Multiplexed Detection of Analytes on Single Test Strips with Antibody-Gated Indicator-Releasing Mesoporous Nanoparticles

This is the peer reviewed version of the following article: Climent, E., Biyikal, M., Gröninger, D., Weller, M. G., Martínez¿Máñez, R., & Rurack, K. (2020). Multiplexed Detection of Analytes on Single Test Strips with Antibody-Gated Indicator-Releasing Mesoporous Nanoparticles. Angewandte Chemie International Edition, 59(52), 23862-23869, which has been published in final form at https://doi.org/10.1002/anie.202009000. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving."[EN] Rapid testing methods for the use directly at a point of need are expected to unfold their true potential especially when offering adequate capabilities for the simultaneous measurement of multiple analytes of interest. Considering the unique modularity, high sensitivity, and selectivity of antibody-gated indicator delivery (gAID) systems, a multiplexed assay for three small-molecule explosives (TATP, TNT, PETN) was thus developed, allowing to detect the analytes simultaneously with a single test strip at lower ppb concentrations in the liquid phase in 2 adsorption/desorption measurements, Y. Salinas and L. E. Santos for support on the materials screening, A. Walter, S. Ramin and A. Hesse for obtaining the sera and R. Gotor and J. Bell for their help in the fabrication of the home-made smartphone periphery. Open access funding enabled and organized by Projekt DEAL.Climent Terol, E.; Biyikal, M.; Gröninger, D.; Weller, MG.; Martínez-Máñez, R.; Rurack, K. (2020). Multiplexed Detection of Analytes on Single Test Strips with Antibody-Gated Indicator-Releasing Mesoporous Nanoparticles. Angewandte Chemie International Edition. 59(52):23862-23869. https://doi.org/10.1002/anie.2020090002386223869595

Antibody-Capped Mesoporous Nanoscopic Materials:Design of a Probe for the Selective Chromo-FluorogenicDetection of Finasteride

[EN] The synthesis of capped mesoporous silica nanoparticles (MSN) conjugated with an antibody (AB) as a gatekeeper has been carried out in order to obtain a delivery system able to release an entrapped cargo (dye) in the presence of a target molecule (antigen) to which the conjugated antibody binds selectively. In particular, MSN loaded with rhodamine B and functionalized on the external surface with a suitable derivative of N-(t-butyl)- 3-oxo-(5a,17b)-4-aza-androst-1-ene-17-carboxamide (finasteride) have been prepared (S1). The addition of polyclonal antibodies against finasteride induced capping of the pores due to the interaction with the anchored hapten-like finasteride derivative to give a MSN¿hapten¿AB nanoparticle S1-AB. It was found that the addition of capped material S1-AB to water solutions containing finasteride resulted in displacement of the antibody, pore uncapping and entrapped-dye release. The response of the gated material is highly selective, and only finasteride, among other steroids, was able to induce a significant uncapping process. Compared with finasteride, the finasteride metabolite was able to release 17% of the dye, whereas the exogen steroids testosterone, metenolone and 16-b-hydroxystanozolol only induced very little release of rhodamine B (lower than 10%) from aqueous suspensions containing sensing solid S1-AB. A detection limit as low as 20 ppb was found for the fluorimetric detection of finasteride. In order to evaluate a possible application of the material for label-free detection of finasteride, the capped material was isolated and stored to give final sensing solid S1-AB-i. It was found to display a similar behavior towards finasteride as to that shown by freshly prepared S1-AB; even after a period of two months, no significant loss of selectivity or sensitivity was noted. Moreover, to study the application for the detection of finasteride in biological samples, this ¿aged¿ material, S1-AB-i, was tested using commercially available blank urine as matrix. Samples containing 70 and 90% blank urine were spiked with a defined amount of finasteride, and the concentration was determined using capped S1-AB-i. Recovery ranges from 94% to 118% were reached.Financial support from the Spanish Government (project MAT2009-14564-C04-01) and the Generalitat Valenciana (Spain) (projects PROMETEO/2009/016 and PROMETEO/2010/008) is gratefully acknowledged. E. C. thanks the Minesterio de Ciencia e Innovacion (MICINN, Spain) for her fellowship.Climent Terol, E.; Martínez Mañez, R.; Maquieira Catala, Á.; Sancenón Galarza, F.; Marcos Martínez, MD.; Brun Sánchez, EM.; Soto Camino, J.... (2012). Antibody-Capped Mesoporous Nanoscopic Materials:Design of a Probe for the Selective Chromo-FluorogenicDetection of Finasteride. ChemistryOpen. 1:251-259. https://doi.org/10.1002/open.201100008S251259

Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the years 2010-2011

This review focuses on examples reported in the years 2010¿2011 dealing with the design of chromogenic and fluorogenic chemosensors or reagents for anions.Santos Figueroa, LE.; Moragues Pons, ME.; Climent Terol, E.; Agostini, A.; Martínez Mañez, R.; Sancenón Galarza, F. (2013). Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the years 2010-2011. Chemical Society Reviews. 42(8):3489-3613. doi:10.1039/C3CS35429FS34893613428Martínez-Máñez, R., & Sancenón, F. (2003). Fluorogenic and Chromogenic Chemosensors and Reagents for Anions. Chemical Reviews, 103(11), 4419-4476. doi:10.1021/cr010421eKatayev, E. A., Ustynyuk, Y. A., & Sessler, J. L. (2006). Receptors for tetrahedral oxyanions. Coordination Chemistry Reviews, 250(23-24), 3004-3037. doi:10.1016/j.ccr.2006.04.013Suksai, C., & Tuntulani, T. (2003). Chromogenic anion sensors. Chemical Society Reviews, 32(4), 192. doi:10.1039/b209598jKim, S. K., Lee, D. H., Hong, J.-I., & Yoon, J. (2009). Chemosensors for Pyrophosphate. Accounts of Chemical Research, 42(1), 23-31. doi:10.1021/ar800003fBeer, P. (2000). Electrochemical and optical sensing of anions by transition metal based receptors. Coordination Chemistry Reviews, 205(1), 131-155. doi:10.1016/s0010-8545(00)00237-xZhou, Y., Xu, Z., & Yoon, J. (2011). Fluorescent and colorimetric chemosensors for detection of nucleotides, FAD and NADH: highlighted research during 2004–2010. Chemical Society Reviews, 40(5), 2222. doi:10.1039/c0cs00169dGunnlaugsson, T., Glynn, M., Tocci (née Hussey), G. M., Kruger, P. E., & Pfeffer, F. M. (2006). Anion recognition and sensing in organic and aqueous media using luminescent and colorimetric sensors. Coordination Chemistry Reviews, 250(23-24), 3094-3117. doi:10.1016/j.ccr.2006.08.017Amendola, V., Esteban-Gómez, D., Fabbrizzi, L., & Licchelli, M. (2006). What Anions Do to N−H-Containing Receptors. Accounts of Chemical Research, 39(5), 343-353. doi:10.1021/ar050195lGunnlaugsson, T., Ali, H. D. P., Glynn, M., Kruger, P. E., Hussey, G. M., Pfeffer, F. M., … Tierney, J. (2005). Fluorescent Photoinduced Electron Transfer (PET) Sensors for Anions; From Design to Potential Application. Journal of Fluorescence, 15(3), 287-299. doi:10.1007/s10895-005-2627-yWiskur, S. L., Ait-Haddou, H., Lavigne, J. J., & Anslyn, E. V. (2001). Teaching Old Indicators New Tricks. Accounts of Chemical Research, 34(12), 963-972. doi:10.1021/ar9600796Nguyen, B. T., & Anslyn, E. V. (2006). Indicator–displacement assays. Coordination Chemistry Reviews, 250(23-24), 3118-3127. doi:10.1016/j.ccr.2006.04.009Xu, Z., Chen, X., Kim, H. N., & Yoon, J. (2010). Sensors for the optical detection ofcyanide ion. Chem. Soc. Rev., 39(1), 127-137. doi:10.1039/b907368jKaur, K., Saini, R., Kumar, A., Luxami, V., Kaur, N., Singh, P., & Kumar, S. (2012). Chemodosimeters: An approach for detection and estimation of biologically and medically relevant metal ions, anions and thiols. Coordination Chemistry Reviews, 256(17-18), 1992-2028. doi:10.1016/j.ccr.2012.04.013Zhou, Y., & Yoon, J. (2012). Recent progress in fluorescent and colorimetric chemosensors for detection ofamino acids. Chem. Soc. Rev., 41(1), 52-67. doi:10.1039/c1cs15159bMoragues, M. E., Martínez-Máñez, R., & Sancenón, F. (2011). Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the year 2009. Chemical Society Reviews, 40(5), 2593. doi:10.1039/c0cs00015aAldrey, A., Núñez, C., García, V., Bastida, R., Lodeiro, C., & Macías, A. (2010). Anion sensing properties of new colorimetric chemosensors based on macrocyclic ligands bearing three nitrophenylurea groups. Tetrahedron, 66(47), 9223-9230. doi:10.1016/j.tet.2010.09.054Odago, M. O., Colabello, D. M., & Lees, A. J. (2010). A simple thiourea based colorimetric sensor for cyanide anion. Tetrahedron, 66(38), 7465-7471. doi:10.1016/j.tet.2010.07.006Piątek, P. (2011). A selective chromogenic chemosensor for carboxylate salt recognition. Chemical Communications, 47(16), 4745. doi:10.1039/c0cc05537aHe, X., Herranz, F., Cheng, E. C.-C., Vilar, R., & Yam, V. W.-W. (2010). Design, Synthesis, Photophysics, and Anion-Binding Studies of Bis(dicyclohexylphosphino)methane-Containing Dinuclear Gold(I) Thiolate Complexes with Urea Receptors. Chemistry - A European Journal, 16(30), 9123-9131. doi:10.1002/chem.201000647Lin, W.-C., Tseng, Y.-P., Lin, C.-Y., & Yen, Y.-P. (2011). Synthesis of alanine-based colorimetric sensors and enantioselective recognition of aspartate and malate anions. Organic & Biomolecular Chemistry, 9(15), 5547. doi:10.1039/c1ob05135kRegueiro-Figueroa, M., Djanashvili, K., Esteban-Gómez, D., de Blas, A., Platas-Iglesias, C., & Rodríguez-Blas, T. (2010). Towards Selective Recognition of Sialic Acid Through Simultaneous Binding to Its cis-Diol and Carboxylate Functions. European Journal of Organic Chemistry, 2010(17), 3237-3248. doi:10.1002/ejoc.201000186Carasel, I. A., Yamnitz, C. R., Winter, R. K., & Gokel, G. W. (2010). Halide Ions Complex and Deprotonate Dipicolinamides and Isophthalamides: Assessment by Mass Spectrometry and UV−Visible Spectroscopy. The Journal of Organic Chemistry, 75(23), 8112-8116. doi:10.1021/jo101749aRostami, A., Colin, A., Li, X. Y., Chudzinski, M. G., Lough, A. J., & Taylor, M. S. (2010). N,N′-Diarylsquaramides: General, High-Yielding Synthesis and Applications in Colorimetric Anion Sensing. The Journal of Organic Chemistry, 75(12), 3983-3992. doi:10.1021/jo100104gAmendola, V., Bergamaschi, G., Boiocchi, M., Fabbrizzi, L., & Milani, M. (2010). The Squaramide versus Urea Contest for Anion Recognition. Chemistry - A European Journal, 16(14), 4368-4380. doi:10.1002/chem.200903190Sola, A., Orenes, R. A., García, M. A., Claramunt, R. M., Alkorta, I., Elguero, J., … Molina, P. (2011). Unprecedented 1,3-Diaza[3]ferrocenophane Scaffold as Molecular Probe for Anions. Inorganic Chemistry, 50(9), 4212-4220. doi:10.1021/ic102314rLee, D. Y., Singh, N., Satyender, A., & Jang, D. O. (2011). An azo dye-coupled tripodal chromogenic sensor for cyanide. Tetrahedron Letters, 52(51), 6919-6922. doi:10.1016/j.tetlet.2011.10.061Haridas, V., Sahu, S., & Praveen Kumar, P. P. (2011). Triazole-based chromogenic and non-chromogenic receptors for halides. Tetrahedron Letters, 52(51), 6930-6934. doi:10.1016/j.tetlet.2011.10.066Park, J. J., Kim, Y.-H., Rhim, S., & Kang, J. (2012). Anion receptors with viologen molecular scaffold. Tetrahedron Letters, 53(2), 247-252. doi:10.1016/j.tetlet.2011.11.040Amendola, V., Fabbrizzi, L., Mosca, L., & Schmidtchen, F.-P. (2011). Urea-, Squaramide-, and Sulfonamide-Based Anion Receptors: A Thermodynamic Study. Chemistry - A European Journal, 17(21), 5972-5981. doi:10.1002/chem.201003411You, J.-M., Jeong, H., Seo, H., & Jeon, S. (2010). A new fluoride ion colorimetric sensor based on dipyrrolemethanes. Sensors and Actuators B: Chemical, 146(1), 160-164. doi:10.1016/j.snb.2010.02.042Farinha, A. S. F., Tomé, A. C., & Cavaleiro, J. A. S. (2010). (E)-3-(meso-Octamethylcalix[4]pyrrol-2-yl)propenal: a versatile precursor for calix[4]pyrrole-based chromogenic anion sensors. Tetrahedron Letters, 51(16), 2184-2187. doi:10.1016/j.tetlet.2010.02.091Lee, G. W., Kim, N.-K., & Jeong, K.-S. (2010). Synthesis of Biindole−Diazo Conjugates as a Colorimetric Anion Receptor. Organic Letters, 12(11), 2634-2637. doi:10.1021/ol100830bBose, P., & Ghosh, P. (2010). Visible and near-infrared sensing of fluoride by indole conjugated urea/thiourea ligands. Chemical Communications, 46(17), 2962. doi:10.1039/b919128cWang, L., He, X., Guo, Y., Xu, J., & Shao, S. (2011). Tris(indolyl)methene molecule as an anion receptor and colorimetric chemosensor: tunable selectivity and sensitivity for anions. Org. Biomol. Chem., 9(3), 752-757. doi:10.1039/c0ob00472cTetilla, M. A., Aragoni, M. C., Arca, M., Caltagirone, C., Bazzicalupi, C., Bencini, A., … Meli, V. (2011). Colorimetric response to anions by a «robust» copper(ii) complex of a [9]aneN3 pendant arm derivative: CN− and I− selective sensing. Chemical Communications, 47(13), 3805. doi:10.1039/c0cc04500dKundu, T., Mobin, S. M., & Lahiri, G. K. (2010). Paramagnetic ruthenium-biimidazole derivatives [(acac)2RuIII(LHn)]m, n/m = 2/+, 1/0, 0/−. Synthesis, structures, solution properties and anion receptor features in solution state. Dalton Transactions, 39(17), 4232. doi:10.1039/b919036hLee, C.-H., Lee, S., Yoon, H., & Jang, W.-D. (2011). Strong Binding Affinity of a Zinc-Porphyrin-Based Receptor for Halides through the Cooperative Effects of Quadruple CH Hydrogen Bonds and Axial Ligation. Chemistry - A European Journal, 17(49), 13898-13903. doi:10.1002/chem.201101884Swinburne, A. N., Paterson, M. J., Fischer, K. H., Dickson, S. J., Wallace, E. V. B., Belcher, W. J., … Steed, J. W. (2010). Colourimetric Carboxylate Anion Sensors Derived from Viologen-Based Receptors. Chemistry - A European Journal, 16(5), 1480-1492. doi:10.1002/chem.200902609Kannappan, R., Bucher, C., Saint-Aman, E., Moutet, J.-C., Milet, A., Oltean, M., … Chaix, C. (2010). Viologen-based redox-switchable anion-binding receptors. New Journal of Chemistry, 34(7), 1373. doi:10.1039/b9nj00757aKumari, N., Jha, S., & Bhattacharya, S. (2011). Colorimetric Probes Based on Anthraimidazolediones for Selective Sensing of Fluoride and Cyanide Ion via Intramolecular Charge Transfer. The Journal of Organic Chemistry, 76(20), 8215-8222. doi:10.1021/jo201290aAmendola, V., Boiocchi, M., Fabbrizzi, L., & Fusco, N. (2011). Putting the Anion into the Cage - Fluoride Inclusion in the Smallest Trisimidazolium Macrotricycle. European Journal of Organic Chemistry, 2011(32), 6434-6444. doi:10.1002/ejoc.201100902Kumar, A., Kumar, V., & Upadhyay, K. K. (2011). A ninhydrin based colorimetric molecular switch for Hg2+ and CH3COO−/F−. Tetrahedron Letters, 52(50), 6809-6813. doi:10.1016/j.tetlet.2011.10.046Bao, X., & Zhou, Y. (2010). Synthesis and recognition properties of a class of simple colorimetric anion chemosensors containing OH and CONH groups. Sensors and Actuators B: Chemical, 147(2), 434-441. doi:10.1016/j.snb.2010.03.068Lou, X., Zhang, Y., Li, Q., Qin, J., & Li, Z. (2011). A highly specific rhodamine-based colorimetric probe for hypochlorites: a new sensing strategy and real application in tap water. Chemical Communications, 47(11), 3189. doi:10.1039/c0cc04911eShang, X.-F., Su, H., Lin, H., & Lin, H.-K. (2010). A supramolecular optic sensor for selective recognition AMP. Inorganic Chemistry Communications, 13(8), 999-1003. doi:10.1016/j.inoche.2010.04.006Mendy, J. S., Saeed, M. A., Fronczek, F. R., Powell, D. R., & Hossain, M. A. (2010). Anion Recognition and Sensing by a New Macrocyclic Dinuclear Copper(II) Complex: A Selective Receptor for Iodide. Inorganic Chemistry, 49(16), 7223-7225. doi:10.1021/ic100686mMahato, P., Ghosh, A., Mishra, S. K., Shrivastav, A., Mishra, S., & Das, A. (2011). Zn(II)−Cyclam Based Chromogenic Sensors for Recognition of ATP in Aqueous Solution Under Physiological Conditions and Their Application as Viable Staining Agents for Microorganism. Inorganic Chemistry, 50(9), 4162-4170. doi:10.1021/ic200223gMahato, P., Ghosh, A., Mishra, S. K., Shrivastav, A., Mishra, S., & Das, A. (2010). Zn(II) based colorimetric sensor for ATP and its use as a viable staining agent in pure aqueous media of pH 7.2. Chemical Communications, 46(48), 9134. doi:10.1039/c0cc01996hDalla Cort, A., Forte, G., & Schiaffino, L. (2011). Anion Recognition in Water with Use of a Neutral Uranyl-salophen Receptor. The Journal of Organic Chemistry, 76(18), 7569-7572. doi:10.1021/jo201213eDas, P., Mandal, A. K., Kesharwani, M. 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Chemistry - A European Journal, 17(25), 7020-7031. doi:10.1002/chem.201100428Chen, Z., Lu, Y., He, Y., & Huang, X. (2010). Recognition of pyrophosphate anion in aqueous solution using the competition displacement method. Sensors and Actuators B: Chemical, 149(2), 407-412. doi:10.1016/j.snb.2010.06.038Müller-Graff, P.-K., Szelke, H., Severin, K., & Krämer, R. (2010). Pattern-based sensing of sulfated glycosaminoglycans with a dynamic mixture of iron complexes. Organic & Biomolecular Chemistry, 8(10), 2327. doi:10.1039/c000420kHu, Z.-Q., Wang, X.-M., Feng, Y.-C., Ding, L., Li, M., & Lin, C.-S. (2011). A novel colorimetric and fluorescent chemosensor for acetate ions in aqueous media based on a rhodamine 6G–phenylurea conjugate in the presence of Fe(iii) ions. Chem. Commun., 47(5), 1622-1624. doi:10.1039/c0cc04136jSingh, N., & Jang, D. O. (2011). A selective ATP chromogenic sensor for use in an indicator displacement assay. Tetrahedron Letters, 52(39), 5094-5097. doi:10.1016/j.tetlet.2011.07.096Ghosh, K., & Ranjan Sarkar, A. (2011). Pyridinium-based symmetrical diamides as chemosensors in visual sensing of citrate through indicator displacement assay (IDA) and gel formation. Organic & Biomolecular Chemistry, 9(19), 6551. doi:10.1039/c1ob05707cAtta, A. K., Ahn, I.-H., Hong, A.-Y., Heo, J., Kim, C. K., & Cho, D.-G. (2012). Fluoride indicator that functions in mixed aqueous media: hydrogen bonding effects. Tetrahedron Letters, 53(5), 575-578. doi:10.1016/j.tetlet.2011.11.099Perry-Feigenbaum, R., Sella, E., & Shabat, D. (2011). Autoinductive Exponential Signal Amplification: A Diagnostic Probe for Direct Detection of Fluoride. Chemistry - A European Journal, 17(43), 12123-12128. doi:10.1002/chem.201101796Rajamalli, P., & Prasad, E. (2011). Low Molecular Weight Fluorescent Organogel for Fluoride Ion Detection. Organic Letters, 13(14), 3714-3717. doi:10.1021/ol201325jBhaumik, C., Das, S., Maity, D., & Baitalik, S. (2011). A terpyridyl-imidazole (tpy-HImzPh3) based bifunctional receptor for multichannel detection of Fe2+ and F− ions. Dalton Transactions, 40(44), 11795. doi:10.1039/c1dt10965kIsaad, J., & Perwuelz, A. (2010). New color chemosensors for cyanide based on water soluble azo dyes. Tetrahedron Letters, 51(44), 5810-5814. doi:10.1016/j.tetlet.2010.08.098Wade, C. R., & Gabbaï, F. P. (2010). Cyanide Anion Binding by a Triarylborane at the Outer Rim of a Cyclometalated Ruthenium(II) Cationic Complex. Inorganic Chemistry, 49(2), 714-720. doi:10.1021/ic9020349Ábalos, T., Jiménez, D., Moragues, M., Royo, S., Martínez-Máñez, R., Sancenón, F., … Gil, S. (2010). Multi-channel receptors based on thiopyrylium functionalised with macrocyclic receptors for the recognition of transition metal cations and anions. 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Biosourced 3-formyl chromenyl-azo dye as Michael acceptor type of chemodosimeter for cyanide in aqueous environment. Tetrahedron, 67(31), 5678-5685. doi:10.1016/j.tet.2011.05.083Isaad, J., & El Achari, A. (2011). A novel cyanide chemodosimeter based on trifluoroacetamide benzhydrol-2 as binding motif: importance of substituent positioning on intra-molecular charge transfer. Tetrahedron, 67(23), 4196-4201. doi:10.1016/j.tet.2011.04.059Park, I. S., Heo, E.-J., & Kim, J.-M. (2011). A photochromic phenoxyquinone based cyanide ion sensor. Tetrahedron Letters, 52(19), 2454-2457. doi:10.1016/j.tetlet.2011.02.105Tang, X., Liu, W., Wu, J., Zhao, W., Zhang, H., & Wang, P. (2011). A colorimetric chemosensor for fast detection of thiols based on intramolecular charge transfer. Tetrahedron Letters, 52(40), 5136-5139. doi:10.1016/j.tetlet.2011.07.111Wei, W., Liang, X., Hu, G., Guo, Y., & Shao, S. (2011). A highly selective colorimetric probe based on 2,2′,2″-trisindolylmethene for cysteine/homocysteine. Tetrahedron Letters, 52(13), 1422-1425. doi:10.1016/j.tetlet.2010.07.182Cui, K., Zhang, D., Zhang, G., & Zhu, D. (2010). A highly selective naked-eye probe for hypochlorite with the p-methoxyphenol-substituted aniline compound. Tetrahedron Letters, 51(46), 6052-6055. doi:10.1016/j.tetlet.2010.09.041Kim, M. H., Kim, S., Jang, H. H., Yi, S., Seo, S. H., & Han, M. S. (2010). A gold nanoparticle-based colorimetric sensing ensemble for the colorimetric detection of cyanide ions in aqueous solution. Tetrahedron Letters, 51(36), 4712-4716. doi:10.1016/j.tetlet.2010.07.002Zhang, S., Wang, J., Han, L., Li, C., Wang, W., & Yuan, Z. (2010). Colorimetric detection of bis-phosphorylated peptides using zinc(ii) dipicolylamine-appended gold nanoparticles. Sensors and Actuators B: Chemical, 147(2), 687-690. doi:10.1016/j.snb.2010.03.071Feng, D.-Q., Liu, G., Zheng, W., Liu, J., Chen, T., & Li, D. (2011). A highly selective and sensitive on–off sensor for silver ions and cysteine by light scattering technique of DNA-functionalized gold nanoparticles. Chemical Communications, 47(30), 8557. doi:10.1039/c1cc12377gCao, R., & Li, B. (2011). A simple and sensitive method for visual detection of heparin using positively-charged gold nanoparticles as colorimetric probes. Chemical Communications, 47(10), 2865. doi:10.1039/c0cc05094fLiu, C.-Y., & Tseng, W.-L. (2011). Colorimetric assay for cyanide and cyanogenic glycoside using polysorbate 40-stabilized gold nanoparticles. Chemical Communications, 47(9), 2550. doi:10.1039/c0cc04591hZhang, M., Liu, Y.-Q., & Ye, B.-C. (2011). Rapid and sensitive colorimetric visualization of phthalates using UTP-modified gold nanoparticles cross-linked by copper(ii). Chemical Communications, 47(43), 11849. doi:10.1039/c1cc14772bLi, H., Li, F., Han, C., Cui, Z., Xie, G., & Zhang, A. (2010). Highly sensitive and selective tryptophan colorimetric sensor based on 4,4-bipyridine-functionalized silver nanoparticles. Sensors and Actuators B: Chemical, 145(1), 194-199. doi:10.1016/j.snb.2009.11.062Sakai, R., Okade, S., Barasa, E. B., Kakuchi, R., Ziabka, M., Umeda, S., … Kakuchi, T. (2010). Efficient Colorimetric Anion Detection Based on Positive Allosteric System of Urea-Functionalized Poly(phenylacetylene) Receptor. Macromolecules, 43(18), 7406-7411. doi:10.1021/ma1016852Sakai, R., Sakai, N., Satoh, T., Li, W., Zhang, A., & Kakuchi, T. (2011). Strict Size Specificity in Colorimetric Anion Detection Based on Poly(phenylacetylene) Receptor Bearing Second Generation Lysine Dendrons. Macromolecules, 44(11), 4249-4257. doi:10.1021/ma200710rIsaad, J., & Salaün, F. (2011). Functionalized poly (vinyl alcohol) polymer as chemodosimeter material for the colorimetric sensing of cyanide in pure water. Sensors and Actuators B: Chemical, 157(1), 26-33. doi:10.1016/j.snb.2011.03.022Isaad, J., & El Achari, A. (2011). Colorimetric sensing of cyanide anions in aqueous media based on functional surface modification of natural cellulose materials. Tetrahedron, 67(26), 4939-4947. doi:10.1016/j.tet.2011.04.061Yao, Z., Bai, H., Li, C., & Shi, G. (2010). Analyte-induced aggregation of conjugated polyelectrolytes: role of the charged moieties and its sensing application. Chemical Communications, 46(28), 5094. doi:10.1039/c002188aKrishnamurthi, J., Ono, T., Amemori, S., Komatsu, H., Shinkai, S., & Sada, K. (2011). Thiourea-tagged poly(octadecyl acrylate) gels as fluoride and acetate responsive polymer gels through selective complexation. Chem. Commun., 47(5), 1571-1573. doi:10.1039/c0cc03256eVallejos, S., Estévez, P., García, F. C., Serna, F., de la Peña, J. L., & García, J. M. (201

Design of new hybrid materials: Study of its application in new detection formats and in controlled release applications

Climent Terol, E. (2012). Design of new hybrid materials: Study of its application in new detection formats and in controlled release applications [Tesis doctoral]. Editorial Universitat Politècnica de València. https://doi.org/10.4995/Thesis/10251/17939Palanci

Selective and sensitive chromo-fluorogenic sensing of anionic surfactants in water using functionalised silica nanoparticles

A new chromo-fluorogenic sensing protocol for anionic surfactants in aqueous environments using silica functionalised nanoparticles containing imidazolium and thiol groups has been developed. © 2011 The Royal Society of Chemistry.Financial support from the Spanish Government (project MAT2009-14564-C04-01) and the Generalitat Valencia (project PROMETEO/2009/016) is gratefully acknowledged. E. C. and C. G. thank the MICINN and the UPV for fellowships.Climent Terol, E.; Giménez Morales, C.; Marcos Martínez, MD.; Martínez Mañez, R.; Sancenón Galarza, F.; Soto Camino, J. (2011). Selective and sensitive chromo-fluorogenic sensing of anionic surfactants in water using functionalised silica nanoparticles. Chemical Communications. 47:6873-6875. https://doi.org/10.1039/c1cc11393cS6873687547Cserháti, T., Forgács, E., & Oros, G. (2002). Biological activity and environmental impact of anionic surfactants. Environment International, 28(5), 337-348. doi:10.1016/s0160-4120(02)00032-6Richardson, S. D. (2007). Water Analysis:  Emerging Contaminants and Current Issues. Analytical Chemistry, 79(12), 4295-4324. doi:10.1021/ac070719qGonzález, S., Barceló, D., & Petrovic, M. (2007). Advanced liquid chromatography-mass spectrometry (LC-MS) methods applied to wastewater removal and the fate of surfactants in the environment. TrAC Trends in Analytical Chemistry, 26(2), 116-124. doi:10.1016/j.trac.2006.12.003Ventura, F., & de Voogt, P. (2003). Chapter 2 Separation and detection. Comprehensive Analytical Chemistry, 51-392. doi:10.1016/s0166-526x(03)40005-6Sánchez, J., & del Valle, M. (2005). Determination of Anionic Surfactants Employing Potentiometric Sensors—A Review. Critical Reviews in Analytical Chemistry, 35(1), 15-29. doi:10.1080/10408340590947899GERLACHE, M., KAUFFMANN, J., QUARIN, G., VIRE, J., BRYANT, G., & TALBOT, J. (1996). Electrochemical analysis of surfactants: An overview. Talanta, 43(4), 507-519. doi:10.1016/0039-9140(95)01787-9Caltagirone, C., & Gale, P. A. (2009). Anion receptor chemistry: highlights from 2007. Chem. Soc. Rev., 38(2), 520-563. doi:10.1039/b806422aAmendola, V., Esteban-Gómez, D., Fabbrizzi, L., & Licchelli, M. (2006). What Anions Do to N−H-Containing Receptors. Accounts of Chemical Research, 39(5), 343-353. doi:10.1021/ar050195lDe Silva, A. P., Gunaratne, H. Q. N., Gunnlaugsson, T., Huxley, A. J. M., McCoy, C. P., Rademacher, J. T., & Rice, T. E. (1997). Signaling Recognition Events with Fluorescent Sensors and Switches. Chemical Reviews, 97(5), 1515-1566. doi:10.1021/cr960386pMartínez-Máñez, R., Sancenón, F., Hecht, M., Biyikal, M., & Rurack, K. (2010). Nanoscopic optical sensors based on functional supramolecular hybrid materials. Analytical and Bioanalytical Chemistry, 399(1), 55-74. doi:10.1007/s00216-010-4198-2Climent, E., Marcos, M. D., Martínez-Máñez, R., Sancenón, F., Soto, J., Rurack, K., & Amorós, P. (2009). The Determination of Methylmercury in Real Samples Using Organically Capped Mesoporous Inorganic Materials Capable of Signal Amplification. Angewandte Chemie International Edition, 48(45), 8519-8522. doi:10.1002/anie.200904243Casasús, R., Aznar, E., Marcos, M. D., Martínez-Máñez, R., Sancenón, F., Soto, J., & Amorós, P. (2006). New Methods for Anion Recognition and Signaling Using Nanoscopic Gatelike Scaffoldings. Angewandte Chemie International Edition, 45(40), 6661-6664. doi:10.1002/anie.200602045Balaji, T., El-Safty, S. A., Matsunaga, H., Hanaoka, T., & Mizukami, F. (2006). Optical Sensors Based on Nanostructured Cage Materials for the Detection of Toxic Metal Ions. Angewandte Chemie International Edition, 45(43), 7202-7208. doi:10.1002/anie.200602453El-Safty, S. A., Ismail, A. A., Matsunaga, H., & Mizukami, F. (2007). Optical Nanosensor Design with Uniform Pore Geometry and Large Particle Morphology. Chemistry - A European Journal, 13(33), 9245-9255. doi:10.1002/chem.200700499Brasola, E., Mancin, F., Rampazzo, E., Tecilla, P., & Tonellato, U. (2003). A fluorescence nanosensor for Cu2+ on silica particlesElectronic supplementary information (ESI) available: experimental procedure; TEM images; NMR, UV-vis and fluorescence spectra; fluoresence titration. See http://www.rsc.org/suppdata/cc/b3/b310582b/. Chemical Communications, (24), 3026. doi:10.1039/b310582bRampazzo, E., Brasola, E., Marcuz, S., Mancin, F., Tecilla, P., & Tonellato, U. (2005). Surface modification of silica nanoparticles: a new strategy for the realization of self-organized fluorescence chemosensors. Journal of Materials Chemistry, 15(27-28), 2687. doi:10.1039/b502052bDescalzo, A. B., Martínez-Máñez, R., Sancenón, F., Hoffmann, K., & Rurack, K. (2006). The Supramolecular Chemistry of Organic–Inorganic Hybrid Materials. Angewandte Chemie International Edition, 45(36), 5924-5948. doi:10.1002/anie.200600734Trewyn, B. G., Slowing, I. I., Giri, S., Chen, H.-T., & Lin, V. S.-Y. (2007). Synthesis and Functionalization of a Mesoporous Silica Nanoparticle Based on the Sol–Gel Process and Applications in Controlled Release. Accounts of Chemical Research, 40(9), 846-853. doi:10.1021/ar600032uCliment, E., Casasús, R., Marcos, M. D., Martínez-Máñez, R., Sancenón, F., & Soto, J. (2008). Chromo-fluorogenic sensing of pyrophosphate in aqueous media using silica functionalised with binding and reactive units. Chemical Communications, (48), 6531. doi:10.1039/b813199fCliment, E., Calero, P., Marcos, M. D., Martínez-Máñez, R., Sancenón, F., & Soto, J. (2009). Selective Chromofluorogenic Sensing of Heparin by using Functionalised Silica Nanoparticles Containing Binding Sites and a Signalling Reporter. Chemistry - A European Journal, 15(8), 1816-1820. doi:10.1002/chem.200802074Climent, E., Martínez-Máñez, R., Sancenón, F., Marcos, M. D., Soto, J., Maquieira, A., & Amorós, P. (2010). Controlled Delivery Using Oligonucleotide-Capped Mesoporous Silica Nanoparticles. Angewandte Chemie International Edition, 49(40), 7281-7283. doi:10.1002/anie.201001847Gadzekpo, V. P. Y., Xiao, K. P., Aoki, H., Bühlmann, P., & Umezawa, Y. (1999). Voltammetric Detection of the Polycation Protamine by the Use of Electrodes Modified with Self-Assembled Monolayers of Thioctic Acid. Analytical Chemistry, 71(22), 5109-5115. doi:10.1021/ac990580mGadzekpo, V. P. Y., Bühlmann, P., Xiao, K. P., Aoki, H., & Umezawa, Y. (2000). Development of an ion-channel sensor for heparin detection. Analytica Chimica Acta, 411(1-2), 163-173. doi:10.1016/s0003-2670(00)00740-6Ros-Lis, J. V., García, B., Jiménez, D., Martínez-Máñez, R., Sancenón, F., Soto, J., … Valldecabres, M. C. (2004). Squaraines as Fluoro−Chromogenic Probes for Thiol-Containing Compounds and Their Application to the Detection of Biorelevant Thiols. Journal of the American Chemical Society, 126(13), 4064-4065. doi:10.1021/ja031987iYoon, J., Kim, S. K., Singh, N. J., & Kim, K. S. (2006). Imidazolium receptors for the recognition of anions. Chemical Society Reviews, 35(4), 355. doi:10.1039/b513733kXu, Z., Kim, S. K., & Yoon, J. (2010). Revisit to imidazolium receptors for the recognition of anions: highlighted research during 2006–2009. Chemical Society Reviews, 39(5), 1457. doi:10.1039/b918937hColl, C., Martínez-Máñez, R., Marcos, M. D., Sancenón, F., & Soto, J. (2007). A Simple Approach for the Selective and Sensitive Colorimetric Detection of Anionic Surfactants in Water. Angewandte Chemie International Edition, 46(10), 1675-1678. doi:10.1002/anie.200603800Ros-Lis, J. V., Martínez-Máñez, R., Sancenón, F., Soto, J., Spieles, M., & Rurack, K. (2008). Squaraines as Reporter Units: Insights into their Photophysics, Protonation, and Metal-Ion Coordination Behaviour. Chemistry - A European Journal, 14(32), 10101-10114. doi:10.1002/chem.200800300Montalti, M., Prodi, L., Zaccheroni, N., & Falini, G. (2002). Solvent-Induced Modulation of Collective Photophysical Processes in Fluorescent Silica Nanoparticles. Journal of the American Chemical Society, 124(45), 13540-13546. doi:10.1021/ja027270

A Rapid and Sensitive Strip-Based Quick Test for Nerve Agents Tabun, Sarin, and Soman Using BODIPY-Modified Silica Materials

Test strips that in combination with a portable fluorescence reader or digital camera can rapidly and selectively detect chemical warfare agents (CWAs) such as Tabun (GA), Sarin (GB), and Soman (GD) and their simulants in the gas phase have been developed. The strips contain spots of a hybrid indicator material consisting of a fluorescent BODIPY indicator covalently anchored into the channels of mesoporous SBA silica microparticles. The fluorescence quenching response allows the sensitive detection of CWAs in the mu g m(-3) range in a few seconds.Financial support from the Alexander von Humboldt Foundation, the German Federal Ministry for Economic Affairs and Energy, European FEDER funds (MAT2012-38429-C04), the Generalitat Valenciana (PROMETEOII/2014/047), and the Spanish Government is gratefully acknowledged. We thank S. Selve (Technical University Berlin) for TEM images, A. Zehl (Humboldt University Berlin) for elemental analysis, D. Pfeifer (BAM, Div. 1.3) for NMR, A. Zimathies (BAM 1.3) for N2 adsorption/desorption, S. Ewald and A. Lehmann (BAM 1.5 & 1.8) for MS support, and T. Fischer (BAM 1.9) for support with the fluorescence decay measurements.Climent Terol, E.; Biyikal, M.; Gawlitza, K.; Dropa, T.; Urban, M.; Costero Nieto, AM.; Martínez-Máñez, R.... (2016). A Rapid and Sensitive Strip-Based Quick Test for Nerve Agents Tabun, Sarin, and Soman Using BODIPY-Modified Silica Materials. Chemistry - A European Journal. 22(32):11138-11142. https://doi.org/10.1002/chem.201601269S1113811142223

A Simple Probe for the Colorimetric Detection of Carbon Dioxide

The present study reports a novel approach for the chromogenic sensing of CO2 using silica nanoparticles N1 functionalized with amino and thiol moieties. The reaction of CO2 present in air with the hybrid silica nanoparticles controlled the access of a squaraine dye to the surface of nanoparticles, due to formation of carbamates between amino groups and carbon dioxide. This competitive reaction results in a simple chromogenic response to CO2. By using these bifunctionalized nanoparticles CO2 detection was achieved using suspensions of N1 in phosphate buffer or by using N1 directly in contact with air containing CO2. The use of nanoparticles that can be easily functionalized with two or more individual groups that are able to react with dyes and CO2, and the possible use of a wide range of different dyes (for signalling), makes this approach highly appealing and versatile for the design of chromo¿fluorogenic dosimeters for the evaluation of the accumulative exposure to CO2 in different environmentsFinancial support from the Spanish Government (project MAT2012-38429-C04-01) and the Generalitat Valencia (project PROMETEO/2009/016) is gratefully acknowledged. A. A. thanks the Generalitat Valencia for a Santiago Grisolia fellowship. M. E. M. is grateful to the Spanish Ministerio de Ciencia e Innovacion for an FPU grant.Climent Terol, E.; Agostini, A.; Moragues Pons, ME.; Martínez Mañez, R.; Sancenón Galarza, F.; Pardo Vicente, MT.; Marcos Martínez, MD. (2013). A Simple Probe for the Colorimetric Detection of Carbon Dioxide. Chemistry - A European Journal. 19:17301-17304. https://doi.org/10.1002/chem.201302991S17301173041

Towards Chemical Communication between Gated Nanoparticles

The design of comparatively simple and modularly configurable artificial systems able to communicate through the exchange of chemical messengers is, to the best of our knowledge, an unexplored field. As a proof-of-concept, we present here a family of nanoparticles that have been designed to communicate with one another in a hierarchical manner. The concept involves the use of capped mesoporous silica supports in which the messenger delivered by a first type of gated nanoparticle is used to open a second type of nanoparticle, which delivers another messenger that opens a third group of gated nanoobjects.We believe that the conceptual idea that nanodevices can be designed to communicate with one another may result in novel applications and will boost further advances towards cooperative systems with complex behavior as a result of the communication between simple abiotic individual components.Financial support from the Spanish government (project MAT2012-38429-C04-01) and the Generalitat Valencia (project PROMETEO/2009/016) is gratefully acknowledged. E.A. thanks the Universitat Politecnica de Valencia (project SP20120795) for support. C.G. is grateful to the Spanish Ministry of Science and Innovation for a grant. E.C. is grateful to the Adolf-Martens-Fonds for a fellowship. We are indebted to M. Dinter (LTB Lasertechnik Berlin GmbH) for assistance with the graphics.Giménez Morales, C.; Climent Terol, E.; Aznar Gimeno, E.; Martínez Mañez, R.; Sancenón Galarza, F.; Marcos Martínez, MD.; Amoros Del Toro, PJ.... (2014). Towards Chemical Communication between Gated Nanoparticles. Angewandte Chemie International Edition. 53(46):12629-12633. https://doi.org/10.1002/anie.201405580S12629126335346Steiger, S., Schmitt, T., & Schaefer, H. M. (2010). The origin and dynamic evolution of chemical information transfer. Proceedings of the Royal Society B: Biological Sciences, 278(1708), 970-979. doi:10.1098/rspb.2010.2285Waters, C. M., & Bassler, B. L. (2005). QUORUM SENSING: Cell-to-Cell Communication in Bacteria. Annual Review of Cell and Developmental Biology, 21(1), 319-346. doi:10.1146/annurev.cellbio.21.012704.131001Van Donk, E. (2007). Chemical information transfer in freshwater plankton. Ecological Informatics, 2(2), 112-120. doi:10.1016/j.ecoinf.2007.03.002Robinson, G. E., & Huang, Z.-Y. (1998). Colony integration in honey bees: genetic, endocrine and social control of division of labor. Apidologie, 29(1-2), 159-170. doi:10.1051/apido:19980109Sbarbati, A., & Osculati, F. (2006). Allelochemical Communication in Vertebrates: Kairomones, Allomones and Synomones. Cells Tissues Organs, 183(4), 206-219. doi:10.1159/000096511Wayne, R. (1994). The excitability of plant cells: With a special emphasis on characean internodal cells. The Botanical Review, 60(3), 265-367. doi:10.1007/bf02960261Pacheco, A. R., & Sperandio, V. (2009). Inter-kingdom signaling: chemical language between bacteria and host. Current Opinion in Microbiology, 12(2), 192-198. doi:10.1016/j.mib.2009.01.006Badri, D. V., Weir, T. L., van der Lelie, D., & Vivanco, J. M. (2009). Rhizosphere chemical dialogues: plant–microbe interactions. Current Opinion in Biotechnology, 20(6), 642-650. doi:10.1016/j.copbio.2009.09.014Janata, J. (2009). Principles of Chemical Sensors. doi:10.1007/b136378Rieth, S., Hermann, K., Wang, B.-Y., & Badjić, J. D. (2011). Controlling the dynamics of molecular encapsulation and gating. Chem. Soc. Rev., 40(3), 1609-1622. doi:10.1039/c005254jKreft, O., Prevot, M., Möhwald, H., & Sukhorukov, G. B. (2007). Shell-in-Shell Microcapsules: A Novel Tool for Integrated, Spatially Confined Enzymatic Reactions. Angewandte Chemie International Edition, 46(29), 5605-5608. doi:10.1002/anie.200701173Kreft, O., Prevot, M., Möhwald, H., & Sukhorukov, G. B. (2007). Effiziente Kopplung räumlich getrennter Enzymreaktionen in «Shell-in-shell»-Mikrokapseln. Angewandte Chemie, 119(29), 5702-5705. doi:10.1002/ange.200701173Coll, C., Bernardos, A., Martínez-Máñez, R., & Sancenón, F. (2012). Gated Silica Mesoporous Supports for Controlled Release and Signaling Applications. Accounts of Chemical Research, 46(2), 339-349. doi:10.1021/ar3001469Yang, P., Gai, S., & Lin, J. (2012). Functionalized mesoporous silica materials for controlled drug delivery. Chemical Society Reviews, 41(9), 3679. doi:10.1039/c2cs15308dLi, Z., Barnes, J. C., Bosoy, A., Stoddart, J. F., & Zink, J. I. (2012). Mesoporous silica nanoparticles in biomedical applications. Chemical Society Reviews, 41(7), 2590. doi:10.1039/c1cs15246gLudlow, R. F., & Otto, S. (2008). Systems chemistry. Chem. Soc. Rev., 37(1), 101-108. doi:10.1039/b611921mTaylor, A. F., Tinsley, M. R., Wang, F., Huang, Z., & Showalter, K. (2009). Dynamical Quorum Sensing and Synchronization in Large Populations of Chemical Oscillators. Science, 323(5914), 614-617. doi:10.1126/science.1166253Dickschat, J. S. (2010). Quorum sensing and bacterial biofilms. Natural Product Reports, 27(3), 343. doi:10.1039/b804469bKerényi, Á., Bihary, D., Venturi, V., & Pongor, S. (2013). Stability of Multispecies Bacterial Communities: Signaling Networks May Stabilize Microbiomes. PLoS ONE, 8(3), e57947. doi:10.1371/journal.pone.0057947Betke, K. M., Wells, C. A., & Hamm, H. E. (2012). GPCR mediated regulation of synaptic transmission. Progress in Neurobiology, 96(3), 304-321. doi:10.1016/j.pneurobio.2012.01.009Aznar, E., Martínez-Máñez, R., & Sancenón, F. (2009). Controlled release using mesoporous materials containing gate-like scaffoldings. Expert Opinion on Drug Delivery, 6(6), 643-655. doi:10.1517/17425240902895980Cotí, K. K., Belowich, M. E., Liong, M., Ambrogio, M. W., Lau, Y. A., Khatib, H. A., … Stoddart, J. F. (2009). Mechanised nanoparticles for drug delivery. Nanoscale, 1(1), 16. doi:10.1039/b9nr00162jWang, C., Li, Z., Cao, D., Zhao, Y.-L., Gaines, J. W., Bozdemir, O. A., … Stoddart, J. F. (2012). Stimulated Release of Size-Selected Cargos in Succession from Mesoporous Silica Nanoparticles. Angewandte Chemie International Edition, 51(22), 5460-5465. doi:10.1002/anie.201107960Wang, C., Li, Z., Cao, D., Zhao, Y.-L., Gaines, J. W., Bozdemir, O. A., … Stoddart, J. F. (2012). Stimulated Release of Size-Selected Cargos in Succession from Mesoporous Silica Nanoparticles. Angewandte Chemie, 124(22), 5556-5561. doi:10.1002/ange.201107960Liu, R., Zhao, X., Wu, T., & Feng, P. (2008). Tunable Redox-Responsive Hybrid Nanogated Ensembles. Journal of the American Chemical Society, 130(44), 14418-14419. doi:10.1021/ja8060886Zhu, C.-L., Lu, C.-H., Song, X.-Y., Yang, H.-H., & Wang, X.-R. (2011). Bioresponsive Controlled Release Using Mesoporous Silica Nanoparticles Capped with Aptamer-Based Molecular Gate. Journal of the American Chemical Society, 133(5), 1278-1281. doi:10.1021/ja110094gSchlossbauer, A., Dohmen, C., Schaffert, D., Wagner, E., & Bein, T. (2011). pH-Responsive Release of Acetal-Linked Melittin from SBA-15 Mesoporous Silica. Angewandte Chemie International Edition, 50(30), 6828-6830. doi:10.1002/anie.201005120Schlossbauer, A., Dohmen, C., Schaffert, D., Wagner, E., & Bein, T. (2011). pH-Responsive Release of Acetal-Linked Melittin from SBA-15 Mesoporous Silica. Angewandte Chemie, 123(30), 6960-6962. doi:10.1002/ange.201005120Wu, S., Huang, X., & Du, X. (2013). Glucose- and pH-Responsive Controlled Release of Cargo from Protein-Gated Carbohydrate-Functionalized Mesoporous Silica Nanocontainers. Angewandte Chemie International Edition, 52(21), 5580-5584. doi:10.1002/anie.201300958Wu, S., Huang, X., & Du, X. (2013). Glucose- and pH-Responsive Controlled Release of Cargo from Protein-Gated Carbohydrate-Functionalized Mesoporous Silica Nanocontainers. Angewandte Chemie, 125(21), 5690-5694. doi:10.1002/ange.201300958Zhang, Z., Balogh, D., Wang, F., & Willner, I. (2013). Smart Mesoporous SiO2 Nanoparticles for the DNAzyme-Induced Multiplexed Release of Substrates. Journal of the American Chemical Society, 135(5), 1934-1940. doi:10.1021/ja311385yYang, X., Pu, F., Chen, C., Ren, J., & Qu, X. (2012). An enzyme-responsive nanocontainer as an intelligent signal-amplification platform for a multiple proteases assay. Chemical Communications, 48(90), 11133. doi:10.1039/c2cc36340bSchlossbauer, A., Kecht, J., & Bein, T. (2009). Biotin-Avidin as a Protease-Responsive Cap System for Controlled Guest Release from Colloidal Mesoporous Silica. Angewandte Chemie International Edition, 48(17), 3092-3095. doi:10.1002/anie.200805818Schlossbauer, A., Kecht, J., & Bein, T. (2009). Biotin-Avidin as a Protease-Responsive Cap System for Controlled Guest Release from Colloidal Mesoporous Silica. Angewandte Chemie, 121(17), 3138-3141. doi:10.1002/ange.200805818Park, C., Kim, H., Kim, S., & Kim, C. (2009). Enzyme Responsive Nanocontainers with Cyclodextrin Gatekeepers and Synergistic Effects in Release of Guests. Journal of the American Chemical Society, 131(46), 16614-16615. doi:10.1021/ja9061085Thornton, P. D., & Heise, A. (2010). Highly Specific Dual Enzyme-Mediated Payload Release from Peptide-Coated Silica Particles. Journal of the American Chemical Society, 132(6), 2024-2028. doi:10.1021/ja9094439Coll, C., Mondragón, L., Martínez-Máñez, R., Sancenón, F., Marcos, M. D., Soto, J., … Pérez-Payá, E. (2011). Enzyme-Mediated Controlled Release Systems by Anchoring Peptide Sequences on Mesoporous Silica Supports. Angewandte Chemie International Edition, 50(9), 2138-2140. doi:10.1002/anie.201004133Coll, C., Mondragón, L., Martínez-Máñez, R., Sancenón, F., Marcos, M. D., Soto, J., … Pérez-Payá, E. (2011). Enzyme-Mediated Controlled Release Systems by Anchoring Peptide Sequences on Mesoporous Silica Supports. Angewandte Chemie, 123(9), 2186-2188. doi:10.1002/ange.201004133Climent, E., Gröninger, D., Hecht, M., Walter, M. A., Martínez-Máñez, R., Weller, M. G., … Rurack, K. (2013). Selective, Sensitive, and Rapid Analysis with Lateral-Flow Assays Based on Antibody-Gated Dye-Delivery Systems: The Example of Triacetone Triperoxide. Chemistry - A European Journal, 19(13), 4117-4122. doi:10.1002/chem.201300031Oroval, M., Climent, E., Coll, C., Eritja, R., Aviñó, A., Marcos, M. D., … Amorós, P. (2013). An aptamer-gated silica mesoporous material for thrombin detection. Chemical Communications, 49(48), 5480. doi:10.1039/c3cc42157kHecht, M., Climent, E., Biyikal, M., Sancenón, F., Martínez-Máñez, R., & Rurack, K. (2013). Gated hybrid delivery systems: En route to sensory materials with inherent signal amplification. Coordination Chemistry Reviews, 257(17-18), 2589-2606. doi:10.1016/j.ccr.2013.03.020Scrimin, P., & Prins, L. J. (2011). Sensing through signal amplification. Chemical Society Reviews, 40(9), 4488. doi:10.1039/c1cs15024cMartínez-Máñez, R., Sancenón, F., Biyikal, M., Hecht, M., & Rurack, K. (2011). 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Selektiver, hoch empfindlicher und schneller Nachweis genomischer DNA mit gesteuerten materialien am beispiel von Mycoplasma

[DE] Mit DNA verschlossene und mit Farbstoff beladene mesoporöse Siliciumdioxid-Nanopartikel wurden zum Nachweis von Mycoplasma bis zu einer Nachweisgrenze von ca. 70 genomischen DNA-Kopien pro mu-L in real kontaminierten Zellkulturmedien ohne die Hilfe von PCR-Techniken eingesetzt.Diese Arbeit wurde durch die Spanische Regierung (MAT2009-14564-C04-01 und SAF2010 15512) und die Generalitat Valenciana (PROMETEO/2009/016 und 2010/005) unterstützt. E.C. dankt dem Spanischen Bildungsministerium für ein StipendiumCliment Terol, E.; Mondragón Martínez, L.; Martínez Mañez, R.; Sancenón Galarza, F.; Marcos Martínez, MD.; Murguía Ibáñez, JR.; Amoros Del Toro, P.... (2013). Selektiver, hoch empfindlicher und schneller Nachweis genomischer DNA mit gesteuerten materialien am beispiel von Mycoplasma. Angewandte Chemie. 125(34):9106-9110. https://doi.org/10.1002/ange.201302954S9106911012534Goodman, R. P. (2005). Rapid Chiral Assembly of Rigid DNA Building Blocks for Molecular Nanofabrication. Science, 310(5754), 1661-1665. doi:10.1126/science.1120367Nishikawa, M., Rattanakiat, S., & Takakura, Y. (2010). DNA-based nano-sized systems for pharmaceutical and biomedical applications. Advanced Drug Delivery Reviews, 62(6), 626-632. doi:10.1016/j.addr.2010.03.006Chhabra, R., Sharma, J., Liu, Y., Rinker, S., & Yan, H. (2010). DNA Self-assembly for Nanomedicine. Advanced Drug Delivery Reviews, 62(6), 617-625. doi:10.1016/j.addr.2010.03.005Schlossbauer, A., Kecht, J., & Bein, T. (2009). Biotin-Avidin as a Protease-Responsive Cap System for Controlled Guest Release from Colloidal Mesoporous Silica. Angewandte Chemie, 121(17), 3138-3141. doi:10.1002/ange.200805818Schlossbauer, A., Kecht, J., & Bein, T. (2009). Biotin-Avidin as a Protease-Responsive Cap System for Controlled Guest Release from Colloidal Mesoporous Silica. Angewandte Chemie International Edition, 48(17), 3092-3095. doi:10.1002/anie.200805818Park, C., Kim, H., Kim, S., & Kim, C. (2009). Enzyme Responsive Nanocontainers with Cyclodextrin Gatekeepers and Synergistic Effects in Release of Guests. Journal of the American Chemical Society, 131(46), 16614-16615. doi:10.1021/ja9061085Bernardos, A., Mondragón, L., Aznar, E., Marcos, M. D., Martínez-Máñez, R., Sancenón, F., … Amorós, P. (2010). Enzyme-Responsive Intracellular Controlled Release Using Nanometric Silica Mesoporous Supports Capped with «Saccharides». ACS Nano, 4(11), 6353-6368. doi:10.1021/nn101499dWang, C., Li, Z., Cao, D., Zhao, Y.-L., Gaines, J. W., Bozdemir, O. A., … Stoddart, J. F. (2012). Stimulated Release of Size-Selected Cargos in Succession from Mesoporous Silica Nanoparticles. Angewandte Chemie, 124(22), 5556-5561. doi:10.1002/ange.201107960Wang, C., Li, Z., Cao, D., Zhao, Y.-L., Gaines, J. W., Bozdemir, O. A., … Stoddart, J. F. (2012). Stimulated Release of Size-Selected Cargos in Succession from Mesoporous Silica Nanoparticles. Angewandte Chemie International Edition, 51(22), 5460-5465. doi:10.1002/anie.201107960Coll, C., Bernardos, A., Martínez-Máñez, R., & Sancenón, F. (2012). Gated Silica Mesoporous Supports for Controlled Release and Signaling Applications. Accounts of Chemical Research, 46(2), 339-349. doi:10.1021/ar3001469Luo, Z., Cai, K., Hu, Y., Zhao, L., Liu, P., Duan, L., & Yang, W. (2010). Mesoporous Silica Nanoparticles End-Capped with Collagen: Redox-Responsive Nanoreservoirs for Targeted Drug Delivery. Angewandte Chemie, 123(3), 666-669. doi:10.1002/ange.201005061Luo, Z., Cai, K., Hu, Y., Zhao, L., Liu, P., Duan, L., & Yang, W. (2010). Mesoporous Silica Nanoparticles End-Capped with Collagen: Redox-Responsive Nanoreservoirs for Targeted Drug Delivery. Angewandte Chemie International Edition, 50(3), 640-643. doi:10.1002/anie.201005061Porta, F., Lamers, G. E. M., Zink, J. I., & Kros, A. (2011). Peptide modified mesoporous silica nanocontainers. Physical Chemistry Chemical Physics, 13(21), 9982. doi:10.1039/c0cp02959aPopat, A., Ross, B. P., Liu, J., Jambhrunkar, S., Kleitz, F., & Qiao, S. Z. (2012). Enzyme-Responsive Controlled Release of Covalently Bound Prodrug from Functional Mesoporous Silica Nanospheres. Angewandte Chemie, 124(50), 12654-12657. doi:10.1002/ange.201206416Popat, A., Ross, B. P., Liu, J., Jambhrunkar, S., Kleitz, F., & Qiao, S. Z. (2012). Enzyme-Responsive Controlled Release of Covalently Bound Prodrug from Functional Mesoporous Silica Nanospheres. Angewandte Chemie International Edition, 51(50), 12486-12489. doi:10.1002/anie.201206416Climent, E., Martínez-Máñez, R., Sancenón, F., Marcos, M. D., Soto, J., Maquieira, A., & Amorós, P. (2010). Controlled Delivery Using Oligonucleotide-Capped Mesoporous Silica Nanoparticles. Angewandte Chemie, 122(40), 7439-7441. doi:10.1002/ange.201001847Climent, E., Martínez-Máñez, R., Sancenón, F., Marcos, M. D., Soto, J., Maquieira, A., & Amorós, P. (2010). Controlled Delivery Using Oligonucleotide-Capped Mesoporous Silica Nanoparticles. Angewandte Chemie International Edition, 49(40), 7281-7283. doi:10.1002/anie.201001847Schlossbauer, A., Warncke, S., Gramlich, P. M. E., Kecht, J., Manetto, A., Carell, T., & Bein, T. (2010). Ein programmierbares, DNA-basiertes molekulares Ventil für kolloidales, mesoporöses Siliciumoxid. Angewandte Chemie, 122(28), 4842-4845. doi:10.1002/ange.201000827Schlossbauer, A., Warncke, S., Gramlich, P. M. E., Kecht, J., Manetto, A., Carell, T., & Bein, T. (2010). A Programmable DNA-Based Molecular Valve for Colloidal Mesoporous Silica. Angewandte Chemie International Edition, 49(28), 4734-4737. doi:10.1002/anie.201000827Zhu, C.-L., Lu, C.-H., Song, X.-Y., Yang, H.-H., & Wang, X.-R. (2011). Bioresponsive Controlled Release Using Mesoporous Silica Nanoparticles Capped with Aptamer-Based Molecular Gate. Journal of the American Chemical Society, 133(5), 1278-1281. doi:10.1021/ja110094gÖzalp, V. C., & Schäfer, T. (2011). Aptamer-Based Switchable Nanovalves for Stimuli-Responsive Drug Delivery. Chemistry - A European Journal, 17(36), 9893-9896. doi:10.1002/chem.201101403Ruiz-Hernández, E., Baeza, A., & Vallet-Regí, M. (2011). Smart Drug Delivery through DNA/Magnetic Nanoparticle Gates. ACS Nano, 5(2), 1259-1266. doi:10.1021/nn1029229Zhang, Y., Yuan, Q., Chen, T., Zhang, X., Chen, Y., & Tan, W. (2012). DNA-Capped Mesoporous Silica Nanoparticles as an Ion-Responsive Release System to Determine the Presence of Mercury in Aqueous Solutions. Analytical Chemistry, 84(4), 1956-1962. doi:10.1021/ac202993pHe, D., He, X., Wang, K., Cao, J., & Zhao, Y. (2012). A Photon-Fueled Gate-Like Delivery System Using i-Motif DNA Functionalized Mesoporous Silica Nanoparticles. Advanced Functional Materials, 22(22), 4704-4710. doi:10.1002/adfm.201201343Chen, Z., Li, Z., Lin, Y., Yin, M., Ren, J., & Qu, X. (2013). Bioresponsive Hyaluronic Acid-Capped Mesoporous Silica Nanoparticles for Targeted Drug Delivery. Chemistry - A European Journal, 19(5), 1778-1783. doi:10.1002/chem.201202038Baeza, A., Guisasola, E., Ruiz-Hernández, E., & Vallet-Regí, M. (2012). Magnetically Triggered Multidrug Release by Hybrid Mesoporous Silica Nanoparticles. Chemistry of Materials, 24(3), 517-524. doi:10.1021/cm203000uTarn, D., Xue, M., & Zink, J. I. (2013). pH-Responsive Dual Cargo Delivery from Mesoporous Silica Nanoparticles with a Metal-Latched Nanogate. Inorganic Chemistry, 52(4), 2044-2049. doi:10.1021/ic3024265Hoffman, A. S. (2008). The origins and evolution of «controlled» drug delivery systems. Journal of Controlled Release, 132(3), 153-163. doi:10.1016/j.jconrel.2008.08.012Vivero-Escoto, J. L., Slowing, I. I., Trewyn, B. G., & Lin, V. S.-Y. (2010). Mesoporous Silica Nanoparticles for Intracellular Controlled Drug Delivery. Small, 6(18), 1952-1967. doi:10.1002/smll.200901789Climent, E., Marcos, M. D., Martínez-Máñez, R., Sancenón, F., Soto, J., Rurack, K., & Amorós, P. (2009). The Determination of Methylmercury in Real Samples Using Organically Capped Mesoporous Inorganic Materials Capable of Signal Amplification. Angewandte Chemie, 121(45), 8671-8674. doi:10.1002/ange.200904243Climent, E., Marcos, M. D., Martínez-Máñez, R., Sancenón, F., Soto, J., Rurack, K., & Amorós, P. (2009). The Determination of Methylmercury in Real Samples Using Organically Capped Mesoporous Inorganic Materials Capable of Signal Amplification. Angewandte Chemie International Edition, 48(45), 8519-8522. doi:10.1002/anie.200904243Choi, Y. L., Jaworski, J., Seo, M. L., Lee, S. J., & Jung, J. H. (2011). Controlled release using mesoporous silica nanoparticles functionalized with 18-crown-6 derivative. Journal of Materials Chemistry, 21(22), 7882. doi:10.1039/c1jm11334hCui, Y., Dong, H., Cai, X., Wang, D., & Li, Y. (2012). Mesoporous Silica Nanoparticles Capped with Disulfide-Linked PEG Gatekeepers for Glutathione-Mediated Controlled Release. 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Selective opening of nanoscopic capped mesoporous inorganic materials with nerve agent simulants; an application to design chromo-fluorogenic probes

A hybrid nanoscopic capped mesoporous material, that is selectively opened in the presence of nerve agent simulants, has been prepared and used as a probe for the chromo-fluorogenic detection of these chemicals. © 2011 The Royal Society of Chemistry.Financial support from the Spanish Government (project MAT2009-14564-C04-01 and -02) and Generalitat Valenciana (project PROMETEO/2009/016) is gratefully acknowledged. I. C. thanks the UPV for her Fellowship. SCSIE (Universidad de Valencia) is gratefully acknowledged for all the equipment employed.Candel Busquets, I.; Bernardos Bau, A.; Climent Terol, E.; Marcos Martínez, MD.; Martínez Mañez, R.; Sancenón Galarza, F.; Soto Camino, J.... (2011). Selective opening of nanoscopic capped mesoporous inorganic materials with nerve agent simulants; an application to design chromo-fluorogenic probes. Chemical Communications. 47:8313-8315. https://doi.org/10.1039/c1cc12727fS8313831547Hill, H. H., & Martin, S. J. (2002). Conventional analytical methods for chemical warfare agents. Pure and Applied Chemistry, 74(12), 2281-2291. doi:10.1351/pac200274122281Eubanks, L. M., Dickerson, T. J., & Janda, K. D. (2007). Technological advancements for the detection of and protection against biological and chemical warfare agents. Chemical Society Reviews, 36(3), 458. doi:10.1039/b615227aRoyo, S., Martínez-Máñez, R., Sancenón, F., Costero, A. M., Parra, M., & Gil, S. (2007). Chromogenic and fluorogenic reagents for chemical warfare nerve agents’ detection. Chemical Communications, (46), 4839. doi:10.1039/b707063bVan Houten, K. A., Heath, D. C., & Pilato, R. S. (1998). Rapid Luminescent Detection of Phosphate Esters in Solution and the Gas Phase Using (dppe)Pt{S2C2(2-pyridyl)(CH2CH2OH)}. Journal of the American Chemical Society, 120(47), 12359-12360. doi:10.1021/ja982365dImaoka, T., Horiguchi, H., & Yamamoto, K. (2003). Metal Assembly in Novel Dendrimers with Porphyrin Cores. Journal of the American Chemical Society, 125(2), 340-341. doi:10.1021/ja0285060Dale, T. J., & Rebek, J. (2006). Fluorescent Sensors for Organophosphorus Nerve Agent Mimics. Journal of the American Chemical Society, 128(14), 4500-4501. doi:10.1021/ja057449iBencic-Nagale, S., Sternfeld, T., & Walt, D. R. (2006). Microbead Chemical Switches:  An Approach to Detection of Reactive Organophosphate Chemical Warfare Agent Vapors. Journal of the American Chemical Society, 128(15), 5041-5048. doi:10.1021/ja057057bWallace, K. J., Morey, J., Lynch, V. M., & Anslyn, E. V. (2005). Colorimetric detection of chemical warfare simulants. New Journal of Chemistry, 29(11), 1469. doi:10.1039/b506100hWallace, K. J., Fagbemi, R. I., Folmer-Andersen, F. J., Morey, J., Lynth, V. M., & Anslyn, E. V. (2006). Detection of chemical warfare simulants by phosphorylation of a coumarin oximate. Chemical Communications, (37), 3886. doi:10.1039/b609861dHan, S., Xue, Z., Wang, Z., & Wen, T. B. (2010). Visual and fluorogenic detection of a nerve agent simulant via a Lossen rearrangement of rhodamine–hydroxamate. Chemical Communications, 46(44), 8413. doi:10.1039/c0cc02881aJenkins, A. L., & Bae, S. Y. (2005). Molecularly imprinted polymers for chemical agent detection in multiple water matrices. Analytica Chimica Acta, 542(1), 32-37. doi:10.1016/j.aca.2004.12.088Southard, G. E., Van Houten, K. A., Ott, E. W., & Murray, G. M. (2007). Luminescent sensing of organophosphates using europium(III) containing imprinted polymers prepared by RAFT polymerization. Analytica Chimica Acta, 581(2), 202-207. doi:10.1016/j.aca.2006.08.027Pavlov, V., Xiao, Y., & Willner, I. (2005). Inhibition of the Acetycholine Esterase-Stimulated Growth of Au Nanoparticles:  Nanotechnology-Based Sensing of Nerve Gases. Nano Letters, 5(4), 649-653. doi:10.1021/nl050054cKong, L., Wang, J., Luo, T., Meng, F., Chen, X., Li, M., & Liu, J. (2010). Novel pyrenehexafluoroisopropanol derivative-decorated single-walled carbon nanotubes for detection of nerve agents by strong hydrogen-bonding interaction. The Analyst, 135(2), 368-374. doi:10.1039/b920266hCostero, A. M., Gil, S., Parra, M., Mancini, P. M. E., Martínez-Máñez, R., Sancenón, F., & Royo, S. (2008). Chromogenic detection of nerve agent mimics. Chemical Communications, (45), 6002. doi:10.1039/b811247aCostero, A. M., Parra, M., Gil, S., Gotor, R., Mancini, P. M. E., Martínez-Máñez, R., … Royo, S. (2010). Chromo-Fluorogenic Detection of Nerve-Agent Mimics Using Triggered Cyclization Reactions in Push-Pull Dyes. Chemistry - An Asian Journal, 5(7), 1573-1585. doi:10.1002/asia.201000058Knapton, D., Burnworth, M., Rowan, S. J., & Weder, C. (2006). Fluorescent Organometallic Sensors for the Detection of Chemical-Warfare-Agent Mimics. Angewandte Chemie International Edition, 45(35), 5825-5829. doi:10.1002/anie.200601634Climent, E., Martínez-Máñez, R., Sancenón, F., Marcos, M. D., Soto, J., Maquieira, A., & Amorós, P. (2010). Controlled Delivery Using Oligonucleotide-Capped Mesoporous Silica Nanoparticles. Angewandte Chemie International Edition, 49(40), 7281-7283. doi:10.1002/anie.201001847Bernardos, A., Aznar, E., Marcos, M. D., Martínez-Máñez, R., Sancenón, F., Soto, J., … Amorós, P. (2009). Enzyme-Responsive Controlled Release Using Mesoporous Silica Supports Capped with Lactose. Angewandte Chemie International Edition, 48(32), 5884-5887. doi:10.1002/anie.200900880Bernardos, A., Mondragón, L., Aznar, E., Marcos, M. D., Martínez-Máñez, R., Sancenón, F., … Amorós, P. (2010). Enzyme-Responsive Intracellular Controlled Release Using Nanometric Silica Mesoporous Supports Capped with «Saccharides». ACS Nano, 4(11), 6353-6368. doi:10.1021/nn101499dCliment, E., Bernardos, A., Martínez-Máñez, R., Maquieira, A., Marcos, M. D., Pastor-Navarro, N., … Amorós, P. (2009). Controlled Delivery Systems Using Antibody-Capped Mesoporous Nanocontainers. Journal of the American Chemical Society, 131(39), 14075-14080. doi:10.1021/ja904456dCliment, E., Marcos, M. D., Martínez-Máñez, R., Sancenón, F., Soto, J., Rurack, K., & Amorós, P. (2009). The Determination of Methylmercury in Real Samples Using Organically Capped Mesoporous Inorganic Materials Capable of Signal Amplification. Angewandte Chemie International Edition, 48(45), 8519-8522. doi:10.1002/anie.200904243Cabrera, S., El Haskouri, J., Guillem, C., Latorre, J., Beltrán-Porter, A., Beltrán-Porter, D., … Amorós *, P. (2000). Generalised syntheses of ordered mesoporous oxides: the atrane route. Solid State Sciences, 2(4), 405-420. doi:10.1016/s1293-2558(00)00152-7Felix, F., Ferguson, J., Guedel, H. U., & Ludi, A. (1980). The electronic spectrum of tris(2,2’-bipyridine)ruthenium(2+). Journal of the American Chemical Society, 102(12), 4096-4102. doi:10.1021/ja00532a019Lytle, F. E., & Hercules, D. M. (1969). Luminescence of tris(2,2’-bipyridine)ruthenium(II) dichloride. Journal of the American Chemical Society, 91(2), 253-257. doi:10.1021/ja01030a00