794 research outputs found
Synthesis and evaluation of a novel pyrenyl-appended triazole-based thiacalix[4]arene as a fluorescent sensor for Ag+ ion
New fluorescent chemosensors 1,3-alternate-1 and 2 with pyrenyl-appended triazole-based on thiacalix[4]arene were synthesized. The fluorescence spectra changes suggested that chemosensors 1 and 2 are highly selective for Ag+ over other metal ions by enhancing the monomer emission of pyrene in neutral solution. However, other heavy metal ions, such as Cu2+, and Hg2+ quench both the monomer and excimer emission of pyrene acutely. The 1H NMR results indicated that Ag+ can be selectively recognized by the triazole moieties on the receptors 1 and 2 together with the ionophoricity cavity formed by the two inverted benzene rings and sulfur atoms of the thiacalix[4]arene
Mimicking tricks from nature with sensory organic-inorganic hybrid materials
Design strategies for (bio)chemical systems that are inspired by nature's accomplishments in system design and operation on various levels of complexity are increasingly gaining in importance. Within the broad field of biomimetic chemistry, this article highlights various attempts toward improved and sophisticated sensory materials that rely on the combination of supramolecular (bio)chemical recognition principles and nanoscopic solid structures. Examples range from more established concepts such as hybrid sensing ensembles with improved sensitivity and selectivity or for target analytes for which selectivity is hard to achieve by conventional methods, which were often inspired by protein binding pockets or ion channels in membranes, to very recent approaches relying on target-gated amplified signalling with functionalised mesoporous inorganic supports and the integration of native biological sensory species such as transmembrane proteins in spherically supported bilayer membranes. Besides obvious mimicry of recognition-based processes, selected approaches toward chemical transduction junctions utilizing artificially organized synapses, hybrid ensembles for improved antibody generation and uniquely colour changing systems are discussed. All of these strategies open up exciting new prospects for the development of sensing concepts and sensory devices at the interface of nanotechnology, smart materials and supramolecular (bio)chemistry. © 2011 The Royal Society of Chemistry.Martínez Mañez, R.; Sancenón Galarza, F.; Biyikal, M.; Hecht, M.; Rurack, K. (2011). Mimicking tricks from nature with sensory organic-inorganic hybrid materials. Journal of Materials Chemistry. 21(34):12588-12604. doi:10.1039/c1jm11210dS12588126042134Ma, M. (2007). Encoding Olfactory Signals via Multiple Chemosensory Systems. Critical Reviews in Biochemistry and Molecular Biology, 42(6), 463-480. doi:10.1080/10409230701693359Leinders-Zufall, T., Lane, A. P., Puche, A. C., Ma, W., Novotny, M. 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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
Anilinopyridine metal complexes for the selective chromogenic sensing of cyanide anion
[EN] Probe 1, which contains an anilinopyridine chromophore and an aza-oxa macrocyclic subunit, presented an absorption band centered at 340 nm in acetonitrile. Addition of Fe(III), Cr(III) and Hg(II) induced the growth of a new absorption band at 430 nm (with color change from colorless to yellow), whereas in the presence of Cu(II), Zn(II) and Pb(II), less marked changes were observed. The color changes observed upon addition of Fe(III), Cr(III) and Hg(II) were ascribed to the formation of 1:1 stoichiometry complexes with probe 1. Coordination of Fe(III), Cr(III) and Hg(II) with the pyridine fragment of 1 induced an enhancement of the charge transfer character accompanied with a marked bathochromic shift that was reflected in a color change from colorless to yellow. The strength of the interaction between probe 1 and Fe(III) cation was modulated upon interaction with anions. Of all the anions tested, only cyanide was able to induce the bleaching of the yellow 1Fe(III) complex solution. This bleaching was ascribed to the formation of 1Fe(III)-CN complex that restored, to some extent, the optical features of the free probe allowing the chromogenic sensing of cyanide. Besides, 1Fe(III) complex was used to detect cyanide in acetonitrile-water 90:10 v/v mixtures with good recoveries.This work was supported by the Generalitat Valenciana [grant number PROMETEOII/2014/047]; Ministerio de Economia y Competitividad [grant number MAT2015-64139-C4-1-R], [grant number AGL2015-70235-C2-2-R (MINECO/FEDER)].Lozano-Torres, B.; Marcos Martínez, MD.; Pardo Vicente, MT.; Sancenón Galarza, F.; Martínez-Máñez, R.; Rurack, K. (2018). Anilinopyridine metal complexes for the selective chromogenic sensing of cyanide anion. Journal of Coordination Chemistry. 71(6):786-796. https://doi.org/10.1080/00958972.2018.1434719S786796716Boening, D. W., & Chew, C. M. (1999). Water, Air, and Soil Pollution, 109(1/4), 67-79. doi:10.1023/a:1005005117439Tylleskar, T., Howlett, W. P., Rwiza, H. T., Aquilonius, S. M., Stalberg, E., Linden, B., … Rosling, H. (1993). Konzo: a distinct disease entity with selective upper motor neuron damage. Journal of Neurology, Neurosurgery & Psychiatry, 56(6), 638-643. doi:10.1136/jnnp.56.6.638(a) WHO. Guidelines for Drinking-Water Quality, p. 342, World Health Organisation, Geneva, Switzerland (2011)Safavi, A., Maleki, N., & Shahbaazi, H. . (2004). Indirect determination of cyanide ion and hydrogen cyanide by adsorptive stripping voltammetry at a mercury electrode. Analytica Chimica Acta, 503(2), 213-221. doi:10.1016/j.aca.2003.10.032Batista, R. M. F., Oliveira, E., Costa, S. P. G., Lodeiro, C., & Raposo, M. M. M. (2013). Cyanide and fluoride colorimetric sensing by novel imidazo-anthraquinones functionalised with indole and carbazole. Supramolecular Chemistry, 26(2), 71-80. doi:10.1080/10610278.2013.824082Santos-Figueroa, L. E., Moragues, M. E., Climent, E., Agostini, A., Martínez-Máñez, R., & Sancenón, F. (2013). Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the years 2010–2011. Chemical Society Reviews, 42(8), 3489. doi:10.1039/c3cs35429fWiskur, 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/ar9600796Kaur, 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.2012.04.013García-Acosta, B., Albiach-Martí, X., García, E., Gil, L., Martínez-Máñez, R., Rurack, K., … Soto, J. (2004). Coordinative and electrostatic forces in action: from the design of differential chromogenic anion sensors to selective carboxylate recognition. Chem. Commun., (7), 774-775. doi:10.1039/b314997hGarcía-Acosta, B., Martínez-Máñez, R., Sancenón, F., Soto, J., Rurack, K., Spieles, M., … Gil, L. (2007). Ditopic N-Crowned 4-(p-Aminophenyl)-2,6-diphenylpyridines: Implications of Macrocycle Topology on the Spectroscopic Properties, Cation Complexation, and Differential Anion Responses. Inorganic Chemistry, 46(8), 3123-3135. doi:10.1021/ic062069zVerhoeven, J. W. (s. f.). Sigma-coupled Charge-transfer Probes of the Fluoroprobe and Fluorotrope Type. Topics in Fluorescence Spectroscopy, 249-284. doi:10.1007/0-387-23335-0_7Kurihara, M., Kawashima, T., & Ozutsumi, K. (2000). Complexation of Cobalt(II), Nickel(II), and Copper(II) Ions with Pyridine, 2-Methylpyridine, 3-Methylpyridine, and 4-Methylpyridine in Acetonitrile. Zeitschrift für Naturforschung B, 55(3-4), 277-284. doi:10.1515/znb-2000-3-409Xu, 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/b907368
Luminescence Lifetime-Based Sensing Platform Based on Cyclometalated Iridium(III) Complexes for the Detection of Perfluorooctanoic Acid in Aqueous Samples
Luminescence lifetimes are an attractive analytical method for detection due to its high sensitivity and stability. Iridium probes exhibit luminescence with long excited-state lifetimes, which are sensitive to the local environment. Perfluorooctanoic acid (PFOA) is listed as a chemical of high concern regarding its toxicity and is classified as a "forever chemical". In addition to strict limits on the presence of PFOA in drinking water, environmental contamination from industrial effluent or chemical spills requires rapid, simple, accurate, and cost-effective analysis in order to aid containment. Herein, we report the fabrication and function of a novel and facile luminescence sensor for PFOA based on iridium modified on gold surfaces. These surfaces were modified with lipophilic iridium complexes bearing alkyl chains, namely, IrC6 and IrC12, and Zonyl-FSA surfactant. Upon addition of PFOA, the modified surfaces IrC6-FSA@Au and IrC12-FSA @Au show the largest change in the red luminescence signal with changes in the luminescence lifetime that allow monitoring of PFOA concentrations in aqueous solutions. The platform was tested for the measurement of PFOA in aqueous samples spiked with known concentrations of PFOA and demonstrated the capacity to determine PFOA at concentrations >100 μg/L (240 nM).</p
Dyes That Bear Thiazolylazo Groups as Chromogenic Chemosensors for Metal Cations
A family of dyes (L 1-L 6) that contain a thiazolylazo group as signalling subunit and several macrocyclic cavities with different ring sizes and type and number of heteroatoms as binding sites has been synthesized and characterized. Solutions of L 1-L 6 in acetonitrile show broad and structureless absorption bands in the 554-577 nm range with typicalmolar absorption coefficients that range from 20000 to 32000 M -1 cm -1. A detailed protonation study was carried out with solutions of L 1, L 2 and L 5 in acetonitrile. Addition of one equivalent of protons to L 1 and L 2 resulted in the development of a new band at 425 and 370 nm, respectively, which was ascribed to protonation in the aniline nitrogen. In contrast, protonation of L 5 resulted in a bathochromic shift of 25 nm of the absorption band that was conceivable with protonation of one of the nitrogen atoms of the azo moiety. These results were in agreement with 1H NMR spectroscopic data. Theoretical studies on the model ligand L 1 and on different possible protonation species were also performed by using density functional theory (DFT) quantum mechanical calculations. Colour modulations in solutions of L 1-L 6 in acetonitrile in the presence of the metal cations Fe 3+, Ni 2+, Zn 2+, Cd 2+, Pb 2+ and Hg 2+ have been studied. A selective chromogenic response of L 4 in the presence of Pb 2+ and L 5 in the presence of Hg 2+ was observed. To get a better insight into the chromophoric nature in the presence of metal cations, the interaction of Hg 2+ with the model compound L 1 in two different coordination modes was studied theoretically by using density functional theory (DFT) quantum mechanical calculations.Financial support by the Spanish Ministerio de Ciencia e Innovacion (MICINN) through projects MAT2009-14564-C04-01, CTQ2010-15364, Molecular Nanoscience (Consolider Ingenio CSD2007-00010) and Generalitat Valenciana (PROMETEO/2009/016 and PROMETEO/2009/108) is gratefully acknowledged.Abalos Aguado, T.; Moragues Pons, ME.; Royo Calvo, S.; Jiménez, D.; Martínez Mañez, R.; Soto Camino, J.; Sancenón Galarza, F.... (2012). Dyes That Bear Thiazolylazo Groups as Chromogenic Chemosensors for Metal Cations. European Journal of Inorganic Chemistry. (1):76-84. doi:10.1002/ejic.201100834S76841Fabbrizzi, L., & Poggi, A. (1995). Sensors and switches from supramolecular chemistry. 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Strip-based lateral flow-type indicator displacement assay for gamma-hydroxybutyric acid (GHB) detection in beverages
[EN] The use of gamma-hydroxybutyric acid (GHB) in drug-facilitated sexual assault has increased due to its availability and high solubility in aqueous solutions and alcoholic beverages, necessitating the development of rapid methods for GHB detection. In this respect, portable testing methods for use in the field, based on lateral flow assays (LFAs) and capable of detecting trace concentrations of target analytes, are particularly attractive and hold enormous potential for the detection of illicit drugs. Using this strategy, here we report a rapid, low cost, easy-tohandle strip-based LFA for GHB analysis employing a smartphone for fluorescence readout. At molecular signalling level, the ensemble is based on a Cu2+ complex with a tetradentate ligand and the fluorescent dye coumarin 343, which indicate GHB through an indicator displacement assay (IDA) in aqueous solution. When incorporated in a LFA-based strip test this system shows a detection limit as low as 0.03 mu M for GHB in MES buffer solution and is able to detect GHB at concentrations of 0.1 mu M in soft drinks and alcoholic beverages in only 1 min.This research was funded by the Ministerio de Ciencia, Innovacion y Universidades (Spanish Government), the Agencia Estatal de Investigacion (AEI), the European Union (PID2021-126304OB-C41) (MCIU/AEI/FEDER, EU), the Conselleria de Innovacion, Universidades, Ciencia y Sociedad Digital, Generalitat Valenciana (PROMETEO CIPROM/2021/007) and the German Research Foundation (DFG; CL 761/1-19). This work was also supported by CIBER-Consorcio Centro de Investigacion Biomedica en Red (CB06/01/2012), Instituto de Salud Carlos III, Ministerio de Ciencia e Innovacion. E. G. is grateful to the Spanish MEC for her FPU grant (FPU16/02464). G. H. thanks to Generalitat Valenciana for his pre-doctoral grant (ACIF/2021/204). V. M.-C. thanks the financial support from Generalitat Valenciana (CIDEGENT/2020/031).Garrido-García, EM.; Hernández-Sigüenza, G.; Climent Terol, E.; Marcos Martínez, MD.; Rurack, K.; Gaviña, P.; Parra, M.... (2023). Strip-based lateral flow-type indicator displacement assay for gamma-hydroxybutyric acid (GHB) detection in beverages. Sensors and Actuators B Chemical. 377. https://doi.org/10.1016/j.snb.2022.13304337
Sensory hybrid host materials for the selective chromo-fluorogenic detection of biogenic amines
Pyrylium-containing mesoporous materials have been used for the chromo-fluorogenic sensing of biogenic amines in an aqueous environment.Amoros del Toro, Pedro Jose, [email protected]
Surface Photochemistry: 3,3′-Dialkylthia and Selenocarbocyanine Dyes Adsorbed onto Microcrystalline Cellulose
In this work, thia and selenocarbocyanines with n-alkyl chains of different length, namely with methyl, ethyl, propyl, hexyl and decyl substituents, were studied in homogeneous and heterogeneous media for comparison purposes. For both carbocyanine dyes adsorbed onto microcrystalline cellulose, a remarkable increase in the fluorescence quantum yields and lifetimes were detected, when compared with solution. Contrary to the solution behaviour, where the increase in the n-alkyl chains length increases to a certain extent the fluorescence emission ΦF and τF, on powdered solid samples a decrease of ΦF and τF was observed. The use of an integrating sphere enabled us to obtain absolute ΦF’s for all the powdered samples. The main difference for liquid homogeneous samples is that the increase of the alkyl chain strongly decreases the ΦF values, both for thiacarbocyanines and selenocarbocyanines. A lifetime distribution analysis for the fluorescence of these dyes adsorbed onto microcrystalline cellulose, evidenced location on the ordered and crystalline part of the substrate, as well as on the more disordered region where the lifetime is smaller. The increase of the n-alkyl chains length decreases the photoisomer emission for the dyes adsorbed onto microcrystalline cellulose, as detected for high fluences of the laser excitation, for most samples
Oligonucleotide-capped mesoporous silica nanoparticles as DNA-responsive dye delivery systems for genomic DNA detection
[EN] New hybrid oligonucleotide-capped mesoporous silica nanoparticles able to detect genomic DNA were designed.Financial support from the Spanish Government (Project MAT2012-38429-C04) and the Generalitat Valencia (Project PROMETEOII/2014/047) is gratefully acknowledged. Ll. P. is grateful to the Universidad Politecnica de Valencia for his grant.Pascual Vidal, L.; Baroja, I.; Aznar Gimeno, E.; Sancenón Galarza, F.; Marcos Martínez, MD.; Murguía Ibáñez, JR.; Amoros Del Toro, PJ.... (2015). Oligonucleotide-capped mesoporous silica nanoparticles as DNA-responsive dye delivery systems for genomic DNA detection. Chemical Communications. 51(8):1414-1416. https://doi.org/10.1039/C4CC08306GS14141416518Agostini, A., Mondragón, L., Bernardos, A., Martínez-Máñez, R., Marcos, M. D., Sancenón, F., … Murguía, J. R. (2012). Targeted Cargo Delivery in Senescent Cells Using Capped Mesoporous Silica Nanoparticles. Angewandte Chemie International Edition, 51(42), 10556-10560. doi:10.1002/anie.201204663Zhang, Q., Wang, X., Li, P.-Z., Nguyen, K. T., Wang, X.-J., Luo, Z., … Zhao, Y. (2013). Biocompatible, Uniform, and Redispersible Mesoporous Silica Nanoparticles for Cancer-Targeted Drug Delivery In Vivo. Advanced Functional Materials, 24(17), 2450-2461. doi:10.1002/adfm.201302988Chen, C., Geng, J., Pu, F., Yang, X., Ren, J., & Qu, X. (2010). Polyvalent Nucleic Acid/Mesoporous Silica Nanoparticle Conjugates: Dual Stimuli-Responsive Vehicles for Intracellular Drug Delivery. Angewandte Chemie International Edition, 50(4), 882-886. doi:10.1002/anie.201005471Zhou, L., Chen, Z., Dong, K., Yin, M., Ren, J., & Qu, X. (2013). DNA-mediated Construction of Hollow Upconversion Nanoparticles for Protein Harvesting and Near-Infrared Light Triggered Release. Advanced Materials, 26(15), 2424-2430. doi:10.1002/adma.201304437Agostini, A., Mondragón, L., Pascual, L., Aznar, E., Coll, C., Martínez-Máñez, R., … Gil, S. (2012). Design of Enzyme-Mediated Controlled Release Systems Based on Silica Mesoporous Supports Capped with Ester-Glycol Groups. Langmuir, 28(41), 14766-14776. doi:10.1021/la303161eColl, 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/ar3001469Climent, E., Martínez-Máñez, R., Maquieira, Á., Sancenón, F., Marcos, M. D., Brun, E. M., … Amorós, P. (2012). Antibody-Capped Mesoporous Nanoscopic Materials: Design of a Probe for the Selective Chromo-Fluorogenic Detection of Finasteride. ChemistryOpen, 1(6), 251-259. doi:10.1002/open.201100008Oroval, 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/c3cc42157kChen, M., Huang, C., He, C., Zhu, W., Xu, Y., & Lu, Y. (2012). A glucose-responsive controlled release system using glucose oxidase-gated mesoporous silica nanocontainers. Chemical Communications, 48(76), 9522. doi:10.1039/c2cc34290aCliment, 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.201001847Climent, E., Mondragón, L., Martínez-Máñez, R., Sancenón, F., Marcos, M. D., Murguía, J. R., … Pérez-Payá, E. (2013). Selective, Highly Sensitive, and Rapid Detection of Genomic DNA by Using Gated Materials:MycoplasmaDetection. Angewandte Chemie International Edition, 52(34), 8938-8942. doi:10.1002/anie.201302954Zhang, Z., Balogh, D., Wang, F., Sung, S. Y., Nechushtai, R., & Willner, I. (2013). Biocatalytic Release of an Anticancer Drug from Nucleic-Acids-Capped Mesoporous SiO2 Using DNA or Molecular Biomarkers as Triggering Stimuli. ACS Nano, 7(10), 8455-8468. doi:10.1021/nn403772jWu, L., Ren, J., & Qu, X. (2014). Target-responsive DNA-capped nanocontainer used for fabricating universal detector and performing logic operations. Nucleic Acids Research, 42(21), e160-e160. doi:10.1093/nar/gku858Drexler, H. G., & Uphoff, C. C. (2002). Cytotechnology, 39(2), 75-90. doi:10.1023/a:1022913015916Matas Andreu, L., Molinos Abós, S., Fernández Rivas, G., González Soler, V., & Ausina Ruiz, V. (2006). Diagnóstico serológico de las infecciones por Mycoplasma pneumoniae. Enfermedades Infecciosas y Microbiología Clínica, 24, 19-23. doi:10.1157/13094274V. Ausina , Infecciones causadas por micoplasmas, Medicina Interna, Elsevier España, 2004, 15th edn, pp. 2363–236
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