Optical detection of scopolamine and ketamine with a BODIPY-Phen conjugate and Cu(II)

[EN] Chemical submission is becoming a global growing threat. Therefore, the development of fast and reliable methods for detecting the presence of chemical submission drugs in drinks is of great interest. For this purpose, a new BODIPY-Phen conjugate consisting of a 1,10-phenanthroline moiety connected through its 4-position to the meso position of a BODIPY dye has been synthesized and characterized by NMR, UV-vis spectroscopy and by single-crystal X-ray diffraction. BODIPY-Phen in combination with Cu(II) was used as a probe for the fluorescent and colorimetric detection of scopolamine and ketamine, two of the drugs used in cases of chemical submission. The determined limits of detection in water were 3 mu M for scopolamine and 2.88 mu M for ketamine. Selectivity of the probe in the presence of other drugs and some possible interferents that could be found in beverages has also been tested. The detection process seems to be due to a reduction of the Cu(II) ion to Cu(I) followed by coordination of Cu(I) to the BODIPY-Phen conjugate, which results in quenching of its fluorescence together with a visible color change. The probe is able to detect by the unaided eye the presence of scopolamine in real soft drinks and alcoholic beverages spiked with the drug.The authors gratefully acknowledge grant PID2021-126304OB-C42 funded by the Spanish MCIN/AEI/10.13039/501100011033 and by "ERDF A way of making Europe, EU", and grant PDC2022-133576-C22 funded by the Spanish MCIN/AEI/10.13039/501100011033 and by the European Union "NextGenerationEU"/PRTR". SCSIE (Universidad de Valencia) is gratefully acknowledged for all the equipment employed. NMR was registered at the U26 facility of ICTS "NAMBIOSIS" at the Universitat of Valencia.Hernandez-Contreras, J.; Madrigal, P.; Arroyo, P.; Liu-González, M.; Gil, S.; Parra, M.; Sáez José A.... (2024). Optical detection of scopolamine and ketamine with a BODIPY-Phen conjugate and Cu(II). Dyes and Pigments. 221. https://doi.org/10.1016/j.dyepig.2023.11180622

Salts of 5-amino-2-sulfonamide-1,3,4-thiadiazole, a structural and analog of acetazolamide, show interesting carbonic anhydrase inhibitory properties, diuretic, and anticonvulsant action

Three salts of 5-amino-2-sulfonamide-1,3,4-thiadiazole (Hats) were prepared and characterized by physico-chemical methods. The p-toluensulfonate, the methylsulfonate, and the chlorhydrate monohydrate salts of Hats were evaluated as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors (CAIs) and as anticonvulsants and diuretics, since many CAIs are clinically used as pharmacological agents. The three Hats salts exhibited diuretic and anticonvulsant activities with little neurotoxicity. The human (h) isoforms hCA I, II, IV, VII, IX, and XII were inhibited in their micromolar range by these salts, whereas pathogenic beta and gamma CAs showed similar, weak inhibitory profiles.Fil: Diaz, Jorge R. A.. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Área Química General e Inorgánica; ArgentinaFil: Camí, Gerardo Enrique. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Liu González, Malva. Universidad de Valencia; EspañaFil: Vega, Daniel Roberto. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigaciones y Aplicaciones no Nucleares. Gerencia de Física (Centro Atómico Constituyentes); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Vullo, Daniela. Università degli Studi di Firenze; ItaliaFil: Juárez, Américo. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; ArgentinaFil: Pedregosa, Jose Carmelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Supuran, Claudiu T.. Università degli Studi di Firenze; Itali

The sodium salt of diethyl 1H-pyrazole-3,5-dicarboxylate as an efficient amphiphilic receptor for dopamine and amphetamines. Crystal structure and solution studies

The sodium salt of the diethyl 1H-pyrazole-3,5-dicarboxylate (2) of amphiphilic character is able to interact with (+)-amphetamine, (+)-methamphetamine, and dopamine, yielding stable complexes. Crystal structure of 2 with (+)-amphetamine leads to a very nice double helical supramolecular structure.Financial support from CICYT (SAF 2003/ 02262 and CTQ2006-15672-CO5-01/BQU) is acknowledged. We also thank Mr. V. Gálvez for technical assistancePeer reviewe

Synthesis and characterization of a Cu(II) complex of 2-benzylmercapto-5- methyl-1,3,4-thiadiazole (C10H10N2S 2)

A Cu(II) complex of 2-benzylmercapto-5-methyl-1,3,4-thiadiazole was synthesized and characterized. The crystal structure of the copper complex and the free ligand were determined by single-crystal X-ray diffraction at room temperature: {[Cu(C10H10N2S2) 2(Cl)2], P1 triclinic, a = 8.1450(2) Å, b = 8.1690(2) Å, c = 10.8180(3) Å, α = 97.4040(12)°, β = 101.6270(11)°, γ = 116.1431(14)°; C10H10N2S2 ligand, Pbca orthorhombic, a = 8.7938(7) Å, b = 9.6491(7) Å, c = 25.3552(18) Å}. The metal complex framework consists of discrete units that provide crystalline stability through a network of van der Waals contacts. The Cu(II) is coordinated by two chloride ions and two 2-benzylmercapto-5-methyl-1,3,4- thiadiazole monodentate ligands showing a distorted square planar configuration. Both thiadiazole ligands coordinate through the N atom bonded to the benzylthio substituted C atom. The FTIR spectroscopic data are consistent with this structural model. Analysis of the magnetic susceptibility from 5 K to room temperature indicates the presence of paramagnetic Cu(II), confirmed by the EPR spectrum.Fil: Camí, Gerardo E.. Universidad Nacional de San Luis; ArgentinaFil: González, Malva Liu. Universidad de Valencia; EspañaFil: Ruiz, Francisco Sanz. Universidad de Valencia; EspañaFil: De Arellano, Carmen Ramírez. Universidad de Valencia; EspañaFil: Sanchez, Rodolfo Daniel. Universidad Nacional de Cuyo; Argentina. Comisión Nacional de Energía Atómica. Gerencia del Área de Energía Nuclear. Instituto Balseiro; Argentina. Comisión Nacional de Energía Atómica. Gerencia del Area de Investigación y Aplicaciones No Nucleares. Gerencia de Física (Centro Atómico Bariloche); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Pedregosa, Jose Carmelo. Universidad Nacional de San Luis; Argentin