Intermolecular charge-transfer complexes between chlorothiazide antihypertensive drug against iodine sigma and picric acid pi acceptors: DFT and molecular docking interaction study with Covid-19 protease

Kirkendall, 1959, Clinical evaluation of chlorothiazide, Circulation, 19, 933, 10.1161/01.CIR.19.6.933 Pilsbury, 1983, J. Pharm. Pharmacol., 17, 1 Argawal, 1982, Pharmazie, 37, 150 Pomier, 2021, Interactions of intrinsically disordered proteins with the unconventional chaperone human serum albumin: from mechanisms of amyloid inhibition to therapeutic opportunities, Biophys. Chem. Cohen, 1962, Polarographic reduction of 1, 2, 4-benzothiadiazine-1, 1-dioxides and related compounds, Anal. Chem., 34, 216, 10.1021/ac60182a018 Ulvi, 1998, Spectrophotometric studies on the photostability of some thiazide diuretics in ethanolic solution, J. Pharmaceut. Biomed. Anal., 17, 77, 10.1016/S0731-7085(97)00171-4 Supurane, 1996, Rev.Roum.Chim., 3, 1 Ibrahim, 1998, Charge transfer complexes of pyrazolones with iodine, Microchem. J., 58, 175, 10.1006/mchj.1997.1515 Ibrahim, 2001, Charge transfer complexes of benzimidazoles with pi-acceptors, Egypt, J. Chem., 44, 151 El-Medani, 2003, Spectroscopic and X-ray crystal structure of 2-aminobenzimidazole-trinitrobenzene charge transfer and 2-aminobenzimidazole-picric acid ion-pair derivatives, J. Mol. Struct., 644, 77, 10.1016/S0022-2860(02)00474-X Mohamed, 2005, Spectroscopic and X-ray crystal structure studies of 2-aminothiazole-3, 5-dinitrobenzoic acid and 3, 5-dinitrosalicylic acid derivatives, J. Indian Chem. Soc., 82, 799 El-Mammli, 2003, Spectrophotometric determination of flucloxacillin in pharmaceutical preparations using some nitrophenols as a complexing agent, Spectrochim. Acta Mol. Biomol. Spectrosc., 59, 771, 10.1016/S1386-1425(02)00237-8 El-Mossalamy, 2004, Charge-transfer complexes of phenylephrine with nitrobenzene derivatives, Spectrochim. Acta Mol. Biomol. Spectrosc., 60, 1161, 10.1016/j.saa.2003.06.003 Refat, 2004, Spectroscopic and physicochemical studies of charge-transfer complexes of some benzanthrone derivatives" luminophore dyes" with iodine as s--acceptor, Can. J. Anal. Sci. Spectrosc., 49, 258 Salman, 2005, Can. J. Anal. Sci. Spectrosc., 49, 245 A Ibrahim, 2021, Study of Charge transfer complexes of chlorothiazide, Aswan Univ. J. Environ. stud., 2, 75, 10.21608/aujes.2021.150024 Frisch, 2009 Becke, A. Density-functional thermochemistry. III. The role of exact exchange (1993) J. Chem. Phys., 98, 5648;. Hariharan, 1972, The effect of d-functions on molecular orbital energies for hydrocarbons, Chem. Phys. Lett., 16, 217, 10.1016/0009-2614(72)80259-8 Zhurko, 2004 O'Boyle, 2011, Open Babel: an open chemical toolbox, J. Cheminf., 3, 1, 10.1186/1758-2946-3-33 Dallakyan, 2008 Chu, 2014, Proteins: Struct., Funct., Bioinf., 82, 1079, 10.1002/prot.24446 Morris, 1998, Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function, J. Comput. Chem., 19, 1639, 10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B Trott, 2010, AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading, J. Comput. Chem., 31, 455, 10.1002/jcc.21334 Pomier, 2021, Interactions of intrinsically disordered proteins with the unconventional chaperone human serum albumin: from mechanisms of amyloid inhibition to therapeutic opportunities, Biophys. Chem. Chakrabarti, 2022, Intrinsically disordered proteins/regions and insight into their biomolecular interactions, Biophys. Chem., 106769, 10.1016/j.bpc.2022.106769 Kiefer, 1972, The UV-laser excited resonance Raman spectrum of the I− 3 ion, Chem. Phys. Lett., 16, 5, 10.1016/0009-2614(72)80442-1 Andrews, 1980, Resonance Raman and ultraviolet absorption spectra of the triiodide ion produced by alkali iodide-iodine argon matrix reactions, Inorg. Chem., 19, 463, 10.1021/ic50204a036 Kaya, 1972, Resonance Raman effect of I− 3 ion by ultraviolet laser excitation, Chem. Phys. Lett., 16, 151, 10.1016/0009-2614(72)80479-2 Nour, 1986, Resonance Raman and far‐infrared studies of charge‐transfer complexes of iodine, J. Raman Spectrosc., 17, 467, 10.1002/jrs.1250170608 Mizuno, 1981, Electronic spectra and structures of polyiodide chain complexes, J. Phys. Chem., 85, 1789, 10.1021/j150613a006 Alhomrani, 2022, Enhancing the antipsychotic effect of risperidone by increasing its binding affinity to serotonin receptor via picric acid: a molecular dynamics simulation, Pharmaceuticals, 15, 285, 10.3390/ph15030285 Benesi, 1949, A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons, J. Am. Chem. Soc., 71, 2703, 10.1021/ja01176a030 Khan, 2020, Synthesis, characterization, antimicrobial and DNA binding properties of an organic charge transfer complex obtained from pyrazole and chloranilic acid, Bioorg. Chem., 99, 10.1016/j.bioorg.2020.103779 Hasan, 2022, Novel thiophene Chalcones-Coumarin as acetylcholinesterase inhibitors: design, synthesis, biological evaluation, molecular docking, ADMET prediction and molecular dynamics simulation, Bioorg. Chem., 119, 10.1016/j.bioorg.2021.105572 Shakya, 2020, Charge transfer complex based real-time colorimetric chemosensor for rapid recognition of dinitrobenzene and discriminative detection of Fe2+ ions in aqueous media and human hemoglobin, J. Photochem. Photobiol. Chem., 392, 10.1016/j.jphotochem.2020.112402 Khan, 2021, Low concentrated phosphorus sorption in aqueous medium on aragonite synthesized by carbonation of seashells: optimization, kinetics, and mechanism study, J. Environ. Manag., 280, 10.1016/j.jenvman.2020.111652 Islam, 2019, Solvatochromic absorbance and fluorescence probe behavior within ionic liquid+ γ-butyrolactone mixture, J. Chem. Eng. Data, 64, 4169, 10.1021/acs.jced.9b00576 Murugavel, 2019, J. Mol. Struct., 1176, 729, 10.1016/j.molstruc.2018.09.010 Alkathiri, 2022, Impedance spectroscopy and DFT/TD-DFT studies of diyttrium trioxide for optoelectronic fields, J. Rare Earths, 10.1016/j.jre.2022.03.010 Khan, 2019, Exploring colorimetric real-time sensing behavior of a newly designed CT complex toward nitrobenzene and Co2+: spectrophotometric, DFT/TD-DFT, and mechanistic insights, ACS Omega, 4, 9983, 10.1021/acsomega.9b01314 Akram, 2020, Multispectroscopic and computational analysis insight into the interaction of cationic diester-bonded gemini surfactants with serine protease α-chymotrypsin, ACS Omega, 5, 3624, 10.1021/acsomega.9b04142 Shakya, 2019, Effect of geraniol against arecoline induced toxicity in the third instar larvae of transgenic Drosophila melanogaster (hsp70-lacZ) Bg9, Toxicol. Mech. Methods, 29, 187, 10.1080/15376516.2018.1534299 Khan, 2021, Synthesis and spectrophotometric studies of CT complex between 1, 2-dimethylimidazole and picric acid in different polar solvents: exploring antimicrobial activities and molecular (DNA) docking, Phys. Chem. Liq., 59, 753, 10.1080/00319104.2020.1810250 Khan, 2021, Synthesis, spectroscopic characterization, antimicrobial activity, molecular docking and DFT studies of proton transfer (H-bonded) complex of 8-aminoquinoline (donor) with chloranilic acid (acceptor), J. Biomol. Struct. Dyn., 1