Synthesis, characterization, evaluation of metabolic enzyme inhibitors and in silico studies of thymol based 2-amino thiol and sulfonic acid compounds

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dc.authoridGenç Bilgiçli, Hayriye/0000-0001-6909-316X
dc.authoridGulcin, ilhami/0000-0001-5993-1668
dc.authoridÜÇ, EDA MEHTAP/0000-0002-9259-5704
dc.authoridalagoz, mehmet abdullah/0000-0001-5190-7196;
dc.authorwosidGenç Bilgiçli, Hayriye/U-4685-2017
dc.authorwosidGulcin, ilhami/F-1428-2014
dc.authorwosidBORA, Rıfat Emin/GWM-8842-2022
dc.authorwosidÜÇ, EDA MEHTAP/AFI-4038-2022
dc.authorwosidalagoz, mehmet abdullah/W-7847-2018
dc.authorwosidZengin, Mustafa/HTT-3124-2023
dc.contributor.authorBora, Rifat Emin
dc.contributor.authorBilgicli, Hayriye Genc
dc.contributor.authorUc, Eda Mehtap
dc.contributor.authorAlagoz, Mehmet Abdullah
dc.contributor.authorZengin, Mustafa
dc.contributor.authorGulcin, Ilhami
dc.date.accessioned2024-08-04T20:52:18Z
dc.date.available2024-08-04T20:52:18Z
dc.date.issued2022
dc.departmentİnönü Üniversitesien_US
dc.description.abstractEight new aminothiols (4a-g and 5) and three new sulfonic acid derivatives (6a-c) were synthesized, and their structures were characterized. Inhibitory effects of the obtained compounds on carbonic anhydrase I and II isoforms (hCA I and hCA II), butyrylcholinesterase (BChE) and acetylcholinesterase (AChE), enzymes were investigated. The newly synthesized compounds have inhibited hCA I with Kis ranging from 7.11 +/- 1.46 nM (6a) to 670.52 +/- 300.41 nM (4b) and, hCA II with Kis ranging from 16.83 +/- 5.72 nM (6a) to 453.34 +/- 208.56 nM (4c). Acetazolamide was employed as the positive control for both hCA isoforms (K-i for hCA I 198.81 +/- 14.13 nM and K-i for hCA II 211.42 +/- 13.10 nM), and among the new compounds obtained, it was observed that there were compounds that were active at much lower nM levels. All compounds were also evaluated for inhibition of AChE and BChE. They inhibited AChE and BChE enzymes in the range of Ki 5.24 +/- 2.27 (6c) -48.44 +/- 21.82 (4g) for AChE and 4.86 +/- 0.64 (6c) -51.75 +/- 12.56 (4a) for BChE, and the results were compared with the standard inhibitor Tacrine (K-i: 14.20 +/- 8.83 nM toward AChE and K-i: 3.39 +/- 1.91 nM for BChE). Cholinesterase (BChE and AChE) inhibitory abilities of all synthesized molecules were also performed in situ and molecular docking and molecular dynamics (MD) simulation studies. The molecular coupling scores of the compounds and the free binding energies calculated by MM/GBSA were found to be compatible. Examining the results obtained from this study shows that it may have the potential to develop new drugs to treat some global patients such as glaucoma and Alzheimer's disease (AD).en_US
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK), Turkey [118Z681]en_US
dc.description.sponsorshipThis study is a part of the project which is supported by Scientific and Technological Research Council of Turkey (TUBITAK Project No: 118Z681) , Turkey.en_US
dc.identifier.doi10.1016/j.cbi.2022.110134
dc.identifier.issn0009-2797
dc.identifier.issn1872-7786
dc.identifier.pmid36057360en_US
dc.identifier.scopus2-s2.0-85137627272en_US
dc.identifier.scopusqualityQ1en_US
dc.identifier.urihttps://doi.org/10.1016/j.cbi.2022.110134
dc.identifier.urihttps://hdl.handle.net/11616/100880
dc.identifier.volume366en_US
dc.identifier.wosWOS:000861651900006en_US
dc.identifier.wosqualityQ1en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherElsevier Ireland Ltden_US
dc.relation.ispartofChemico-Biological Interactionsen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject2-Aminothiolen_US
dc.subjectAcetylcholinesteraseen_US
dc.subjectEnzyme inhibitionen_US
dc.subjectCarbonic anhydraseen_US
dc.subjectButyrylcholinesteraseen_US
dc.titleSynthesis, characterization, evaluation of metabolic enzyme inhibitors and in silico studies of thymol based 2-amino thiol and sulfonic acid compoundsen_US
dc.typeArticleen_US

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