Synthesis of new 7-amino-3,4-dihydroquinolin-2(1H)-one-peptide derivatives and their carbonic anhydrase enzyme inhibition, antioxidant, and cytotoxic activities

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dc.authoridYesilada, Ozfer/0000-0003-0038-6575
dc.authoridKUCUKBAY, HASAN/0000-0002-7180-9486
dc.authoridTekin, Zehra/0000-0003-3682-3044
dc.authoridSupuran, Claudiu/0000-0003-4262-0323
dc.authoridangeli, andrea/0000-0002-1470-7192
dc.authoridBartolucci, Gianluca/0000-0002-5631-8769
dc.authorwosidYesilada, Ozfer/ABI-1335-2020
dc.authorwosidTEKİN, zehra/HSH-9254-2023
dc.authorwosidKUCUKBAY, HASAN/A-5050-2019
dc.authorwosidTekin, Zehra/GLR-6001-2022
dc.contributor.authorKucukbay, Hasan
dc.contributor.authorGonul, Zeynep
dc.contributor.authorKucukbay, Fatumetuzzehra Zehra
dc.contributor.authorTekin, Zehra
dc.contributor.authorAngeli, Andrea
dc.contributor.authorBartolucci, Gianluca
dc.contributor.authorSupuran, Claudiu T.
dc.date.accessioned2024-08-04T20:50:26Z
dc.date.available2024-08-04T20:50:26Z
dc.date.issued2021
dc.departmentİnönü Üniversitesien_US
dc.description.abstractSix new monopeptides, seven new dipeptides, and two deprotected monopeptide dihydroquinolinone conjugates were prepared by the benzothiazole-mediated method and their structures were confirmed by nuclear magnetic resonance, mass, infrared spectroscopy, and elemental analysis methods. The human carbonic anhydrase (hCA) I and hCA II enzyme inhibition activities of the compounds were determined using the stopped-flow instrument. The synthesized peptide-dihydroquinolinone conjugates 2, 3, 6, 10, 13, and 15 showed inhibition against the hCA II enzyme in the range of 15.7-65.7 mu M. However, none of the compounds showed inhibition of hCA I at a concentration of 100 mu M. The antioxidant activities of the compounds were also examined using the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging method at concentrations of 12.5-125 mu g/ml, but when compared with the standard antioxidant compounds alpha-tocopherol and butylated hydroxyanisole (BHA), weak antioxidant activities were detected. The cytotoxic effects of four compounds against the A549 and BEAS-2B cell lines were also investigated. Among the compounds studied, compound 7 was found to be most effective, with the IC50 values on the A549 cells for 48 and 72 h being 26.87 and 9.979 mu g/ml, respectively, and the IC50 values on the BEAS-2B cells being >100 mu g/ml. None of the tested compounds showed antimicrobial activity in the concentration range (800-1.56 mu g/ml) studied.en_US
dc.description.sponsorshipInonu University Research Fund [FYL-2018-909]en_US
dc.description.sponsorshipThis study was financially supported by the Inonu University Research Fund (FYL-2018-909).en_US
dc.identifier.doi10.1002/ardp.202100122
dc.identifier.issn0365-6233
dc.identifier.issn1521-4184
dc.identifier.issue11en_US
dc.identifier.pmid34313324en_US
dc.identifier.scopus2-s2.0-85111095877en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1002/ardp.202100122
dc.identifier.urihttps://hdl.handle.net/11616/100063
dc.identifier.volume354en_US
dc.identifier.wosWOS:000677723600001en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherWiley-V C H Verlag Gmbhen_US
dc.relation.ispartofArchiv Der Pharmazieen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectantioxidanten_US
dc.subjectcarbonic anhydraseen_US
dc.subjectcytotoxicityen_US
dc.subjectpeptideen_US
dc.subjectpeptide-dihydroquinolin-2-one conjugatesen_US
dc.subjectquinolonesen_US
dc.titleSynthesis of new 7-amino-3,4-dihydroquinolin-2(1H)-one-peptide derivatives and their carbonic anhydrase enzyme inhibition, antioxidant, and cytotoxic activitiesen_US
dc.typeArticleen_US

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