Synthesis and molecular modeling studies of naphthazarin derivatives as novel selective inhibitors of ?-glucosidase and ?-amylase

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dc.authorid0000-0002-3909-0694en_US
dc.authorid0000-0002-8325-8116en_US
dc.authorid0000-0003-2811-1872en_US
dc.authorid0000-0001-9386-4892en_US
dc.contributor.authorAbadan, Şebnem
dc.contributor.authorSağlam, Mehmet F.
dc.contributor.authorKoca, Mehmet Serdar
dc.contributor.authorBingül, Murat
dc.contributor.authorŞahin, Hasan
dc.contributor.authorZorlu, Yunus
dc.contributor.authorŞengül, İbrahim F.
dc.date.accessioned2023-08-09T06:42:33Z
dc.date.available2023-08-09T06:42:33Z
dc.date.issued2023en_US
dc.departmentDicle Üniversitesi, Eczacılık Fakültesi, Temel Eczacılık Bilimleri Bölümüen_US
dc.description.abstractDiabetes mellitus is known as one of the most life-threatening diseases and has attracted the attention of medicinal chemists. The design and synthesis of novel potential candidates for the inhibition of αamylase and α-glucosidase enzymes which are responsible for the digestion of dietary carbohydrates are an important approach for the treatment of diabetes. In this current work, a range of novel mono and naphthazarin derivatives were successfully synthesized by the esterification reaction of naphthazarin with different benzoyl chlorides and heterocyclic acyl chlorides. The synthesized compounds were subjected to in vitro antidiabetic activities through α-glucosidase and α-amylase inhibition properties. Despite the limited inhibition potential against α-amylase enzymes, naphthazarin derivatives would be promising targets for antidiabetic study due to the specificity for α-glucosidase enzyme. The compound 18 revealed a dual inhibition behavior, however all the other active compounds were detected as specific for α-glucosidase inhibition and quite potent compared to the standard acarbose which is promising for eliminating the side effects associated with the non-selectivity of acarbose. The compound 19 was the best candidate for inhibition with IC50 value of 7.4 μM and resulted 150-fold better activity compared to the standard. Free energy calculations support the experimental binding affinity of compound 19 found as the most promising drug candidate for α-glucosidase among the synthesized compounds. The plausible binding mode and the interaction of compound 19 complexed with α-glucosidase has been revealed by MD simulations.en_US
dc.identifier.citationAbadan, Ş., Sağlam, M. F., Koca, M. S., Bingül, M., Şahin, H., Zorlu, Y. ve diğerleri. (2023). Synthesis and molecular modeling studies of naphthazarin derivatives as novel selective inhibitors of α-glucosidase and α-amylase. Journal of Molecular Structure, (1278), 1-12.en_US
dc.identifier.doi10.1016/j.molstruc.2023.134954
dc.identifier.endpage12en_US
dc.identifier.issn0022-2860
dc.identifier.issue1278en_US
dc.identifier.scopus2-s2.0-85146420730
dc.identifier.scopusqualityQ1
dc.identifier.startpage1en_US
dc.identifier.urihttps://www.sciencedirect.com/science/article/pii/S0022286023000558?via%3Dihub
dc.identifier.urihttps://hdl.handle.net/11468/12453
dc.identifier.wosWOS:000996516100001
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorBingül, Murat
dc.institutionauthorŞahin, Hasan
dc.language.isoenen_US
dc.publisherElsevier B.V.en_US
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectNaphthazarinen_US
dc.subjectα-amylaseen_US
dc.subjectα-glucosidaseen_US
dc.subjectEnzyme inhibitionen_US
dc.subjectMolecular modelingen_US
dc.titleSynthesis and molecular modeling studies of naphthazarin derivatives as novel selective inhibitors of ?-glucosidase and ?-amylaseen_US
dc.titleSynthesis and molecular modeling studies of naphthazarin derivatives as novel selective inhibitors of ?-glucosidase and ?-amylase
dc.typeArticleen_US

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