Absolute Configuration and Biological Profile of Pyrazoline Enantiomers as Mao Inhibitory Activity

dc.contributor.authorGoksen, Umut Salgin
dc.contributor.authorSarıgül, Sevgi
dc.contributor.authorBultinck, Patrick
dc.contributor.authorHerrebout, Wouter
dc.contributor.authorDoğan, İlknur
dc.contributor.authorYelekçi, Kemal
dc.contributor.authorUçar, Gülberk
dc.contributor.authorKelekçi, Nesrin Gökhan
dc.date.accessioned2019-06-27T08:02:31Z
dc.date.available2019-06-27T08:02:31Z
dc.date.issued2019
dc.departmentFakülteler, Mühendislik ve Doğa Bilimleri Fakültesi, Biyoinformatik ve Genetik Bölümüen_US
dc.description.abstractA new racemic pyrazoline derivative was synthesized and resolved to its enantiomers using analytic and semipreparative high-pressure liquid chromatography. The absolute configuration of both fractions was established using vibrational circular dichroism. The in vitro monoamine oxidase (MAO) inhibitory profiles were evaluated for the racemate and both enantiomers separately for the two isoforms of the enzyme. The racemic compound and both enantiomers were found to inhibit hMAO-A selectively and competitively. In particular the R enantiomer was detected as an exceptionally potent and a selective MAO-A inhibitor (K-i = 0.85 x 10(-3) +/- 0.05 x 10(-3) mu M and SI: 2.35 x 10(-5)) whereas S was determined as poorer compound than R in terms of K-i and SI (0.184 +/- 0.007 and 0.001). The selectivity of the enantiomers was explained by molecular modeling docking studies based on the PDB enzymatic models of MAO isoforms.en_US]
dc.identifier.citation18
dc.identifier.doi10.1002/chir.23027en_US
dc.identifier.endpage33
dc.identifier.issn0899-0042en_US
dc.identifier.issn1520-636Xen_US
dc.identifier.issn0899-0042
dc.identifier.issn1520-636X
dc.identifier.issue1
dc.identifier.pmid30468523en_US
dc.identifier.scopus2-s2.0-85057123364en_US
dc.identifier.scopusqualityQ2
dc.identifier.startpage21en_US
dc.identifier.urihttps://hdl.handle.net/20.500.12469/637
dc.identifier.urihttps://doi.org/10.1002/chir.23027
dc.identifier.volume31en_US
dc.identifier.wosWOS:000454123000003en_US
dc.institutionauthorYelekçi, Kemalen_US
dc.institutionauthorYelekçi, Kemal
dc.language.isoenen_US
dc.publisherWileyen_US
dc.relation.journalChiralityen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subject2-pyrazolineen_US
dc.subjectMolecular modeling dockingen_US
dc.subjectMonoamine oxidase inhibitory activityen_US
dc.subjectSpecific rotationen_US
dc.subjectStereochemistryen_US
dc.subjectVibrational circular dichroismen_US
dc.titleAbsolute Configuration and Biological Profile of Pyrazoline Enantiomers as Mao Inhibitory Activityen_US
dc.typeArticleen_US
dspace.entity.typePublication
relation.isAuthorOfPublication9407938e-3d31-453b-9199-aaa8280a66c5
relation.isAuthorOfPublication.latestForDiscovery9407938e-3d31-453b-9199-aaa8280a66c5

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