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Quantum chemical modeling of the inhibition mechanism of monoamine oxidase by oxazolidinone and analogous heterocyclic compounds

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dc.contributor.authorERDEM, SAFİYE
dc.contributor.authorsErdem, Safiye Sag; Ozpinar, Gul Altinbas; Boz, Umut
dc.date.accessioned2022-03-14T10:58:06Z
dc.date.available2022-03-14T10:58:06Z
dc.date.issued2014-02-01
dc.description.abstractMonoamine oxidase (MAO, EC 1.4.3.4) is responsible from the oxidation of a variety of amine neurotransmitters. MAO inhibitors are used for the treatment of depression or Parkinson's disease. They also inhibit the catabolism of dietary amines. According to one hypothesis, inactivation results from the formation of a covalent adduct to a cysteine residue in the enzyme. If the adduct is stable enough, the enzyme is inhibited for a long time. After a while, enzyme can turn to its active form as a result of adduct breakdown by beta-elimination. In this study, the proposed inactivation mechanism was modeled and tested by quantum chemical calculations. Eight heterocyclic methylthioamine derivatives were selected to represent the proposed covalent adducts. Activation energies related to their beta-elimination reactions were calculated using ab initio and density functional theory methods. Calculated activation energies were in good agreement with the relative stabilities of the hypothetical adducts predicted in the literature by enzyme inactivation measurements.
dc.identifier.doi10.3109/14756366.2012.753882
dc.identifier.eissn1475-6374
dc.identifier.issn1475-6366
dc.identifier.pubmed23323992
dc.identifier.urihttps://hdl.handle.net/11424/245621
dc.identifier.wosWOS:000330850300014
dc.language.isoeng
dc.publisherTAYLOR & FRANCIS LTD
dc.relation.ispartofJOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectAdduct dissociation
dc.subjectadduct stability
dc.subjectdihydrofuranone
dc.subjectenzyme inhibition
dc.subjectoxazolidinone
dc.subjectpyrrolidinone
dc.subjectACTIVE-SITE
dc.subjectAMINE-OXIDATION
dc.subjectB INACTIVATORS
dc.subjectAROMATIC CAGE
dc.subjectDRUG TARGET
dc.subject1-PHENYLCYCLOPROPYLAMINE
dc.subjectBENZYLAMINE
dc.titleQuantum chemical modeling of the inhibition mechanism of monoamine oxidase by oxazolidinone and analogous heterocyclic compounds
dc.typearticle
dspace.entity.typePublication
local.avesis.idaabba976-8a46-4600-8068-5be7ea4b02f5
local.import.packageSS16
local.indexed.atWOS
local.indexed.atSCOPUS
local.indexed.atPUBMED
local.journal.numberofpages6
oaire.citation.endPage86
oaire.citation.issue1
oaire.citation.startPage81
oaire.citation.titleJOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
oaire.citation.volume29
relation.isAuthorOfPublication99f2f09c-7e48-402f-9bb9-ccdd73c27ec2
relation.isAuthorOfPublication.latestForDiscovery99f2f09c-7e48-402f-9bb9-ccdd73c27ec2

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