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In vitro and in silico investigation of inhibitory activities of 3-arylcoumarins and 3-phenylazo-4-hydroxycoumarin on MAO isoenzymes

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dc.contributor.authorDANIŞ, ÖZKAN
dc.contributor.authorDEMİR, SERAP
dc.contributor.authorERDEM, SAFİYE
dc.contributor.authorOGAN, AYŞE
dc.contributor.authorsYuce-Dursun B., DANIŞ Ö., Ozalp L., Sahin E., DEMİR S., ERDEM S., OGAN A.
dc.date.accessioned2022-12-19T11:01:47Z
dc.date.available2022-12-19T11:01:47Z
dc.date.issued2022-11-01
dc.description.abstractA series of 3-aryl coumarin derivatives and 3-phenylazo-4-hydroxycoumarin were evaluated for their monoamine oxidase (MAO) A and B inhibitory activity and selectivity by fluorometric enzymological assays. Among 21 coumarin derivatives, compound 21 (3-phenylazo-4-hydroxycoumarin) displayed a good inhibitory activity (0.12 +/- 0.02 mu M) and very high selectivity for MAO-B (SI > 833.33). The inhibition was determined as mixed-type and not time-dependent. Docking studies, molecular dynamics and molecular mechanics/Poisson-Boltzmann surface area (MM/PBSA) calculations were performed to elucidate in vitro results. Our results reveal that the insertion of an azo linker between coumarin and phenyl rings in 3-arylcoumarins enhances MAO-B selectivity enormously since such a linker leads to the perfect alignment of the coumarin ring in the aromatic cage and the phenyl ring in the entrance cavity of MAO-B active site. Hydrogen bond interactions with Cys172 in the active site entrance of MAO-B also contributes to the remarkably higher inhibitory activity and selectivity for MAO-B.
dc.identifier.citationYuce-Dursun B., DANIŞ Ö., Ozalp L., Sahin E., DEMİR S., ERDEM S., OGAN A., "In vitro and in silico investigation of inhibitory activities of 3-arylcoumarins and 3-phenylazo-4-hydroxycoumarin on MAO isoenzymes", STRUCTURAL CHEMISTRY, 2022
dc.identifier.doi10.1007/s11224-022-02092-x
dc.identifier.issn1040-0400
dc.identifier.urihttps://hdl.handle.net/11424/283705
dc.language.isoeng
dc.relation.ispartofSTRUCTURAL CHEMISTRY
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectKimya
dc.subjectBiyokimya
dc.subjectAlkoloidler
dc.subjectFizikokimya
dc.subjectSıvı Kristaller ve Sıvı Kristal Polimerler
dc.subjectTemel Bilimler
dc.subjectChemistry
dc.subjectBiochemistry
dc.subjectAlcaloides
dc.subjectPhysical Chemistry
dc.subjectLiquid Crystals and LCP
dc.subjectNatural Sciences
dc.subjectKİMYA, MULTİDİSİPLİNER
dc.subjectTemel Bilimler (SCI)
dc.subjectKİMYA, FİZİKSEL
dc.subjectKRİSTALLOGRAFİ
dc.subjectCHEMISTRY, MULTIDISCIPLINARY
dc.subjectCHEMISTRY
dc.subjectNatural Sciences (SCI)
dc.subjectCHEMISTRY, PHYSICAL
dc.subjectCRYSTALLOGRAPHY
dc.subjectYüzeyler ve Arayüzler
dc.subjectYüzeyler, Kaplamalar ve Filmler
dc.subjectFiziksel ve Teorik Kimya
dc.subjectKimya (çeşitli)
dc.subjectGenel Kimya
dc.subjectFizik Bilimleri
dc.subjectSurfaces and Interfaces
dc.subjectSurfaces, Coatings and Films
dc.subjectPhysical and Theoretical Chemistry
dc.subjectChemistry (miscellaneous)
dc.subjectGeneral Chemistry
dc.subjectPhysical Sciences
dc.subjectEnzyme inhibition
dc.subjectCoumarin
dc.subjectDrug design
dc.subjectMonoamine oxidase a/b
dc.subjectMolecular docking
dc.subjectMolecular dynamics
dc.subjectMONOAMINE-OXIDASE-B
dc.subjectVALENCE-BOND SIMULATIONS
dc.subjectHYDRIDE-TRANSFER STEP
dc.subjectCOUMARIN DERIVATIVES
dc.subject2H-CHROMEN-2-ONE DERIVATIVES
dc.subjectCATALYZED METABOLISM
dc.subjectANTIOXIDANT ACTIVITY
dc.subjectOXIDATION MECHANISM
dc.subjectMOLECULAR-DYNAMICS
dc.subjectDUAL INHIBITORS
dc.subjectEnzyme inhibition · Coumarin · Drug design · Monoamine oxidase a/b · Molecular docking · Molecular dynamics
dc.titleIn vitro and in silico investigation of inhibitory activities of 3-arylcoumarins and 3-phenylazo-4-hydroxycoumarin on MAO isoenzymes
dc.typearticle
dspace.entity.typePublication
local.avesis.id987bf8d1-ad41-4e11-ac90-c06122283640
local.indexed.atWOS
local.indexed.atSCOPUS
relation.isAuthorOfPublication91b82a1e-bb32-4e40-ad53-90dcac92bacd
relation.isAuthorOfPublication2790d85f-c14d-4e37-8567-e89f9e168058
relation.isAuthorOfPublication99f2f09c-7e48-402f-9bb9-ccdd73c27ec2
relation.isAuthorOfPublication58db3332-a5f8-4224-a021-aeea795f52fa
relation.isAuthorOfPublication.latestForDiscovery91b82a1e-bb32-4e40-ad53-90dcac92bacd

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