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dc.creatorOstojić, Bojana
dc.creatorĐorđević, Dragana
dc.date.accessioned2019-01-30T17:45:57Z
dc.date.available2019-01-30T17:45:57Z
dc.date.issued2015
dc.identifier.issn0304-3894
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/1737
dc.description.abstractThe equilibrium geometries, relative energies, IR and Raman spectra, vertical ionization potentials (IP), vertical electron affinities (EA), dipole moments (mu), electronic dipole polarizabilities (alpha), and molecular electrostatic potentials (MEP) of two species that show very high mutagenicity, 1-nitro-6-azabenzo[a]pyrene N-oxide (1-N-6-ABPO) and 3-nitro-6-azabenzo[a]pyrene N-oxide (3-N-6-ABPO), are investigated by means of Density Functional Theory (DFT) using B3LYP functional with different basis sets. The 3-N-6-ABPO isomer was estimated to be much more mutagenic in Salmonella typhimurium tester strain TA98 (396 000 revertants/nmol) than 1-N-6-ABPO (36 100 revertants/nmol) (Fukuhara et al., 1992). The results show that for both isomers the structural, energetic, and vibrational properties are similar. The orientation of the nitro group with respect to the plane of the aromatic system as well as the nitroreduction and oxidation reaction and polarizability seem not be important for the determination of different mutagenic behavior of these isomers. However, the dipole moment of 3-N-6-ABPO is about 3 times that of 1-N-6-ABPO. The larger dipole moment and the different electronic charge distribution of 3-N-6-ABPO compared to 1-N-6-ABPO imply stronger electrostatic and inductive molecular interactions so that the active site of the enzyme involved in the mutagenic activation can more effectively bind 3-N-6-ABPO compared to 1-N-6-ABPO.en
dc.publisherElsevier Science Bv, Amsterdam
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172001/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/171017/RS//
dc.rightsrestrictedAccess
dc.sourceJournal of Hazardous Materials
dc.subject1-Nitro-6-azabenzo[a]pyreneen
dc.subject3-Nitro-6-azabenzo[a]pyreneen
dc.subjectEnvironmental pollutantsen
dc.subjectDFT calculationsen
dc.subjectMutagenic activityen
dc.titleTwo nitro derivatives of azabenzo[a]pyrene N-oxide: Electronic properties and their relation to mutagenic activityen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractОстојић, Бојана; Ђорђевић, Драгана;
dc.citation.volume285
dc.citation.spage94
dc.citation.epage102
dc.citation.other285: 94-102
dc.citation.rankaM21
dc.identifier.pmid25497021
dc.identifier.doi10.1016/j.jhazmat.2014.11.032
dc.identifier.rcubConv_3296
dc.identifier.scopus2-s2.0-84917706347
dc.identifier.wos000349880100012
dc.type.versionpublishedVersion


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