Two nitro derivatives of azabenzo[a]pyrene N-oxide: Electronic properties and their relation to mutagenic activity
Abstract
The 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.
Keywords:
1-Nitro-6-azabenzo[a]pyrene / 3-Nitro-6-azabenzo[a]pyrene / Environmental pollutants / DFT calculations / Mutagenic activitySource:
Journal of Hazardous Materials, 2015, 285, 94-102Publisher:
- Elsevier
Funding / projects:
- The study of physicochemical and biochemical processes in living environment that have impacts on pollution and the investigation of possibilities for minimizing the consequences (RS-172001)
- Modeling and Numerical Simulations of Complex Many-Body Systems (RS-171017)
DOI: 10.1016/j.jhazmat.2014.11.032
ISSN: 0304-3894
PubMed: 25497021
WoS: 000349880100012
Scopus: 2-s2.0-84917706347
Collections
Institution/Community
IHTMTY - JOUR AU - Ostojić, Bojana AU - Đorđević, Dragana PY - 2015 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1737 AB - The 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. PB - Elsevier T2 - Journal of Hazardous Materials T1 - Two nitro derivatives of azabenzo[a]pyrene N-oxide: Electronic properties and their relation to mutagenic activity VL - 285 SP - 94 EP - 102 DO - 10.1016/j.jhazmat.2014.11.032 ER -
@article{ author = "Ostojić, Bojana and Đorđević, Dragana", year = "2015", abstract = "The 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.", publisher = "Elsevier", journal = "Journal of Hazardous Materials", title = "Two nitro derivatives of azabenzo[a]pyrene N-oxide: Electronic properties and their relation to mutagenic activity", volume = "285", pages = "94-102", doi = "10.1016/j.jhazmat.2014.11.032" }
Ostojić, B.,& Đorđević, D.. (2015). Two nitro derivatives of azabenzo[a]pyrene N-oxide: Electronic properties and their relation to mutagenic activity. in Journal of Hazardous Materials Elsevier., 285, 94-102. https://doi.org/10.1016/j.jhazmat.2014.11.032
Ostojić B, Đorđević D. Two nitro derivatives of azabenzo[a]pyrene N-oxide: Electronic properties and their relation to mutagenic activity. in Journal of Hazardous Materials. 2015;285:94-102. doi:10.1016/j.jhazmat.2014.11.032 .
Ostojić, Bojana, Đorđević, Dragana, "Two nitro derivatives of azabenzo[a]pyrene N-oxide: Electronic properties and their relation to mutagenic activity" in Journal of Hazardous Materials, 285 (2015):94-102, https://doi.org/10.1016/j.jhazmat.2014.11.032 . .