STRUCTURE-ACTIVITY RELATIONSHIP OF GENOTOXIC POLYCYCLIC AROMATIC NITRO-COMPOUNDS - FURTHER EVIDENCE FOR THE IMPORTANCE OF HYDROPHOBICITY AND MOLECULAR-ORBITAL ENERGIES IN GENETIC TOXICITY

被引：25

作者：

DEBNATH, AK

HANSCH, C

机构：

[1] Chemistry Department, Pomona College, Claremont, California

来源：

ENVIRONMENTAL AND MOLECULAR MUTAGENESIS | 1992年 / 20卷 / 02期

关键词：

QSAR; SOS CHROMOTEST; ESCHERICHIA-COLI PQ37; BETA-GALACTOSIDASE;

D O I：

10.1002/em.2850200210

中图分类号：

X [环境科学、安全科学];

学科分类号：

08 ; 0830 ;

摘要：

A quantitative structure-activity relationship (QSAR) has been formulated for 15 polycyclic aromatic nitro compounds acting on E. coli PQ37. Upon damage of DNA by these substances beta-galactosidase is induced and can be easily assayed colorimetrically, hence, this is a short-term test for mutagenicity. The QSAR (log SOSIP = 1.07 log P - 1.57 epsilon(LUMO) - 6.41) is strikingly similar to that found earlier with nitroaromatics acting in the Ames test (TA100) and differs significantly for that found using TA98 organisms. The QSAR brings out in a unique manner the underlying similarity in the two test systems.

引用

收藏

页码：140 / 144

页数：5

相关论文

共 24 条

[1] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].

ALLEN, FH ;

KENNARD, O ;

WATSON, DG ;

BRAMMER, L ;

ORPEN, AG ;

TAYLOR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19

[2]

COMPADRE RLL, 1990, ENVIRON MOL MUTAGEN, V15, P44

[3]

COMPADRE RLL, 1988, INT J QUANTUM CHEM, V34, P91

[4] STRUCTURE ACTIVITY RELATIONSHIP OF MUTAGENIC AROMATIC AND HETEROAROMATIC NITRO-COMPOUNDS - CORRELATION WITH MOLECULAR-ORBITAL ENERGIES AND HYDROPHOBICITY [J].

DEBNATH, AK ;

DECOMPADRE, RLL ;

DEBNATH, G ;

SHUSTERMAN, AJ ;

HANSCH, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :786-797

[5] A QSAR INVESTIGATION OF THE ROLE OF HYDROPHOBICITY IN REGULATING MUTAGENICITY IN THE AMES TEST .1. MUTAGENICITY OF AROMATIC AND HETEROAROMATIC AMINES IN SALMONELLA-TYPHIMURIUM TA98 AND TA100 [J].

DEBNATH, AK ;

DEBNATH, G ;

SHUSTERMAN, AJ ;

HANSCH, C .

ENVIRONMENTAL AND MOLECULAR MUTAGENESIS, 1992, 19 (01) :37-52

[6] QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP INVESTIGATION OF THE ROLE OF HYDROPHOBICITY IN REGULATING MUTAGENICITY IN THE AMES TEST .2. MUTAGENICITY OF AROMATIC AND HETEROAROMATIC NITRO-COMPOUNDS IN SALMONELLA-TYPHIMURIUM TA100 [J].

DEBNATH, AK ;

DECOMPADRE, RLL ;

SHUSTERMAN, AJ ;

HANSCH, C .

ENVIRONMENTAL AND MOLECULAR MUTAGENESIS, 1992, 19 (01) :53-70

[7]

DEBNATH AK, IN PRESS MUTAT RES

[8] EVALUATION OF THE MUTAGENIC AND GENOTOXIC ACTIVITIES OF 48 NITROIMIDAZOLES AND RELATED IMIDAZOLE DERIVATIVES BY THE AMES TEST AND THE SOS CHROMOTEST [J].

DEMEO, M ;

VANELLE, P ;

BERNADINI, E ;

LAGET, M ;

MALDONADO, J ;

JENTZER, O ;

CROZET, MP ;

DUMENIL, G .

ENVIRONMENTAL AND MOLECULAR MUTAGENESIS, 1992, 19 (02) :167-181

[9]

DENNIS M J, 1984, Food Additives and Contaminants, V1, P29, DOI 10.1080/02652038409385820

[10] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].

DEWAR, MJS ;

ZOEBISCH, EG ;

HEALY, EF ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909