NOVEL ACTIVATION MECHANISM FOR THE PROMUTAGENIC HERBICIDE DIALLATE

被引：44

作者：

SCHUPHAN, I ^{[1
]}

ROSEN, JD ^{[1
]}

CASIDA, JE ^{[1
]}

机构：

[1] UNIV CALIF BERKELEY,DEPT ENTOMOL SCI,PESTICIDE CHEM & TOXICOL LAB,BERKELEY,CA 94720

来源：

SCIENCE | 1979年 / 205卷 / 4410期

关键词：

D O I：

10.1126/science.472719

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

The potent bacterial mutagen 2-chloroacrolein is formed from the carcinogenic herbicide S-2,3-dichloroallyl diisopropylthiocarbamate (diallate) on incubation with hepatic microsomal monooxygenases or on reaction with m-chloroperbenzoic acid. A proposed activation mechanism for this promutagen involves sulfoxidation followed by [2,3] sigmatropic rearrangement and 1,2-elimination reactions. A portion of the highly reactive intermediate, diallate sulfoxide (proximate mutagen), is attacked by glutathione in a reaction which competes with its transformation to the ultimate mutagen, 2-chloroacrolein.

引用

页码：1013 / 1015

页数：3

共 15 条

[1] METHODS FOR DETECTING CARCINOGENS AND MUTAGENS WITH SALMONELLA-MAMMALIAN-MICROSOME MUTAGENICITY TEST [J].

AMES, BN ;

MCCANN, J ;

YAMASAKI, E .

MUTATION RESEARCH, 1975, 31 (06) :347-363

[2]

Casida J E, 1975, Environ Qual Saf Suppl, V3, P675

[3] SULFOXIDATION OF THIOCARBAMATE HERBICIDES AND METABOLISM OF THIOCARBAMATE SULFOXIDES IN LIVING MICE AND LIVER-ENZYME SYSTEMS [J].

CASIDA, JE ;

KIMMEL, EC ;

OHKAWA, H ;

OHKAWA, R .

PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 1975, 5 (01) :1-11

[4] THIOCARBAMATE SULFOXIDES - POTENT, SELECTIVE, AND BIODEGRADABLE HERBICIDES [J].

CASIDA, JE ;

GRAY, RA ;

TILLES, H .

SCIENCE, 1974, 184 (4136) :573-574

[5] THIOCARBAMATE HERBICIDE METABOLISM - MICROSOMAL OXYGENASE METABOLISM OF EPTC INVOLVING MONO-OXYGENATION AND DIOXYGENATION AT SULFUR AND HYDROXYLATION AT EACH ALKYL CARBON [J].

CHEN, YS ;

CASIDA, JE .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1978, 26 (01) :263-267

[6] S-CHLOROALLYL THIOCARBAMATE HERBICIDES - MOUSE HEPATIC MICROSOMAL L LYSOGENASE AND RAT-METABOLISM OF CIS-[C-14=O]DIALLATE AND TRANS-O]DIALLATE-C-14 [J].

CHEN, YS ;

SCHUPHAN, I ;

CASIDA, JE .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1979, 27 (04) :709-712

[7]

DELORENZO F, 1978, CANCER RES, V38, P13

[8] METABOLIC-FATE OF N,N-DIALKYLCARBAMOYL MOIETY OF THIOCARBAMATE HERBICIDES IN RATS AND CORN [J].

HUBBELL, JP ;

CASIDA, JE .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1977, 25 (02) :404-413

[9]

INNES JRM, 1969, JNCI-J NATL CANCER I, V42, P1101

[10]

SCHUPHAN I, 1979, TETRAHEDRON LETT, P841

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