Kinetic constraints for the thiolysis of 4-methyl-5-(pyrazin-2-yl)-1,2-dithiole-3-thione (oltipraz) and related dithiole-3-thiones in aqueous solution

Chemical Research in Toxicology

Volumn 14, Issue 8, 2001, Pages 939-945

  Carey, K A ^a   Kensler, T W ^b   Fishbein, J C ^a  

^a UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

^b JOHNS HOPKINS BLOOMBERG SCHOOL OF PUBLIC HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; DITHIOL DERIVATIVE; DITHIOTHREITOL; GLUTATHIONE; MERCAPTOETHANOL; OLTIPRAZ; PROPANE; THIOGLYCOLIC ACID; THIOL DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; LYSIS; PH; REACTION ANALYSIS;

ANTICARCINOGENIC AGENTS; HYDROGEN-ION CONCENTRATION; KINETICS; PYRAZINES; SULFHYDRYL COMPOUNDS; TEMPERATURE; TOLUENE; WATER;

EID: 0034873552     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0100340     Document Type: Article

References (32)

1. Ring opening and closing rates for thiosugars
2. Inhibition of carcinogenic and toxic effects of polycyclic hydrocarbons by phenolic antioxidants and ethoxyquin
3. Indentification of a common chemical signal regulating the induction of enzymes that protect against chemical carcinogenesis
4. Chemical and molecular regulation of enzymes that detoxify carcinogens
5. Role of transcription factor Nrf2 in the induction of hepatic phase 2 and antioxidative enzymes in vivo by the chemopreventive agent 3H-1,2-dithiole-3-thione
6. An Nrf2/small Maf heterodimer mediates the induction of phase II detoxifying enzyme genes through antioxidant response elements
7. Keap1 represses nuclear activation of antioxidant responsive elements by Nrf2 through binding to the amino-terminal Neh2 domain
8. Potency of Michael reaction acceptors as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups
9. Oltipraz: A laboratory and clinical review
10. Chemopreventive activity of oltipraz
11. Mechanisms of chemoprotection by 1,2-dithiole-3-thiones
12. Chemoprevention by inducers of carcinogen detoxication enzymes
13. Regulation of phase 2 enzyme induction by oltipraz and other dithiolethiones
14. Sensitivity to carcinogenesis is increased and chemoprotective efficacy of enzyme inducers is lost in Nrf2 transcription factor-deficient mice
15. Development of cancer chemopreventive agents: Oltipraz as a paradigm
16. Metabolism of oltipraz and glutathione reductase inhibition
17. A bridge to control
18. Activation of the OxyR transcription factor by reversible disulfide bond formation
19. Reactivity of substituted 1,2-dithiole-3-thiones with sodium ethanethiolate: A convenient route to a novel heterocycle
20. Studies of the reaction of 1,2-dithiole-thiones with nucleophiles
21. Toward an understanding of the schistosomocidal effect of 4-methyl-5-(2-pyrazinyl)-1,2-dithiole-3-thione
22. Evidence for thiol-dependent production of oxygen radicals by 4-methyl-5-pyrazinyl-3H-1,2-dithiole-3-thione and 3H-1,2-dithiole-thione: Possible relevance to the anticarcinogenic properties of 1,2-dithiole-3-thiones
23. Oltipraz stimulates the transcription of the MnSOD gene in rat hepatocytes
24. Antioxidant and redox regulation of gene transcription
25. Tissue sulfhydryl groups
26. Ellman's reagent: 5.5′-dithiobis(2-nitrobenzoic acid) - A reexamination
27. Rates of thiol disulfide interchange reactions between mono- and di-thiols and Ellman's reagent
28. Rate constants and equilibrium constants for thiol-disulfide interchange reactions involving oxidized glutathione
29. Structure-reactivity correlations for the thiol-disulfide interchange reaction
30. Water/octanol partition coefficients of 1,2-dithiole-3-thiones
31. Correlations between n-octanol/water partition coefficients and the RP-HPLC capacity factors of 1,2-dithiole-3-thiones and 1,2-dithiole-3-ones