Detoxication of sulfur half-mustards by nucleophilic scavengers: Robust activity of thiopurines

Chemical Research in Toxicology

Volumn 23, Issue 3, 2010, Pages 488-496

  Liu, Jinyun ^a   Powell, K Leslie ^a   Thames, Howard D ^b   MacLeod, Michael C ^a  

^a UNIVERSITY OF TEXAS   (United States)

^b UNIVERSITY OF TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 MERCAPTOPURINE DERIVATIVE; ACETYLCYSTEINE; CHLORMETHINE; DNA; ELECTROPHILE; GLUTATHIONE; MUSTARD GAS; PURINE DERIVATIVE; SCAVENGER; SULFONIUM DERIVATIVE; THIOL DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CELL DAMAGE; CHEMICAL REACTION; CONTROLLED STUDY; CROSS LINKING; DETOXIFICATION; HYDROLYSIS; MACROMOLECULE; MOLECULAR WEIGHT; PH; SYNTHESIS;

CHEMICAL WARFARE AGENTS; MUSTARD GAS; PURINES; THIONUCLEOSIDES;

BRASSICACEAE;

EID: 77949418282     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx900190j     Document Type: Article

References (24)

1. Dacre, J. C., and Goldman, M. (1996) Toxicology and pharmacology of the chemical warfare agent sulfur mustard. Pharmacol. ReV. 48, 289-326.
2. Emad, A., and Rezaian, G. R. (1999) Immunoglobulins and cellular constituents of the BAL fluid of patients with sulfur mustard gasinduced pulmonary fibrosis. Chest 115, 1346-1351.
3. Drasch, G., Kretschmer, E., Kauert, G., and von Meyer, L. (1987) Concentrations of mustard gas [bis(2-chloroethyl)sulfide] in the tissues of a victim of a vesicant exposure. J. Forensic Sci. 32, 1788-1793.
4. Hattersley, I. J., Jenner, J., Dalton, C., Chilcott, R. P., and Graham, J. S. (2008) The skin reservoir of sulphur mustard. Toxicol. In Vitro 22, 1539-1546.
5. Fidder, A., Moes, G. W., Scheffer, A. G., van der Schans, G. P., Baan, R. A., de Jong, L. P., and Benschop, H. P. (1994) Synthesis, characterization, and quantitation of the major adducts formed between sulfur mustard and DNA of calf thymus and human blood. Chem. Res. Toxicol. 7, 199-204.
6. Lawley, P. D., and Brookes, P. (1967) Interstrand cross-linking of DNA by difunctional alkylating agents. J. Mol. Biol. 25, 143-160.
7. Lawley, P. D., Lethbridge, J. H., Edwards, P. A., and Shooter, K. V. (1969) Inactivation of bacteriophage T7 by mono-and difunctional sulphur mustards in relation to cross-linking and depurination of bacteriophage DNA. J. Mol. Biol. 39, 181-198.
8. Ludlum, D. B., Austin-Ritchie, P., Hagopian, M., Niu, T. Q., and Yu, D. (1994) Detection of sulfur mustard-induced DNA modifications. Chem.-Biol. Interact. 91, 39-49.
9. Noort, D., Benschop, H. P., and Black, R. M. (2002) Biomonitoring of exposure to chemical warfare agents: a review. Toxicol. Appl. Pharmacol. 184, 116-126.
10. Bartlett, P. D., and Swain, C. G. (1949) Kinetics of hydrolysis and displacement reactions of beta, beta1-dichlorodiethyl sulfide and of beta-chloro-beta1-hydroxydiethyl sulfide. J. Am. Chem. Soc. 71, 1406-1415.
11. Yang, Y. C., Ward, J. R., and Luteran, T. (1986) Hydrolysis of mustard derivatives in aqueous acetone-water and ethanol-water mixtures. J. Org. Chem. 51, 2756-2759.
12. Kircher, M., Fleer, R., Ruhland, A., and Brendel, M. (1979) Biological and chemical effects of mustard gas in yeast. Mutat. Res. 63, 273-289.
13. Matijasevic, Z., Precopio, M. L., Snyder, J. E., and Ludlum, D. B. (2001) Repair of sulfur mustard-induced DNA damage in mammalian cells measured by a host cell reactivation assay. Carcinogenesis 22, 661-664.
14. MacLeod, M. C., Humphrey, R. M., Bickerstaff, T., and Daylong, A. (1990) Inhibition by 6-mercaptopurine of the binding of a benzo(a)pyrene diol-epoxide to DNA in Chinese hamster ovary cells. Cancer Res. 50, 4355-4359.
15. MacLeod, M. C., Stewart, E., Daylong, A., Lew, L. K., and Evans, F. E. (1991) Reaction of a chemotherapeutic agent, 6-mercaptopurine, with a direct-acting, electrophilic carcinogen, benzo[a]pyrene-7,8-diol 9,10-epoxide. Chem. Res. Toxicol. 4, 453-462.
16. MacLeod, M. C., Qing, W. G., Powell, K. L., Daylong, A., and Evans, F. E. (1993) Reaction of nontoxic, potentially chemopreventive purinethiols with a direct-acting, electrophilic carcinogen, benzo[a]pyrene-7,8-diol 9,10-epoxide. Chem. Res. Toxicol. 6, 159-167.
17. Qing, W.-G., Powell, K. L., and MacLeod, M. C. (1996) Kinetics of the reaction of a potential chemopreventive agent, 2,6-dithiopurine, and its major metabolite, 2,6-dithiouric acid, with multiple classes of electrophilic toxicants. Chem. Res. Toxicol. 9, 1298-1304.
18. MacLeod, M. C., Mann, K. L., Thai, G., Conti, C. J., and Reiners, J. J., Jr. (1991) Inhibition by 2,6-dithiopurine and thiopurinol of binding of a benzo(a)pyrene diol epoxide to DNA in mouse epidermis and of the initiation phase of two-stage tumorigenesis. Cancer Res. 51, 4859-4864.
19. Plagemann, P. G., Marz, R., Wohlhueter, R. M., Graff, J. C., and Zylka, J. M. (1981) Facilitated transport of 6-mercaptopurine and 6-thioguanine and non-mediated permeation of 8-azaguanine in Novikoff rat hepatoma cells and relationship to intracellular phosphoribosylation. Biochim. Biophys. Acta 647, 49-62.
20. Ogston, A. G., Holiday, E. R., Philpot, J. S. L., and Stocken, L. A. (1946) The replacement reactions of---'-dichlorodiethyl sulphide and of some analogues in aqueous solution: The isolation of--chloro--'-hydroxydiethyl sulphide. Trans. Faraday Soc. 44, 45-52.
21. Tilley, R. I. (1993) The hydrolysis of Bis(2-chloroethyl) sulfide (sulfur mustard) in aqueous mixtures of ethanol, acetone and dimethyl sulfoxide. Aust. J. Chem. 46, 293-300.
22. Qing, W. G., Powell, K. L., Stoica, G., Szumlanski, C. L., Weinshilboum, R. M., and Macleod, M. C. (1995) Toxicity and metabolism in mice of 2,6-dithiopurine, a potential chemopreventive agent. Drug Metab. Dispos. 23, 854-860.
23. Yang, Y. C., Szafraniec, L. L., Beaudry, W. T., and Ward, J. R. (1988) Kinetics and mechanism of the hydrolysis of 2-chloroethyl sulfides. J. Org. Chem. 53, 3293-3297.
24. Stein, W. H., and Fruton, J. S. (1946) Chemical reactions of mustard gas and related compounds. IV. Chemical reactions of--chloroethyl--'- hydroxyethylsulfide. J. Org. Chem. 11, 686-691.