Renal and spermatozoal toxicity of α-bromohydrin, 3-bromolactate and 3-bromopyruvate

Journal of Applied Toxicology

Volumn 16, Issue 1, 1996, Pages 57-63

  Jones, A R ^a   Porter, K E ^a   Dobbie, M S ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

Bromohydrin; (R) Bromohydrin; 3 Bromopropan 1,2 diol; 3 Bromopyruvate; 3 Chlorolactate; Boar spermatozoa; Diuresis; Male antifertility; Nephrotoxicity; Rat kidney tubules

Indexed keywords

1,2 BROMOHYDRIN; 3 BROMOLACTATE; BROMOPYRUVIC ACID; HALOGENATED HYDROCARBON; LACTIC ACID DERIVATIVE; PYRUVIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTRACEPTION; CONTROLLED STUDY; DIURESIS; GLUCOSURIA; IN VITRO STUDY; KIDNEY TUBULE; MALE; NEPHROTOXICITY; NONHUMAN; PRIORITY JOURNAL; RAT; REPRODUCTIVE TOXICITY; SPERMATOZOON;

ANIMALS; ENZYME INHIBITORS; GLYCOSURIA; KIDNEY DISEASES; KIDNEY TUBULES; LACTATES; MALE; PROPYLENE GLYCOLS; PYRUVATE DEHYDROGENASE COMPLEX; PYRUVATES; RATS; RATS, SPRAGUE-DAWLEY; SPERMATOCIDAL AGENTS; SPERMATOZOA; SWINE;

EID: 0030042636     PISSN: 0260437X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1263(199601)16:1<57::AID-JAT305>3.0.CO;2-R     Document Type: Article

References (35)

1. A. R. Jones, G. Fakhouri and P. Gadiel, The metabolism of the soil fumigant 1,2-dibromo-3-chloropropane in the rat. Experientia 35, 1432-1434 (1979).
2. A. R. Jones, Antifertility actions of α-chlorohydrin in the male. Aust. J. Biol. Sci. 36, 333-350 (1983).
3. E. Dybing, J. G. Omichinski, E. J. Soderlund, G. Brunborg, M. Låg, J. A. Holme and S. D. Nelson, Mutagenicity and organ damage of 1,2-dibromo-3-chloropropane (DBCP) and tris(2,3-dibromopropyl) phosphate. Rev. Biochem. Toxicol. 10, 139-186 (1989).
4. E. Dybing, E. J. Soderlund, M. Låg, G. Brunborg, J. A. Holme, J. G. Omichinski, P.G. Pearson and S. D. Nelson, Testicular metabolism and toxicity of halogenated propanes. Adv. Exp. Med. Biol. 283, 471-476 (1991).
5. T. R. Torkelson, S. E. Sadek, V. R. Rowe, J. K. Kodama, H. H. Anderson, G. S. Loquvam and C. H. Hine, Toxicologic investigations of 1,2-dibromo-3-chloropropane. Toxicol. Appl. Pharmacol. 3, 545-559 (1961).
6. D. Whorton, R. M. Krauss, S. Marshall and R. M. Milby, Infertility in male pesticide workers. Lancet ii, 1259-1261 (1977).
7. Environmental Protection Agency, Dibromochloropropane. Fed. Reg. 42, 48915-48922 (1977).
8. W. M. Kluwe, B. N. Gupta and J. C. Lamb, The comparative effects of 1,2-dibromo-3-chloropropane (DBCP) and its metabolites, 3-chloro-1,2-propane-oxide (epi-chlorohydrin), 3-chloro-1,2-propanediol alpha-chlorohydin), and oxalic acid, on the urogenital system of male rats. Toxicol. Appl. Pharmacol. 70, 67-86 (1983).
9. W. M. Kluwe, Chemical modulation of 1,2-dibromo-3-chloropropane toxicity. Toxicology 27, 287-299 (1983).
10. M. S. Dobbie, K. E. Porter and A. R. Jones, Is the nephrotoxicity of (R)-3-chlorolactate in the rat caused by 3-chloropyruvate? Xenobiotica 18, 1389-1399 (1988).
11. A. R. Jones and L. A. Chantrill, Oxidative metabolic activity of boar spermatozoa: a system for assessing anti-glycolytic activity of potential inhibitors in vivo. Reprod. Fertil. Dev. 1, 357-367 (1989).
12. S. Winstein and L. Goodman, Neighbouring groups in addition. II Hydroxyl and acetoxy groups in allyl derivatives. J. Am. Chem. Soc. 76, 4368-4372 (1954).
13. J. J. Baldwin, A. W. Raab, K. Mensler, B. H. Arison and D. E. McClure, Synthesis of (R)- and (S)- epichlorohydrin. J. Org. Chem. 43, 4876-4878 (1978).
14. C. F. Koelsch, A sulfur analog of glyceric acid. Betathioglyceric acid. J. Am. Chem. Soc. 52, 1105-1108 (1930).
15. A. R. Jones, D. H. Milton and C- Murcott, The oxidative metabolism of α-chlorohydrin in the male rat and the formation of spermatocoeles. Xenobiotica 8, 573-582 (1978).
16. H. A. Krebs, D. A. H. Bennett, P. De Gasquet, T. Gascoyne and T. Yoshida, Renal gluconeogenesis. The effect of diet on the gluconeogenic capacity of rat-kidney-cortex slices. Biochem. J. 86, 22-27 (1963).
17. D. Stevenson and A. R. Jones, Production of (S)-3-chlorolactaldehyde from (S)-α-chlorohydrin by boar spermatozoa and the inhibition of glyceraldehyde 3-phosphate dehydrogenase in vitro. J. Reprod. Fertil. 74, 157-165 (1985).
18. A. G. Dawson, Preparation and some properties of a suspension of fragmented tubules from rat kidney. Biochem. J. 130, 525-532 (1972).
19. A. G. Dawson, Contribution of pH-sensitive metabolic processes to pH homeostasis in isolated rat kidney tubules. Biochim. Biophys. Acta 499, 85-98 (1977).
20. G. Michal, D-Fructose-1,6-bisphosphate, dihydroxyacetone phosphate and D-glyceraldehyde 3-phosphate. In Methods of Enzymatic Analysis, 3rd Edn, Vol. 6, ed. by H. U. Bergmeyer, pp. 342-350. Verlag Chemie, Weinheim (1985).
21. H. U. Bergmeyer, M. Grassl and H. E. Walter, Biochemical reagents for general use: enzymes. In Methods of Enzymatic Analysis, 3rd Edn, Vol. 2, ed. by H. U. Bergmeyer, pp. 126-327. Verlag Chemie, Weinheim (1985).
22. O. H. Lowry, N. J. Roseborough, A. L. Farr and R. J. Randall, Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193, 265-275 (1951).
23. K. E. Porter and A. R. Jones, The effect of the isomers of α-chlorohydrin and racemic β-chlorolactate on the rat kidney. Chem.-Biol. Interact. 41, 95-104 (1982).
24. K. E. Porter and A. R. Jones. The renal toxicity of (R)-3-chlorolactate in the rat. Chem. Biol. Interact. 62, 157-166 (1987).
25. R. R. Pitts, Physiology of the Kidney and Body Fluids, p. 259. Medical Publishers, Chicago (1974).
26. U. K. Banik, T. Tanikella and S. Rakhit, Oral antifertility effects of halo propanediol derivatives in male rats. J. Reprod. Fertil. 30, 117-124 (1972).
27. N. Rashed and B. R. Rabin, Inhibition of yeast alcohol dehydrogenase by alkylating agents. Eur. J. Biochem. 5, 147-150 (1968).
28. J. P. Baker and B. R. Rabin, Effects of bromopyruvate on the control and catalytic properties of glutamate dehydrogenase. Eur. J. Biochem. 11, 154-159 (1969).
29. G. Chang and R. Y. Hsu, The substrate analog bromopyruvate as a substrate, an inhibitor and an alkylating agent of malic enzyme of pigeon liver. Biochim. Biophys. Res. Commun. 55, 580-587 (1973).
30. G. Tunnicliff and T. T. Ngo, Mechanism of inactivation of brain glutamic decarboxylase by 3-bromopyruvate. Int. J. Biochem. 9, 249-252 (1978).
31. 3H]N-phenylmaleimide. Biochem. J. 196, 471-479 (1981).
32. M. L. Fonda, Bromopyruvate inactivation of glutamate apodecarboxylase. Kinetics and specificity. J. Biol. Chem. 251, 229-235 (1976).
33. M. L. Fonda and R. F. DeGrella, Inactivation of glutamate decarboxylase by bromopyruvate. Biochim. Biophys. Res. Commun. 56, 451-458 (1974).
34. M. A. Apfel, B. H. Ikeda, D. C. Speckhard and P. A. Frey, Escherichia coli pyruvate dehydrogenase complex. Thiamin pyrophosphate-dependent inactivation by 3-bromopyruvate. J. Biol. Chem. 259, 2905-2909 (1984).
35. P. N. Lowe and R. N. Perham, Bromopyruvate as an activesite-directed inhibitor of the pyruvate dehydrogenase multienzyme complex from Escherichia coli. Biochemistry 23, 91-97 (1984).