Formation of N-alkylprotoporphyrin IX from metabolism of diallyl sulfone in lung and liver

Drug Metabolism and Disposition

Volumn 34, Issue 6, 2006, Pages 895-900

  Black, Gordon P ^a   Collins, Kathy S ^a   Blacquiere, Dylan P ^a   Forkert, Poh Gek ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DIALLYL SULFONE; N ALKYLPROTOPORPHYRIN 9; RECOMBINANT CYTOCHROME P450 2E1; RECOMBINANT ENZYME; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; FEMALE; FLUOROMETRY; HUMAN; HUMAN CELL; HUMAN TISSUE; LIVER METABOLISM; LIVER MICROSOME; LUNG ALVEOLUS CELL; LUNG EMBOLISM; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; SPECTROPHOTOMETRY;

ALKYLATION; ALLYL COMPOUNDS; ANIMALS; CYTOCHROME P-450 CYP2E1; FEMALE; HUMANS; KINETICS; LIVER; LUNG; MALE; MICE; MICROSOMES, LIVER; PROTOPORPHYRINS; RECOMBINANT PROTEINS; SEX FACTORS; SULFONES;

ALLIUM SATIVUM; ANIMALIA; MURINAE;

EID: 33646821349     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.106.009928     Document Type: Article

References (22)

1. Block E (1985) The chemistry of garlic and onion. Sci Am 252:114-119.
2. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254.
3. Brady JF, Li DC, Ishizaki H, Fukuto JM, Lin MC, Fadel A, Gapac JM, and Yang CS (1991a) Inhibition of cytochrome P-450 2E1 by diallyl sulfide and its metabolites. Chem Res Toxicol 4:642-647.
4. Brady JF, Wang M-H, Hong J-Y, Xiao F, Li Y, Yoo J-SH, Ning SM, Lee M-J, Fukuto JM, Gapac JM, et al. (1991b) Modulation of rat hepatic microsomal monooxygenase enzymes and cytotoxicity by diallyl sulfide. Toxicol Appl Pharmacol 108:342-354.
5. De Matteis F, Gibbs AH, Cantoni L, and Francis J (1980) Substrate-dependent irreversible inactivation of cytochrome P-450: conversion of its haem moiety into modified porphyrins. Ciba Found Symp 76:119-139.
6. Forkert PG (1995) CYP2E1 is preferentially expressed in Clara cells of mouse lung: localization by in situ hybridization and immunohistochemical methods. Am J Respir Cell Mol Biol 12:589-596.
7. Forkert PG, Dowsley TF, Lee RP, Hong J-Y, and Ulreich JB (1996a) Differential formation of 1,1-dichloroethylene-metabolites in the lungs of adult and weanling male and female mice: correlation with severities of bronchiolar cytotoxicity. J Pharmacol Exp Ther 279:1484-1490.
8. Forkert PG, Lee RP, Dowsley TF, Hong J-F, and Ulreich JB (1996b) Protection from 1,1-dichloroethylene-induced Clara cell injury by diallyl sulfone, a derivative of garlic. J Pharmacol Exp Ther 277:1665-1671.
9. Forkert PG, Lee RP, and Reid K (2001) Involvement of CYP2E1 and carboxylesterase enzymes in vinyl carbamate metabolism in human lung microsomes. Drug Metab Dispos 29:258-263.
10. Forkert PG, Premdas PD, and Bowers RJ (2000) Epoxide formation from diallyl sulfone is associated with CYP2E1 inactivation in murine and human lungs. Am J Respir Cell Mol Biol 23:687-695.
11. Halpert JR, Guengerich FP, Bend JR, and Correia MA (1994) Selective inhibitors of cytochromes P450. Toxicol Appl Pharmacol 125:163-175.
12. Hayes MA, Rushmore TH, and Goldberg MT (1987) Inhibition of hepatic carcinogenic responses to 1,2-dimethylhydrazine by diallyl sulfide, a component of garlic oil. Carcinogenesis (Lond) 8:1155-1157.
13. Jin L and Baillie TA (1997) Metabolism of the chemoprotective agent diallyl sulfide to glutathione conjugates in rats. Chem Res Toxicol 10:318-327.
14. Kimmett SM and Marks GS (1992) Thin-layer chromatographic separation of the ferrochelatase-inhibitory ring A and ring B regioisomers of N-ethylprotoporphyrin from a mixture of the four regioisomers. J Pharmacol Toxicol Methods 28:113-117.
15. Lavigne JA, Nakatsu K, and Marks GS (2002) Identification of human hepatic cytochrome P450 sources of N-alkylprotoporphyrin IX after interaction with porphyrinogenic xenobiotics, implications for detection of xenobiotic-induced porphyria in humans. Drug Metab Dispos 30:788-794.
16. Ortiz de Montellano PR and Correia MA (1983) Suicidal destruction of cytochrome P-450 during oxidative drug metabolism. Annu Rev Pharmacol Toxicol 23:481-503.
17. Ortiz de Montellano PR and Correia MA (1995) Inhibition of cytochrome P450 enzymes, in Cytochrome P450: Structure, Mechanism and Biochemistry (Ortiz de Montellano PR ed) pp 305-364, Plenum Press, New York.
18. Ortiz de Montellano PR and Mico BA (1981) Destruction of cytochrome P-450 by allylisopropylacetamide is a suicidal process. Arch Biochem Biophys 206:43-50.
19. Premdas PD, Bowers RJ, and Forkert PG (2000) Inactivation of hepatic CYP2E1 by an epoxide of diallyl sulfone. J Pharmacol Exp Ther 293:1112-1120.
20. Sparnins VL, Barany G, and Wattenberg LW (1988) Effects of organosulfur compounds from garlic and onions on benzo[a]pyrene-induced neoplasia and glutathione S-transferase activity in the mouse. Carcinogenesis 9:131-134.
21. Wong SG, Kobus SM, McNamee JP, and Marks GS (1998) Gender differences in N-alkylprotoporphyrin IX production in rats after the administration of porphyrinogenic xenobiotics. Drug Metab Dis 26:739-744.
22. Wong SG and Marks GS (1999) Formation of N-alkylprotoporphyrin IX after interaction of porphyrinogenic xenobiotics with rat liver microsomes. J Pharmacol 42:107-113.