Intracellular cysteine and glutathione delivery systems

Journal of the American College of Nutrition

Volumn 5, Issue 2, 1986, Pages 137-151

  Meister, Alton ^a   Anderson, Mary E ^a   Hwang, Onyou ^a  

^a WEILL CORNELL MEDICAL COLLEGE   (United States)

Author keywords

5 oxoprolinase; Acetaminophen; Glutathione ester; L 2 OxothiazoIidine 4 carboxylate; Radiation; Toxicity; Y glutamyl cysteinyl glycyl ethyl ester; Y glutamylcyst(e)ine

Indexed keywords

2 OXO 4 THIAZOLIDINECARBOXYLIC ACID; CYSTEINE; GAMMA GLUTAMYLCYSTEINE; GLUTAMIC ACID; GLUTATHIONE; GLUTATHIONE DERIVATIVE; PARACETAMOL; RADIOISOTOPE;

2 OXO 4 THIAZOLIDINECARBOXYLIC ACID S 35; CELL CULTURE; CELL PROTECTION; CYSTINYLBISGLYCINE; DRUG ACCUMULATION; DRUG DELIVERY SYSTEM; DRUG METABOLISM; GAMMA GLUTAMYLCYSTEINE DISULFIDE; GLUTAMYLCYSTEINE; GLUTATHIONE[GLYCINE ETHYL ESTER]; GLUTATHIONE[GLYCINE METHYL ESTER]; IN VITRO STUDY; NONHUMAN; RADIATION;

ACETAMINOPHEN; ANIMAL; BIOLOGICAL TRANSPORT, ACTIVE; CYSTEINE; DIPEPTIDES; GLUTATHIONE; INTRACELLULAR FLUID; KIDNEY; LIVER; MICE; MODELS, BIOLOGICAL; PYROGLUTAMATE HYDROLASE; SULFUR; THIAZOLES;

EID: 0022460516     PISSN: 07315724     EISSN: 15411087     Source Type: Journal    
DOI: 10.1080/07315724.1986.10720121     Document Type: Article

References (55)

1. Larsson A, Orrenius S, Holmgren A, Man-nervik B (eds): “Functions of Glutathione— Biochemical, Physiological and Toxicological Aspects.” (Fifth Karolinska Institute Nobel Conference, Skokloster, Sweden May 23-27, 1982) New York: Raven Press, 1983.
2. Meister A, Anderson ME: Glutathione. Ann Rev Biochem 52:711-760, 1983.
3. Meister A: “Glutathione synthesis. The Enzymes (3rd ed). Voi. 10.” New York: Academic Press, 1974, pp 671-697.
4. Richman P, Meister A: Regulation of 7-glutamyl-cysteine synthetase by nonallosteric feedback inhibition by glutathione. J Biol Chem 250:1422-1426, 1975.
5. Meister A: 5-Oxoprolinuria (pyroglutamic aciduria) and other disorders of the 7-gluta-myl cycle. In “Metabolic Basis of Inherited Diseases.” New York: McGraw Hill, 1983, Stanbury JB, et al (eds): pp 348-359.
6. Wellner VP, Sekura R, Meister A, Larsson A: Glutathione synthetase deficiency, an inborn error of metabolism involving the 7-glutamyl cycle in patients with 5-oxoprolinu-ria (pyroglutamic aciduria). Proc Natl Acad Sci USA 71:2505-2509, 1974.
7. Meister A: Selective modification of glutathione metabolism. Science 220:471-477, 1983.
8. Griffith OW, Anderson ME, Meister A: Inhibition of glutathione biosynthesis by prothi-onine sulfoximine (S-n-propyl-homocysteine sulfoximine), a selective inhibitor of 7-gluta-mylcysteine synthetase. J Biol Chem 254:1205-1210, 1979.
9. Griffith OW, Meister A: Potent and specific inhibition of glutathione synthesis by buthio-nine sulfoximine (S-n-butyl homocysteine sulfoximine). J Biol Chem 254:7558-7560, 1979.
10. Meister A: New aspects of glutathione biochemistry and transport. Selective alteration of glutathione metabolism (William C. Rose Award Lecture) Nutr Rev 42:397-410, 1984.
11. Birnbaum SM, Winitz M, Greenstein JP: Quantitative nutritional studies with water-soluble, chemically defined diets. III. Individual amino acids as sources of “non-essential” nitrogen. Arch Biochem Biophys 72:428-436, 1957.
12. Olney JW, Ho OL, Rhee V: Cytotoxic effects of acidic and sulphur containing amino acids on the infant mouse central nervous system. Exp Brain Res 14:61-76, 1971.
13. Karlsen RL, Grofova I, Malthe-Sorenssen D, Fonnum F: Morphological changes in rat brain induced by L-cysteine injection in newborn animals. Brain Res 208:167-180, 1981.
14. Nishiuch Y, Sasaki M, Nakayasu M, Oikawa A: Cytotoxicity of cysteine in culture media. In Vitro 12:635-638, 1976.
15. Cooper AJL, Haber MT, Meister A: On the chemistry and biochemistry of 3-mercaptopy-ruvic acid, the a-keto acid analog of cysteine. J Biol Chem 257:816-826, 1982.
16. Williamson JM, Meister A: Stimulation of hepatic glutathione formation by administration of L-2-Oxothiazolidine-4-carboxylate, a 5-oxo-L-prolinase substrate. Proc Natl Acad Sci USA 78:936-939, 1981.
17. Van Der Werf P, Orlowski M, Meister A: Enzymatic conversion of 5-oxo-L-proline (L-pyrrolidone carboxylate) to L-glutamate, a reaction in the 7-glutamyl cycle. Proc Natl Acad Sci USA 68:2982-2985, 1971.
18. Van Der Werf P, Griffith OW, Meister A: 5-oxo-L-prolinase (L-pyroglutamate hydrolase). Purification and catalytic properties. J Biol Chem 250:6686-6692, 1975.
19. Williamson JM, Meister A: Effect of sulfhy-dryl group modification on the activities of 5-oxo-L-prolinase, J Biol Chem 257:9161-9169, 1982.
20. Seddon AP, Li L, Meister A: Resolution of 5-oxo-L-prolinase into 5-oxo-L-proline-depen-dent ATPase and a coupling protein. J Biol Chem 259:8091-8094, 1984.
21. Griffith OW, Meister A: Interaction of 5-oxo-L-prolinase with nucleotide triphosphates. Evidence suggesting substrate-dependent conformational change. J Biol Chem 257:43924397, 1982.
22. Williamson JM, Meister A: New substrates of 5-oxo-L-prolinase. J Biol Chem 257:12039-12042, 1982.
23. Williamson JM, Boettcher B, Meister A: An intracellular cysteine delivery system that protects against toxicity by promoting glutathione synthesis. Proc Natl Acad Sci USA 79:6246-6249, 1982.
24. Birnbaum SM, Levintow L, Kingsley RB, Greenstein JP: Specificity of amino acid acy-lases. J Biol Chem 194:455-470, 1952.
25. Mitchell JR, Jollow DJ, Potter WZ, Davis DC, Gillette JR, Brodie BB: Acetaminophen-induced hepatic necrosis. I. Role of drug metabolism. J. Pharmacol Exp Ther 187:185-194, 1973.
26. Jollow DJ, Mitchell JR, Potter WZ, Davis DC, Gillette JR, Brodie BB: Acetaminophen-induced hepatic necrosis. II. Role of covalent binding in vivo. J. Pharmacol Exp Ther 187:195-202, 1973.
27. Potter WZ, Davis DC, Mitchell JR, Jollow DJ, Gillette JR, Brodie BB: Acetaminophen-induced necrosis. III. Cytochrome P-450-me-diated covalent binding in vitro. J Pharmacol Exp Ther 187:203-210, 1973.
28. Mitchell JR, Jollow DJ, Potter WZ, Gillette JR, Brodie BB: Acetaminophen-induced hepatic necrosis. IV. Protective role of glutathione. J. Pharmacol Exp Ther 187:211-217, 1973.
29. Jones DP, Stead AH, Moldeus P, Orrenius S: Glutathione and glutathione conjugate metabolism in isolated liver and kidney cells. In Sies H, Wendel A (eds): “Functions of Glutathione in Liver and Kidney.” Berlin: Springer Verlag, 1978, pp 194-200.
30. Tietze F: Enzymic method for quantitative determination of nanogram amounts of total and oxidized glutathione: Applications to mammalian blood and other tissues. Anal Biochem 27:502-522, 1969.
31. Owens CWI, Belcher RV: A colorimetric micro-method for the determination of glutathione. Biochem J 94:705-711, 1965.
32. Griffith OW: Determination of glutathione and glutathione disulfide using glutathione reductase and 2-vinylpyridine. Anal Biochem 106:207-212, 1980.
33. Anderson ME, Meister A: Transport and direct utilization of 7-glutamylcyst(e)ine for glutathione synthesis. Proc Natl Acad Sci USA 80:707-711, 1983.
34. Newton GL, Dorian R, Fahey RC: Analysis of biological thiols: Derivatization with mono-bromobimane and separation by reverse-phase high performance liquid chromatography. Anal Biochem 114:383-387, 1981.
35. Boettcher B, Meister A: Synthesis of L-2-oxo-thiazolidine-4-carboxylic acid. Anal Biochem 138:449-450, 1984
36. Sturman JA: Methionine metabolism in developing neural tissue. In Cavallini D, Gaull GE, Zappia V (eds): “Natural Sulfur Compounds, Novel Biochemical and Structural Aspects.” New York, Plenum Press 1980, pp 107-119.
37. Burns RA, Milner JA: Sulfur amino acid requirements of immature beagle dogs. J Nutr 111:2117-2124, 1981.
38. Wellner, Meister A: A survey of inborn errors of amino acid metabolism and transport in man. Anni Rev Biochem 50:911-968, 1981.
39. Horowitz JH, Rypins EB, Henderson JM, Heymsfield SB, Moffitt SD, Bain RP, Chawla RK, Bleier JC, Rudman D: Evidence for impairment of transsulfuration pathway in cirrhosis. Gastroenterology 81:668-676, 1981.
40. Debey Ш, Mackenzie JB, Mackenzie CG: The replacement by thiazolidinecarboxylic acid of exogenous cystine and cysteine. J Nutr 66:607-619, 1958.
41. Meister A: “Biochemistry of Amino Acids, 2nd ed; Voi. 2.” New York: Academic Press, 1965, pp. 813-814.
42. Mackenzie CG, Harris J: N-Formylcysteine synthesis in mitochondria from formaldehyde and L-cysteine via thiazolidinecarboxylic acid. J Biol Chem 227:393-406, 1957.
43. Nagasawa HT, Goon DJW, Muldoon WP, Zera RT: 2-Substituted thiazolidine-4-(R)-carboxylic acids as prodrugs of L-cysteine. Protection of mice against acetaminophen hepatoxicity. J Med Chem 27:591-596, 1984.
44. Nagasawa HT, Goon DJW, Muldoon WP, Zera RT: Products of L-cysteine as liver-protective agents. 2(RS)-methylthiazolidine-4(R)-carboxylic acid, a latent cysteine. J Med Chem 25:489-491, 1982.
45. Griffith OW, Bridges RJ, Meister A: Transport of y-glutamyl amino acids; role of glutathione and y-glutamyl transpeptidase. Proc Natl Acad Sci USA 76:6319-6322, 1979.
46. Puri RN, Meister A: Transport of glutathione, as y-glutamylcysteinylglycyl ester, into liver and kidney. Proc Natl Acad Sci USA 80:52585260, 1983.
47. Wellner VP, Anderson ME, Puri RN, Jensen GL, Meister A: Radioprotection by glutathione esther. Transport of glutathione ester into human lymphoid cells and fibroblasts. Proc Natl Acad Sci USA 81:4732-4735, 1984.
48. Jensen GL, Meister A: Radioprotection of human lymphoid cells by exogenously-supplied glutathione is mediated by y-glutamyl transpeptidase. Proc Natl Acad Sci USA 80:47144717, 1983.
49. Griffith OW, Meister A: Translocation of intracellular glutathione to membrane-bound y-glutamyl transpeptidase as a discrete step in the y-glutamyl cycle. Glutathionuria after inhibition of transpeptidase. Proc Natl Acad Sci USA 76:268-272, 1979.
50. Lauterburg BH, Adams JD, Mitchel JR: Hepatic glutathione homeostasis in the rat: Efflux accounts for glutathione turnover. Hepatology 4:586-590, 1984.
51. Womack M, Kemmerer KS, Rose WC: The relation of cystine and methionine to growth. J Biol Chem 121:403-410, 1937.
52. Womack M, Rose WC: The partial replacement of dietary methionine by cystine for purposes of growth. J Biol Chem 141:375-379, 1941.
53. Anderson ME, Bridges RJ, Meister A: Direct evidence for inter-organ transport of glutathione and that the non-filtration renal mechanism for glutathione utilization involves y-glutamyl transpeptidase. Biochem Biophys Res Commun 96:848-853, 1980.
54. Griffith OW, Meister A: Glutathione: Interorgan translocation, turnover and metabolism. Proc Natl Acad Sci USA 76:5606-5610, 1979.
55. Abbott WA, Bridges RJ, Meister A: Extracellular metabolism of glutathione accounts for its disappearance from the basolateral circulation of the kidney. J Biol Chem 259:1539315,400, 1984.