5-Hydroxy-4-oxo-L-norvaline Depletes Intracellular Glutathione: A New Modulator of Drug Resistance

Bioscience, Biotechnology and Biochemistry

Volumn 63, Issue 11, 1999, Pages 1953-1958

  Tagashira, Motoyuki ^a   Nozato, Naoko ^a   Isonishi, Seiji ^b   Okamoto, Aikou ^b   Ochiai, Kazunori ^b   Ohtake, Yasuyuki ^a  

^a ASAHI BREWERIES LTD   (Japan)

^b JIKEI UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

5 hydroxy 4 oxo L norvaline; Buthionine sulfoximine; Cisplatin; Drug resistance; Glutathione

Indexed keywords

2 AMINO 5 HYDROXY 4 OXOVALERIC ACID; 2-AMINO-5-HYDROXY-4-OXOPENTANOIC ACID; AMINOLEVULINIC ACID; BUTHIONINE SULFOXIMINE; DRUG DERIVATIVE; GLUTAMATE CYSTEINE LIGASE; GLUTATHIONE; GLUTATHIONE SYNTHASE;

ARTICLE; CELL CULTURE; CHEMISTRY; DRUG EFFECT; FEMALE; HUMAN; ISOLATION AND PURIFICATION; METABOLISM; MICROBIOLOGY; MULTIDRUG RESISTANCE; OVARY TUMOR; SACCHAROMYCES CEREVISIAE; STREPTOMYCES;

AMINOLEVULINIC ACID; BUTHIONINE SULFOXIMINE; DRUG RESISTANCE, MULTIPLE; FEMALE; GLUTAMATE-CYSTEINE LIGASE; GLUTATHIONE; GLUTATHIONE SYNTHASE; HUMANS; OVARIAN NEOPLASMS; SACCHAROMYCES CEREVISIAE; SOIL MICROBIOLOGY; STREPTOMYCES; TUMOR CELLS, CULTURED;

EID: 0033219407     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.63.1953     Document Type: Article

References (28)

1. Redwood, W. R. and Colvin, M., Transport of melphalan by sensitive and resistant L1210 cells. Cancer Res., 40, 1144-1149 (1980).
2. Wang, A. L. and Tew, K. D., Increased glutathione 5-transferase activity in a cell line with acquired resistance to nitrogen mustards. Cancer Treat. Rep., 69, 677-682 (1985).
3. 6-alkylguanine-DNA alkyltran-sferase: regulation and importance in response to alkylating carcinogenic and therapeutic agents. Cancer Res., 50, 6119-6129 (1990).
4. Godwin, A. K., Meister, A., O’Dwyer, P. J., Huang, C. S., Hamilton, T. C., and Anderson, A. E., High resistance to cispla-tin in human ovarian cancer cell lines is associated with marked increase of glutathione synthesis. Proc. Natl. Acad. Sci. USA., 89, 3070-3074 (1992).
5. Goto, S., Yoshida, K., Morikawa, T., Urata, Y., Suzuki, K., and Kondo T., Augmentation of transport for cisplatin-glutathione adduct in cisplatin-resistant cancer cells. Cancer Res., 55, 4297-4301 (1995).
6. Berhane, K., Widersten, M., Engstrom, A., Kozarich, J. W., and Mannervik, B., Detoxication of base propenals and other a,β-unsaturated aldehyde products of radical reactions and lipid peroxidation by human glutathione transrases. Proc. Natl. Acad. Sci. USA, 91, 1480-1484 (1994).
7. Sollod, C. C., Jenns, A. E., and Daub, M. E., Cell surface redox potential as a mechanism of defense against photosensitizers in fungi. Appl. Environ. Microbiol., 58, 444-449 (1992).
8. Perego, P., Weghe, J. V., Ow, D. W., and Howell, S. B., Role of determinans of cadmium sensitivity in the tolerance of Schizosaccharomycespombe to cisplatin. Molecul. Pharmacol., 51, 12-18 (1997).
9. Martinoia, E., Grill, E., Tommasini, R., Kreuz K., and Amrhein, N., ATP-dependent glutathione 5-conjugate ‘export’ pump in the vacuolar membrane of plants. Nature, 364, 247-249 (1993).
10. Ishikawa, T., Wright, C. D., and Ishizuka, H., GS-X pump is functionally overexpressed in cA-diamminedichloro-platinum(II)-resistant human leukemia HL-60 cells and down-regulated by cell differentiation. J. Biol. Chem., 269, 29085-29093 (1994).
11. Novogrodsky, A., Nehring, R. E. Jr., and Meister, A., Inhibition of amino acid transport into lymphoid cells by the glutamine analog L-2-amino-4-oxo-5-chloropentanoate. Proc. Natl. Acad. Sci. USA, 76, 4932-4935 (1979).
12. Fortuniak, A., Zadzinski, R., Bilinski, T., and Bartosz, G., Glutathione depletion in the yeast Saccharomyces cerevisiae. Biochem. Molecul. Biol. Int., 38, 901-910 (1996).
13. Andrews, P. A., Murphy, M. P., and Howell, S. B., Differential potentiation of alkylating and platinating agent cytotoxicity in human ovarian carcinoma cells by glutathione depletion. Cancer Res., 45, 6250-6253 (1985).
14. Chen, Z-S., Mutoh, M., Sumizawa, T., Furukawa, T., Haraguchi, M., Tani, A., and Akiyama, S., Reversal of heavy metal resistance in multidrug-resistant human KB carcinoma cells. Biochem. Biophys. Res. Commn., 236, 586-590 (1997).
15. Wickner, R. B., Chromosomal and nonchromosomal mutations affecting the “killer character” of Saccharomyces cerevisiae. Genetics, 76, 423-432 (1974).
16. Ohtake, Y. and Okumura, Y., Establishing a high glutathione producing yeast species. Bioscience to Industry (in Japanese), 50, 29-34 (1992).
17. Disaia, P. J., Sinkovics, J. G., Rutledge, F. N., and Smith, J. P., Cell-mediated immunity to human malignant cells. Am. J. Obstet. Gynecol. 114, 979-989 (1972).
18. Isonishi, S., Ochiai, K., Yasuda, M., Ohkawa, K., and Terashima, Y., Mehcanism-related circumvention of cisplatin resistance in human ovarian carcinoma cells by (-)-(R)-2-aminomethylpyrrolidine(l, 1 -cyclobutanedicarboxylato)-plati-num(II) monohydrate and modulation of its sensitivity by 12-0-tetradecanoylphorbol-13-acetate. Int. J. Oncol., 5, 1309-1314 (1994).
19. Kistler, M., Summer, K. H., and Eckardt, F., Isolation of glutathione-deficient mutants of the yeast Saccharomyces cerevisiae. Mutant. Res., 173, 117-120 (1986).
20. Ohtake, Y., Satou, A., and Yabuuchi, Y., Isolation and Characterization of Glutathione Biosynthesis-dependent Mutans in Saccharomyces cerevisiae. Agric. Biol. Chem., 54, 3145-3150 (1990).
21. Riche, J. P. Jr. and Lang, C. A., The determination of glutathione, cysteine, and other thiols and disulfides in biological samples using high-performance liquid chromatography with dual electrochemical detection. Anal. Biochem., 163, 9-15 (1987).
22. Miyake, A., α-Hydroxy-y-oxo-L-norvaline, a new antitubercular antibiotic (2). synthetic studies. Chem. Pharm. Bull., 8, 1074-1079 (1960).
23. Schmidt, U., Stabler, F., and Lieberknecht, A., Stereoselective Synthesis of the Antibiotics (+)-Negamycin and (-)-HON (RI-331). Synthesis, 482-486 (1992).
24. Tatsuoka, S., Miyake, A., Hitomi, H., Ueyanagi, J., Iwasaki, H., and Yamaguchi, T., HON, a new antibiotic produced by StreptomycesAkiyoshiensis Nov. sp. J. Antibiot. Ser. A. 14, 39-43 (1961).
25. Yamaguchi, H., Uchida, K., Hiratani, T., Nagate, T., Watanabe, N., and Omura, S., RI-331, a new antifungal antibiotic. Ann. N. Y. Acad. Sci., 544, 188-190 (1988).
26. Yamaguchi, M., Yamaki, H., Shinoda, T., Tago, Y., Suzuki, H., Nishimura, T., and Yamaguchi, H., The mode of antifungal action of (S) 2-amino-4-oxo-5-hydroxypentanoic acid, RI-331. J. Antibiot. 43, 411-416 (1990).
27. Yamaki, H., Yamaguchi, M., Imamura, H., Suzuki, H., Nishimura, T., Saito, H., and Yamaguchi, H., The mechanism of antifungal action of (S)-2-amino-4-oxo-5-hydroxypentanoic acid, RI-331: the inhibition of homoserine dehydrogenase in Sac-charomyces cerevisiae. Biochem. Biophys. Res. Commun., 168, 837-843 (1990).
28. O’Dwyer, P. J., Hamilton, T. C., and Young, R. C., Delection of glutathione in normal and malignant human cells in vivo by buthionine sulfoximine: clinical and biochemical results. J. Natl. Cancer Inst., 84, 264-267 (1992).