Formation, Intracellular distribution and efflux of glutathione-bimane conjugates in drug-sensitive and -resistant MCF-7 cells

Cancer Chemotherapy and Pharmacology

Volumn 40, Issue 2, 1997, Pages 101-111

  Millis, Kevin K ^a   Lesko, Stephen A ^b   Gamcsik, Michael P ^a,c  

^a JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b JOHNS HOPKINS BLOOMBERG SCHOOL OF PUBLIC HEALTH   (United States)

^c DUKE UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

Confocal; Epifluorescence; Glutathione S transferase; Microscopy; Monochlorobimane

Indexed keywords

4 HYDROPEROXYCYCLOPHOSPHAMIDE; BROMOBIMANE; BUTHIONINE SULFOXIMINE; DOXORUBICIN; GLUTATHIONE;

ANTIBIOTIC RESISTANCE; ARTICLE; CELL CULTURE; CELL LINE; CELL STRAIN MCF 7; CELLULAR DISTRIBUTION; CONFOCAL MICROSCOPY; CONTROLLED STUDY; DRUG CONJUGATION; DRUG METABOLISM; FLUORESCENCE MICROSCOPY; GLUTATHIONE METABOLISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IN VITRO STUDY; INTERMETHOD COMPARISON; PRIORITY JOURNAL; TECHNIQUE;

ADENOCARCINOMA; ANTIBIOTICS, ANTINEOPLASTIC; ANTINEOPLASTIC AGENTS; BICYCLO COMPOUNDS; BREAST NEOPLASMS; CYCLOPHOSPHAMIDE; DOXORUBICIN; DRUG RESISTANCE, NEOPLASM; FLUORESCENT DYES; GLUTATHIONE; HUMANS; MICROSCOPY, CONFOCAL; MICROSCOPY, FLUORESCENCE; PYRAZOLES; TUMOR CELLS, CULTURED;

EID: 0031007917     PISSN: 03445704     EISSN: None     Source Type: Journal    
DOI: 10.1007/s002800050633     Document Type: Article

References (57)

1. Agard DA, Hiraoka Y, Shaw P, Sedat JW (1989) Fluorescence microscopy in three dimensions. Methods Cell Biol 30: 353
2. Akerboom TPM. Sies H (1981) Assay of glutathione, glutathione disulfide, and glutathione-mixed disulfides in biological samples. Methods Enzymol 77: 373
3. Asghar K, Reddy BG, Krishna G (1975) Histochemical localization of elutathione in tissues. J Histochem Cytochem 23: 774
4. Barhoumi R, Bailey R, Burghardt RC (1995) Kinetic analysis of glutathione in anchored cell with monochlorobimane. Cytometry 19: 226
5. Batist G, Tulpule A, Sinha BK, Katki AG, Myers CE, Cowan KH (1986) Overexpression of a novel anionic glutathione transferase in multidrug-resistant human breast cancer cells. J Biol Chem 261: 15544
6. Batist G, Schecter R, Woo A, Greene D, Lehnert S (1991) Glutathione depletion in human and rat multi-drug resistant breast cancer cell lines. Biochem Pharmacol 41: 631
7. Bellomo G, Vairetti M, Stivala L, Mirabelli F, Richelmi P, Orrenius S (1992) Demonstration of nuclear compartmentalization of glutathione in hepatocytes. Proc Natl Acad Sci USA 89: 4412
8. Britten RA, Green JA, Broughton C, Browning PGW, White R, Warenius HM (1991) The relationship between nuclear glutathione levels and resistance to melphalan in human ovarian tumour cells. Biochem Pharmacol 41: 647
9. Briviba K, Fraser G, Sies H, Ketterer B (1993) Distribution of the monochlorobimane-glutathione conjugate between nucleus and cytosol in isolated hepatocytes. Biochem J 294: 631
10. Burghardt RC, Barhomi R, Lewis EH, Bailey RH, Pyle KA, Clement BA, Phillips TD (1992) Patulin-induced toxicity: a vital fluorescence study. Toxicol Appl Pharmacol 112: 235
11. Chen G, Waxman DJ (1994) Role of cellular glutathione and glutathione S-transferase in the expression of alkylating agent cytotoxicity in human breast cancer cells. Biochem Pharmacol 47: 1079
12. Cook JA, Iype SN, Mitchell JB (1991) Differential specificity of monochlorobimane for isozymes of human and rodent glutathione S-transferases. Cancer Res 51: 1606
13. Cook JA, Pass HI, Iype SN, Friedman N, DeGraff W, Russo A, Mitchell JB (1991) Cellular glutathione and thiol measurements from surgically resected human lung tumor and normal lung tissue. Cancer Res 51: 4287
14. Cowan KH, Batist G, Tulpule A, Sinha BK, Myers CE (1986) Similar biochemical changes associated with multidrug resistance in human breast cancer cells and carcinogen-induced resistance to xenobioties in rats. Proc Natl Acad Sci USA 83: 9328
15. Edgren MR (1987) Nuclear glutathione and oxygen enhancement of radiosensitivity. Int J Radiat Biol 51: 3
16. Edgren M, Révész L (1987) Compartmentalised depletion of glutathione in cells treated with buthionine sulphoximine. Br J Radiol 60: 723
17. Frei E III, Teicher B, Cucchi C, Rosowsky A, Flatow J, Kelley M, Genereux P (1988) Resistance to alkylating agents: Basic studies and therapeutic implications. In: Wooley III P. Tew K (eds) Mechanisms of drug resistance in neoplastic cells. Academic Press, New York, p 69
18. Gamcsik MP, Millis KK (1995) Measuring the rate of glutathione synthesis and degradation in drug-resistant MCF-7 cells. Proceedings of the 86th Annual Meeting of the American Association of Cancer Research, Toronto, Cadmus, Linthicum, MD. p 316
19. Gamcsik MP, Millis KK, Colvin OM (1995) Noninvasive detection of elevated glutathione levels in MCF-7 cells resistant to 4-hydroperoxycyclophosphamide. Cancer Res 55: 2012
20. Gottesmun MM, Paslan I (1993) Biochemistry of multidrug resistance mediated by the multidrug transporter. Annu Rev Biochem 62: 385
21. Griffith OW, Meister A (1979) Potent and specific inhibition of glutathione synthesis by buthionine sulfoximine (S-n-butyl homocysteine sulfoximine). J Biol Chem 254: 7558
22. Hedley DW, Chow S (1994) Evaluation of methods for measuring cellular glutathione content using flow cytometry. Cytometry 15: 349
23. Jedlilschky G, Leier I, Buchholz U, Center M, Keppler D (1994) ATP-dependent transport of glutathione S-conjugates by the multidrug resistance-associated protein. Cancer Res 54: 4833
24. Jevtovic-Todorovic V, Guenthner TM (1992) Depletion of a discrete nuclear glutathione pool by oxidative stress, but not by buthionine sulfoximine. Biochem Pharmacol 44: 1383
25. Jocelyn PC (1975) Some properties of mitochondrial glutathione. Biochin Biophys Acta 396: 427
26. Kosower NS, Kosower EM (1987) Thiol labeling with bromohimunes. Methods Enzymol 143: 76
27. Kosower NS, Kosower EM, Newton GL, Ranny HM (1979) Bimane fluorescent labels: labeling of normal human red cells under physiological conditions. Proc Natl Acad Sci USA 76: 3382
28. Kosower EM, Pazhenshevsky B, Dodiuk H, Kanety H, Faust D (1981) Bimanes. 6. Reactive halogen derivatives of synand anti-1,5-diazabieyclo[3.3.0]octadienedione(9.10-dioxabimanes). J Org Chem 46: 1666
29. Kramer RA, Zakher J, Kim G (1988) Role of the glutathione redox cycle in acquired and de novo multidrug resistance. Science 241: 694
30. Lange JHM de, Schipper NW, Schuurhuis GJ, Kate TK ten, Heuningen THM van, Pinedo HM, Lankelma J, Baak JPA (1992) Quantification by laser-scan microscopy of intracellular doxorubicin distribution. Cytometry 13: 571
31. Larrauri A, Lopez P, Gomez-Lechon M-J, Castell JV (1987) A cytochemical stain for glutathione in rat hepatocytes cultured on plastic. J Histochem Cytochem 35: 271
32. Lewis AD, Forrester LM, Haves JD, Wareing CJ, Carmichael J. Harris AL, Mooghen M, Wolf CR (1989) Glutathione S-transferase isoenzymes in human tumours and tumour derived cell lines. Br J Cancer 60: 327
33. Meister A (1991) Glutathione deficiency produced by inhibition of its synthesis, and its reversal: applications in research and therapy. Pharmacol Ther 51: 155
34. Meister A (1994) Glutathione, ascorbate, and cellular protection. Cancer Res [Suppl] 54: 1969s
35. Meredith MJ, Reed DJ (1982) Status of the mitochondrial pool of glutathione in the isolated hepatocyte. J Biol Chem 257: 3747
36. Mitchell JB, Russo A (1987) The role of glutathione in radiation and drug induced cytotoxicity. Br J Cancer 55: 96
37. Nair S, Singh SV, Krishan A (1991) Flow cytometric monitoring of glutathione content and anthracycline retention in tumor cells. Cytometry 12: 336
38. Newton GL, Dorian R, Fahey RC (1981) Analysis of biological thiols: Derivatization with monobromobimane and separation by reverse-phase high performance liquid chromatography. Anal Biochem 114: 383
39. O'Connor JE, Kimler BF, Morgan MC, Terysas KHJ (1988) A flow cytometric assay for intracellular nonprotein thiols using mercury orange. Cytometry 9: 529
40. O'Dwyer PJ, Hamilton TC, Yao KS, Tew KD, Ozols RF (1995) Modulation of glutathione and related enzymes in reversal of resistance to anticancer drugs. Hematol Oncol Clin N Am 9: 383
41. Orwar O, Fishman HA, Ziv N, Scheller RH, Zare RN (1995) Use of 2,3-naphthalenedicarboxaldehyde derivatization for single-cell analysis of glutathione by capillary electorphoresis and histochemical localization by fluorescence microscopy. Anal Chem 67: 4261
42. Ozols RF (1985) Pharmacologic reversal of drug resistance in ovarian cancer. Semin Oncol XII: 7
43. Ozols RF, Louie KG, Plowman J, Behrens BC, Fine RL, Dykes, K, Hamilton TC (1987) Enhanced melphalan cytotoxicity in human ovarian cancer in vitro and in tumour-bearing nude mice by buthionine sulfoximine depletion of glutathione . Biochem Pharmacol 36: 147
44. Ozols RF, O'Dwyer PJ. Hamilton TC, Young RC (1990) The role of glutathione in drug resistance. Cancer Treat Rev 17: 45
45. Poot M, Kavanagh TJ, Kang HC, Haugland RP, Rabinovitch PS (1991) Flow cytometric analysis of cell cycle-dependent changes in cell thiol level by combining a new laser dye with Hoeschst 33342. Cytometry 12: 184
46. Rice GC, Bump EA, Shrieve DL, Lee W, Kovacs M (1986) Quantitative analysis of cellular glutathione by flow cytometryutilizing monochlorobimane: some applications to radiation and drug resistance in vitro and in vivo. Cancer Res 46: 6105
47. Ross D (1988) Glutathione, free radicals and chemotherapeutic agents. Pharmacol Ther 37: 231
48. Russo A, Carmichael J, Friedman N, DeGraff W, Tochner A, Glatstein E, Mitchell JB (1986) The role of intracellular glutathione in antineoplastic chemotherapy. Int J Radiat Oncol Biol Phys 12: 1347
49. Schneider E, Horton JK, Yang C-H, Nakagawa M, Cowan KH (1994) Multidrug resistance-associated protein gene overexpression and reduced drug sensitivity of topoisomerase II in a human breast carcinoma MCF7 cell line selected for etoposide resistance. Cancer Res 54: 152
50. Schneider E, Yamazaki H, Sinha BK, Cowan KH (1995) Buthionine sulphoximine-mediated sensitisation of etoposide-resistant human breast cancer MCF7 cells overexpressing the multidrug resistance-associated protein involves increased drug accumulation. Br J Cancer 71: 738
51. Thomas M, NickleeT, Hedley DW (1995) Differential effects of depleting agents on cytoplasmic and nuclear non-protein sulphydryls: a fluorescence image cytometry study. Br J Cancer 72: 45
52. Tietze F (1969) Enzymic method for quantitative determination of nanogram amounts of total and oxidized glutathione: Applications to mammalian blood and other tissues. Anal Biochem 27: 502
53. Tirmenstein MA, Reed DJ (1988) The glutathione status of rat kidney nuclei following administration of buthionine sulfoximine. Biochem Biophys Res Commun 155: 956
54. Treuman J, Valet G (1986) Flow-cytometric determination of glutathione alterations in vital cells by o-phthaldialdehyde. Staining Exp Cell Res 163: 518
55. Ublacker GA, Johnson JA, Siegel FL, Mulcahy RT (1991) Influence of glutathione S-transferases on cellular glutathione determination by flow cytometry using monochlorobimane. Cancer Res 51: 1783
56. Ven AJAM van der, Mier P, Peters WHM, Dolstra H, Erp PEJ van, Koopmans PP, Meer JWM van der (1994) Monochlorobimane does not selectively label glutathione in peripheral blood mononuclear cells. Anal Biochem 217: 41
57. Young PR, Connors White AL, Dzido GA (1994) Kinetic analysis of the intracellular conjugation of monochlorobimane by IC-21 murine macrophage glutathione -S-transferase. Biochim Biophys Acta 1201: 461