Reversal of resistance against doxorubicin by a newly developed compound, oxalyl bis(N-phenyl)hydroxamic acid in vitro

Anti-Cancer Drugs

Volumn 9, Issue 9, 1998, Pages 825-832

  Choudhuri, S K ^a   Chatterjee, Amitava ^a  

^a CHITTARANJAN NATIONAL CANCER INSTITUTE   (India)

Author keywords

Ehrlich ascites carcinoma; Glutathione S transferase; Multidrug resistance (MDR); Oxalyl bis(N phenyl)hydroxamic acid; Reduced glutathione; Resistance modifying agent

Indexed keywords

ANTINEOPLASTIC AGENT; CISPLATIN; DOXORUBICIN; GLUTATHIONE; GLUTATHIONE TRANSFERASE; HYDROXAMIC ACID DERIVATIVE; OXALYL BIS(N PHENYL)HYDROXAMIC ACID; SUCCINYL BIS(N PHENYL)HYDROXAMIC ACID; UNCLASSIFIED DRUG; VINBLASTINE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; CROSS RESISTANCE; DRUG RESISTANCE; EHRLICH ASCITES TUMOR CELL; IMMUNOBLOTTING; IMMUNOFLUORESCENCE; MALE; MOUSE; MULTIDRUG RESISTANCE; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; ANTINEOPLASTIC AGENTS; BENZENEACETAMIDES; CALCIUM CHANNEL BLOCKERS; CARCINOMA, EHRLICH TUMOR; DOXORUBICIN; DRUG INTERACTIONS; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; GLUTATHIONE; GLUTATHIONE TRANSFERASE; HELA CELLS; HUMANS; HYDROXAMIC ACIDS; MALE; MICE; OXALATES; P-GLYCOPROTEIN; VERAPAMIL;

EID: 0031788426     PISSN: 09594973     EISSN: None     Source Type: Journal    
DOI: 10.1097/00001813-199810000-00013     Document Type: Article

References (49)

1. Crown KH, Batist G, Tulpul A, Sinha BK, Myers CE. Similar biochemical changes associated with multidrug resistance in human breast cancer cells and carcinogen-induced resistance to xenobiotics in rats. Proc Natl Acad Sci USA 1986; 83: 9328-32.
2. Tew KD. Glutathione associated enzyme in anticancer drug resistance. Cancer Res 1994; 54: 4313-20.
3. Dano K. Active outward transport of daunomycin in resistant Ehrlich ascites tumor cells. Biochem Biophys Acta 1973; 323: 466-83.
4. Incaba M, Jhonson RK. Uptake and retention of adriamycin and daunorubicin by sensitive and anthracycline-resistant sublines of P 388 leukemia. Biochem Pharmacol 1978; 27: 2123-30.
5. Fojo A, Akiama S, Gottesman MM, Patsan I. Reduced drug accumulation in multiple drug-resistant human KB carcinoma cell lines. Cancer Res 1985; 45: 3002-7.
6. Tsuoro T, Satio HI, Kawabata H, Oh-hara T, Hamada H, Utakoji T. Characteristics of resistance to adriamycin in human myelogenous leukemia K562 resistant to adriamycin and in isolated clones. Jpn J Cancer Res 1986; 77: 682-92.
7. Shen DW, Cardarelli C, Hawang J, et al. Multiple drug-resistant human KB carcinoma cells independently selected for high level resistance to colchicine, adriamycin or vinblastine show changes in expression of specific proteins. J Biol Chem 1986; 261: 7762-70.
8. Cornwell MM, Safa AR, Felsted RL, Gottesman MM, Pastan I. Membrane vesicles from multidrug resistant cancer cells contain a 150 to 170 kDa protein detected by photoaffinity labeling. Proc Natl Acad Sci USA 1986; 83: 3847-50.
9. Safa AR, Glover CJ, Mayers MB, Biedler JL, Felsted RL. Vinblastine photoaffinity labeling of a high molecular weight surface membrane glycoprotein specific for multidrug-resistant cells. J Biol Chem 1986; 261: 6137-40.
10. Edincott JA, Ling V. The biochemistry of P-glycoprotein mediated multidrug resistance. Annu Rev Biochem 1989; 58: 137-71.
11. Gottesman MM, Pastan I. Biochemistry of multidrug resistance mediated by the multidrug transporter. Annu Rev Biochem 1993; 62: 385-427.
12. Ford JM, Hait WN. Pharmacology of drugs that alter multidrug resistance in cancer. Pharmacol Rev 1990; 42: 155-98.
13. Suzukake K, Petro BJ, Vistica DT. Reduction in glutathione content of L-PAM resistant L1210 cells confers drug sensitivity. Biochem Pharmacol 1982; 31: 121-4.
14. Suzuka K, Vistica BP, Vistica DT. Dechlorination of L-phenylalanine mustard by sensitive and resistant tumor cells and its relationship to intracellular glutathione content. Biochem Pharmacol 1983; 32: 165-7.
15. Prezioso JA, Fitzgerald GB, Wick MM. Melanoma cytotoxicity of buthionine sulphoxamine (BSO) alone and in combination with 3,4,-dihydroxybenzylamine and melphalan. J Invest Dermatol 1992; 99: 289-93
16. La Creta FP, Brennam JM, Hamilton TC, Ozols RF, O'Dwyer PJ. Streoselective pharmacokinetics of L-buthionine SR-sulphoxamine in patients with cancer. Drug Metab Disp 1994; 22: 835-42.
17. Ciaccio PJ, Tew KD, La Creta FP. The spontaneous and glutathione S-transferase mediated reaction of chlorambucil with glutathione. Cancer Commun 1990; 2: 279-86.
18. Ahamad H, Singhal SS, Awasthi S. The inhibition of the α, μ and π class isozymes of glutathione S-transferases by sulphasalazine, 5-aminosalicylic acid and sulphapyridine. Biochem Arch 1992; 8: 355-61.
19. Pillante SL, Lisek CA, Dulik DM, Fenselau C. Glutathione conjugate. Immobilized enzyme synthesis and characterisation by fast atom bombardment mass spectroscopy. Drug Metab Disp 1986; 14: 313-8.
20. Ploemen JHTM, Van Ommen B, Van Bladeren PJ. Inhibition of rat and human glutathione S-transferase isoenzymes by ethacrynic acid and its glutathione conjugate. Biochem Pharmacol 1990; 40: 1631-5.
21. Philips MF, Mantle TJ. The initial rate-kinetics of mouse glutathione S-transferase YfYYf. Evidence for an allosteric site for ethacrynic acid. Biocbem J 1991; 275: 703-9.
22. Tsuoro T, Iada H, Tsukagoshi S, Sakurai Y. Overcoming of vincristine resistance in P388 leukemia in vivo and in vitro through enhanced cytotoxicity of vincristine and vinblastine by verapamil. Cancer Res 1981; 41: 1967-72.
23. Kartner N, Shales M, Riordan JR, Ling V. Daunorubicin resistant Chinese hamster ovary cells expressing multidrug resistance and cell surface P-glycoprotein. Cancer Res 1983; 43: 4413-9.
24. Ling V, Kartner N, Sudo T, Siminovitch L, Riordan JR. Multidrug resistance phenotype in Chinese hamster ovary cells. Cancer Treat Rep 1983; 67: 869-74.
25. O'Dwyer PJ, La Creta F, Nash S, et al. Phase 1 study of thio TEPA in combination with glutathione transferase inhibitor ethacrynic acid. Cancer Res 1991; 51: 6059-65.
26. Choudhuri SK, Roy PS, Ghose AK. Oxalyl-bis(N-phenyl/N-p-tolyl) hydroxamic acids as coordinating ligands: coordination compounds with organotins. Indian J Chem 1984; 23: 917-9.
27. Ghose NN, Sarkar DK. Succinyl bis(N-phenyl) hydroxamic acid. J Indian Chem Soc 1968; 45: 550-2.
28. Friche E, Danks MK, Beck WT. Characterization of tumor cell resistance to 4-deoxy-4-iododoxorubicin developed in Ehrlich ascites cells in vivo. Cancer Res 1992; 52: 5701-6.
29. Kueng W, Silber E, Eppenberger U. Quantification of cells cultured on 96 well plates. Anal Biocbem 1989; 182: 16-9.
30. Hu X, Yang H, Pan QR, Zhen S. Does p-glycoprotein play a pivotal role in the drug resistance of an MDR variant, K562/Dox? Chemotherapy 1995; 41: 296-305.
31. Lowry OH, Rosenberg NJ, Farr AL, Randal RJ. Protein measurement with folin phenol reagent. J Biol Chem 1951; 196: 265-71.
32. Laemmli, UK. Cleavage of structural proteins during the assembly of the head of bacteriofage T4. Nature 1970; 227: 680-5.
33. Towbin H, Stachelin T, Gorden J. Electrophoretic transfer of proteins form polyacrylamide gels to nitrocellulose sheets: procedure and some applications. Proc Natl Acad Sci USA 1979; 76: 4350-4.
34. Kartner N, Evernden-Porelle D, Bradley G, Ling V. Detection of P-glycoprotein in multidrug-resistant cell lines by monoclonal antibodies. Nature 1985; 316: 1985.
35. Chen CJ, Chin JE, Ueda K, et al. Internal duplication and homology with bacterial transport proteins in the mdr-1 (P-glycoprotein) gene from multidrug-resistant human cells. Cell 1986; 47: 381-9.
36. 6-alkylguanine-DNA alkyltransferase as potential indicators of constitutive drug resistance in human colorectal tumors. Cancer Res 1991; 51: 2092-7.
37. Freeman JW, Chatterjee A, Ross BE, Busch H. Epitope distribution and immunochemical characterisation of nuclear phosphoprotein C23 using ten monoclonal antibodies. Mol Cell Biochem 1985; 68: 87-96.
38. Sedlack J, Lindsay RN. Estimation of total protein-bound and non protein sulphohydral groups in tissues with Ellmans reagent. Anal Biochem 1968; 25: 192-205.
39. Cohn VH, Lyle J. A fluorometric assay for glutathione. Anal Biochem 1966; 14: 434-90.
40. Habig WH, Pabst MJ, Jakoby WB. Glutathione S-transferase. The first enzymatic step in marcapturic acid formation. J Biol Chem 1974; 249: 7130-9.
41. O'Brien ML, Tew KD. Glutathione and related enzymes in multidrug resistance. Br J Cancer 1966; 32: 967-78.
42. O'Brien PJ. Molecular mechanism of quinone cytotoxicity. Chem-Biol Interact 1991; 80: 1-41.
43. Al-Kabban M, Stewart MJ, Watson ID, Reglinski J. The effect of doxorubicin on the glutathione content and viability of cultured human lung cancer cell lines A549 and GLC4 210. Clin Chem Acta 1990; 194: 121-9.
44. Meijer C, Mulder NH, Timmer-Bosscha H, Linter WJ, Meersma GJ, de Vries EG. Relationship of cellular glutathione to cytotoxicity and resistance of seven platinum compounds. Cancer Res 1993; 52: 6885-9.
45. Sellin S, Holmquist B, Mannervik B, Vallee BL. Oxidation and reduction of 4-hydroxyalkenals catalysed by isozymes of human alcohol dehydrogenase. Biochemistry 1991; 30: 2514-8.
46. Versantvoort CHM, Broxterman HJ, Bagrich T, Scheper RJ, Tweentyman PR. Regulation by glutathione of drug transport in multidrug-resistant human lung tumor cell lines overexpressing multidrug resistance-associated protein. Br J Cancer 1995; 72: 82-9.
47. Cole SPC, Bhardawaj G, Gerlach JH, et al. Overexpression of a novel transport gene in a multidrug resistant human lung cancer cell line. Science 1992; 258: 1650-4.
48. Vargese AJ. Glutathione conjugates of Misonidazole. Biochem Biophys Res Commun 1983; 112: 1013-20.
49. Takanuki K, Igarashi I, Hata K, et al. Glutathione depletion by 2-nitromidazole-1-acetohydroxamic acid as a radiosensitizer in hypoxic rat hepatocytes. Biochem Int 1988; 17: 155-62.