Glutathione S-conjugates as prodrugs to target drug-resistant tumors

Frontiers in Pharmacology

Volumn 5 JUL, Issue , 2014, Pages

  Ramsay, Emma E ^a   Dilda, Pierre J ^a  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

Cancer; Drug resistance; Gamma glutamyl transferase; Glutathione s conjugate; Glutathione transferase; Prodrug

Indexed keywords

4 [N (S GLUTATHIONYLACETYL)AMINO]PHENYLARSONOUS ACID; ACETYLCYSTEINE; ANTHRACYCLINE DERIVATIVE; ANTINEOPLASTIC AGENT; ARSENIC TRIOXIDE; BETA LYASE; CANFOSFAMIDE; CHLORMETHINE; CYCLOPHOSPHAMIDE; DARINAPARSIN; DOPA; DOXORUBICIN; GAMMA GLUTAMINYL 4 HYDROXYBENZENE; GAMMA GLUTAMINYL 4 IODOBENZENE; GAMMA GLUTAMYL DERMORPHIN; GAMMA GLUTAMYLTRANSFERASE; GLUTATHIONE; GLUTATHIONE CONJUGATE; GLUTATHIONE TRANSFERASE; LYASE; MELARSOPROL; MERCAPTOPURINE; N ACETYL S (4 CHLOROPHENYLCARBAMOYL)CYSTEINE; PLATINUM COMPLEX; PRODRUG; S NITROSOGLUTATHIONE; SULOFENUR; TAXANE DERIVATIVE; TIOGUANINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACUTE LYMPHOBLASTIC LEUKEMIA; ANTIPROLIFERATIVE ACTIVITY; B CELL LYMPHOMA; BREAST CANCER; BREAST CARCINOMA; CANCER RESISTANCE; COLON CANCER; DNA METHYLATION; DRUG ACTIVATION; DRUG EFFICACY; DRUG MECHANISM; DRUG METABOLISM; DRUG RESISTANT TUMOR; ENDOMETRIUM CARCINOMA; GENETIC POLYMORPHISM; HUMAN; IN VITRO STUDY; IN VIVO STUDY; KIDNEY CANCER; LIVER CELL CARCINOMA; LUNG CANCER; LUNG NON SMALL CELL CANCER; MULTIPLE MYELOMA; NEOPLASM; NEPHROTOXICITY; NONHUMAN; OVARY CANCER; PANCREAS ADENOCARCINOMA; PROMYELOCYTIC LEUKEMIA; PROSTATE CANCER; PROTEIN EXPRESSION; REVIEW; STOMACH CANCER;

EID: 84904756151     PISSN: None     EISSN: 16639812     Source Type: Journal    
DOI: 10.3389/fphar.2014.00181     Document Type: Review

References (206)

1. AGALLIU, I., LANGEBERG, W. J., LAMPE, J. W., SALINAS, C. A. & STANFORD, J. L. 2006. Glutathione S-transferase M1, T1, and P1 polymorphisms and prostate cancer risk in middleaged men. Prostate, 66, 146-156
2. AGHIL, O., BIBBY, M. C., CARRINGTON, S. J., DOUBLE, J., DOUGLAS, K. T., PHILLIPS, R. M. & SHING, T. K. 1992. Synthesis and cytotoxicity of shikimate analogues. Structure:activity studies based on 1-crotonyloxymethyl-3R,4R,5R-trihydroxycyclohex-2-enone. Anticancer DrugDes, 7, 67-82
3. AHMAD, S. T., ARJUMAND, W., SETH, A., SAINI, A. K. & SULTANA, S. 2012. Impact of glutathione transferase M1, T1, and P1 gene polymorphisms in the genetic susceptibility of North Indian population to renal cell carcinoma. DNA and Cell Biology, 31, 636-643
4. ANGELI, V., TACITO, A., PAOLICCHI, A., BARSACCHI, R., FRANZINI, M., BALDASSINI, R., VECOLI, C., POMPELLA, A. & BRAMANTI, E. 2009. A kinetic study of gammaglutamyltransferase (GGT)-mediated S-nitrosoglutathione catabolism. Archives of Biochemistry and Biophysics, 481, 191-196
5. APTE, M. V. & WILSON, J. S. 2012. Dangerous liaisons: pancreatic stellate cells and pancreatic cancer cells. J GastroenterolHepatol, 27 Suppl 2, 69-74
6. ARAI, K., SUMI, S. H., YOSHIDA, K. I. & KOMODA, T. 1995. A precursor form of human kidney γ-glutamyl transferase in normal and cancerous tissues, and its possible post-translational modification. Biochimica et Biophysica Acta - Protein Structure and Molecular Enzymology, 1253,33-38
7. ARMSTRONG, R. N. 1997. Structure, catalytic mechanism, and evolution of the glutathione transferases. ChemRes Toxicol, 10, 2-18
8. AXARLI, I., LABROU, N. E., PETROU, C., RASSIAS, N., CORDOPATIS, P. & CLONIS, Y. D. 2009. Sulphonamide-based bombesin prodrug analogues for glutathione transferase, useful in targeted cancer chemotherapy. Eur JMed Chem, 44, 2009-16
9. BALLATORI, N., KRANCE, S. M., MARCHAN, R. & HAMMOND, C. L. 2009. Plasma membrane glutathione transporters and their roles in cell physiology and pathophysiology. Mol Aspects Med, 30, 13-28
10. BARD, S., NOEL, P., CHAUVIN, F. & QUASH, G. 1986. γ-glutamyltranspeptidase activity in human breast lesions: An unfavourable prognostic sign. British Journal of Cancer, 53, 637-642
11. BLAIR, S. L., HEERDT, P., SACHAR, S., ABOLHODA, A., HOCHWALD, S., CHENG, H. & BURT, M. 1997. Glutathione metabolism in patients with non-small cell lung cancers. Cancer Research, 57, 152-155
12. BORUD, O., MORTENSEN, B., MIKKELSEN, I. M., LEROY, P., WELLMAN, M. & HUSEBY, N. E. 2000. Regulation of γ-glutamyltransferase in cisplatin-resistant and -sensitive colon carcinoma cells after acute cisplatin and oxidative stress exposures. International Journal of Cancer, 88, 464-468
13. BRAMANTI, E., ANGELI, V., FRANZINI, M., VECOLI, C., BALDASSINI, R., PAOLICCHI, A., BARSACCHI, R. & POMPELLA, A. 2009. Exogenous vs. endogenous γ-glutamyltransferase activity: Implications for the specific determination of S-nitrosoglutathione in biological samples. Archives of Biochemistry andBiophysics, 487, 146-152
14. BRONIOWSKA, K. A., DIERS, A. R. & HOGG, N. 2013. S-Nitrosoglutathione. Biochimica et Biophysica Acta - General Subjects, 1830,3173-3181
15. BUDY, B., O'NEILL, R., DIBELLO, P. M., SENGUPTA, S. & JACOBSEN, D. W. 2006. Homocysteine transport by human aortic endothelial cells: identification and properties of import systems. Arch Biochem Biophys, 446, 119-30
16. CALONGHI, N., BOGA, C., CAPPADONE, C., PAGNOTTA, E., BERTUCCI, C., FIORI, J. & MASOTTIA, L. 2002. Cytotoxic and cytostatic effects induced by 4-hydroxynonenal in human osteosarcoma cells. Biochemical and Biophysical Research Communications, 293, 1502-1507
17. CERBONE, A., TOALDO, C., LAURORA, S., BRIATORE, F., PIZZIMENTI, S., DIANZANI, M. U., FERRETTI, C. & BARRERA, G. 2007. 4-Hydroxynonenal and PPARγ ligands affect proliferation, differentiation, and apoptosis in colon cancer cells. Free Radical Biology and Medicine, 42, 1661-1670
18. CHAN, Q. K. Y., KHOO, U.-S., CHAN, K. Y. K., NGAN, H. Y. S., LI, S.-S., CHIU, P.-M., MAN, L.-S., IP, P. P. C., XUE, W.-C. & CHEUNG, A. N. Y. 2005. Promoter Methylation and Differential Expression of π-Class Glutathione S-Transferase in Endometrial Carcinoma. The Journal of Molecular Diagnostics, 7, 8-16
19. CHEN, G. Q., ZHOU, L., STYBLO, M., WALTON, F., JING, Y., WEINBERG, R., CHEN, Z. & WAXMAN, S. 2003. Methylated metabolites of arsenic trioxide are more potent than arsenic trioxide as apoptotic but not differentiation inducers in leukemia and lymphoma cells. Cancer Res, 63, 1853-9
20. CHEN, J. C., STEVENS, J. L., TRIFILLIS, A. L. & JONES, T. W. 1990. Renal cysteine conjugate β-lyase-mediated toxicity studied with primary cultures of human proximal tubular cells. Toxicology and Applied Pharmacology, 103, 463-473
21. CHEN, W., SEEFELDT, T., YOUNG, A., ZHANG, X. & GUAN, X. 2011. Design, synthesis, and biological evaluation of N-acetyl-S-(p-chlorophenylcarbamoyl)cysteine and its analogs as a novel class of anticancer agents. Bioorganic & Medicinal Chemistry, 19, 287-294
22. CHENG, J. C., MATSEN, C. B., GONZALES, F. A., YE, W., GREER, S., MARQUEZ, V. E., JONES, P. A. & SELKER, E. U. 2003. Inhibition of DNA methylation and reactivation of silenced genes by zebularine. Journal of the National Cancer Institute, 95, 399-409
23. CHUNG, S., DECOLLOGNE, S., LUK, P., SHEN, H., HA, W., DAY, B., STRINGER, B., HOGG, P. J. & MCDONALD, K. L. 2013. Preclinical evaluation of PENAO: a potent mitochondrial specific, arsenical-based inhibitor for Glioblastoma. 4th Quadrennial Meeting of the World Federation of Neuro-Oncology, San Francisco, November 21st-24th, Neuro-Oncology, 15,iii40
24. CHUNG, S., MC DONALD, K. L., SHEN, H., DAY, B. W., STRINGER, B. W., JOHN, T., DECOLLOGNE, S., TEO, C., HOGG, P. J. & DILDA, P. J. 2011. Targeting glioblastoma metabolism with a novel arsenic-based metabolic inhibitor, PENAO. SNO Scientific Meeting, Orange County, November 17-20th, NJeuro-Oncology, 13, 118
25. COMMANDEUR, J. N., ANDREADOU, I., ROOSEBOOM, M., OUT, M., DE LEUR, L. J., GROOT, E. & VERMEULEN, N. P. 2000. Bioactivation of selenocysteine Se-conjugates by a highly purified rat renal cysteine conjugate beta-lyase/glutamine transaminase K. J PharmacolExp Ther, 294, 753-61
26. COMMANDEUR, J. N., STIJNTJES, G. J. & VERMEULEN, N. P. 1995. Enzymes and transport systems involved in the formation and disposition of glutathione S-conjugates. Role in bioactivation and detoxication mechanisms of xenobiotics. Pharmacol Rev, 47, 271-330
27. COOPER, A. J. 1998. Mechanisms of cysteine S-conjugate beta-lyases. Adv Enzymol Relat Areas MolBiol, 72, 199-238
28. CORTI, A., FRANZINI, M., PAOLICCHI, A. & POMPELLA, A. 2010. Gammaglutamyltransferase of cancer cells at the crossroads of tumor progression, drug resistance and drug targeting. Anticancer Research, 30, 1169-1181
29. CUMMINGS, B. S. & LASH, L. H. 2000. Metabolism and toxicity of trichloroethylene and S-(1,2-dichlorovinyl)-L-cysteine in freshly isolated human proximal tubular cells. Toxicological Sciences, 53, 458-466
30. DAHLLOF, B., MARTINSSON, T., MANNERVIK, B., JENSSON, H. & LEVAN, G. 1987. Characterization of multidrug resistance in SEWA mouse tumor cells: increased glutathione transferase activity and reversal of resistance with verapamil. Anticancer Res, 7, 65-9
31. DAUBEUF, S., BALIN, D., LEROY, P. & VISVIKIS, A. 2003. Different mechanisms for γ-glutamyltransferase-dependent resistance to carboplatin and cisplatin. Biochemical Pharmacology, 66, 595-604
32. DAUBEUF, S., LEROY, P., PAOLICCHI, A., POMPELLA, A., WELLMAN, M., GALTEAU, M. M. & VISVIKIS, A. 2002. Enhanced resistance of HeLa cells to cisplatin by overexpression of γ-glutamyltransferase. Biochemical Pharmacology, 64, 207-216
33. DAY, B. W., JIN, R. & KAROL, M. H. 1996. In vivo and in vitro reactions of toluene diisocyanate isomers with guinea pig hemoglobin. Chem Res Toxicol, 9, 568-73
34. DEL BELLO, B., PAOLICCHI, A., COMPORTI, M., POMPELLA, A. & MAELLARO, E. 1999. Hydrogen peroxide produced during γ-glutamyl transpeptidase activity is involved in prevention of apoptosis and maintenance of proliferation in U937 cells. FASEB Journal, 13, 69-79
35. DEMPO, K., ELLIOTT, K. A. C., DESMOND, W. & FISHMAN, W. H. 1981. Demonstration of gamma-glutamyl transferase, alkaline phosphatase, CEA and HCG in human lung cancer. Oncodevelopmental Biology and Medicine, 2, 21-37
36. DI ILIO, C., DEL BOCCIO, G., ACETO, A. & FEDERICI, G. 1987. Alteration of glutathione transferase isoenzyme concentrations in human renal carcinoma. Carcinogenesis, 8, 861-864
37. DIAZ, Z., MANN, K. K., MARCOUX, S., KOURELIS, M., COLOMBO, M., KOMARNITSKY, P. B. & MILLER, W. H., JR. 2008. A novel arsenical has antitumor activity toward As2O3-resistant and MRP1/ABCC1-overexpressing cell lines. Leukemia, 22, 1853-63
38. DIERGAARDE, B., BRAND, R., LAMB, J., CHEONG, S. Y., STELLO, K., BARMADA, M. M., FEINGOLD, E. & WHITCOMB, D. C. 2010. Pooling-based genome-wide association study implicates gamma-glutamyltransferase 1 (GGT1) gene in pancreatic carcinogenesis. Pancreatology, 10, 194-200
39. DILDA, P. J., DECOLLOGNE, S., ROSSITER-THORNTON, M. & HOGG, P. J. 2005a. Para to ortho repositioning of the arsenical moiety of the angiogenesis inhibitor 4-(N-(Sglutathionylacetyl) amino)phenylarsenoxide results in a markedly increased cellular accumulation and antiproliferative activity. Cancer Res, 65, 11729-34
40. DILDA, P. J., DECOLLOGNE, S., WEERAKOON, L., NORRIS, M. D., HABER, M., ALLEN, J. D. & HOGG, P. J. 2009. Optimization of the antitumor efficacy of a synthetic mitochondrial toxin by increasing the residence time in the cytosol. Journal of Medicinal Chemistry, 52, 6209-6216
41. DILDA, P. J., DON, A. S., TANABE, K. M., HIGGINS, V. J., ALLEN, J. D., DAWES, I. W. & HOGG, P. J. 2005b. Mechanism of selectivity of an angiogenesis inhibitor from screening a genome-wide set of Saccharomyces cerevisiae deletion strains. JNatl Cancer Inst, 97, 1539-47
42. DILDA, P. J. & HOGG, P. J. 2007. Arsenical-based cancer drugs. Cancer Treat Rev, 33, 542-64.
43. DILDA, P. J., RAMSAY, E. E., CORTI, A., POMPELLA, A. & HOGG, P. J. 2008. Metabolism of the tumor angiogenesis inhibitor 4-(N-(S-Glutathionylacetyl)amino)phenylarsonous acid. Journal of Biological Chemistry, 283, 35428-35434
44. DON, A. S., KISKER, O., DILDA, P., DONOGHUE, N., ZHAO, X., DECOLLOGNE, S., CREIGHTON, B., FLYNN, E., FOLKMAN, J. & HOGG, P. J. 2003. A peptide trivalent arsenical inhibits tumor angiogenesis by perturbing mitochondrial function in angiogenic endothelial cells. Cancer Cell, 3, 497-509
45. DONOGHUE, N., YAM, P. T. W., JIANG, X. M. & HOGG, P. J. 2000. Presence of closely spaced protein thiols on the surface of mammalian cells. Protein Science, 9, 2436-2445
46. DOURADO, D. F. A. R., FERNANDES, P. A., RAMOS, M. J. & MANNERVIK, B. 2013. Mechanism of glutathione transferase P1-1-catalyzed activation of the prodrug canfosfamide (TLK286, TELCYTA). Biochemistry, 52, 8069-8078
47. DROZDZ, R., PARMENTIER, C., HACHAD, H., LEROY, P., SIEST, G. & WELLMAN, M. 1998. γ-glutamyltransferase dependent generation of reactive oxygen species from a glutathione/transferrin system. Free Radical Biology and Medicine, 25, 786-792
48. DURHAM, J. R., FRIERSON JR, H. F. & HANIGAN, M. H. 1997. Gamma-glutamyl transpeptidase immunoreactivity in benign and malignant breast tissue. Breast Cancer Research and Treatment, 45, 55-62
49. EKLUND, B. I., GUNNARSDOTTIR, S., ELFARRA, A. A. & MANNERVIK, B. 2007. Human glutathione transferases catalyzing the bioactivation of anticancer thiopurine prodrugs. Biochem Pharmacol, 73, 1829-41
50. ELFARRA, A. A., DUESCHER, R. J., HWANG, I. Y., SICURI, A. R. & NELSON, J. A. 1995. Targeting 6-thioguanine to the kidney with S-(guanin-6-yl)-L-cysteine. J Pharmacol Exp Ther, 274, 1298-304
51. ELFARRA, A. A., JAKOBSON, I. & ANDERS, M. W. 1986. Mechanism of S-(1,2-dichlorovinyl)glutathione-induced nephrotoxicity. Biochemical Pharmacology, 35, 283-288
52. ENOIU, M., HERBER, R., WENNIG, R., MARSON, C., BODAUD, H., LEROY, P., MITREA, N., SIEST, G. & WELLMAN, M. 2002. γ-glutamyltranspeptidase-dependent metabolism of 4-hydroxynonenal-glutathione conjugate. Archives of Biochemistry and Biophysics, 397, 18-27
53. ESTELLER, M., CORN, P. G., URENA, J. M., GABRIELSON, E., BAYLIN, S. B. & HERMAN, J. G. 1998. Inactivation of glutathione S-transferase P1 gene by promoter hypermethylation in human neoplasia. Cancer Research, 58,4515-4518
54. FAN, Y., ZHANG, W., SHI, C. Y. & CAI, D. F. 2013. Associations of GSTM1 and GSTT1 polymorphisms with pancreatic cancer risk: Evidence from a meta-analysis. Tumor Biology, 34,705-712
55. FIALA, S., TROUT JR, E. C., TEAGUE, C. A. & FIALA, E. S. 1980. γ-Glutamyltransferase, a common marker of human epithelial tumors? Cancer Detection and Prevention, 3, 471-485
56. FINDLAY, V. J., TOWNSEND, D. M., SAAVEDRA, J. E., BUZARD, G. S., CITRO, M. L., KEEFER, L. K., JI, X. & TEW, K. D. 2004. Tumor cell responses to a novel glutathione Stransferase-activated nitric oxide-releasing prodrug. Mol Pharmacol, 65, 1070-9
57. FIRDOUS, A. P. & KUTTAN, R. 2012. Amelioration of cisplatin-induced toxicity in mice by carotenoid meso-zeaxanthin. Human and Experimental Toxicology, 31, 710-717
58. FORRESTER, L. M., HAYES, J. D., MILLIS, R., BARNES, D., HARRIS, A. L., SCHLAGER, J. J., POWIS, G. & WOLF, C. R. 1990. Expression of glutathione S-transferases and cytochrome P450 in normal and tumor breast tissue. Carcinogenesis, 11, 2163-2170
59. FRANZINI, M., CORTI, A., LORENZINI, E., PAOLICCHI, A., POMPELLA, A., DE CESARE, M., PEREGO, P., GATTI, L., LEONE, R., APOSTOLI, P. & ZUNINO, F. 2006. Modulation of cell growth and cisplatin sensitivity by membrane γ-glutamyltransferase in melanoma cells. European Journal of Cancer, 42, 2623-2630
60. FU, J., LIU, L., HUANG, Z., LAI, Y., JI, H., PENG, S., TIAN, J. & ZHANG, Y. 2013. Hybrid molecule from O2-(2,4-dinitrophenyl)diazeniumdiolate and oleanolic acid: A glutathione Stransferase π-activated nitric oxide prodrug with selective anti-human hepatocellular carcinoma activity and improved stability. Journal of Medicinal Chemistry, 56, 4641-4655
61. FUJISAWA, K., KURIHARA, N., NISHIKAWA, H., KIMURA, A. & KOJIMA, M. 1976. Carcinoembryonic character of gamma glutamyltranspeptidase in primary hepatocellular carcinoma. Gastroenterologia Japonica, 11,380-386
62. FURUHASHI, S., SUGITA, H., TAKAMORI, H., HORINO, K., NAKAHARA, O., OKABE, H., MIYAKE, K., TANAKA, H., BEPPU, T. & BABA, H. 2012. NO donor and MEK inhibitor synergistically inhibit proliferation and invasion of cancer cells. International Journal of Oncology, 40,807-815
63. GARNIER, N., PETRUCCELLI, L. A., MOLINA, M. F., KOURELIS, M., KWAN, S., DIAZ, Z., SCHIPPER, H. M., GUPTA, A., DEL RINCON, S. V., MANN, K. K. & MILLER, W. H., JR. 2013. The novel arsenical Darinaparsin circumvents BRG1-dependent, HO-1-mediated cytoprotection in leukemic cells. Leukemia, 27, 2220-8
64. GARNIER, N., REDSTONE, G. G., DAHABIEH, M. S., NICHOL, J. N., DEL RINCON, S. V., GU, Y., BOHLE, D. S., SUN, Y., CONKLIN, D. S., MANN, K. K. & MILLER, W. H., JR. 2014. The novel arsenical darinaparsin is transported by cystine importing systems. Mol Pharmacol, 85, 576-85
65. GASPAR, J., RODRIGUES, S., GIL, O. M., MANITA, I., FERREIRA, T. C., LIMBERT, E., GONÇALVES, L., PINA, J. E. & RUEFF, J. 2004. Combined effects of glutathione Stransferase polymorphisms and thyroid cancer risk. Cancer Genetics and Cytogenetics, 151, 60-67
66. GERBER, M. A. & THUNG, S. N. 1980. Enzyme patterns in human hepatocellular carcinoma. American Journal of Pathology, 98, 395-400
67. GHOSH, P., ROY, S. S., CHAKRABORTY, P., GHOSH, S. & BHATTACHARYA, S. 2013. Effects of organoselenium compound 2-(5-selenocyanatopentyl)- benzo[de]isoquinoline 1,3-dione on cisplatin induced nephrotoxicity and genotoxicity: An investigation of the influence of the compound on oxidative stress and antioxidant enzyme system. BioMetals, 26, 61-73
68. GIOMMARELLI, C., CORTI, A., SUPINO, R., FAVINI, E., PAOLICCHI, A., POMPELLA, A. & ZUNINO, F. 2008. Cellular response to oxidative stress and ascorbic acid in melanoma cells overexpressing γ-glutamyltransferase. European Journal of Cancer, 44, 750-759
69. GRIMM, C., HOFSTETTER, G., AUST, S., MUTZ-DEHBALAIE, I., BRUCH, M., HEINZE, G., RAHHAL-SCHUPP, J., REINTHALLER, A., CONCIN, N. & POLTERAUER, S. 2013. Association of gamma-glutamyltransferase with severity of disease at diagnosis and prognosis of ovarian cancer. British Journal of Cancer, 109, 610-614
70. GUAN, X., HOFFMAN, B. N., MCFARLAND, D. C., GILKERSON, K. K., DWIVEDI, C., ERICKSON, A. K., BEBENSEE, S. & PELLEGRINI, J. 2002. Glutathione and mercapturic acid conjugates of sulofenur and their activity against a human colon cancer cell line. Drug MetabDispos, 30, 331-5
71. GUILBERT, C., ANNIS, M. G., DONG, Z., SIEGEL, P. M., MILLER JR, W. H. & MANN, K. K. 2013. Arsenic trioxide overcomes rapamycin-induced feedback activation of akt and erk signaling to enhance the anti-tumor effects in breast cancer. PLoS ONE, 8
72. GUNNARSDOTTIR, S. & ELFARRA, A. A. 2004. Cytotoxicity of the novel glutathione-activated thiopurine prodrugs cis-AVTP [cis-6-(2-acetylvinylthio)purine] and trans-AVTG [trans-6-(2-acetylvinylthio)guanine] results from the National Cancer Institute's anticancer drug screen. Drug Metab Dispos, 32,321-7
73. GUNNARSDOTTIR, S., RUCKI, M. & ELFARRA, A. A. 2002. Novel glutathione-dependent thiopurine prodrugs: evidence for enhanced cytotoxicity in tumor cells and for decreased bone marrow toxicity in mice. J Pharmacol Exp Ther, 301, 77-86
74. HALESTRAP, A. P., MCSTAY, G. P. & CLARKE, S. J. 2002. The permeability transition pore complex: another view. Biochimie, 84, 153-166
75. HAMADA, S., KAMADA, M., FURUMOTO, H., HIRAO, T. & AONO, T. 1994. Expression of glutathione S-transferase-pi in human ovarian cancer as an indicator of resistance to chemotherapy. Gynecol Oncol, 52,313-9
76. HAMILTON, D. S., DING, Z., GANEM, B. & CREIGHTON, D. J. 2002. Glutathionyl transferase catalyzed addition of glutathione to COMC: a new hypothesis for antitumor activity. Org Lett, 4, 1209-12
77. HAMILTON, D. S., ZHANG, X., DING, Z., HUBATSCH, I., MANNERVIK, B., HOUK, K. N., GANEM, B. & CREIGHTON, D. J. 2003. Mechanism of the glutathione transferasecatalyzed conversion of antitumor 2-crotonyloxymethyl-2-cycloalkenones to GSH adducts. J Am Chem Soc, 125, 15049-58
78. HANIGAN, M. H. 1995. Expression of gamma-glutamyl transpeptidase provides tumor cells with a selective growth advantage at physiologic concentrations of cyst(e)ine. Carcinogenesis, 16, 181-185
79. HANIGAN, M. H. & FRIERSON, H. F., JR. 1996. Immunohistochemical detection of gammaglutamyl transpeptidase in normal human tissue. JHistochem Cytochem, 44, 1101-8
80. HANIGAN, M. H., FRIERSON JR, H. F., BROWN, J. E., LOVELL, M. A. & TAYLOR, P. T. 1994. Human ovarian tumors express γ-glutamyl transpeptidase. Cancer Research, 54, 286-290
81. HANIGAN, M. H., FRIERSON JR., H. F., SWANSON, P. E. & DE YOUNG, B. R. 1999a. Altered expression of gamma-glutamyl transpeptidase in human tumors. Human Pathology, 30, 300-305
82. HANIGAN, M. H., GALLAGHER, B. C., TOWNSEND, D. M. & GABARRA, V. 1999b. γ-glutamyl transpeptidase accelerates tumor growth and increases the resistance of tumors to cisplatin in vivo. Carcinogenesis, 20, 553-559
83. HAO, X. Y., WIDERSTEN, M., RIDDERSTROM, M., HELLMAN, U. & MANNERVIK, B. 1994. Co-variation of glutathione transferase expression and cytostatic drug resistance in HeLa cells: establishment of class Mu glutathione transferase M3-3 as the dominating isoenzyme. Biochem J, 297 (Pt 1), 59-67
84. HAYDEN, P. J. & STEVENS, J. L. 1990. Cysteine conjugate toxicity, metabolism, and binding to macromolecules in isolated rat kidney mitochondria. MolPharmacol, 37, 468-76
85. HENSON, S. E., NICHOLS, T. C., HOLERS, V. M. & KARP, D. R. 1999. The ectoenzyme γ-glutamyl transpeptidase regulates antiproliferative effects of S-nitrosoglutathione on human T and B lymphocytes. Journal of Immunology, 163, 1845-1852
86. HETLAND, T. E., NYMOEN, D. A., EMILSEN, E., KÆRN, J., TROPÉ, C. G., FLORENES, V. A. & DAVIDSON, B. 2012. MGST1 expression in serous ovarian carcinoma differs at various anatomic sites, but is unrelated to chemoresistance or survival. Gynecologic Oncology, 126, 460-465
87. HINCHMAN, C. A., REBBEOR, J. F. & BALLATORI, N. 1998. Efficient hepatic uptake and concentrative biliary excretion of a mercapturic acid. Am JPhysiol, 275, G612-9
88. HO, Y. S., LIU, H. L., DUH, J. S., CHEN, R. J., HO, W. L., JENG, J. H., WANG, Y. J. & LIN, J. K. 1999. Induction of apoptosis by S-nitrosoglutathione and Cu2+ or Ni2+ ion through modulation of bax, bad, and bcl-2 proteins in human colon adenocarcinoma cells. Molecular Carcinogenesis, 26, 201-211
89. HOCHWALD, S. N., HARRISON, L. E., ROSE, D. M., ANDERSON, M. & BURT, M. E. 1996. γ-glutamyl transpeptidase mediation of tumor glutathione utilization in vivo. Journal of the National Cancer Institute, 88, 193-197
90. HOGG, N., SINGH, R. J., KONOREV, E., JOSEPH, J. & KALYANARAMAN, B. 1997. Snitrosoglutathione as a substrate for γ-glutamyl transpeptidase. Biochemical Journal, 323, 477-481
91. HORSLEY, L., CUMMINGS, J., MIDDLETON, M., WARD, T., BACKEN, A., CLAMP, A., DAWSON, M., FARMER, H., FISHER, N., HALBERT, G., HALFORD, S., HARRIS, A., HASAN, J., HOGG, P., KUMARAN, G., LITTLE, R., PARKER, G. J. M., POTTER, P., SAUNDERS, M., ROBERTS, C., SHAW, D., SMITH, N., SMYTHE, J., TAYLOR, A., TURNER, H., WATSON, Y., DIVE, C. & JAYSON, G. C. 2013. A phase 1 trial of intravenous 4-(N-(S-glutathionylacetyl)amino) phenylarsenoxide (GSAO) in patients with advanced solid tumours. Cancer Chemotherapy and Pharmacology, 72, 1343-1352
92. HOSEIN, P. J., CRAIG, M. D., TALLMAN, M. S., BOCCIA, R. V., HAMILTON, B. L., LEWIS, J. J. & LOSSOS, I. S. 2012. A multicenter phase II study of darinaparsin in relapsed or refractory Hodgkin's and non-Hodgkin's lymphoma. Am JHematol, 87, 111-4
93. HOWBERT, J. J., GROSSMAN, C. S., CROWELL, T. A., RIEDER, B. J., HARPER, R. W., KRAMER, K. E., TAO, E. V., AIKINS, J., POORE, G. A., RINZEL, S. M. & ET AL. 1990. Novel agents effective against solid tumors: the diarylsulfonylureas. Synthesis, activities, and analysis of quantitative structure-activity relationships. JMedChem, 33, 2393-407
94. HOWIE, A. F., FORRESTER, L. M., GLANCEY, M. J., SCHLAGER, J. J., POWIS, G., BECKETT, G. J., HAYES, J. D. & WOLF, C. R. 1990. Glutathione S-transferase and glutathione peroxidase expression in normal and tumour human tissues. Carcinogenesis, 11, 451-8
95. HUTTUNEN, K. M. & RAUTIO, J. 2011. Prodrugs - An efficient way to breach delivery and targeting barriers. Current Topics in Medicinal Chemistry, 11, 2265-2287
96. HWANG, I. Y. & ELFARRA, A. A. 1991. Kidney-selective prodrugs of 6-mercaptopurine: biochemical basis of the kidney selectivity of S-(6-purinyl)-L-cysteine and metabolism of new analogs in rats. J Pharmacol Exp Ther, 258, 171-7
97. IWANAMI, A., CLOUGHESY, T. F., CAVENEE, W. K. & MISCHEL, P. S. 2013. Arsenic reverses glioblastoma resistance to mTOR-targeted therapies. Cell Cycle, 12, 1473-1474
98. JENSEN, G. L. & MEISTER, A. 1983. Radioprotection of human lymphoid cells by exogenously supplied glutathione is mediated by γ-glutamyl transpeptidase. Proceedings of the National Academy of Sciences of the United States of America, 80,4714-4717
99. JERREMALM, E., WALLIN, I., YACHNIN, J. & EHRSSON, H. 2006. Oxaliplatin degradation in the presence of important biological sulphur-containing compounds and plasma ultrafiltrate. European Journal of Pharmaceutical Sciences, 28, 278-283
100. JOCHHEIM, C. M., DAVIS, M. R., BAILLIE, K. M., EHLHARDT, W. J. & BAILLIE, T. A. 2002. Glutathione-dependent metabolism of the antitumor agent sulofenur. Evidence for the formation of p-chlorophenyl isocyanate as a reactive intermediate. Chem Res Toxicol, 15,240-8
101. JUNG, H. J., CHEN, Z. & MCCARTY, N. 2012. Synergistic anticancer effects of arsenic trioxide with bortezomib in mantle cell lymphoma. American Journal of Hematology, 87, 1057-1064
102. KAMTHAN, A., SCARFFE, J. H., WALLING, J., HATTY, S., PETERS, B., COLEMAN, R. & SMYTH, J. F. 1992. A phase II study of sulofenur (LY186641) in gastric cancer. Anticancer Drugs, 3,331-5
103. KAVANAGH, J. J., LEVENBACK, C. F., RAMIREZ, P. T., WOLF, J. L., MOORE, C. L., JONES, M. R., MENG, L., BROWN, G. L. & BAST, R. C. 2010. Phase 2 study of canfosfamide in combination with pegylated liposomal doxorubicin in platinum and paclitaxel refractory or resistant epithelial ovarian cancer. Journal of Hematology and Oncology, 3
104. KIRSCH, M., LEHNIG, M., KORTH, H. G., SUSTMANN, R. & DE GROOT, H. 2001. Inhibition of peroxynitrite-induced nitration of tyrosine by glutathione in the presence of carbon dioxide through both radical repair and peroxynitrate formation. Chemistry - A European Journal, 7, 3313-3320
105. KIZILTEPE, T., HIDESHIMA, T., ISHITSUKA, K., OCIO, E. M., RAJE, N., CATLEY, L., LI, C. Q., TRUDEL, L. J., YASUI, H., VALLET, S., KUTOK, J. L., CHAUHAN, D., MITSIADES, C. S., SAAVEDRA, J. E., WOGAN, G. N., KEEFER, L. K., SHAMI, P. J. & ANDERSON, K. C. 2007. JS-K, a GST-activated nitric oxide generator, induces DNA double-strand breaks, activates DNA damage response pathways, and induces apoptosis in vitro and in vivo in human multiple myeloma cells. Blood, 110, 709-18
106. KNICKELBEIN, R. G., INGBAR, D. H., SERES, T., SNOW, K., JOHNSTON JR, R. B., FAYEMI, O., GUMKOWSKI, F., JAMIESON, J. D. & WARSHAW, J. B. 1996. Hyperoxia enhances expression of γ-glutamyl transpeptidase and increases protein S-glutathiolation in rat lung. American Journal of Physiology - Lung Cellular and Molecular Physiology, 270, L1 15-L1 22
107. KOEPLINGER, K. A., ZHAO, Z., PETERSON, T., LEONE, J. W., SCHWENDE, F. S., HEINRIKSON, R. L. & TOMASSELLI, A. G. 1999. Activated sulfonamides are cleaved by glutathione-S-transferases. DrugMetab Dispos, 27, 986-91
108. KRYEZIU, K., JUNGWIRTH, U., HODA, M. A., FERK, F., KNASMÜLLER, S., KARNTHALERBENBAKKA, C., KOWOL, C. R., BERGER, W. & HEFFETER, P. 2013. Synergistic anticancer activity of arsenic trioxide with erlotinib is based on inhibition of EGFR-mediated DNA double-strand break repair. Molecular Cancer Therapeutics, 12, 1073-1084
109. KUGELMAN, A., CHOY, H. A., LIU, R., SHI, M. M., GOZAL, E. & FORMAN, H. J. 1994. γ-Glutamyl transpeptidase is increased by oxidative stress in rat alveolar L2 epithelial cells. American Journal of Respiratory Cell and Molecular Biology, 11, 586-592
110. KUMAR, V., YADAV, C. S., DATTA, S. K., SINGH, S., AHMED, R. S., GOEL, S., GUPTA, S., MUSTAFA, M., GROVER, R. K. & BANERJEE, B. D. 2011. Association of GSTM1 and GSTT1 polymorphism with lipid peroxidation in benign prostate hyperplasia and prostate cancer: A pilot study. Disease Markers, 30, 163-169
111. LA THANGUE, N. B. & KERR, D. J. 2011. Predictive biomarkers: a paradigm shift towards personalized cancer medicine. Nature Reviews Clinical Oncology, 8, 587-596
112. LAFUENTE, A., GIRALT, M., CERVELLO, I., PUJOL, F. & MALLOL, J. 1990. Glutathione-Stransferase activity in human superficial transitional cell carcinoma of the bladder comparison with healthy controls. Cancer, 65, 2064-2068
113. LALLEMAND-BREITENBACH, V., ZHU, J., CHEN, Z. & DE THE, H. 2012. Curing APL through PML/RARA degradation by As2O3. TrendsMolMed, 18,36-42
114. LASCHAK, M., SPINDLER, K. D., SCHRADER, A. J., HESSENAUER, A., STREICHER, W., SCHRADER, M. & CRONAUER, M. V. 2012. JS-K, a glutathione/glutathione S-transferaseactivated nitric oxide releasing prodrug inhibits androgen receptor and WNT-signaling in prostate cancer cells. BMC Cancer, 12, 130
115. LASH, L. H., ELFARRA, A. A. & ANDERS, M. W. 1986. Renal cysteine conjugate β-lyase. Bioactivation of nephrotoxic cysteine S-conjugates in mitochondrial outer membrane. Journal of Biological Chemistry, 261, 5930-5935
116. LASH, L. H., SHIVNANI, A., MAI, J., CHINNAIYAN, P., KRAUSE, R. J. & ELFARRA, A. A. 1997. Renal cellular transport, metabolism, and cytotoxicity of S-(6-purinyl)glutathione, a prodrug of 6-mercaptopurine, and analogues. Biochem Pharmacol, 54, 1341-9
117. LEE, J. S. 2007. GSTP1 promoter hypermethylation is an early event in breast carcinogenesis. Virchows Archiv, 450, 637-642
118. LEE, M. R. 1990. Five years' experience with γ-L-glutamyl-L-dopa: A relatively renally specific dopaminergic prodrug in man. Journal ofAutonomic Pharmacology, 10, s103-s108
119. LEWIS, A. D., HAYES, J. D. & WOLF, C. R. 1988. Glutathione and glutathione-dependent enzymes in ovarian adenocarcinoma cell lines derived from a patient before and after the onset of drug resistance: Intrinsic differences and cell cycle effects. Carcinogenesis, 9, 1283-1287
120. LI, J., LONG, J., HU, Y., TAN, A., GUO, X. & ZHANG, S. 2012. Glutathione S-transferase M1, T1, and P1 polymorphisms and thyroid cancer risk: A meta-analysis. Cancer Epidemiology, 36, e333-e340
121. LIU, D., LIU, Y., RAN, L., SHANG, H. & LI, D. 2013. GSTT1 and GSTM1 polymorphisms and prostate cancer risk in Asians: A systematic review and meta-analysis. Tumor Biology, 34, 2539-2544
122. LIU, L., FU, J., LI, T., CUI, R., LING, J., YU, X., JI, H. & ZHANG, Y. 2012. NG, a novel PABA/NO-based oleanolic acid derivative, induces Human hepatoma cell apoptosis via a ROS/MAPK-dependent mitochondrial pathway. European Journal of Pharmacology, 691, 61-68
123. LIU, Q., CHAN, S. T. F. & MAHENDRAN, R. 2003. Nitric oxide induces cyclooxygenase expression and inhibits cell growth in colon cancer cell lines. Carcinogenesis, 24, 637-642
124. LIU, R. M., SHI, M. M., GIULIVI, C. & FORMAN, H. J. 1998. Quinones increase γ-glutamyl transpeptidase expression by multiple mechanisms in rat lung epithelial cells. American Journal of Physiology - Lung Cellular and Molecular Physiology, 274, L330-L336
125. LU, S. C. 2013. Glutathione synthesis. Biochimica et Biophysica Acta - General Subjects, 1830, 3143-3153
126. LYTTLE, M. H., SATYAM, A., HOCKER, M. D., BAUER, K. E., CALDWELL, C. G., HUI, H. C., MORGAN, A. S., MERGIA, A. & KAUVAR, L. M. 1994. Glutathione-S-transferase activates novel alkylating agents. JMedChem, 37, 1501-7
127. MAELLARO, E., DOMINICI, S., DEL BELLO, B., VALENTINI, M. A., PIERI, L., PEREGO, P., SUPINO, R., ZUNINO, F., LORENZINI, E., PAOLICCHI, A., COMPORTI, M. & POMPELLA, A. 2000. Membrane gamma-glutamyl transpeptidase activity of melanoma cells: effects on cellular H2O2 production, cell surface protein thiol oxidation and NF-ΚB activation status. Journal of Cell Science, 113, 2671-2678
128. MAHJOUBI, M., KATTAN, J., BONNAY, M., SCHMITT, H. & DROZ, J. P. 1993. Phase II trial of LY 186641 in advanced renal cancer. Invest New Drugs, 11, 323-8
129. MANNERVIK, B., BOARD, P. G., HAYES, J. D., LISTOWSKY, I. & PEARSON, W. R. 2005. Nomenclature for mammalian soluble glutathione transferases. Methods Enzymol, 401, 1-8
130. MAREŠ, V., STREMENOVÁ, J., LISÁ, V., KOZÁKOVÁ, H., MAREK, J., SYRŮČEK, M., ŠOULA, O. & ŠEDO, A. 2012. Compartment- and malignance-dependent up-regulation of γ-glutamyltranspeptidase and dipetidylpeptidase-IV activity in human brain gliomas. Histology and Histopathology, 27, 931-940
131. MATULIS, S. M., MORALES, A. A., YEHIAYAN, L., CROUTCH, C., GUTMAN, D., CAI, Y., LEE, K. P. & BOISE, L. H. 2009. Darinaparsin induces a unique cellular response and is active in an arsenic trioxide-resistant myeloma cell line. Mol Cancer Ther, 8, 1197-206
132. MCSTAY, G. P., CLARKE, S. J. & HALESTRAP, A. P. 2002. Role of critical thiol groups on the matrix surface of the adenine nucleotide translocase in the mechanism of the mitochondrial permeability transition pore. Biochemical Journal, 367, 541-548
133. MISICKA, A., MASZCZYNSKA, I., LIPKOWSKI, A. W., STROPOVA, D., YAMAMURA, H. I. & HRUBY, V. J. 1996. Synthesis and biological properties of gamma-glutamyl-dermorphin, a prodrug. Life Sciences, 58, 905-911
134. MOHAMADI, F., SPEES, M. M. & GRINDEY, G. B. 1992. Sulfonylureas: a new class of cancer chemotherapeutic agents. JMedChem, 35, 3012-6
135. MOON, D. O., KIM, B. Y., JANG, J. H., KIM, M. O., JAYASOORIYA, R. G. P. T., KANG, C. H., CHOI, Y. H., MOON, S. K., KIM, W. J., AHN, J. S. & KIM, G. Y. 2012. K-RAS transformation in prostate epithelial cell overcomes H2O2-induced apoptosis via upregulation of gamma-glutamyltransferase-2. Toxicology in Vitro, 26,429-434
136. MOORGHEN, M., CAIRNS, J., FORRESTER, L. M., HAYES, J. D., HALL, A., CATTAN, A. R., WOLF, C. R. & HARRIS, A. L. 1991. Enhanced expression of glutathione S-transferases in colorectal carcinoma compared to non-neoplastic mucosa. Carcinogenesis, 12, 13-17
137. MORGAN, A. S., SANDERSON, P. E., BORCH, R. F., TEW, K. D., NIITSU, Y., TAKAYAMA, T., VON HOFF, D. D., IZBICKA, E., MANGOLD, G., PAUL, C., BROBERG, U., MANNERVIK, B., HENNER, W. D. & KAUVAR, L. M. 1998. Tumor efficacy and bone marrow-sparing properties of TER286, a cytotoxin activated by glutathione S-transferase. Cancer Res, 58,2568-75
138. MORIARTY-CRAIGE, S. E. & JONES, D. P. 2004. Extracellular thiols and thiol/disulfide redox in metabolism. Annu Rev Nutr, 24, 481-509
139. MOSKALUK, C. A., DURAY, P. H., COWAN, K. H., LINEHAN, M. & MERINO, M. J. 1997. Immunohistochemical expression of π-class glutathione S-transferase is down-regulated in adenocarcinoma of the prostate. Cancer, 79, 1595-1599
140. MUNSHI, N. C., SEITZ, D. E., FOSSELLA, F., LIPPMAN, S. M. & EINHORN, L. H. 1993. Phase II study of sulofenur (LY 186641). A novel antineoplastic agent in advanced non-small cell lung cancer. Invest New Drugs, 11, 87-90
141. MURATA, J. I., RICCIARDI-CASTAGNOLI, P., MANGE, P. D. L., MARTIN, F. & JUILLERATJEANNERET, L. 1997. Microglial cells induce cytotoxic effects toward colon carcinoma cells: Measurement of tumor cytotoxicity with a γ-glutamyl transpeptidase assay. InternationalJournal of Cancer, 70, 169-174
142. NIELSEN, T. H., JOHNSON, N., GARNIER, N., KWAN, S., YAO, L., COCOLAKIS, E., HEBERT, J., MORGAN, R. A., PAQUET, E., CALLAHAN, K. P., JORDAN, C. T., ASSOULINE, S., MILLER, W. H., JR. & MANN, K. K. 2013. Monitoring Response and Resistance to the Novel Arsenical Darinaparsin in an AML Patient. Front Pharmacol, 4, 9
143. NOH, E. K., KIM, H., PARK, M. J., BAEK, J. H., PARK, J. H., CHA, S. J., WON, J. H. & MIN, Y. J. 2010. Gefitinib enhances arsenic tri oxide (AS2O3)-induced differentiation of acute promyelocytic leukemia cell line. Leukemia Research, 34, 1501-1505
144. O'BRIEN, M. E., HARDY, J., TAN, S., WALLING, J., PETERS, B., HATTY, S. & WILTSHAW, E. 1992. A phase II study of sulofenur, a novel sulfonylurea, in recurrent epithelial ovarian cancer. Cancer Chemother Pharmacol, 30, 245-8
145. O'BRIEN, M. L. & TEW, K. D. 1996. Glutathione and related enzymes in multidrug resistance. Eur J Cancer, 32A, 967-78
146. OGUZTUZUN, S., SEZGIN, Y., YAZiCi, S., Fi{dotless}RAT, P., OZHAVZALi, M. & OZEN, H. 2011. Expression of glutathione-S-transferases isoenzymes and p53 in exfoliated human bladder cancer cells. Urologic Oncology: Seminars and Original Investigations, 29, 538-544
147. PACIFICI, G. M., FRANCHI, M., BENCINI, C., REPETTI, F., DI LASCIO, N. & MURARO, G. B. 1988. Tissue distribution of drug-metabolizing enzymes in humans. Xenobiotica, 18, 849-56
148. PANKIV, S., MØLLER, S., BJØRKØY, G., MOENS, U. & HUSEBY, N. E. 2006. Radiationinduced upregulation of γ-glutamyltransferase in colon carcinoma cells is mediated through the Ras signal transduction pathway. Biochimica et Biophysica Acta, 1760, 151-157
149. PAOLICCHI, A., DOMINICI, S., PIERI, L., MAELLARO, E. & POMPELLA, A. 2002. Glutathione catabolism as a signaling mechanism. Biochemical Pharmacology, 64, 1027-1035
150. PAOLICCHI, A., POMPELLA, A., TONARELLI, P., GADDUCCI, A., GENAZZANI, A. R., ZUNINO, F., PRATESI, G. & TONGIANI, R. 1996. Gamma-glutamyltranspeptidase activity in human ovarian carcinoma. Anticancer Research, 16, 3053-3058
151. PAOLICCHI, A., SOTIROPUOLOU, M., PEREGO, P., DAUBEUF, S., VISVIKIS, A., LORENZINI, E., FRANZINI, M., ROMITI, N., CHIELI, E., LEONE, R., APOSTOLI, P., COLANGELO, D., ZUNINO, F. & POMPELLA, A. 2003. γ-Glutamyl transpeptidase catalyses the extracellular detoxification of cisplatin in a human cell line derived from the proximal convoluted tubule of the kidney. European Journal of Cancer, 39, 996-1003
152. PARK, D., CHIU, J., PERRONE, G. G., DILDA, P. J. & HOGG, P. J. 2012. The tumour metabolism inhibitors GSAO and PENAO react with cysteines 57 and 257 of mitochondrial adenine nucleotide translocase. Cancer Cell International, 12
153. PARK, D. & DILDA, P. J. 2010. Mitochondria as targets in angiogenesis inhibition. Mol Aspects Med, 31, 113-31
154. PATEL, N. J., FULLONE, J. S. & ANDERS, M. W. 1993. Brain uptake of S-(1,2-dichlorovinyl)glutathione and S-(1,2-dichlorovinyl)-L-cysteine, the glutathione and cysteine S-conjugates of the neurotoxin dichloroacetylene. Molecular Brain Research, 17, 53-58
155. PETERS, W. H. M., WORMSKAMP, N. G. M. & THIES, E. 1990. Expression of glutathione Stransferases in normal gastric mucosa and in gastric tumors. Carcinogenesis, 11, 1593-1596
156. PETTAZZONI, P., PIZZIMENTI, S., TOALDO, C., SOTOMAYOR, P., TAGLIAVACCA, L., LIU, S., WANG, D., MINELLI, R., ELLIS, L., ATADJA, P., CIAMPORCERO, E., DIANZANI, M. U., BARRERA, G. & PILI, R. 2011. Induction of cell cycle arrest and DNA damage by the HDAC inhibitor panobinostat (LBH589) and the lipid peroxidation end product 4-hydroxynonenal in prostate cancer cells. Free Radical Biology and Medicine, 50, 313-322
157. PLUMB, J. A., STRATHDEE, G., SLUDDEN, J., KAYE, S. B. & BROWN, R. 2000. Reversal of drug resistance in human tumor xenografts by 2'-deoxy-5-azacytidine-induced demethylation of the hMLH1 gene promoter. Cancer Research, 60, 6039-6044
158. POMPELLA, A., DE TATA, V., PAOLICCHI, A. & ZUNINO, F. 2006. Expression of γ-glutamyltransferase in cancer cells and its significance in drug resistance. Biochemical Pharmacology, 71,231-238
159. PREZIOSO, J. A., DAMODARAN, K. M., WANG, N. & BLOOMER, W. D. 1993. Mechanism(s) regulating inhibition of thymidylate synthase and growth by γ-L-glutaminyl-4-hydroxy-3-iodobenzene, a novel melanin precursor, in melanogenic melanoma cells. Biochemical Pharmacology, 45, 473-481
160. PREZIOSO, J. A., HUGHEY, R. P., WANG, N., DAMODARAN, K. M. & BLOOMER, W. D. 1994a. γ-Glutamyltranspeptidase expression regulates the growth-inhibitory activity of the anti-tumor prodrug γ-L-glutaminyl-4-hydroxy-3-iodobenzene. International Journal of Cancer, 56, 874-879
161. PREZIOSO, J. A., SHIELDS, D., WANG, N. & ROSENSTEIN, M. 1994b. Role of γ-glutamyltranspeptidase-mediated glutathione transport on the radiosensitivity of B16 melanoma variant cell lines. International Journal of Radiation Oncology Biology Physics, 30,373-381
162. RAMSAY, E. E., DECOLLOGNE, S., JOSHI, S., CORTI, A., APTE, M., POMPELLA, A., HOGG, P. J. & DILDA, P. J. 2014. Employing Pancreatic Tumor γ-Glutamyltransferase for Therapeutic Delivery. Molecular Pharmaceutics
163. REBBECK, T. R. 1997. Molecular epidemiology of the human glutathione S-transferase genotypes GSTM1 and GSTT1 in cancer susceptibility. Cancer Epidemiology Biomarkers and Prevention, 6, 733-743
164. REBBECK, T. R., WALKER, A. H., JAFFE, J. M., WHITE, D. L., WEIN, A. J. & MALKOWICZ, S. B. 1999. Glutathione S-transferase-μ (GSTM1) and -Θ (GSTT1) genotypes in the etiology of prostate cancer. Cancer Epidemiology Biomarkers and Prevention, 8, 283-287
165. ROOMI, M. W., GAAL, K., YUAN, Q. X., FRENCH, B. A., FU, P., BARDAG-GORCE, F. & FRENCH, S. W. 2006. Preneoplastic liver cell foci expansion induced by thioacetamide toxicity in drug-primed mice. Experimental and Molecular Pathology, 81, 8-14
166. RUZZA, P., ROSATO, A., ROSSI, C. R., FLOREANI, M. & QUINTIERI, L. 2009. Glutathione transferases as targets for cancer therapy. Anticancer AgentsMed Chem, 9, 763-77
167. SABATINO, M. A., GERONI, C., GANZINELLI, M., CERUTI, R. & BROGGINI, M. 2013. Zebularine partially reverses GST methylation in prostate cancer cells and restores sensitivity to the DNA minor groove binder brostallicin. Epigenetics, 8
168. SADIQ, S., BERNDT, T. J., NATH, K. A. & KNOX, F. G. 2000. Effect of γ-L-glutamyl-L-DOPA on phosphate excretion. Journal of Laboratory and Clinical Medicine, 135, 52-56
169. SATYAM, A., HOCKER, M. D., KANE-MAGUIRE, K. A., MORGAN, A. S., VILLAR, H. O. & LYTTLE, M. H. 1996. Design, synthesis, and evaluation of latent alkylating agents activated by glutathione S-transferase. J Med Chem, 39, 1736-47
170. SAXENA, A., DHILLON, V. S., SHAHID, M., KHALIL, H. S., RANI, M., DAS, T. P., HEDAU, S., HUSSAIN, A., NAQVI, R. A., DEO, S. V. S., SHUKLA, N. K., DAS, B. C. & HUSAIN, S. A. 2012. GSTP1 methylation and polymorphism increase the risk of breast cancer and the effects of diet and lifestyle in breast cancer patients. Experimental and Therapeutic Medicine, 4, 1097-1103
171. SCHÄFER, C., FELS, C., BRUCKE, M., HOLZHAUSEN, H. J., BAHN, H., WELLMAN, M., VISVIKIS, A., FISCHER, P. & RAINOV, N. G. 2001. Gamma-glutamyl transferase expression in higher-grade astrocytic glioma. Acta Oncologica, 40, 529-535
172. SENER, M. T., SENER, E., TOK, A., POLAT, B., CINAR, I., POLAT, H., AKCAY, F. & SULEYMAN, H. 2012. Biochemical and histologic study of lethal cisplatin nephrotoxicity prevention by mirtazapine. Pharmacological Reports, 64, 594-602
173. SEQUIST, L. V., FIDIAS, P. M., TEMEL, J. S., KOLEVSKA, T., RABIN, M. S., BOCCIA, R. V., BURRIS, H. A., BELT, R. J., HUBERMAN, M. S., MELNYK, O., MILLS, G. M., ENGLUND, C. W., CALDWELL, D. C., KECK, J. G., MENG, L., JONES, M., BROWN, G. L., EDELMAN, M. J. & LYNCH, T. J. 2009. Phase 1-2a multicenter dose-ranging study of canfosfamide in combination with carboplatin and paclitaxel as first-line therapy for patients with advanced non-small cell lung cancer. Journal of Thoracic Oncology, 4, 1389-1396
174. SHAMI, P. J., SAAVEDRA, J. E., WANG, L. Y., BONIFANT, C. L., DIWAN, B. A., SINGH, S. V., GU, Y., FOX, S. D., BUZARD, G. S., CITRO, M. L., WATERHOUSE, D. J., DAVIES, K. M., JI, X. & KEEFER, L. K. 2003. JS-K, a glutathione/glutathione S-transferase-activated nitric oxide donor of the diazeniumdiolate class with potent antineoplastic activity. Mol Cancer Ther, 2,409-17
175. SHIOZAWA, M., YAMASHITA, S., AISO, S. & YASUDA, K. 1989. A monoclonal antibody against human kidney gamma-glutamyl transpeptidase: preparation, immunochemical, and immunohistochemical characterization. JHistochem Cytochem, 37, 1053-61
176. SONG, K., YI, J., SHEN, X. & CAI, Y. 2012. Genetic Polymorphisms of Glutathione S-Transferase Genes GSTM1, GSTT1 and Risk of Hepatocellular Carcinoma. PLoS ONE, 7
177. SPENCER, P. S. & SCHAUMBURG, H. H. 1985. Organic solvent neurotoxicity: Facts and research needs. Scandinavian Journal of Work, Environment and Health, 11, 53-60
178. STARK, A. A. & GLASS, G. A. 1997. Role of copper and ceruloplasmin in oxidative mutogenesis induced by the glutathione-γ-glutamyl transpeptidase system and by other thiols. Environmental and Molecular Mutagenesis, 29, 63-72
179. STARK, A. A., ZEIGER, E. & PAGANO, D. A. 1993. Glutathione metabolism by γ-glutamyltranspeptidase leads to lipid peroxidation: characterization of the system and relevance to hepatocarcinogenesis. Carcinogenesis, 14, 183-189
180. STEVENS, J. L., HATZINGER, P. B. & HAYDEN, P. J. 1989. Quantitation of multiple pathways for the metabolism of nephrotoxic cysteine conjugates using selective inhibitors of L-alphahydroxy acid oxidase (L-amino acid oxidase) and cysteine conjugate beta-lyase. DrugMetab Dispos, 17,297-303
181. SUPINO, R., MAPELLI, E., SANFILIPPO, O. & SILVESTRO, L. 1992. Biological and enzymatic features of human melanoma clones with different invasive potential. Melanoma Research, 2, 377-384
182. TALBOT, D. C., SMITH, I. E., NICOLSON, M. C., POWLES, T. J., BUTTON, D. & WALLING, J. 1993. Phase II trial of the novel sulphonylurea sulofenur in advanced breast cancer. Cancer Chemother Pharmacol, 31, 419-22
183. TATEISHI, N., HIGASHI, T., NOMURA, T., NARUSE, A. & NAKASHIMA, K. 1976. Higher transpeptidation activity and broad acceptor specificity of γ glutamyltransferases of tumors. Gann, The Japanese Journal of Cancer Research, 67, 215-222
184. TERRACINI, B. & PARKER, V. H. 1965. A pathological study on the toxicity of S-dichlorovinyl-Lcysteine. Food and Cosmetics Toxicology, 3, 67-7 4
185. TIAN, J., DOI, H., SAAR, M., SANTOS, J., LI, X., PEEHL, D. M. & KNOX, S. J. 2013. Radioprotection and cell cycle arrest of intestinal epithelial cells by darinaparsin, a tumor radiosensitizer. Int JRadiat OncolBiolPhys, 87, 1179-85
186. TIAN, J., ZHAO, H., NOLLEY, R., REESE, S. W., YOUNG, S. R., LI, X., PEEHL, D. M. & KNOX, S. J. 2012. Darinaparsin: solid tumor hypoxic cytotoxin and radiosensitizer. Clin Cancer Res, 18,3366-76
187. TOWNSEND, D. M., DENG, M., ZHANG, L., LAPUS, M. G. & HANIGAN, M. H. 2003. Metabolism of Cisplatin to a nephrotoxin in proximal tubule cells. J Am Soc Nephrol, 14, 1-10
188. TOWNSEND, D. M., SHEN, H., STAROS, A. L., GATÉ, L. & TEW, K. D. 2002. Efficacy of a glutathione s-transferase π-activated prodrug in platinum-resistant ovarian cancer cells. Molecular Cancer Therapeutics, 1, 1089-1095
189. TSIMBERIDOU, A. M., CAMACHO, L. H., VERSTOVSEK, S., NG, C., HONG, D. S., UEHARA, C. K., GUTIERREZ, C., DARING, S., STEVENS, J., KOMARNITSKY, P. B., SCHWARTZ, B. & KURZROCK, R. 2009. A phase I clinical trial of darinaparsin in patients with refractory solid tumors. Clin Cancer Res, 15, 4769-76
190. TSOLI, M., LUK, P., DILDA, P. J., HABER, M. & ZIEGLER, D. 2013. Targeting mitochondria and metabolism as a novel therapeutic approach in the treatment of diffuse intrinsic pontine glioma. 2nd Annual Pediatric Neuro-Oncology Basic and Translational Research Conference, Fort Lauderdale, May 16-17th, Neuro-Oncology, 15, 21
191. TSUCHIDA, S., SEKINE, Y., SHINEHA, R., NISHIHIRA, T. & SATO, K. 1989. Elevation of the placental glutathione S-transferase form (GST-Π) in tumor tissues and the levels in sera of patients with cancer. Cancer Research, 49, 5225-5229
192. TSUTSUMI, M., SAKAMURO, D., TAKADA, A., ZANG, S. C., FURUKAWA, T. & TANIGUCHI, N. 1996. Detection of a unique γ-glutamyl transpeptidase messenger RNA species closely related to the development of hepatocellular carcinoma in humans: A new candidate for early diagnosis of hepatocellular carcinoma. Hepatology, 23, 1093-1097
193. TURCHI, J. J. 2006. Nitric oxide and cisplatin resistance: NO easy answers. Proceedings of the National Academy of Sciences of the United States of America, 103, 4337-4338
194. VERGOTE, I., FINKLER, N. J., HALL, J. B., MELNYK, O., EDWARDS, R. P., JONES, M., KECK, J. G., MENG, L., BROWN, G. L., RANKIN, E. M., BURKE, J. J., BOCCIA, R. V., RUNOWICZ, C. D. & ROSE, P. G. 2010. Randomized phase III study of canfosfamide in combination with pegylated liposomal doxorubicin compared with pegylated liposomal doxorubicin alone in platinum-resistant ovarian cancer. International Journal of Gynecological Cancer, 20, 772-780
195. WANG, Y., TEICHER, B. A., SHEA, T. C., HOLDEN, S. A., ROSBE, K. W., AL-ACHI, A. & HENNER, W. D. 1989. Cross-resistance and glutathione-S-transferase-π levels among four human melanoma cell lines selected for alkylating agent resistance. Cancer Research, 49, 6185-6192
196. WANG, Z., HE, W., YANG, G., WANG, J., WANG, Z., NESLAND, J. M., HOLM, R. & SUO, Z. 2010. Decreased expression of GST pi is correlated with a poor prognosis in human esophageal squamous carcinoma. BMC Cancer, 10
197. WAXMAN, S. & ANDERSON, K. C. 2001. History of the development of arsenic derivatives in cancer therapy. Oncologist, 6 Suppl 2, 3-10
198. WILK, S., MIZOGUCHI, H. & ORLOWSKI, M. 1978. γ-glutamyl dopa: a kidney-specific dopamine precursor. Journal of Pharmacology and Experimental Therapeutics, 206, 227-232
199. WORTH, D. P., HARVEY, J. N., BROWN, J. & LEE, M. R. 1985. γ-L-glutamyl-L-dopa is a dopamine pro-drug, relatively specific for the kidney in normal subjects. Clinical Science, 69, 207-214
200. WU, J., HENDERSON, C., FEUN, L., VAN VELDHUIZEN, P., GOLD, P., ZHENG, H., RYAN, T., BLASZKOWSKY, L. S., CHEN, H., COSTA, M., ROSENZWEIG, B., NIERODZIK, M., HOCHSTER, H., MUGGIA, F., ABBADESSA, G., LEWIS, J. & ZHU, A. X. 2010. Phase II study of darinaparsin in patients with advanced hepatocellular carcinoma. Invest New Drugs, 28, 670-6
201. YOON, H. Y., KIM, Y. W., KANG, H. W., KIM, W. T., YUN, S. J., LEE, S. C., KIM, W. J. & KIM, Y. J. 2012. DNA methylation of GSTP1 in human prostate tissues: Pyrosequencing analysis. Korean Journal of Urology, 53, 200-205
202. ZHANG, L. & HANIGAN, M. H. 2003. Role of cysteine S-conjugate beta-lyase in the metabolism of cisplatin. J Pharmacol Exp Ther, 306, 988-94
203. ZHANG, Q., KULCZYNSKA, A., WEBB, D. J., MEGSON, I. L. & BOTTING, N. P. 2013a. A new class of NO-donor pro-drugs triggered by γ-glutamyl transpeptidase with potential for renoselective vasodilatation. Chemical Communications, 49, 1389-1391
204. ZHANG, Q., MILLIKEN, P., KULCZYNSKA, A., SLAWIN, A. M. Z., GORDON, A., KIRKBY, N. S., WEBB, D. J., BOTTING, N. P. & MEGSON, I. L. 2013b. Development and characterization of glutamyl-protected N-hydroxyguanidines as reno-active nitric oxide donor drugs with therapeutic potential in acute renal failure. Journal of Medicinal Chemistry, 56, 5321-5334
205. ZHAO, Z., KOEPLINGER, K. A., PETERSON, T., CONRADI, R. A., BURTON, P. S., SUARATO, A., HEINRIKSON, R. L. & TOMASSELLI, A. G. 1999. Mechanism, structure-activity studies, and potential applications of glutathione S-transferase-catalyzed cleavage of sulfonamides. DrugMetab Dispos, 27, 992-8
206. ZHONG, S., TANG, M. W., YEO, W., LIU, C., LO, Y. M. D. & JOHNSON, P. J. 2002. Silencing of GSTP1 gene by CpG island DNA hypermethylation in HBV-associated hepatocellular carcinomas. Clinical Cancer Research, 8, 1087-1092