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Volumn 1, Issue 13, 2002, Pages 1211-1220

The glutathione-activated thiopurine prodrugs trans-6-(2-acetylvinylthio) guanine and cis-6-(2-acetylvinylthio)purine cause less in vivo toxicity than 6-thioguanine after single- and multiple-dose regimens

Author keywords

[No Author keywords available]

Indexed keywords

6 (2 ACETYLVINYLTHIO)GUANINE; 6-(2-ACETYLVINYLTHIO)GUANINE; 6-THIOGUANYLIC ACID; ALANINE AMINOTRANSFERASE; ANTINEOPLASTIC AGENT; ASPARTATE AMINOTRANSFERASE; DRUG DERIVATIVE; GLUTATHIONE; GUANINE; GUANINE NUCLEOTIDE; NUCLEOTIDE; PRODRUG; THIOGUANOSINE PHOSPHATE;

EID: 0038474099     PISSN: 15357163     EISSN: 15388514     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (10)

References (40)
  • 1
    • 0000082652 scopus 로고
    • Structure-activity relationships among purines related to 6-mercaptopurine
    • Clarke, D. A., Elion, G. B., Hitchings, G. H., and Stock, C. C. Structure-activity relationships among purines related to 6-mercaptopurine. Cancer Res., 18: 445-456, 1958.
    • (1958) Cancer Res. , vol.18 , pp. 445-456
    • Clarke, D.A.1    Elion, G.B.2    Hitchings, G.H.3    Stock, C.C.4
  • 2
    • 0001957721 scopus 로고
    • Purine and pyrimidine biochemistry, and some relevant clinical and preclinical cancer chemotherapy research
    • G. Powis and R. A. Prough (eds.), New York: Taylor and Francis
    • Martin, D. S. Purine and pyrimidine biochemistry, and some relevant clinical and preclinical cancer chemotherapy research. In: G. Powis and R. A. Prough (eds.), Metabolism and Action of Anti-Cancer Drug, pp. 91-140. New York: Taylor and Francis, 1987.
    • (1987) Metabolism and Action of Anti-Cancer Drug , pp. 91-140
    • Martin, D.S.1
  • 3
    • 0022401174 scopus 로고
    • The pharmacology and metabolism of the thiopurine drugs 6-mercaptopurine and azathioprine
    • van Scoik, K. G., Johnson, C. A., and Porter, W. R. The pharmacology and metabolism of the thiopurine drugs 6-mercaptopurine and azathioprine. Drug Metab. Rev., 16: 157-174, 1985. (Pubitemid 16191932)
    • (1985) Drug Metabolism Reviews , vol.16 , Issue.1-2 , pp. 157-174
    • Van Scoik, K.G.1    Johnson, C.A.2    Porter, W.R.3
  • 4
    • 0029073930 scopus 로고
    • Methylation of mercaptopurine, thioguanine and their nucleotide metabolites by heterologously expressed human thiopurine S-methyltransferase
    • Krynetski, E. Y., Krynetskaia, N. F., Yanishevski, Y., and Evans, W. E. Methylation of mercaptopurine, thioguanine and their nucleotide metabolites by heterologously expressed human thiopurine S-methyltransferase. Mol. Pharmacol., 47: 1141-1147, 1995.
    • (1995) Mol. Pharmacol. , vol.47 , pp. 1141-1147
    • Krynetski, E.Y.1    Krynetskaia, N.F.2    Yanishevski, Y.3    Evans, W.E.4
  • 5
    • 0026758498 scopus 로고
    • The clinical pharmacology of 6-mercaptopurine
    • Lennard, L. The clinical pharmacology of 6-mercaptopurine. Eur. J. Clin. Pharmacol., 43: 329-339, 1992.
    • (1992) Eur. J. Clin. Pharmacol. , vol.43 , pp. 329-339
    • Lennard, L.1
  • 6
    • 72849178625 scopus 로고
    • A comparison of the metabolism of 6-mercaptopurine and its 6-methyl analog in the rat
    • Sarcione, E. J., and Stutzman, L. A comparison of the metabolism of 6-mercaptopurine and its 6-methyl analog in the rat. Cancer Res., 20: 387-392, 1960.
    • (1960) Cancer Res. , vol.20 , pp. 387-392
    • Sarcione, E.J.1    Stutzman, L.2
  • 7
    • 0024554561 scopus 로고
    • The purine path to chemotherapy
    • Elion, G. B. The purine path to chemotherapy. Science (Wash. DC), 244: 41-47, 1989. (Pubitemid 19130741)
    • (1989) Science , vol.244 , Issue.4900 , pp. 41-47
    • Elion, G.B.1
  • 8
    • 0027973369 scopus 로고
    • The cytotoxicity of thioguanine vs mercaptopurine in acute lymphoblastic leukemia
    • DOI 10.1016/0145-2126(94)90159-7
    • Adamson, P. C., Poplack, D. G., and Balis, F. M. The cytotoxicity of thioguanine versus mercaptopurine in acute lymphoblastic leukemia. Leuk. Res., 18: 805-810, 1994. (Pubitemid 24338172)
    • (1994) Leukemia Research , vol.18 , Issue.11 , pp. 805-810
    • Adamson, P.C.1    Poplack, D.G.2    Balis, F.M.3
  • 10
    • 70449185495 scopus 로고
    • 6-Mercaptopurine in childhood leukemia. Comparison of large dose interrupted with small dose continuous therapy
    • Hymen, C. B., Brubaker, C., and Sturgeon, P. 6-Mercaptopurine in childhood leukemia. Comparison of large dose interrupted with small dose continuous therapy. Cancer Res., 17: 851-856, 1957.
    • (1957) Cancer Res. , vol.17 , pp. 851-856
    • Hymen, C.B.1    Brubaker, C.2    Sturgeon, P.3
  • 11
    • 0002360109 scopus 로고
    • Comparative clinical toxicity of 6-mercaptopurine (NSC-755) and 6-mercaptopurine ribonucleoside (NSC-4911) administered intravenously to patients with advanced cancer
    • Regelson, W., Holland, J. F., Frei, E., III, Gold, G. L., Hall, T., Krant, M., and Miller, S. O. Comparative clinical toxicity of 6-mercaptopurine (NSC-755) and 6-mercaptopurine ribonucleoside (NSC-4911) administered intravenously to patients with advanced cancer. Cancer Chemother. Rep., 36: 41-48, 1964.
    • (1964) Cancer Chemother. Rep. , vol.36 , pp. 41-48
    • Regelson, W.1    Holland, J.F.2    Frei III, E.3    Gold, G.L.4    Hall, T.5    Krant, M.6    Miller, S.O.7
  • 12
    • 0000378195 scopus 로고
    • Hepatotoxicity of mercaptopurine
    • Einhorn, M., and Davidshon, I. Hepatotoxicity of mercaptopurine. J. Am. Med. Assoc., 188: 802-806, 1964.
    • (1964) J. Am. Med. Assoc. , vol.188 , pp. 802-806
    • Einhorn, M.1    Davidshon, I.2
  • 13
    • 0016832011 scopus 로고
    • Phase II trials with procarbazine (NSC-77213), streptozotocin (NSC-85998), 6-thioguanine (NSC-752), and CCNU (NSC-79037) in patients with metastatic cancer of the large bowel
    • Horton, J., Mittelman, A., Taylor, S. G., III, Jurkowitz, L., Bennett, J. M., Ezdinli, E., Colsky, J., and Hanley, J. A. Phase II trials with procarbazine (NSC-77213), streptozotocin (NSC-85998), 6-thioguanine (NSC-752), and CCNU (NSC-79037) in patients with metastatic cancer of the large bowel. Cancer Chemother. Rep., 59: 333-340, 1975.
    • (1975) Cancer Chemother. Rep. , vol.59 , pp. 333-340
    • Horton, J.1    Mittelman, A.2    Taylor III, S.G.3    Jurkowitz, L.4    Bennett, J.M.5    Ezdinli, E.6    Colsky, J.7    Hanley, J.A.8
  • 15
    • 0038135110 scopus 로고
    • The effectiveness of 2-amino-6-[(1-methyl-4-nitro-5-imidazolyl)thio] purine (B.W. 57-323) in metastatic squamous cell carcinoma of the oropharynx and larynx
    • Frank, W., and Tornyos, K. The effectiveness of 2-amino-6-[(1-methyl-4- nitro-5-imidazolyl)thio]purine (B.W. 57-323) in metastatic squamous cell carcinoma of the oropharynx and larynx. Cancer Chemother. Rep., 20: 113-115, 1962.
    • (1962) Cancer Chemother. Rep. , vol.20 , pp. 113-115
    • Frank, W.1    Tornyos, K.2
  • 17
    • 0024365674 scopus 로고
    • Implications for therapy of drug-metabolizing enzymes in human colon cancer
    • Mekhail-Ishak, K., Hudson, N., Tsao, M-S., and Batist, G. Implications for therapy of drug-metabolizing enzymes in human colon cancer. Cancer Res., 49: 4866-4869, 1989. (Pubitemid 19213639)
    • (1989) Cancer Research , vol.49 , Issue.17 , pp. 4866-4869
    • Mekhail-Ishak, K.1    Hudson, N.2    Tsao, M.-S.3    Batist, G.4
  • 18
    • 0030907575 scopus 로고    scopus 로고
    • Breast cancer: Pretreatment drug resistance parameters (GSH-system, ATase, P-glycoprotein) in tumor tissue and their correlation with clinical and prognostic characteristics
    • DOI 10.1023/A:1008202723066
    • Buser, K., Joncourt, F., Altermatt, H-J., Bacchi, M., Oberli, A., and Cerny, T. Breast cancer: pretreament drug resistance parameters (GSH-system, ATase, P-glycoprotein) in tumor tissue and their correlation with clinical and prognostic characteristics. Ann. Oncol., 8: 335-341, 1997. (Pubitemid 27230973)
    • (1997) Annals of Oncology , vol.8 , Issue.4 , pp. 335-341
    • Buser, K.1    Joncourt, F.2    Altermatt, H.-J.3    Bacchi, M.4    Oberli, A.5    Cerny, T..6
  • 21
    • 0033953170 scopus 로고    scopus 로고
    • GSH extrusion and the mitochondrial pathway of apoptotic signalling
    • Coppola, S., and Ghibelli, L. GSH extrusion and the mitochondrial pathway of apoptotic signalling. Biochem. Soc. Trans., 28: 56-61, 2000. (Pubitemid 30103213)
    • (2000) Biochemical Society Transactions , vol.28 , Issue.2 , pp. 56-61
    • Coppola, S.1    Ghibelli, L.2
  • 22
    • 0033088957 scopus 로고    scopus 로고
    • The role of glutathione in the regulation of apoptosis
    • DOI 10.1046/j.1365-2362.1999.00447.x
    • Hall, A. G. The role of glutathione in the regulation of apoptosis. Eur. J. Clin. Investig., 29: 238-245, 1999. (Pubitemid 29106315)
    • (1999) European Journal of Clinical Investigation , vol.29 , Issue.3 , pp. 238-245
    • Hall, A.G.1
  • 23
    • 0032143389 scopus 로고    scopus 로고
    • Multiple drug resistance parameter expression in ovarian cancer
    • DOI 10.1006/gyno.1998.5085
    • Joncourt, F., Buser, K., Altermatt, H., Bacchi, M., Oberli, A., and Cerny, T. Multiple drug resistance parameter expression in ovarian cancer. Gynecol. Oncol., 70: 176-182, 1998. (Pubitemid 28430925)
    • (1998) Gynecologic Oncology , vol.70 , Issue.2 , pp. 176-182
    • Joncourt, F.1    Buser, K.2    Altermatt, H.3    Bacchi, M.4    Oberli, A.5    Cerny, T.6
  • 24
    • 0027272622 scopus 로고
    • Glutathione levels and variability in breast tumor and normal tissue
    • Phila.
    • Perry, R. R., Mazetta, J., Levin, M., and Barranco, S. C. Glutathione levels and variability in breast tumor and normal tissue. Cancer (Phila.), 72: 786-787, 1993.
    • (1993) Cancer , vol.72 , pp. 786-787
    • Perry, R.R.1    Mazetta, J.2    Levin, M.3    Barranco, S.C.4
  • 25
    • 0025331750 scopus 로고
    • P-170 glycoprotein, glutathione and associated enzymes in relation to chemoresistance of primary human renal cell carcinomas
    • Mickisch, G., Bier, H., Bergler, W., Bak, M., Tschada, R., and Alken, P. P-170 glycoprotein, glutathione and associated enzymes in relation to chemoresistance of primary human renal cell carcinomas. Urol. Int., 45: 170-176, 1990. (Pubitemid 20172046)
    • (1990) Urologia Internationalis , vol.45 , Issue.3 , pp. 170-176
    • Mickisch, G.1    Bier, H.2    Bergler, W.3    Bak, M.4    Tschada, R.5    Alken, P.6
  • 26
    • 0029954846 scopus 로고    scopus 로고
    • Glutathione and related enzymes in multidrug resistance
    • O'Brien, M. L., and Tew, K. D. Glutathione and related enzymes in multidrug resistance. Eur. J. Cancer, 32A: 967-978, 1996.
    • (1996) Eur. J. Cancer , vol.32 A , pp. 967-978
    • O'Brien, M.L.1    Tew, K.D.2
  • 28
    • 0036129205 scopus 로고    scopus 로고
    • Novel glutathione-dependent thiopurine prodrugs: Evidence for enhanced cytotoxicity in tumor cells and for decreased bone marrow toxicity in mice
    • DOI 10.1124/jpet.301.1.77
    • Gunnarsdottir, S., Rucki, M., and Elfarra, A. A. Novel glutathionedependent thiopurine prodrugs: evidence for enhanced cytotoxicity in tumor cells and for decreased bone marrow toxicity in mice. J. Pharmacol. Exp. Ther., 301: 77-86, 2002. (Pubitemid 34250282)
    • (2002) Journal of Pharmacology and Experimental Therapeutics , vol.301 , Issue.1 , pp. 77-86
    • Gunnarsdottir, S.1    Rucki, M.2    Elfarra, A.A.3
  • 29
    • 84880287342 scopus 로고    scopus 로고
    • Novel glutathione-activated thiopurine prodrugs exhibit less bone marrow and intestinal toxicity than 6-thioguanine
    • Gunnarsdottir, S., Rucki, M., Phillips, L. A., Young, K. M., and Elfarra, A. A. Novel glutathione-activated thiopurine prodrugs exhibit less bone marrow and intestinal toxicity than 6-thioguanine. Proc. Am. Assoc. Cancer Res., 43: 79, 2002.
    • (2002) Proc. Am. Assoc. Cancer Res. , vol.43 , pp. 79
    • Gunnarsdottir, S.1    Rucki, M.2    Phillips, L.A.3    Young, K.M.4    Elfarra, A.A.5
  • 30
    • 0004934556 scopus 로고
    • The enzymatic oxidation of 6-mercaptopurine to 6-thiouric acid
    • Bergmann, F., and Ungar, H. The enzymatic oxidation of 6-mercaptopurine to 6-thiouric acid. J. Am. Chem. Soc., 82: 3957-3960, 1960.
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 3957-3960
    • Bergmann, F.1    Ungar, H.2
  • 31
    • 84965043979 scopus 로고
    • The hematological alterations resulting from repeated injections of 6-mercaptopurine into AKR mice
    • Latta, J. S., and Gentry, R. P. The hematological alterations resulting from repeated injections of 6-mercaptopurine into AKR mice. Anat. Rec., 132: 1-23, 1958.
    • (1958) Anat. Rec. , vol.132 , pp. 1-23
    • Latta, J.S.1    Gentry, R.P.2
  • 35
    • 0022652352 scopus 로고
    • Formation of 6-thioguanine and 6-mercaptopurine from their 9-alkyl derivatives in mice
    • Nelson, J. A., and Vidale, E. Formation of 6-thioguanine and 6-mercaptopurine from their 9-alkyl derivatives in mice. Cancer Res., 46: 137-140, 1986. (Pubitemid 16189042)
    • (1986) Cancer Research , vol.46 , Issue.1 , pp. 137-140
    • Nelson, J.A.1    Vidale, E.2
  • 36
    • 84965082063 scopus 로고
    • Inhibition by cytotoxic drugs of bone marrow regeneration after irradiation and marrow transplantation
    • Hollingsworth, J. W. Inhibition by cytotoxic drugs of bone marrow regeneration after irradiation and marrow transplantation. Cancer Res., 19: 165-169, 1959.
    • (1959) Cancer Res. , vol.19 , pp. 165-169
    • Hollingsworth, J.W.1
  • 37
    • 0037797348 scopus 로고
    • A summary of investigations with 2-amino-6-[(1-methyl-4-nitro-5- imidazolyl)thio]purine (B.W. 57-323) in animals
    • Elion, G. B., Bieber, S., and Hitchings, G. H. A summary of investigations with 2-amino-6-[(1-methyl-4-nitro-5-imidazolyl)thio]purine (B.W. 57-323) in animals. Cancer Chemother. Rep., 8: 36-43, 1960.
    • (1960) Cancer Chemother. Rep. , vol.8 , pp. 36-43
    • Elion, G.B.1    Bieber, S.2    Hitchings, G.H.3
  • 38
    • 0002539411 scopus 로고
    • A summary of investigations with 6-[(1-methyl-4-nitro-5-imidazolyl) thio]purine (B.W. 57-322)
    • Elion, G. B., Callahan, S., Bieber, S., Hitchings, G. H., and Rundles, R. W. A summary of investigations with 6-[(1-methyl-4-nitro-5-imidazolyl) thio]purine (B.W. 57-322). Cancer Chemother. Rep., 14: 93-98, 1961.
    • (1961) Cancer Chemother. Rep. , vol.14 , pp. 93-98
    • Elion, G.B.1    Callahan, S.2    Bieber, S.3    Hitchings, G.H.4    Rundles, R.W.5
  • 39
    • 0025342366 scopus 로고
    • Pharmacokinetics of oral 6-mercaptopurine: Relationship between plasma levels and urine excretion of parent drug
    • Endresen, L., Lie, S. O., Storm-Mathisen, I., Rugstad, H. E., and Stokke, O. Pharmacokinetics of oral 6-mercaptopurine: relationship between plasma levels and urine excretion of parent drug. Ther. Drug Monit., 12: 227-234, 1990. (Pubitemid 20150886)
    • (1990) Therapeutic Drug Monitoring , vol.12 , Issue.3 , pp. 227-234
    • Endresen, L.1    Lie, S.O.2    Storm-Mathisen, I.3    Rugstad, H.E.4    Stokke, O.5
  • 40
    • 0031874260 scopus 로고    scopus 로고
    • Pharmacokinetics and metabolism of thiopurines in children with acute lymphoblastic leukemia receiving 6-thioguanine versus 6-mercaptopurine
    • DOI 10.1007/s002800050816
    • Erb, N., Harms, D. O., and Janka-Schaub, G. Pharmacokinetics and metabolism of thiopurines in children with acute lymphoplastic leukemia given 6-thioguanine versus 6-mercaptopurine. Cancer Chemother. Pharmacol., 42: 266-272, 1998. (Pubitemid 28393842)
    • (1998) Cancer Chemotherapy and Pharmacology , vol.42 , Issue.4 , pp. 266-272
    • Erb, N.1    Harms, D.O.2    Janka-Schaub, G.3


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