메뉴 건너뛰기




Volumn 76, Issue 9, 1997, Pages 1170-1180

5-Ethynyluracil (GW776): Effects on the formation of the toxic catabolites of 5-fluorouracil, fluoroacetate and fluorohydroxypropionic acid in the isolated perfused rat liver model

Author keywords

2 fluoro 3 hydroxypropionic acid; 5 ethynyluracil (GW776); 5 fluorouracil; 19F nuclear magnetic resonance; Fluoroacetate; Isolated perfused rat liver; Modulation of 5 fluorouracil metabolism

Indexed keywords

5 ETHYNYLURACIL; ALPHA FLUORO BETA ALANINE; DIHYDROPYRIMIDINE DEHYDROGENASE; FLUORINE; FLUOROACETIC ACID; FLUOROURACIL; PROPIONIC ACID DERIVATIVE;

EID: 0030845828     PISSN: 00070920     EISSN: None     Source Type: Journal    
DOI: 10.1038/bjc.1997.529     Document Type: Article
Times cited : (21)

References (39)
  • 1
    • 0028280275 scopus 로고
    • Fluorouracil cardiotoxicity
    • Anand AJ (1994) Fluorouracil cardiotoxicity. Ann Pharmacother 28: 374-378
    • (1994) Ann Pharmacother , vol.28 , pp. 374-378
    • Anand, A.J.1
  • 2
    • 0347650146 scopus 로고
    • First demonstration that the anticancer drug, 5-fluorouracil, is metabolized in the isolated perfused rat liver into highly cardiotoxic fluoroacetate
    • Arellano M, Malet-Martino M and Martino R (1994) First demonstration that the anticancer drug, 5-fluorouracil, is metabolized in the isolated perfused rat liver into highly cardiotoxic fluoroacetate. Proc Soc Magnetic Resonance 1320.
    • (1994) Proc Soc Magnetic Resonance , pp. 1320
    • Arellano, M.1    Malet-Martino, M.2    Martino, R.3
  • 3
    • 0027489763 scopus 로고
    • 5-ethynyluracil (776C85): A potent modulator of the pharmacokinetics and antitumor efficacy of 5-fluorouracil
    • Baccanari DP, Davis ST, Knick VC and Spector T (1993) 5-ethynyluracil (776C85): a potent modulator of the pharmacokinetics and antitumor efficacy of 5-fluorouracil. Proc Natl Acad Sci USA 90: 11064-11068
    • (1993) Proc Natl Acad Sci USA , vol.90 , pp. 11064-11068
    • Baccanari, D.P.1    Davis, S.T.2    Knick, V.C.3    Spector, T.4
  • 5
    • 0038085032 scopus 로고
    • Isolated rat liver preparation. Bile production and other basic properties
    • Brauer RW, Pessotti RL and Pizzolato P (1951) Isolated rat liver preparation. Bile production and other basic properties. Proc Soc Exp Biol Med 78: 174-181
    • (1951) Proc Soc Exp Biol Med , vol.78 , pp. 174-181
    • Brauer, R.W.1    Pessotti, R.L.2    Pizzolato, P.3
  • 6
    • 0028281781 scopus 로고
    • 5-ethynyluracil (776C85): Modulation of 5-fluorouracil efficacy and therapeutic index in rats bearing advanced colorectal carcinoma
    • Cao S, Rustum YM and Spector T (1994) 5-ethynyluracil (776C85): modulation of 5-fluorouracil efficacy and therapeutic index in rats bearing advanced colorectal carcinoma. Cancer Res 54: 1507-1510
    • (1994) Cancer Res , vol.54 , pp. 1507-1510
    • Cao, S.1    Rustum, Y.M.2    Spector, T.3
  • 7
    • 0028106211 scopus 로고
    • 5-ethynyluracil (776C85): Protection from 5-fluorouracil-induced neurotoxicity in dogs
    • Davis ST, Joyner SS, Baccanari DP and Spector T (1994) 5-ethynyluracil (776C85): protection from 5-fluorouracil-induced neurotoxicity in dogs. Biochem Pharmacol 48: 233-236
    • (1994) Biochem Pharmacol , vol.48 , pp. 233-236
    • Davis, S.T.1    Joyner, S.S.2    Baccanari, D.P.3    Spector, T.4
  • 8
    • 0344248958 scopus 로고
    • 5-ethynyluracil (5EU, 776C85): Effects on thymidylate synthase (TS) inhibition and incorporation of 5-FU into RNA in mice bearing s.c. MOPC-315 tumors
    • Davis ST, Baccanari DP and Spector T (1995) 5-ethynyluracil (5EU, 776C85): effects on thymidylate synthase (TS) inhibition and incorporation of 5-FU into RNA in mice bearing s.c. MOPC-315 tumors. Proc Am Assoc Cancer Res 36: 292
    • (1995) Proc Am Assoc Cancer Res , vol.36 , pp. 292
    • Davis, S.T.1    Baccanari, D.P.2    Spector, T.3
  • 10
    • 37049107127 scopus 로고
    • Stereochemistry of catabolism of the DNA base thymine and of the anti-cancer drug 5-fluorouracil
    • Gani D, Hitchcock PB and Young DW (1985) Stereochemistry of catabolism of the DNA base thymine and of the anti-cancer drug 5-fluorouracil. J Chem Soc Perkin Trans 1, 1363-1372
    • (1985) J Chem Soc Perkin Trans , vol.1 , pp. 1363-1372
    • Gani, D.1    Hitchcock, P.B.2    Young, D.W.3
  • 11
    • 0023187085 scopus 로고
    • Clinical pharmacokinetics of 5-fluorouracil and its metabolites in plasma, urine, and bile
    • Heggie GD, Sommadossi JP, Cross DS, Huster WJ and Diasio RB (1987) Clinical pharmacokinetics of 5-fluorouracil and its metabolites in plasma, urine, and bile. Cancer Res 47: 2203-2206
    • (1987) Cancer Res , vol.47 , pp. 2203-2206
    • Heggie, G.D.1    Sommadossi, J.P.2    Cross, D.S.3    Huster, W.J.4    Diasio, R.B.5
  • 12
    • 0023931286 scopus 로고
    • 19F nuclear magnetic resonance spectroscopy, for patients receiving chemotherapy with or without methotrexate pretreatment
    • 19F nuclear magnetic resonance spectroscopy, for patients receiving chemotherapy with or without methotrexate pretreatment. Cancer Res 48: 1680-1688
    • (1988) Cancer Res , vol.48 , pp. 1680-1688
    • Hull, W.E.1    Port, R.E.2    Herrmann, R.3    Britsch, B.4    Kunz, W.5
  • 14
    • 0014834207 scopus 로고
    • Biochemical basis for fluorouracil neurotoxicity
    • Koenig H and Patel A (1970) Biochemical basis for fluorouracil neurotoxicity. Arch Neurol 23: 155-160
    • (1970) Arch Neurol , vol.23 , pp. 155-160
    • Koenig, H.1    Patel, A.2
  • 15
    • 0026665811 scopus 로고
    • Cardiotoxicity of commercial 5-fluorouracil vials stems from the alkaline hydrolysis of this drug
    • Lemaire L, Malet-Martino MC, De Forni M, Martino R and Lasserre B (1992) Cardiotoxicity of commercial 5-fluorouracil vials stems from the alkaline hydrolysis of this drug. Br J Cancer 66: 119-127
    • (1992) Br J Cancer , vol.66 , pp. 119-127
    • Lemaire, L.1    Malet-Martino, M.C.2    De Forni, M.3    Martino, R.4    Lasserre, B.5
  • 16
    • 0028105304 scopus 로고
    • The Tris formulation of 5-fluorouracil is more cardiotoxic than the sodium salt formulations
    • Lemaire L, Malet-Martino MC, Martino R, De Forni M and Lasserre B (1994) The Tris formulation of 5-fluorouracil is more cardiotoxic than the sodium salt formulations. Oncol Rep 1: 173-174
    • (1994) Oncol Rep , vol.1 , pp. 173-174
    • Lemaire, L.1    Malet-Martino, M.C.2    Martino, R.3    De Forni, M.4    Lasserre, B.5
  • 18
    • 0026491216 scopus 로고
    • Magnetic resonance spectroscopy: A powerful tool for drug metabolism studies
    • Malet-Martino MC and Martino R (1992) Magnetic resonance spectroscopy: a powerful tool for drug metabolism studies. Biochimie 74: 785-800
    • (1992) Biochimie , vol.74 , pp. 785-800
    • Malet-Martino, M.C.1    Martino, R.2
  • 19
    • 0023818907 scopus 로고
    • 19F NMR spectrometry evidence for bile acid conjugates of α-fluoro-β-alanine as the main biliary metabolites of antineoplastic fluoropyrimidines in humans
    • 19F NMR spectrometry evidence for bile acid conjugates of α-fluoro-β-alanine as the main biliary metabolites of antineoplastic fluoropyrimidines in humans. Drug Metab Dispos 16: 78-84
    • (1988) Drug Metab Dispos , vol.16 , pp. 78-84
    • Malet-Martino, M.C.1    Bernadou, J.2    Martino, R.3    Armand, J.P.4
  • 20
    • 0021995130 scopus 로고
    • Release of fluoride ion from 5′-deoxy-5-fluorouridine, an antineoplastic fluoropyrimidine, in humans
    • Martino R, Lopez A, Malet-Martino MC, Bernadou J and Armand JP (1985) Release of fluoride ion from 5′-deoxy-5-fluorouridine, an antineoplastic fluoropyrimidine, in humans. Drug Metab Dispos 13: 116-118
    • (1985) Drug Metab Dispos , vol.13 , pp. 116-118
    • Martino, R.1    Lopez, A.2    Malet-Martino, M.C.3    Bernadou, J.4    Armand, J.P.5
  • 21
    • 0023522785 scopus 로고
    • 19F NMR analysis of the carbamate reaction of α-fluoro-β-alanine, the major catabolite of fluoropyrimidines. Application to FBAL carbamate determination in body fluids of patients treated with 5′-deoxy-5-fluorouridine
    • 19F NMR analysis of the carbamate reaction of α-fluoro-β-alanine, the major catabolite of fluoropyrimidines. Application to FBAL carbamate determination in body fluids of patients treated with 5′-deoxy-5-fluorouridine. Drug Metab Dispos 15: 897-904
    • (1987) Drug Metab Dispos , vol.15 , pp. 897-904
    • Martino, R.1    Malet-Martino, M.C.2    Vialaneix, C.3    Lopez, A.4    Bon, M.5
  • 22
    • 85028628281 scopus 로고
    • The use of sodium fluoroacetate (compound 1080) for the control of the rabbit in Tasmania
    • Meldrum GK and Bignell JT (1957) The use of sodium fluoroacetate (compound 1080) for the control of the rabbit in Tasmania. The Aust Vet J 33: 186-196
    • (1957) The Aust Vet J , vol.33 , pp. 186-196
    • Meldrum, G.K.1    Bignell, J.T.2
  • 24
    • 0021268296 scopus 로고
    • Neuropathologic study on chronic neurotoxicity of 5-fluorouracil and its masked compounds in dogs
    • Okeda R, Karakama T, Kimura S, Toizumi S, Mitsushima T and Yokoyama Y (1984) Neuropathologic study on chronic neurotoxicity of 5-fluorouracil and its masked compounds in dogs. Acta Neuropathol 63: 334-343
    • (1984) Acta Neuropathol , vol.63 , pp. 334-343
    • Okeda, R.1    Karakama, T.2    Kimura, S.3    Toizumi, S.4    Mitsushima, T.5    Yokoyama, Y.6
  • 25
    • 0025010640 scopus 로고
    • Experimental neurotoxicity of 5-fluorouracil and its derivatives is due to poisoning by the monofluorinated organic metabolites, monofluoroacetic acid and α-fluoro-β-alanine
    • Okeda R, Shibutani M, Matsuo T, Kuroiwa T, Shimokawa R and Tajima T (1990) Experimental neurotoxicity of 5-fluorouracil and its derivatives is due to poisoning by the monofluorinated organic metabolites, monofluoroacetic acid and α-fluoro-β-alanine. Acta Neuropathol 81: 66-73
    • (1990) Acta Neuropathol , vol.81 , pp. 66-73
    • Okeda, R.1    Shibutani, M.2    Matsuo, T.3    Kuroiwa, T.4    Shimokawa, R.5    Tajima, T.6
  • 26
    • 0025786725 scopus 로고
    • 19F nuclear magnetic resonance analysis of 5-fluorouracil metabolism in four differently pigmented strains of Nectria haematococca
    • 19F nuclear magnetic resonance analysis of 5-fluorouracil metabolism in four differently pigmented strains of Nectria haematococca. Appl Environ Microbiol 57: 3605-3612
    • (1991) Appl Environ Microbiol , vol.57 , pp. 3605-3612
    • Parisot, D.1    Malet-Martino, M.C.2    Martino, R.3    Crasnier, P.4
  • 28
    • 0026701936 scopus 로고
    • Mechanism-based inactivation of dihydropyrimidine dehydrogenase by 5-ethynyluracil
    • Porter DJT, Chestnut WG, Merrill BM and Spector T (1992) Mechanism-based inactivation of dihydropyrimidine dehydrogenase by 5-ethynyluracil. J Biol Chem 267: 5236-5242
    • (1992) J Biol Chem , vol.267 , pp. 5236-5242
    • Porter, D.J.T.1    Chestnut, W.G.2    Merrill, B.M.3    Spector, T.4
  • 31
    • 0027135995 scopus 로고
    • 5-ethynyluracil (776C85): Inactivation of dihydropyrimidine dehydrogenase in vivo
    • Spector T, Harrington JA and Porter DJT (1993) 5-ethynyluracil (776C85): inactivation of dihydropyrimidine dehydrogenase in vivo. Biochem Pharmacol 46: 2243-2248
    • (1993) Biochem Pharmacol , vol.46 , pp. 2243-2248
    • Spector, T.1    Harrington, J.A.2    Porter, D.J.T.3
  • 33
    • 0017802994 scopus 로고
    • Biochemical and ultrastructural evaluation of isolated rat liver systems perfused with a hemoglobin-free medium
    • Sugano T, Suda K, Shimada M and Oshino N (1978) Biochemical and ultrastructural evaluation of isolated rat liver systems perfused with a hemoglobin-free medium. J Biochem 83: 995-1007
    • (1978) J Biochem , vol.83 , pp. 995-1007
    • Sugano, T.1    Suda, K.2    Shimada, M.3    Oshino, N.4
  • 34
    • 0023934756 scopus 로고
    • Formation of conjugates of 2-fluoro-beta-alanine and bile acids during the metabolism of 5-fluorouracil and 5-fluoro-2-deoxyuridine in the isolated perfused rat liver
    • Sweeny DJ, Barnes S and Diasio RB (1988) Formation of conjugates of 2-fluoro-beta-alanine and bile acids during the metabolism of 5-fluorouracil and 5-fluoro-2-deoxyuridine in the isolated perfused rat liver. Cancer Res 48: 2010-2014
    • (1988) Cancer Res , vol.48 , pp. 2010-2014
    • Sweeny, D.J.1    Barnes, S.2    Diasio, R.B.3
  • 35
    • 0020760615 scopus 로고
    • Oxygen consumption by rat liver: Effects of taurocholate and sulfobromophthalein transport, glucagon, and cation substitution
    • Van Dyke RW, Gollan JL and Scharschmidt BF (1983) Oxygen consumption by rat liver: effects of taurocholate and sulfobromophthalein transport, glucagon, and cation substitution. Am J Physiol 244: G523-G531
    • (1983) Am J Physiol , vol.244
    • Van Dyke, R.W.1    Gollan, J.L.2    Scharschmidt, B.F.3
  • 36
    • 0015738891 scopus 로고
    • Rales of synthesis of ribosomal protein and total ribonucleic acid through the cell cycle of the fission yeast Schizosaccharomyces pombe
    • Wain WH and Staatz WD (1973) Rales of synthesis of ribosomal protein and total ribonucleic acid through the cell cycle of the fission yeast Schizosaccharomyces pombe. Exp Cell Res 81: 269-278
    • (1973) Exp Cell Res , vol.81 , pp. 269-278
    • Wain, W.H.1    Staatz, W.D.2
  • 37
    • 0028577519 scopus 로고
    • Acute confusion induced by a high-dose infusion of 5-fluorouracil and folinic acid
    • Yeh KH and Cheng AL (1994) Acute confusion induced by a high-dose infusion of 5-fluorouracil and folinic acid. J Formos Med Assoc 93: 721-723
    • (1994) J Formos Med Assoc , vol.93 , pp. 721-723
    • Yeh, K.H.1    Cheng, A.L.2
  • 38
    • 0026526790 scopus 로고
    • Pharmacokinetics and tissue distribution of 2-fluoro-β-alanine in rats. Potential relevance to toxicity pattern of 5-fluorouracil
    • Zhang R, Soong SJ, Liu T, Barnes E and Diasio RB (1992) Pharmacokinetics and tissue distribution of 2-fluoro-β-alanine in rats. Potential relevance to toxicity pattern of 5-fluorouracil. Drug Metab Dispos 20: 113-119
    • (1992) Drug Metab Dispos , vol.20 , pp. 113-119
    • Zhang, R.1    Soong, S.J.2    Liu, T.3    Barnes, E.4    Diasio, R.B.5
  • 39
    • 0027288254 scopus 로고
    • A mathematical model of the kinetics and tissue distribution of 2-fluoro-β-alanine, the major catabolite of 5-fluorouracil
    • Zhang R, Liu T, Soong SJ and Diasio RB (1993) A mathematical model of the kinetics and tissue distribution of 2-fluoro-β-alanine, the major catabolite of 5-fluorouracil. Biochem Pharmacol 45: 2063-2069
    • (1993) Biochem Pharmacol , vol.45 , pp. 2063-2069
    • Zhang, R.1    Liu, T.2    Soong, S.J.3    Diasio, R.B.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.