Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 37, 2007 - Issue 3
138
Views
11
CrossRef citations to date
0
Altmetric
Research Article

Nafamostat is hydrolysed by human liver cytosolic long-chain acyl-CoA hydrolase

, , , , , , , , & show all
Pages 260-270 | Received 16 Oct 2006, Accepted 12 Dec 2006, Published online: 22 Sep 2008

References

  • Abe T, Kinoshita T, Matsuda J, Ogushi T, Kawasugi K, Yoshimura Y, Otomo M. Phase I study of FUT-175-single and multiple dose study (in Japanese). Japanese Pharmacology and Therapeutics 1984; 12: 65–88
  • Aoyama T, Okutome T, Nakayama T, Yaegashi T, Matsui R, Nunomura S, Kurumi M, Sakurai Y, Fujii S. Synthesis and structure–activity study of protease inhibitors. IV. Amidinonaphthols and related acyl derivatives. Chemical and Pharmaceutical Bulletin 1985; 33: 1458–1471
  • Berge RK, Vollset SE, Farstad M. Intracellular localization of palmitoyl-CoA hydrolase and palmitoyl-CoA synthetase in human blood platelets and liver. Scandinavian Journal of Clinical and Laboratory Investigation 1980; 40: 271–278
  • Broustas CG, Hajra AK. Purification, properties, and specificity of rat brain cytosolic fatty acyl coenzyme A hydrolase. Journal of Neurochemistry 1995; 64: 2345–2353
  • Deykin D, Goodman DS. The hydrolysis of long-chain fatty acid esters of cholesterol with rat liver enzymes. Journal of Biological Chemistry 1962; 237: 3649–3656
  • Fujii S, Hitomi Y. New synthetic inhibitors of C1r, C1 esterase, thrombin, plasmin, kallikrein and trypsin. Biochimica et Biophysica Acta 1981; 661: 342–345
  • Hitomi Y, Ikari N, Fujii S. Inhibitory effect of a new synthetic protease inhibitor (FUT-175) on the coagulation system. Haemostasis 1985; 15: 164–168
  • Hosokawa M, Endo T, Fujisawa M, Hara S, Iwata N, Sato Y, Satoh T. Interindividual variation in carboxylesterase levels in human liver microsomes. Drug Metabolism and Disposition 1995; 23: 1022–1027
  • Huhtinen K, O’Byrne J, Lindquist PJ, Contreras JA, Alexson SE. The peroxisome proliferator-induced cytosolic type I acyl-CoA thioesterase (CTE-I) is a serine-histidine-aspartic acid α/β hydrolase. Journal of Biological Chemistry 2002; 277: 3424–3432
  • Hunt MC, Yamada J, Maltais LJ, Wright MW, Podesta EJ, Alexson SE. A revised nomenclature for mammalian acyl-CoA thioesterases/hydrolases. Journal of Lipid Research 2005; 46: 2029–2032
  • Lindquist PJ, Svensson LT, Alexson SE. Molecular cloning of the peroxisome proliferator-induced 46-kDa cytosolic acyl-CoA thioesterase from mouse and rat liver — recombinant expression in Escherichia coli, tissue expression, and nutritional regulation. European Journal of Biochemistry 1998; 251: 631–640
  • Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. Protein measurement with Folin–phenol reagent. Journal of Biological Chemistry 1951; 193: 265–275
  • McCracken NW, Blain PG, Williams FM. Human xenobiotic metabolizing esterases in liver and blood. Biochemical Pharmacology 1993; 46: 1125–1129
  • Mori S, Itoh Y, Shinohata R, Sendo T, Oishi R, Nishibori M. Nafamostat mesilate is an extremely potent inhibitor of human tryptase. Journal of Pharmacological Sciences 2003; 92: 420–423
  • Nanpo T, Ohtsuki T, Jin Y, Matsunaga K, Takahashi M, Shibuya M, Sasaki H, Kurumi M. Pharmacokinetic study of FUT-175 (nafamostat mesilate). (1) Blood level profiles, tissue distribution, metabolism and excretion in rats after intravenous administration. Clinical Report 1984; 18: 467–488
  • Natarajan R, Ghosh S, Grogan W. Catalytic properties of the purified rat hepatic cytosolic cholesteryl ester hydrolase. Biochemical and Biophysical Research Communications 1996; 225: 413–419
  • Robbi M, Van Schaftingen E, Beaufay H. Cloning and sequencing of rat liver carboxylesterase ES-4 (microsomal palmitoyl-CoA hydrolase). Biochemical Journal 1996; 313: 821–826
  • Satoh T, Hosokawa M. The mammalian carboxylesterases: From molecules to functions. Annual Review of Pharmacology and Toxicology 1998; 38: 257–288
  • Segel IH. Enzyme kinetics: Behavior and analysis of rapid equilibrium and steady-state enzyme systems. Wiley, New York, NY 1975
  • Sonnenborn U, Eiteljorge G, Trzeciak WH, Kunau WH. Identical catalytic subunit in both molecular forms of hormone-sensitive cholesterol esterase from bovine adrenal cortex. FEBS Letters 1982; 145: 271–276
  • Tabata T, Katoh M, Tokudome S, Hosakawa M, Chiba K, Nakajima M, Yokoi T. Bioactivation of capecitabine in human liver: Involvement of the cytosolic enzyme on 5′-deoxy-5-fluorocytidine formation. Drug Metabolism and Disposition 2004a; 32: 762–767
  • Tabata T, Katoh M, Tokudome S, Nakajima M, Yokoi T. Identification of the cytosolic carboxylesterase catalyzing the 5′-deoxy-5-fluorocytidine formation from capecitabine in human liver. Drug Metabolism and Disposition 2004b; 32: 1103–1110
  • Testa B, Mayer JM. Hydrolysis in Drug and Prodrug Metabolism: Chemistry, Biochemistry, and Enzymology. Wiley-VCH, Weinheim 2003
  • Watanabe K, Matsunaga T, Yamamoto I, Funae Y, Yoshimura H. Involvement of CYP2C in the metabolism of cannabinoids by human hepatic microsomes from an old woman. Biological and Pharmaceutical Bulletin 1995; 18: 1138–1141
  • Wilcke M, Alexson SE. Characterization of acyl-CoA thioesterase activity in isolated rat liver peroxisomes. Partial purification and characterization of a long-chain acyl-CoA thioesterase. European Journal of Biochemistry 1994; 222: 803–811
  • Williams FM, Mutch EM, Nicholson E, Wynne H, Wright P, Lambert D, Rawlins MD. Human liver and plasma aspirin esterase. Journal of Pharmacy and Pharmacology 1989; 41: 407–409
  • Xu G, Zhang W, Ma MK, McLeod HL. Human carboxylesterase 2 is commonly expressed in tumor tissue and is correlated with activation of irinotecan. Clinical Cancer Research 2002; 8: 2605–2611
  • Yamada J, Furihata T, Iida N, Watanabe T, Hosokawa M, Satoh T, Someya A, Nagaoka I, Suga T. Molecular cloning and expression of cDNAs encoding rat brain and liver cytosolic long-chain acyl-CoA hydrolases. Biochemical and Biophysical Research Communications 1997; 232: 198–203
  • Yamada J, Matsumoto I, Furihata T, Sakuma M, Suga T. Purification and properties of long-chain acyl-CoA hydrolases from the liver cytosol of rats treated with peroxisome proliferator. Archives of Biochemistry and Biophysics 1994; 308: 118–125
  • Yamaori S, Fujiyama N, Kushihara M, Funahashi T, Kimura T, Yamamoto I, Sone T, Isobe M, Ohshima T, Matsumura K, Oda M, Wakanabe K. Involvement of human blood arylesterases and liver microsomal carboxylesterases in nafamostat hydrolysis. Drug Metabolism and Pharmacokinetics 2006; 21: 147–155
  • Yang H, Henkin J, Kim KH, Greer J. Selective inhibition of urokinase by substituted phenylguanidines: Quantitative structure–activity relationship analyses. Journal of Medicinal Chemistry 1990; 33: 2956–2961

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.