Genomic Structure and Transcriptional Regulation of the Rat, Mouse, and Human Carboxylesterase Genes

REFERENCES

• Aida K., Moore R., Negishi M. Cloning and nucleotide sequence of a novel, male-predominant carboxylesterase in mouse liver. Biochim. Biophys. Acta 1993; 1174: 72–74
   PubMed Web of Science ®Google Scholar
• Alam M., Vance D. E., Lehner R. Structure-function analysis of human triacylglycerol hydrolase by site-directed mutagenesis: identification of the catalytic triad and a glycosylation site. Biochemistry 2002; 41: 6679–6687
   PubMed Web of Science ®Google Scholar
• Aldridge W. N. The esterases: perspectives and problems. Chem. Biol. Interact. 1993; 87: 5–13
   PubMed Web of Science ®Google Scholar
• Bencharit S., Morton C. L., Howard-Williams E. L., Danks M. K., Potter P. M., Redinbo M. R. Structural insights into CPT-11 activation by mammalian carboxylesterases. Nat. Struct. Biol. 2002; 9: 337–342
   PubMedGoogle Scholar
• Bencharit S., Morton C. L., Hyatt J. L., Kuhn P., Danks M. K., Potter P. M., Redinbo M. R. Crystal structure of human carboxylesterase 1 complexed with the Alzheimer's drug tacrine: from binding promiscuity to selective inhibition. Chem. Biol. 2003a; 10: 341–349
   PubMed Web of Science ®Google Scholar
• Bencharit S., Morton C. L., Xue Y., Potter P. M., Redinbo M. R. Structural basis of heroin and cocaine metabolism by a promiscuous human drug-processing enzyme. Nat. Struct. Biol. 2003b; 10: 349–356
   PubMedGoogle Scholar
• Cygler M., Schrag J. D., Sussman J. L., Harel M., Silman I., Gentry M. K., Doctor B. P. Relationship between sequence conservation and three-dimensional structure in a large family of esterases, lipases, and related proteins. Protein Sci. 1993; 2: 366–382
   PubMed Web of Science ®Google Scholar
• Dolinsky V. W., Sipione S., Lehner R., Vance D. E. The cloning and expression of a murine triacylglycerol hydrolase cDNA and the structure of its corresponding gene. Biochim. Biophys. Acta 2001; 1532: 162–172
   PubMed Web of Science ®Google Scholar
• Frey P. A., Whitt S. A., Tobin J. B. A low-barrier hydrogen bond in the catalytic triad of serine proteases. Science 1994; 264: 1927–1930
   PubMed Web of Science ®Google Scholar
• Furihata T., Hosokawa M., Fujii A., Derbel M., Satoh T., Chiba K. Dexamethasone-induced methylprednisolone hemisuccinate hydrolase: Its identification as a member of the rat carboxylesterase 2 family and its unique existence in plasma. Biochem. Pharmacol. 2005; 69: 1287–1297
   PubMed Web of Science ®Google Scholar
• Furihata T., Hosokawa M., Koyano N., Nakamura T., Satoh T., Chiba K. Identification of di-(2-ethylhexyl) phthalate-induced carboxylesterase 1 in C57BL/6 mouse liver microsomes: Purification, cDNA cloning, and baculovirus-mediated expression. Drug Metab. Dispos. 2004a; 32: 1170–1177
   PubMed Web of Science ®Google Scholar
• Furihata T., Hosokawa M., Masuda M., Satoh T., Chiba K. Hepatocyte nuclear factor-4 alphaplays pivotal roles in the regulation of mouse carboxylesterase 2 gene transcription in mouse liver. Arch. Biochem. Biophys. 2006; 447: 107–117
   PubMed Web of Science ®Google Scholar
• Furihata T., Hosokawa M., Nakata F., Satoh T., Chiba K. Purification, molecular cloning, and functional expression of inducible liver acylcarnitine hydrolase in C57BL/6 mouse, belonging to the carboxylesterase multigene family. Arch. Biochem. Biophys. 2003; 416: 101–109
   PubMed Web of Science ®Google Scholar
• Furihata T., Hosokawa M., Satoh T., Chiba K. Synergistic role of specificity proteins and upstream stimulatory factor 1 in transactivation of the mouse carboxylesterase 2/microsomal acylcarnitine hydrolase gene promoter. Biochem. J. 2004b; 384: 101–110
   PubMed Web of Science ®Google Scholar
• Hattori K., Igarashi M., Itoh M., Tomisawa H., Ozawa N., Tateishi M. Purification and characterization of glucocorticoid-inducible steroid esterase in rat hepatic microsomes:Specific induction by glucocorticoids of steroid esterase in rat hepatic microsomes and its release into serum. Biochem. Pharmacol. 1992; 43: 1929–1937
   PubMed Web of Science ®Google Scholar
• Hosokawa M., Hirata K., Nakata F., Suga T., Satoh T. Species differences in the induction of hepatic microsomal carboxylesterases caused by dietary exposure to di(2-ethylhexyl)phthalate, a peroxisome proliferator. Drug Metab. Dispos. 1994; 22: 889–894
   PubMed Web of Science ®Google Scholar
• Hosokawa M., Maki T., Satoh T. Multiplicity and regulation of hepatic microsomal carboxylesterases in rats. Mol. Pharmacol. 1987; 31: 579–584
   PubMed Web of Science ®Google Scholar
• Hosokawa M., Maki T., Satoh T. Differences in the induction of carboxylesterase isozymes in rat liver microsomes by xenobiotics. Biochem. Pharmacol. 1988; 37: 2708–2711
   PubMed Web of Science ®Google Scholar
• Hosokawa M., Maki T., Satoh T. Characterization of molecular species of liver microsomal carboxylesterases of several animal species and humans. Arch. Biochem. Biophys. 1990; 277: 219–227
   PubMed Web of Science ®Google Scholar
• Howarth J. A., Price S. C., Dobrota M., Kentish P. A., Hinton R. H. Effects on male rats of di-(2-ethylhexyl) phthalate and di-n-hexylphthalate administered alone or in combination. Toxicol. Lett. 2001; 121: 35–43
   PubMed Web of Science ®Google Scholar
• Imai T., Yoshigae Y., Hosokawa M., Chiba K., Otagiri M. Evidence for the involvement of a pulmonary first-pass effect via carboxylesterase in the disposition of a propranolol ester derivative after intravenous administration. J. Pharmacol. Exp. Ther. 2003; 307: 1234–1242
   PubMed Web of Science ®Google Scholar
• Inoue M., Morikawa M., Tsuboi M., Sugiura M. Species difference and characterization of intestinal esterase on the hydrolizing activity of ester-type drugs. Jpn. J. Pharmacol. 1979; 29: 9–16
   PubMedGoogle Scholar
• Kamendulis L. M., Brzezinski M. R., Pindel E. V., Bosron W. F., Dean R. A. Metabolism of cocaine and heroin is catalyzed by the same human liver carboxylesterases. J. Pharmacol. Exp. Ther. 1996; 279: 713–717
   PubMed Web of Science ®Google Scholar
• Korza G., Ozols J. Complete covalent structure of 60-kDa esterase isolated from 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced rabbit liver. J. Biol. Chem. 1988; 263: 3486–3495
   PubMed Web of Science ®Google Scholar
• Kroetz D. L., McBride O. W., Gonzalez F. J. Glycosylation-dependent activity of baculovirus-expressed human liver carboxylesterases: cDNA cloning and characterization of two highly similar enzyme forms. Biochemistry 1993; 32: 11606–11617
   PubMed Web of Science ®Google Scholar
• Kusano K., Seko T., Tanaka S., Shikata Y., Ando T., Ida S., Hosokawa M., Satoh T., Yuzuriha T., Horie T. Purification and characterization of monkey liver amidohydrolases and its relationship to a metabolic polymorphism of E6123, a platelet activating factor receptor antagonist. Drug. Metab. Dispos. 1996; 24: 1186–1191
   PubMed Web of Science ®Google Scholar
• Langmann T., Becker A., Aslanidis C., Notka F., Ullrich H., Schwer H., Schmitz G. Structural organization and characterization of the promoter region of a human carboxylesterase gene. Biochim. Biophys. Acta 1997; 1350: 65–74
   PubMed Web of Science ®Google Scholar
• Maki T., Hosokawa M., Satoh T., Sato K. Changes in carboxylesterase isoenzymes of rat liver microsomes during hepatocarcinogenesis. Jpn. J. Cancer Res. 1991; 82: 800–806
   PubMedGoogle Scholar
• Medda S., Takeuchi K., Devore-Carter D., von Deimling O., Heymann E., Swank R.T. An accessory protein identical to mouse egasyn is complexed with rat microsomal beta-glucuronidase and is identical to rat esterase-3. J. Biol. Chem. 1987; 262: 7248–7253
   PubMed Web of Science ®Google Scholar
• Mentlein R., Suttorp M., Heymann E. Specificity of purified monoacylglycerol lipase, palmitoyl-CoA hydrolase, palmitoyl-carnitine hydrolase, and nonspecific carboxylesterase from rat liver microsomes. Arch. Biochem. Biophys. 1984; 228: 230–246
   PubMed Web of Science ®Google Scholar
• Miyazaki M., Kamiie K., Soeta S., Taira H., Yamashita T. Molecular cloning and characterization of a novel carboxylesterase-like protein that is physiologically present at high concentration in the urine of domestic cats (Felis catus). Biochem. J. 2003; 15: 101–110
   Web of Science ®Google Scholar
• Mori M., Hosokawa M., Ogasawara Y., Tsukada E., Chiba K. cDNA cloning, characterization and stable expression of novel human brain carboxylesterase. FEBS Lett. 1999; 458: 17–22
   PubMed Web of Science ®Google Scholar
• Ohtsuka K., Inoue S., Kameyama M., Kanetoshi A., Fujimoto T., Takaoka K., Araya Y., Shida A. Intracellular conversion of irinotecan to its active form, SN-38, by native carboxylesterase in human non-small cell lung cancer. Lung Cancer 2003; 41: 187–198
   PubMed Web of Science ®Google Scholar
• Ovnic M., Swank R. T., Fletcher C., Zhen L., Novak E. K., Baumann H., Heintz N., Ganschow R. E. Characterization and functional expression of a cDNA encoding egasyn (esterase-22): the endoplasmic reticulum-targeting protein of beta- glucuronidase. Genomics 1991a; 11: 956–967
   PubMed Web of Science ®Google Scholar
• Ovnic M., Tepperman K., Medda S., Elliott R. W., Stephenson D. A., Grant S. G., Ganschow R. E. Characterization of a murine cDNA encoding a member of the carboxylesterase multigene family. Genomics 1991b; 9: 344–354
   PubMed Web of Science ®Google Scholar
• Ozols J. Isolation, properties, and the complete amino acid sequence of a second form of 60-kDa glycoprotein esterase. J. Biol. Chem. 1989; 264: 12533–12545
   PubMed Web of Science ®Google Scholar
• Pelham H. R. The retention signal for soluble proteins of the endoplasmic reticulum. Trends Biochem. Sci. 1990; 15: 483–486
   PubMed Web of Science ®Google Scholar
• Pindel E. V., Kedishvili N. Y., Abraham T. L., Brzezinski M. R., Zhang J., Dean R. A., Bosron W. F. Purification and cloning of a broad substrate specificity human liver carboxylesterase that catalyzes the hydrolysis of cocaine and heroin. J. Biol. Chem. 1997; 272: 14769–14775
   PubMed Web of Science ®Google Scholar
• Prueksaritanont T., Gorham L. M., Hochman J. H., Tran L. O., Vyas K. P. Comparative studies of drug-metabolizing enzymes in dog, monkey, and human small intestines, and in Caco-2 cells. Drug Metab. Dispos. 1996; 24: 634–642
   PubMed Web of Science ®Google Scholar
• Robbi M., Beaufay H. Cloning and sequencing of rat liver carboxylesterase ES-3 (egasyn). Biochem. Biophys. Res. Commun. 1994; 203: 1404–1411
   PubMed Web of Science ®Google Scholar
• Robbi M., Beaufay H., Octave J. N. Nucleotide sequence of cDNA coding for rat liver pI 6.1 esterase (ES-10), a carboxylesterase located in the lumen of the endoplasmic reticulum. Biochem. J. 1990; 269: 451–458
   PubMed Web of Science ®Google Scholar
• Sanghani S. P., Quinney S. K., Fredenburg T. B., Sun Z., Davis W. I., Murry D. J., Cummings O. W., Seitz D. E., Bosron W. F. Carboxylesterases expressed in human colon tumor tissue and their role in CPT-11 hydrolysis. Clin. Cancer Res. 2003; 9: 4983–4991
   PubMed Web of Science ®Google Scholar
• Satoh T., Hosokawa M. The mammalian carboxylesterases: from molecules to functions. Annu. Rev. Pharmacol. Toxicol. 1998; 38: 257–288
   PubMed Web of Science ®Google Scholar
• Satoh T., Hosokawa M., Atsumi R., Suzuki W., Hakusui H., Nagai E. Metabolic activation of CPT-11, 7-ethyl-10-[4-(1-piperidino)-1- piperidino]carbonyloxycamptothecin, a novel antitumor agent, by carboxylesterase. Biol. Pharm. Bull. 1994; 17: 662–664
   PubMed Web of Science ®Google Scholar
• Satoh T., Taylor P., Bosron W. F., Sanghani S. P., Hosokawa M., La Du B. N. Current progress on esterases: from molecular structure to function. Drug Metab. Dispos. 2002; 30: 488–493
   PubMed Web of Science ®Google Scholar
• Shibata F., Takagi Y., Kitajima M., Kuroda T., Omura T. Molecular cloning and characterization of a human carboxylesterase gene. Genomics 1993; 17: 76–82
   PubMed Web of Science ®Google Scholar
• 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 Metab. Dispos. 2004; 32: 1103–1110
   PubMed Web of Science ®Google Scholar
• Takai S., Matsuda A., Usami Y., Adachi T., Sugiyama T., Katagiri Y., Tatematsu M., Hirano K. Hydrolytic profile for ester- or amide-linkage by carboxylesterases pI 5.3 and 4.5 from human liver. Biol. Pharm. Bull. 1997; 20: 869–873
   PubMed Web of Science ®Google Scholar
• Takayama H., Watanabe A., Hosokawa M., Chiba K., Satoh T., Aimi N. Synthesis of a new class of camptothecin derivatives, the long-chain fatty acid esters of 10-hydroxycamptothecin, as a potent prodrug candidate, and their in vitro metabolic conversion by carboxylesterases. Bioorg. Med. Chem. Lett. 1998; 8: 415–418
   PubMed Web of Science ®Google Scholar
• Tang B. K., Kalow W. Variable activation of lovastatin by hydrolytic enzymes in human plasma and liver. 4. Eur. J. Clin. Pharmacol. 1995; 47: 449–451
   PubMed Web of Science ®Google Scholar
• von Heijne G. Patterns of amino acids near signal-sequence cleavage sites. Eur. J. Biochem. 1983; 133: 17–21
   PubMedGoogle Scholar
• Wallace T. J., Ghosh S., McLean Grogan W. Molecular cloning and expression of rat lung carboxylesterase and its potential role in the detoxification of organophosphorus compounds. Am. J. Respir. Cell. Mol. Biol. 1999; 20: 1201–1208
   PubMed Web of Science ®Google Scholar
• Watanabe K., Kayano Y., Matsunaga T., Yamamoto I., Yoshimura H. Purification and characterization of a novel 46.5-kilodalton esterase from mouse hepatic microsomes. Biochem. Mol. Biol. Int. 1993; 31: 25–30
   PubMedGoogle Scholar
• Wong H., Schotz M. C. The lipase gene family. J. Lipid Res. 2002; 43: 993–999
   PubMed Web of Science ®Google Scholar
• Xie M., Yang D., Wu M., Xue B., Yan B. Mouse liver and kidney carboxylesterase (M‐LK) rapidly hydrolyzes antitumor prodrug irinotecan and the N-terminal three quarter sequence determines substrate selectivity. Drug Metab. Dispos. 2003; 31: 21–27
   PubMed Web of Science ®Google Scholar
• Zhang J., Burnell J. C., Dumaual N., Bosron W. F. Binding and hydrolysis of meperidine by human liver carboxylesterase hCE-1. J. Pharmacol. Exp. Ther. 1999; 290: 314–318
   PubMed Web of Science ®Google Scholar
• Zhu W., Song L., Zhang H., Matoney L., LeCluyse E., Yan B. Dexamethasone differentially regulates expression of carboxylesterase genes in humans and rats. Drug Metab. Dispos. 2000; 28: 186–191
   PubMed Web of Science ®Google Scholar
• Zschunke F., Salmassi A., Kreipe H., Buck F., Parwaresch M. R., Radzun H. J. cDNA cloning and characterization of human monocyte/macrophage serine esterase-1. Blood 1991; 78: 506–512
   PubMed Web of Science ®Google Scholar