메뉴 건너뛰기




Volumn 58, Issue 18, 2015, Pages 7164-7172

Discovery of Selective Small Molecule Inhibitors of Monoacylglycerol Acyltransferase 3

Author keywords

[No Author keywords available]

Indexed keywords

ACYLGLYCEROL PALMITOYLTRANSFERASE; ACYLTRANSFERASE INHIBITOR; DEUTERIUM; DIACYLGLYCEROL ACYLTRANSFERASE 1; DIACYLGLYCEROL ACYLTRANSFERASE 2; GLYCEROL; MONOACYLGLYCEROL ACYLTRANSFERASE 3; N (2 CYCLOBUTYL 2H 1,2,3 TRIAZOL 4 YL) 2 [2 (3 METHOXYPHENYL)ACETYL]ISOINDOLINE 5 SULFONAMIDE; UNCLASSIFIED DRUG; 2-ACYLGLYCEROL O-ACYLTRANSFERASE; ACYLTRANSFERASE; DIACYLGLYCEROL ACYLTRANSFERASE; ISOINDOLE DERIVATIVE; PF-06471553; SULFONAMIDE; TRIACYLGLYCEROL;

EID: 84942314032     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b01008     Document Type: Article
Times cited : (15)

References (39)
  • 1
    • 0036182137 scopus 로고    scopus 로고
    • Lipotoxic diseases
    • Unger, R. H. Lipotoxic diseases Annu. Rev. Med. 2002, 53, 319-336 10.1146/annurev.med.53.082901.104057
    • (2002) Annu. Rev. Med. , vol.53 , pp. 319-336
    • Unger, R.H.1
  • 2
    • 0037122801 scopus 로고    scopus 로고
    • Fat in all the wrong places
    • Friedman, J. Fat in all the wrong places Nature 2002, 415, 268-269 10.1038/415268a
    • (2002) Nature , vol.415 , pp. 268-269
    • Friedman, J.1
  • 3
    • 0038509036 scopus 로고    scopus 로고
    • Lipotoxicity: When tissues overeat
    • Schaffer, J. E. Lipotoxicity: when tissues overeat Curr. Opin. Lipidol. 2003, 14, 281-287 10.1097/00041433-200306000-00008
    • (2003) Curr. Opin. Lipidol. , vol.14 , pp. 281-287
    • Schaffer, J.E.1
  • 4
    • 67650096808 scopus 로고    scopus 로고
    • Beyond triglyceride synthesis: The dynamic functional roles of MGAT and DGAT enzymes in energy metabolism
    • Shi, Y.; Cheng, D. Beyond triglyceride synthesis: the dynamic functional roles of MGAT and DGAT enzymes in energy metabolism Am. J. Physiol. Endocrinol. Metab. 2009, 297, E10-E18 10.1152/ajpendo.90949.2008
    • (2009) Am. J. Physiol. Endocrinol. Metab. , vol.297 , pp. E10-E18
    • Shi, Y.1    Cheng, D.2
  • 5
    • 58149457426 scopus 로고    scopus 로고
    • Thematic review series: Glycerolipids. DGAT enzymes and triacylglycerol biosynthesis
    • Yen, C. L.; Stone, S. J.; Koliwad, S.; Harris, C.; Farese, R. V., Jr Thematic review series: glycerolipids. DGAT enzymes and triacylglycerol biosynthesis J. Lipid Res. 2008, 49, 2283-2301 10.1194/jlr.R800018-JLR200
    • (2008) J. Lipid Res. , vol.49 , pp. 2283-2301
    • Yen, C.L.1    Stone, S.J.2    Koliwad, S.3    Harris, C.4    Farese, R.V.5
  • 7
    • 0035914356 scopus 로고    scopus 로고
    • Cloning of DGAT2, a second mammalian diacylglycerol acyltransferase, and related family members
    • Cases, S.; Stone, S. J.; Zhou, P.; Yen, E.; Tow, B.; Lardizabal, K. D.; Voelker, T.; Farese, R. V., Jr. Cloning of DGAT2, a second mammalian diacylglycerol acyltransferase, and related family members J. Biol. Chem. 2001, 276, 38870-38876 10.1074/jbc.M106219200
    • (2001) J. Biol. Chem. , vol.276 , pp. 38870-38876
    • Cases, S.1    Stone, S.J.2    Zhou, P.3    Yen, E.4    Tow, B.5    Lardizabal, K.D.6    Voelker, T.7    Farese, Jr.R.V.8
  • 8
    • 0038751862 scopus 로고    scopus 로고
    • Cloning and functional characterization of a mouse intestinal acyl-CoA: Monoacylglycerol acyltransferase, MGAT2
    • Cao, J.; Lockwood, J.; Burn, P.; Shi, Y. Cloning and functional characterization of a mouse intestinal acyl-CoA: monoacylglycerol acyltransferase, MGAT2 J. Biol. Chem. 2003, 278, 13860-13866 10.1074/jbc.M300139200
    • (2003) J. Biol. Chem. , vol.278 , pp. 13860-13866
    • Cao, J.1    Lockwood, J.2    Burn, P.3    Shi, Y.4
  • 9
    • 0037790713 scopus 로고    scopus 로고
    • MGAT2, a monoacylglycerol acyltransferase expressed in the small intestine
    • Yen, C. L.; Farese, R. V., Jr. MGAT2, a monoacylglycerol acyltransferase expressed in the small intestine J. Biol. Chem. 2003, 278 (28) 18532-18537 10.1074/jbc.M301633200
    • (2003) J. Biol. Chem. , vol.278 , Issue.28 , pp. 18532-18537
    • Yen, C.L.1    Farese, R.V.2
  • 10
    • 0037477454 scopus 로고    scopus 로고
    • Properties of the mouse intestinal acyl-CoA:monoacylglycerol acyltransferase, MGAT2
    • Cao, J.; Burn, P.; Shi, Y. Properties of the mouse intestinal acyl-CoA:monoacylglycerol acyltransferase, MGAT2 J. Biol. Chem. 2003, 278 (28) 25657-25663 10.1074/jbc.M302835200
    • (2003) J. Biol. Chem. , vol.278 , Issue.28 , pp. 25657-25663
    • Cao, J.1    Burn, P.2    Shi, Y.3
  • 11
    • 0037172964 scopus 로고    scopus 로고
    • Identification of a gene encoding MGAT1, a monoacylglycerol acyltransferase
    • Yen, C. L.; Stone, S. J.; Cases, S.; Zhou, P.; Farese, R. V., Jr. Identification of a gene encoding MGAT1, a monoacylglycerol acyltransferase Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 8512-8517 10.1073/pnas.132274899
    • (2002) Proc. Natl. Acad. Sci. U. S. A. , vol.99 , pp. 8512-8517
    • Yen, C.L.1    Stone, S.J.2    Cases, S.3    Zhou, P.4    Farese, R.V.5
  • 12
    • 0038075340 scopus 로고    scopus 로고
    • Identification of acyl coenzyme A: Monoacylglycerol acyltransferase 3, an intestinal specific enzyme implicated in dietary fat absorption
    • Cheng, D.; Nelson, T. C.; Chen, J.; Walker, S. G.; Wardwell-Swanson, J.; Meegalla, R.; Taub, R.; Billheimer, J. T.; Ramaker, M.; Feder, J. N. Identification of acyl coenzyme A: monoacylglycerol acyltransferase 3, an intestinal specific enzyme implicated in dietary fat absorption J. Biol. Chem. 2003, 278 (16) 13611-13614 10.1074/jbc.C300042200
    • (2003) J. Biol. Chem. , vol.278 , Issue.16 , pp. 13611-13614
    • Cheng, D.1    Nelson, T.C.2    Chen, J.3    Walker, S.G.4    Wardwell-Swanson, J.5    Meegalla, R.6    Taub, R.7    Billheimer, J.T.8    Ramaker, M.9    Feder, J.N.10
  • 13
    • 84889100046 scopus 로고    scopus 로고
    • Current Status of the Research and Development of Diacylglycerol O-Acyltransferase 1 (Dgat1) Inhibitors
    • DeVita, R. J.; Pinto, S. Current Status of the Research and Development of Diacylglycerol O-Acyltransferase 1 (Dgat1) Inhibitors J. Med. Chem. 2013, 56, 9820-9825 10.1021/jm4007033
    • (2013) J. Med. Chem. , vol.56 , pp. 9820-9825
    • DeVita, R.J.1    Pinto, S.2
  • 14
    • 84911947801 scopus 로고    scopus 로고
    • Acyl-Coa: Diacylglycerol Acyltransferase-1 Inhibition as an Approach to the Treatment of Type 2 Diabetes
    • Dow, R. L. Acyl-Coa: Diacylglycerol Acyltransferase-1 Inhibition as an Approach to the Treatment of Type 2 Diabetes RSC Drug Discovery Ser. 2012, 27, 215-248 10.1039/9781849735322-00215
    • (2012) RSC Drug Discovery Ser. , vol.27 , pp. 215-248
    • Dow, R.L.1
  • 17
    • 39849093869 scopus 로고    scopus 로고
    • Knockdown of acyl-CoA:diacylglycerol acyltransferase 2 with antisense oligonucleotide reduces VLDL, TG and ApoB secretion in mice
    • Liu, Y.; Millar, J. S.; Cromley, D. A.; Graham, M.; Crooke, R.; Billheimer, J. T.; Rader, D. J. Knockdown of acyl-CoA:diacylglycerol acyltransferase 2 with antisense oligonucleotide reduces VLDL, TG and ApoB secretion in mice Biochim. Biophys. Acta, Mol. Cell Biol. Lipids 2008, 1781 (3) 97-104 10.1016/j.bbalip.2008.01.001
    • (2008) Biochim. Biophys. Acta, Mol. Cell Biol. Lipids , vol.1781 , Issue.3 , pp. 97-104
    • Liu, Y.1    Millar, J.S.2    Cromley, D.A.3    Graham, M.4    Crooke, R.5    Billheimer, J.T.6    Rader, D.J.7
  • 18
    • 23044450772 scopus 로고    scopus 로고
    • Antisense oligonucleotide reduction of DGAT2 expression improves hepatic steatosis and hyperlipidemia in obese mice
    • Yu, X. X.; Murray, S. F.; Pandey, S. K.; Booten, S. L.; Bao, D.; Song, X. Z.; Kelly, S.; Chen, S.; McKay, R.; Monia, B. P.; Bhanot, S. Antisense oligonucleotide reduction of DGAT2 expression improves hepatic steatosis and hyperlipidemia in obese mice Hepatology 2005, 42 (2) 362-371 10.1002/hep.20783
    • (2005) Hepatology , vol.42 , Issue.2 , pp. 362-371
    • Yu, X.X.1    Murray, S.F.2    Pandey, S.K.3    Booten, S.L.4    Bao, D.5    Song, X.Z.6    Kelly, S.7    Chen, S.8    McKay, R.9    Monia, B.P.10    Bhanot, S.11
  • 20
    • 64149083743 scopus 로고    scopus 로고
    • Deficiency of the intestinal enzyme acyl CoA:monoacylglycerol acyltransferase-2 protects mice from metabolic disorders induced by high-fat feeding
    • Yen, C. L.; Cheong, M. L.; Grueter, C.; Zhou, P.; Moriwaki, J.; Wong, J. S.; Hubbard, B.; Marmor, S.; Farese, R. V., Jr. Deficiency of the intestinal enzyme acyl CoA:monoacylglycerol acyltransferase-2 protects mice from metabolic disorders induced by high-fat feeding Nat. Med. 2009, 15 (4) 442-446 10.1038/nm.1937
    • (2009) Nat. Med. , vol.15 , Issue.4 , pp. 442-446
    • Yen, C.L.1    Cheong, M.L.2    Grueter, C.3    Zhou, P.4    Moriwaki, J.5    Wong, J.S.6    Hubbard, B.7    Marmor, S.8    Farese, R.V.9
  • 24
    • 33947104623 scopus 로고    scopus 로고
    • Catalytic properties of MGAT3, a putative triacylgycerol synthase
    • Cao, J.; Cheng, L.; Shi, Y. Catalytic properties of MGAT3, a putative triacylgycerol synthase J. Lipid Res. 2006, 48, 583-591 10.1194/jlr.M600331-JLR200
    • (2006) J. Lipid Res. , vol.48 , pp. 583-591
    • Cao, J.1    Cheng, L.2    Shi, Y.3
  • 25
    • 33845977414 scopus 로고    scopus 로고
    • Membrane topology and identification of key functional amino acid residues of murine acyl-CoA:diacylglycerol acyltransferase-2
    • Stone, S. J.; Levin, M. C.; Farese, R. V., Jr. Membrane topology and identification of key functional amino acid residues of murine acyl-CoA:diacylglycerol acyltransferase-2 J. Biol. Chem. 2006, 281 (52) 40273-40282 10.1074/jbc.M607986200
    • (2006) J. Biol. Chem. , vol.281 , Issue.52 , pp. 40273-40282
    • Stone, S.J.1    Levin, M.C.2    Farese, R.V.3
  • 27
    • 77957804992 scopus 로고    scopus 로고
    • Role of Physicochemical Properties and Ligand Lipophilicity Efficiency in Addressing Drug Safety Risks
    • Edwards, M. P.; Price, D. A. Role of Physicochemical Properties and Ligand Lipophilicity Efficiency in Addressing Drug Safety Risks Annu. Rep. Med. Chem. 2010, 45, 380-391 10.1016/S0065-7743(10)45023-X
    • (2010) Annu. Rep. Med. Chem. , vol.45 , pp. 380-391
    • Edwards, M.P.1    Price, D.A.2
  • 28
    • 0035147471 scopus 로고    scopus 로고
    • The Prediction of Human Clearance from Hepatic Microsomal Metabolism Data
    • Obach, R. S. The Prediction of Human Clearance from Hepatic Microsomal Metabolism Data Curr. Opin. Drug Discovery Dev. 2001, 4, 36-44
    • (2001) Curr. Opin. Drug Discovery Dev. , vol.4 , pp. 36-44
    • Obach, R.S.1
  • 30
    • 70349083023 scopus 로고    scopus 로고
    • Modulation of the Partition Coefficient between Octanol and Buffer at Ph 7.4 and pKa to Achieve the Optimum Balance of Blood Clearance and Volume of Distribution for a Series of Tetrahydropyran Histamine Type 3 Receptor Antagonists
    • LogD values were determined using the shake-flask method with an octanol/water partition at pH 7.4. The assay method was adapted from published protocol using MS rather than HPLC for sample analysis: Hay, T.; Jones, R.; Beaumont, K.; Kemp, M. Modulation of the Partition Coefficient between Octanol and Buffer at Ph 7.4 and pKa to Achieve the Optimum Balance of Blood Clearance and Volume of Distribution for a Series of Tetrahydropyran Histamine Type 3 Receptor Antagonists Drug Metab. Dispos. 2009, 37, 1864-1870 10.1124/dmd.109.027888
    • (2009) Drug Metab. Dispos. , vol.37 , pp. 1864-1870
    • Hay, T.1    Jones, R.2    Beaumont, K.3    Kemp, M.4
  • 31
    • 84655169669 scopus 로고    scopus 로고
    • Dirlotapide as a model substrate to refine structure-based drug design strategies on CYP3A4-catalyzed metabolism
    • Sun, H.; Bessire, A. J.; Vaz, A. Dirlotapide as a model substrate to refine structure-based drug design strategies on CYP3A4-catalyzed metabolism Bioorg. Med. Chem. Lett. 2012, 22, 371-6 10.1016/j.bmcl.2011.10.121
    • (2012) Bioorg. Med. Chem. Lett. , vol.22 , pp. 371-376
    • Sun, H.1    Bessire, A.J.2    Vaz, A.3
  • 32
    • 80051714529 scopus 로고    scopus 로고
    • Metabolism of 4-Aminopiperidine Drugs by Cytochrome P450s: Molecular and Quantum Mechanical Insights into Drug Design
    • Sun, H.; Scott, D. O. Metabolism of 4-Aminopiperidine Drugs by Cytochrome P450s: Molecular and Quantum Mechanical Insights into Drug Design ACS Med. Chem. Lett. 2011, 2, 638-643 10.1021/ml200117z
    • (2011) ACS Med. Chem. Lett. , vol.2 , pp. 638-643
    • Sun, H.1    Scott, D.O.2
  • 33
    • 4143143372 scopus 로고    scopus 로고
    • The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-A resolution
    • For CYP2C9 crystal structure (PBD ID: 1R9O), see: Wester, M. R.; Yano, J. K.; Schoch, G. A.; Yang, C.; Griffin, K. J.; Stout, C. D.; Johnson, E. F. The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-A resolution J. Biol. Chem. 2004, 279, 35630-7 10.1074/jbc.M405427200
    • (2004) J. Biol. Chem. , vol.279 , pp. 35630-35637
    • Wester, M.R.1    Yano, J.K.2    Schoch, G.A.3    Yang, C.4    Griffin, K.J.5    Stout, C.D.6    Johnson, E.F.7
  • 34
    • 84855216769 scopus 로고    scopus 로고
    • Systematic and pairwise analysis of the effects of aromatic halogenation and trifluoromethyl substitution on human liver microsomal clearance
    • Pairwise analysis suggests this improvement is not driven only by decreased lipophilicity. See: Sun, H.; Keefer, C. E.; Scott, D. O. Systematic and pairwise analysis of the effects of aromatic halogenation and trifluoromethyl substitution on human liver microsomal clearance Drug Metab. Lett. 2011, 5, 232-242 10.2174/187231211798472575
    • (2011) Drug Metab. Lett. , vol.5 , pp. 232-242
    • Sun, H.1    Keefer, C.E.2    Scott, D.O.3
  • 35
    • 77957847870 scopus 로고    scopus 로고
    • General solution to the synthesis of N-2-substituted 1,2,3-triazoles
    • Wang, X.; Zhang, L.; Krishnamurthy, D.; Senanayake, C. H.; Wipf, P. General solution to the synthesis of N-2-substituted 1,2,3-triazoles Org. Lett. 2010, 12, 4632-4635 10.1021/ol101965a
    • (2010) Org. Lett. , vol.12 , pp. 4632-4635
    • Wang, X.1    Zhang, L.2    Krishnamurthy, D.3    Senanayake, C.H.4    Wipf, P.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.