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Volumn 15, Issue 1, 2011, Pages 69-81

Computer-aided design and synthesis of tetra-aryl-substituted alkenes and their bioevaluation as a selective modulator of estrogen-related receptor γ

Author keywords

Antagonist; Computational docking; Estrogen receptor (ER ); Estrogen related receptor (ERR ); Inverse agonist; Tamoxifen analogs

Indexed keywords

4 [1 [4 (2 (DIMETHYLAMINO)ETHOXY]PHENYL] 2,2 BIS(3 FLUORO PHENYL)VINYL PHENYL PIVALATE; 4 [1 [4 (2 (DIMETHYLAMINO)ETHOXY]PHENYL] 2,2 BIS(4 FLUORO PHENYL)VINYL PHENYL PIVALATE; 4 [1 [4 (2 (DIMETHYLAMINO)ETHOXY]PHENYL] 2,2 DI(1H PYRAZOL 4 YL)VINYL PHENYL PIVALATE; 4 [1 [4 (2 (DIMETHYLAMINO)ETHOXY]PHENYL] 2,2 DI(FURAN 3 YL)VINYL PHENOL; 4 [1 [4 (2 (DIMETHYLAMINO)ETHOXY]PHENYL] 2,2 DI(FURAN 3 YL)VINYL PHENYL PIVALATE; 4 [1 [4 (2 (DIMETHYLAMINO)ETHOXY]PHENYL] 2,2 DI(PYRIDIN 3 YL)VINYL PHENOL; 4 [1 [4 (2 (DIMETHYLAMINO)ETHOXY]PHENYL] 2,2 DI(PYRIDIN 3 YL)VINYL PHENYL PIVALATE; 4 [1 [4 (2 (DIMETHYLAMINO)ETHOXY]PHENYL] 2,2 DI(PYRIDIN 4 YL)VINYL PHENOL; 4 [1 [4 (2 (DIMETHYLAMINO)ETHOXY]PHENYL] 2,2 DI(PYRIDIN 4 YL)VINYL PHENYL PIVALATE; 4 [1 [4 (2 (DIMETHYLAMINO)ETHOXY]PHENYL] 2,2 DI(PYRIMIDIN 5 YL)VINYL PHENOL; 4 [1 [4 (2 (DIMETHYLAMINO)ETHOXY]PHENYL] 2,2 DI(THIOPHEN 2 YL)VINYL PHENYL PIVALATE; 4 [1 [4 (2 (DIMETHYLAMINO)ETHOXY]PHENYL] 2,2 DI(THIOPHEN 3 YL)VINYL PHENYL PIVALATE; 4 [2,2 DIBROMO 1] (4 HYDROXYPHENYL)VINYL PHENYL PIVALATE; 4 [2,2 DIBROMO [1 4 (2 (DIMETHYLAMINO)ETHOXY)PHENYL] VINYL] PHENYL PIVALATE; 4,4' (2,2 DIBROMOETHENE 1,1 DIYL)BIS(4,1PHENYLENE) BIS(2,2 DIMETHYLPROPANOATE); 4,4' CARBONYLBIS(4,1 PHENYLENE)BIS(2,2 DIMETHYLPROPANOATE); AFIMOXIFENE; ALKENE; ANTIESTROGEN; CELL NUCLEUS RECEPTOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RELATED RECEPTOR GAMMA; STEROID RECEPTOR; TAMOXIFEN; UNCLASSIFIED DRUG;

EID: 79953318868     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-010-9224-y     Document Type: Conference Paper
Times cited : (13)

References (30)
  • 1
    • 0032526489 scopus 로고    scopus 로고
    • Isolation of a gene encoding a novel member of the nuclear receptor superfamily from the critical region of usher syndrome type IIa at 1q41
    • DOI 10.1006/geno.1998.5345
    • Eudy JD, Yao S, Weston MD, Ma-Edmonds M, Talmadge CB, Cheng JJ, Kimberling WJ, Sumegi J (1998) Isolation of a gene encoding a novelmember of the nuclear receptor superfamily from the critical region of Usher syndrome type IIa at 1q41. Genomics 50:382-384 (Pubitemid 28328760)
    • (1998) Genomics , vol.50 , Issue.3 , pp. 382-384
    • Eudy, J.D.1    Yao, S.2    Weston, M.D.3    Ma-Edmonds, M.4    Talmadge, C.B.5    Cheng, J.J.6    Kimberling, W.J.7    Sumegi, J.8
  • 2
    • 0033529498 scopus 로고    scopus 로고
    • Hormone-independent transcriptional activation and coactivator binding by novel orphan nuclear receptorERR3
    • doi:10.1074/jbc.274.32.22618
    • Hong H, Yang L, Stallcup MR (1999) Hormone-independent transcriptional activation and coactivator binding by novel orphan nuclear receptorERR3. J Biol Chem 274: 22618-22626. doi:10.1074/jbc.274.32.22618
    • (1999) J Biol Chem , vol.274 , pp. 22618-22626
    • Hong, H.1    Yang, L.2    Stallcup, M.R.3
  • 3
    • 0034335415 scopus 로고    scopus 로고
    • Human ERR γ, a third member of the estrogen receptor-related receptor (ERR) subfamily of orphan nuclear receptors: Tissue-specific isoforms are expressed during development and in the adult
    • doi:10.1210/me.14.3.382
    • Heard DJ, Norby PL, Holloway J, Vissing H (2000) Human ERR γ , a third member of the estrogen receptor-related receptor (ERR) subfamily of orphan nuclear receptors: tissue-specific isoforms are expressed during development and in the adult. Mol Endocrinol 14:382-392. doi:10.1210/me.14.3.382
    • (2000) Mol Endocrinol , vol.14 , pp. 382-392
    • Heard, D.J.1    Norby, P.L.2    Holloway, J.3    Vissing, H.4
  • 5
    • 0037112441 scopus 로고    scopus 로고
    • Estrogen-related receptor α and estrogen-related receptor γ associate with unfavorable and favorable biomarkers, respectively, in human breast cancer
    • Ariazi EA, Clark GM, Mertz JE (2002) Estrogen-related receptor α and estrogen-related receptor γ associate with unfavorable and favorable biomarkers, respectively, in human breast cancer. Cancer Res 62:6510-6518 (Pubitemid 35364116)
    • (2002) Cancer Research , vol.62 , Issue.22 , pp. 6510-6518
    • Ariazi, E.A.1    Clark, G.M.2    Mertz, J.E.3
  • 8
    • 0037174798 scopus 로고    scopus 로고
    • Peroxisome proliferator-activated receptor coactivator-1α (PGC-1α) coactivates the cardiac-enriched nuclear receptors estrogen-related receptor-α and -γ: Identification of novel Leucine-rich interaction motif within PGC-1alpha
    • DOI 10.1074/jbc.M206324200
    • Huss JM, Kopp RP, Kelly DP (2002) Peroxisome proliferator- activated receptor coactivator-1alpha (PGC-1α) coactivates the cardiac-enriched nuclear receptors estrogen-related receptor- α and - γ . Identification of novel leucinerich interaction motif within PGC-1 alpha. J Biol Chem 277:40265-40274. doi:10.1074/jbc.M206324200 (Pubitemid 35215598)
    • (2002) Journal of Biological Chemistry , vol.277 , Issue.43 , pp. 40265-40274
    • Huss, J.M.1    Kopp, R.P.2    Kelly, D.P.3
  • 9
    • 34250371424 scopus 로고    scopus 로고
    • ERRγ suppresses cell proliferation and tumor growth of androgen-sensitive and androgen-insensitive prostate cancer cells and its implication as a therapeutic target for prostate cancer
    • DOI 10.1158/0008-5472.CAN-06-3855
    • Yu S, Wang X, Ng C-F, Chen S, Chan FL (2007) ERR γ suppresses cell proliferation and tumor growth of androgensensitive and androgen-insensitive prostate cancer cells and its implications as a therapeutic target for prostate cancer. Cancer Res 67:4904-4914. doi:10.1158/0008-5472.CAN-06-3855 (Pubitemid 46915313)
    • (2007) Cancer Research , vol.67 , Issue.10 , pp. 4904-4914
    • Yu, S.1    Wang, X.2    Ng, C.-F.3    Chen, S.4    Chan, F.L.5
  • 10
    • 0347989301 scopus 로고    scopus 로고
    • Estrogen receptor-related receptors: Orphan receptors desperately seeking a ligand
    • DOI 10.1677/jme.0.0310349
    • Horard B, Vanacker J-M (2003) Estrogen receptor-related receptors: orphan receptors desperately seeking a ligand. J Mol Endo 31:349-357. doi:10.1677/jme.0.0310349 (Pubitemid 38054510)
    • (2003) Journal of Molecular Endocrinology , vol.31 , Issue.3 , pp. 349-357
    • Horard, B.1    Vanacker, J.-M.2
  • 11
    • 0036633114 scopus 로고    scopus 로고
    • To ERR in the estrogen pathway
    • doi:10.1016/S1043-2760(02)00592-1
    • Giguère V (2002) To ERR in the estrogen pathway. Trend Endocrinol Metab 13:220-225. doi:10.1016/S1043-2760(02)00592-1
    • (2002) Trend Endocrinol Metab , vol.13 , pp. 220-225
    • Giguère, V.1
  • 13
    • 70349330695 scopus 로고    scopus 로고
    • Efficient discovery of selective small molecule agonists of estrogen-related receptor γ using combinatorial approach
    • doi:10.1021/cc900081j
    • Kim Y, Koh M, Kim D-K, Choi H-S, Park SB (2009) Efficient discovery of selective small molecule agonists of estrogen-related receptor γ using combinatorial approach. J Comb Chem 11: 928-937. doi:10.1021/cc900081j
    • (2009) J Comb Chem , vol.11 , pp. 928-937
    • Kim, Y.1    Koh, M.2    Kim, D.-K.3    Choi, H.-S.4    Park, S.B.5
  • 14
    • 64749110949 scopus 로고    scopus 로고
    • Structure-based design of molecular cancer therapeutics
    • doi:10.1016/j.tibtech.2009.02.003
    • Montfort RLM, Workman P (2009) Structure-based design of molecular cancer therapeutics. Trend Biotech 27:315-328. doi:10.1016/j.tibtech.2009.02.003
    • (2009) Trend Biotech , vol.27 , pp. 315-328
    • Montfort, R.L.M.1    Workman, P.2
  • 16
    • 33646112903 scopus 로고    scopus 로고
    • Antibacterial drug discovery and structure-based design
    • doi:10.1016/j.drudis.2006.03.001
    • Barker JJ (2006) Antibacterial drug discovery and structure-based design. Drug Discov Today 11:391-404. doi:10.1016/j.drudis.2006.03.001
    • (2006) Drug Discov Today , vol.11 , pp. 391-404
    • Barker, J.J.1
  • 17
    • 0344391944 scopus 로고    scopus 로고
    • Simple and efficient production of (Z)- 4-Hydroxytamoxifen, a potent estrogen receptor modulator
    • doi:10.1021/jo035164n
    • Yu DD, FormanBM (2003) Simple and efficient production of (Z)- 4-Hydroxytamoxifen, a potent estrogen receptor modulator. J Org Chem 68:9489-9491. doi:10.1021/jo035164n
    • (2003) J Org Chem , vol.68 , pp. 9489-9491
    • Yu, D.D.1    Forman, B.M.2
  • 18
    • 79953326599 scopus 로고    scopus 로고
    • 10188 Telesis Court, Suite 100 San Diego, CA 92121, USA
    • Accelrys Software Inc. 10188 Telesis Court, Suite 100 San Diego, CA 92121, USA. http://accelrys.com
  • 20
    • 4043176291 scopus 로고    scopus 로고
    • Structural basis for the deactivation of the estrogen-related receptor γ by diethylstilbestrol or 4-hydroxytamoxifen and determinants of selectivity
    • DOI 10.1074/jbc.M402195200
    • Greschik H, Flaig R, Renaud J-P, Moras D (2004) Structural basis for the deactivation of the estrogen-related receptor γ by diethylstilbestrol or 4-hydroxytamoxifen and determinants of selectivity. J Biol Chem 279:33639-33646. doi:10.1074/jbc.M402195200 (Pubitemid 39063013)
    • (2004) Journal of Biological Chemistry , vol.279 , Issue.32 , pp. 33639-33646
    • Greschik, H.1    Flaig, R.2    Renaud, J.-P.3    Moras, D.4
  • 21
    • 33846021285 scopus 로고    scopus 로고
    • X-ray crystal structures of the estrogen-related receptor-γ ligand binding domain in three functional states reveal the molecular basis of small molecule regulation
    • DOI 10.1074/jbc.M608410200
    • Wang L, Zuercher WJ, Consler TG, Lambert MH, Miller AB, Orband-Miller LA, McKee DD, Willson TM, Nolte RT (2006) X-ray crystal structures of the estrogen-related receptor- γ ligand binding domain in three functional states reveal the molecular basis of small molecule regulation. J Biol Chem 281:37773-37781. doi:10.1074/jbc.M608410200 (Pubitemid 46042080)
    • (2006) Journal of Biological Chemistry , vol.281 , Issue.49 , pp. 37773-37781
    • Wang, L.1    Zuercher, W.J.2    Consler, T.G.3    Lambert, M.H.4    Miller, A.B.5    Orband-Miller, L.A.6    McKee, D.D.7    Willson, T.M.8    Nolte, R.T.9
  • 22
    • 0028987866 scopus 로고
    • TAMOXIFEN: Toxicities and drug resistance during the treatment and prevention of breast cancer
    • doi:10.1146/annurev.pa.35.040195.001211
    • Jordan VC (1995) TAMOXIFEN: toxicities and drug resistance during the treatment and prevention of breast cancer. Annu Rev Pharmacol Toxicol 35:195-211. doi:10.1146/annurev.pa.35.040195.001211
    • (1995) Annu Rev Pharmacol Toxicol , vol.35 , pp. 195-211
    • Jordan, V.C.1
  • 23
    • 0021348096 scopus 로고
    • Bioactivities, estrogen receptor interactions, and plasminogen activator-inducing activities of tamoxifen and hydroxytamoxifen isomers in MCF-7 human breast cancer cells
    • Katzenellenbogen BS, Norman MJ, Eckert RL, Peltz SW, Mangel WF (1984) Bioactivities, estrogen receptor interactions, and plasminogen activator-inducing activities of tamoxifen and hydroxytamoxifen isomers in MCF-7 human breast cancer cells. Cancer Res 44:112-119 (Pubitemid 14178070)
    • (1984) Cancer Research , vol.44 , Issue.1 , pp. 112-119
    • Katzenellenbogen, B.S.1    Norman, M.J.2    Eckert, R.L.3
  • 24
    • 0042706825 scopus 로고    scopus 로고
    • Cis-Trans isomerization of organic molecules and biomolecules: Implications and applications
    • doi:10.1021/cr0104375
    • Dugave C, Demange L (2003) Cis-Trans isomerization of organic molecules and biomolecules: implications and applications. Chem Rev 103:2475-2532. doi:10.1021/cr0104375
    • (2003) Chem Rev , vol.103 , pp. 2475-2532
    • Dugave, C.1    Demange, L.2
  • 25
    • 0036325773 scopus 로고    scopus 로고
    • Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: Formation of the 4-hydroxy, 4′-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen
    • DOI 10.1124/dmd.30.8.869
    • Crewe HK, Notley LM, Wunsch RM, Lennard MS, Gillam EJ (2002) Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy,4′-hydroxy and N-desmethyl metabolite and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos 30:869-874. doi:10.1124/dmd.30.8.869 (Pubitemid 34815415)
    • (2002) Drug Metabolism and Disposition , vol.30 , Issue.8 , pp. 869-874
    • Crewe, H.K.1    Notley, L.M.2    Wunsch, R.M.3    Lennard, M.S.4    Gillam, E.M.J.5
  • 26
    • 34748865637 scopus 로고    scopus 로고
    • Elimination of antiestrogenic effects of active tamoxifen metabolites by glucuronidation
    • DOI 10.1124/dmd.107.016279
    • Zheng Y, Sun D, Sharma AK, Chen G, Amin S, Lazarus P (2007) Elimination of antiestrogenic effects of active tamoxifen metabolites by glucuronidation. Drug Metab Dispos 35: 1942-1948. doi:10.1124/dmd.107.016279 (Pubitemid 47481590)
    • (2007) Drug Metabolism and Disposition , vol.35 , Issue.10 , pp. 1942-1948
    • Zheng, Y.1    Sun, D.2    Sharma, A.K.3    Chen, G.4    Amin, S.5    Lazarus, P.6
  • 27
    • 0020033521 scopus 로고
    • Tamoxifen antiestrogens. A comparison of the activity, pharmacokinetics, and metabolic activation of the cis and trans isomers of tamoxifen
    • Robertson DW, Katzenellenbogen JA, Logn DJ, Rorke EA, Katzenellenbogen BS (1982) Tamoxifen antiestrogens. A comparison of the activity, pharmacokinetics, and metabolic activation of the cis and trans isomers of tamoxifen. J Ster Biochem 16:1-13 (Pubitemid 12158097)
    • (1982) Journal of Steroid Biochemistry , vol.16 , Issue.1 , pp. 1-13
    • Robertson, D.W.1    Katzenellenbogen, J.A.2    Long, D.J.3
  • 28
    • 84986512474 scopus 로고
    • CHARMM: A program for macromolecular energy minimization and dynamics calculations
    • doi:10.1002/jcc.540040211
    • Brooks BR, Bruccoleri RE, Olafson BD, States DJ, Swaminathan S, Karplus M (1983) CHARMM: a program for macromolecular energy minimization and dynamics calculations. J Comput Chem 4:187-217. doi:10.1002/jcc.540040211
    • (1983) J Comput Chem , vol.4 , pp. 187-217
    • Brooks, B.R.1    Bruccoleri, R.E.2    Olafson, B.D.3    States, D.J.4    Swaminathan, S.5    Karplus, M.6
  • 29
    • 0000344537 scopus 로고
    • A synthetic method for formyl → ethynyl conversion (RCHO→RC≡CH or RC≡CR′)
    • doi:10.1016/S0040-4039(01)94157-7
    • Corey EJ, Fuchs PL (1972) A synthetic method for formyl → ethynyl conversion (RCHO→RC≡CH or RC≡CR′). Tetrahedron Lett 13:3769-3772. doi:10.1016/S0040-4039(01)94157-7
    • (1972) Tetrahedron Lett , vol.13 , pp. 3769-3772
    • Corey, E.J.1    Fuchs, P.L.2
  • 30
    • 0035128543 scopus 로고    scopus 로고
    • Suzuki arylation of 1,1-Dibromo-1-alkenes: Synthesis of tetra-substituted alkenes
    • Bauer A, Miller MW, Vice SF, McCombie SW (2001) Suzuki arylation of 1,1-dibromo-1-alkenes: synthesis of tetra-substituted alkenes. Synlett 2:254-256. doi:10.1055/s-2001-10776 (Pubitemid 32154243)
    • (2001) Synlett , Issue.2 , pp. 254-256
    • Bauer, A.1    Miller, M.W.2    Vice, S.F.3    McCombie, S.W.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.