메뉴 건너뛰기




Volumn 49, Issue 14, 2006, Pages 4208-4215

Back door modulation of the farnesoid X receptor: Design, synthesis, and biological evaluation of a series of side chain modified chenodeoxycholic acid derivatives

Author keywords

[No Author keywords available]

Indexed keywords

23 N (CARBO 2' ADAMANTYLOXY) 3ALPHA,7ALPHA DIHYDROXY 24 NOR 5BETA CHOLAN 23 AMINE; 23 N (CARBO 4 CARBOXYBENZYLOXY) 3ALPHA,7ALPHA DIHYDROXY 24 NOR 5BETA CHOLAN 23 AMINE; 23 N (CARBO 4 METHOXYBENZYLOXY) 3ALPHA,7ALPHA DIHYDROXY 24 NOR 5BETA CHOLAN 23 AMINE; 23 N (CARBOBENZYLOXY) 3ALPHA,7ALPHA DIHYDROXY 24 NOR 5BETA CHOLAN 23 AMINE; 23 N (CARBOCINNAMYLOXY) 3ALPHA,7ALPHA DIHYDROXY 24 NOR 5BETA CHOLAN 23 AMINE; 23 N (CARBOISOPROPYLOXY) 3ALPHA,7ALPHA DIHYDROXY 24 NOR 5BETA CHOLAN 23 AMINE; 23 N (CARBOTHIOPHENE 2' METHYLOXY) 3ALPHA,7ALPHA DIHYDROXY 24 NOR 5BETA CHOLAN 23 AMINE; 23 N (CARBOXYCYCLOHEXYLOXY) 3ALPHA,7ALPHA DIHYDROXY 24 NOR 5BETA CHOLAN 23 AMINE; 3 [2 [2 CHLORO 4 [3 (2,6 DICHLOROPHENYL) 5 ISOPROPYL 4 ISOXAZOLYLMETHOXY]PHENYL]VINYL]BENZOIC ACID; 3ALPHA,7ALPHA DIFORMYLOXY 5BETA CHOLAN 24 OIC ACID; 6ALPHA ETHYL CHENODEOXYCHOLIC ACID; BILE ACID; CARBOXYL GROUP; CHENODEOXYCHOLIC ACID DERIVATIVE; FARNESOID X RECEPTOR; FARNESOID X RECEPTOR AGONIST; FEXARAMINE; INT 747; LUCIFERASE; SELECTIVE ESTROGEN RECEPTOR MODULATOR; UNCLASSIFIED DRUG;

EID: 33745852636     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060294k     Document Type: Article
Times cited : (53)

References (33)
  • 1
    • 23944521260 scopus 로고    scopus 로고
    • Farnesoid X receptor: From structure to potential clinical applications
    • Pellicciari, R.; Costantino, G.; Fiorucci, S. Farnesoid X receptor: from structure to potential clinical applications J. Med. Chem. 2005, 48, 5383-5403.
    • (2005) J. Med. Chem. , vol.48 , pp. 5383-5403
    • Pellicciari, R.1    Costantino, G.2    Fiorucci, S.3
  • 2
    • 0033026760 scopus 로고    scopus 로고
    • Endogenous bile acids are ligands for the nuclear receptor FXR/BAR
    • Wang, H.; Chen, J.; Hollister, K.; Sowers, L. C.; Forman, B. M. Endogenous bile acids are ligands for the nuclear receptor FXR/BAR. Mol. Cell 1999, 3, 543-553.
    • (1999) Mol. Cell , vol.3 , pp. 543-553
    • Wang, H.1    Chen, J.2    Hollister, K.3    Sowers, L.C.4    Forman, B.M.5
  • 11
    • 0034664729 scopus 로고    scopus 로고
    • Targeted disruption of the nuclear receptor FXR/BAR impairs bile acid and lipid homeostasis
    • Sinal, C. J.; Tohkin, M.; Miyata, M.; Ward, J. M.; Lambert, G.; Gonzales, F. J. Targeted disruption of the nuclear receptor FXR/BAR impairs bile acid and lipid homeostasis. Cell 2000, 102, 731-744.
    • (2000) Cell , vol.102 , pp. 731-744
    • Sinal, C.J.1    Tohkin, M.2    Miyata, M.3    Ward, J.M.4    Lambert, G.5    Gonzales, F.J.6
  • 14
    • 14544270531 scopus 로고    scopus 로고
    • Potential regulatory role of the farnesoid X receptor in the metabolic syndrome
    • Duran-Sandoval, D.; Cariou, B.; Fruchart, J.-C.; Staels, B. Potential regulatory role of the farnesoid X receptor in the metabolic syndrome. Biochimie 2005, 87, 93-98.
    • (2005) Biochimie , vol.87 , pp. 93-98
    • Duran-Sandoval, D.1    Cariou, B.2    Fruchart, J.-C.3    Staels, B.4
  • 19
    • 0035942197 scopus 로고    scopus 로고
    • Crystallographic structures of the ligand-binding domains of the androgen receptor and its T877A mutant complexed with the natural agonist dihydrotestosterone
    • Sack, J. S.; Kish, K. F.; Wang, C.; Attar, R. M.; Kiefer, S. E.; An, Y.; Wu, G. Y.; Scheffler, J. E.; Salvati, M. E.; Krystek, S. R.; et al. Crystallographic structures of the ligand-binding domains of the androgen receptor and its T877A mutant complexed with the natural agonist dihydrotestosterone. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 4904-4909.
    • (2001) Proc. Natl. Acad. Sci. U.S.A. , vol.98 , pp. 4904-4909
    • Sack, J.S.1    Kish, K.F.2    Wang, C.3    Attar, R.M.4    Kiefer, S.E.5    An, Y.6    Wu, G.Y.7    Scheffler, J.E.8    Salvati, M.E.9    Krystek, S.R.10
  • 20
    • 0032446607 scopus 로고    scopus 로고
    • The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen
    • Shiau, A. K.; Barstad, D.; Loria, P. M.; Cheng, L.; Kushner, P. J.; Agard, D. A.; Greene, G. L. The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell 1998, 95, 927-937.
    • (1998) Cell , vol.95 , pp. 927-937
    • Shiau, A.K.1    Barstad, D.2    Loria, P.M.3    Cheng, L.4    Kushner, P.J.5    Agard, D.A.6    Greene, G.L.7
  • 21
    • 0032575057 scopus 로고    scopus 로고
    • Atomic structure of progesterone complexed with its receptor
    • (e) Williams, S. P.; Sigler, P. B. Atomic structure of progesterone complexed with its receptor. Nature 1998, 393, 392-396.
    • (1998) Nature , vol.393 , pp. 392-396
    • Williams, S.P.1    Sigler, P.B.2
  • 22
    • 27444441918 scopus 로고    scopus 로고
    • Is antagonism of E/Z-guggulsterone at the farnesoid X receptor mediated by a noncanonical binding site? a molecular modeling study
    • Meyer, U.; Costantino, G.; Macchiarulo, A.; Pellicciari, R. Is antagonism of E/Z-guggulsterone at the farnesoid X receptor mediated by a noncanonical binding site? A molecular modeling study. J. Med. Chem. 2005, 48, 6948-6955.
    • (2005) J. Med. Chem. , vol.48 , pp. 6948-6955
    • Meyer, U.1    Costantino, G.2    Macchiarulo, A.3    Pellicciari, R.4
  • 23
    • 4143056853 scopus 로고    scopus 로고
    • Bile acid derivatives as ligands of the farnesoid X receptor. Synthesis, evaluation, and structure-activity relationship of a series of body and side chain modified analogues of chenodeoxycholic acid
    • Pellicciari, R.; Costantino, G.; Camaioni, E.; Sadeghpour, B. M.; Entrena, A.; Willson, T. M.; Fiorucci, S.; Clerici, C.; Gioiello, A. Bile acid derivatives as ligands of the farnesoid X receptor. Synthesis, evaluation, and structure-activity relationship of a series of body and side chain modified analogues of chenodeoxycholic acid. J. Med. Chem. 2004, 47, 4559-4569.
    • (2004) J. Med. Chem. , vol.47 , pp. 4559-4569
    • Pellicciari, R.1    Costantino, G.2    Camaioni, E.3    Sadeghpour, B.M.4    Entrena, A.5    Willson, T.M.6    Fiorucci, S.7    Clerici, C.8    Gioiello, A.9
  • 25
    • 0018476938 scopus 로고
    • Synthesis of monosulfates of unconjugated bile acids
    • Goto, J.; Kato, H.; Hasegawa, F.; Nambara, T. Synthesis of monosulfates of unconjugated bile acids. Chem. Pharm. Bull. 1979, 27, 1402-1411.
    • (1979) Chem. Pharm. Bull. , vol.27 , pp. 1402-1411
    • Goto, J.1    Kato, H.2    Hasegawa, F.3    Nambara, T.4
  • 26
    • 18244361820 scopus 로고    scopus 로고
    • Molecular dynamics simulation of the ligand binding domain of farnesoid X receptor. Insight into helix-12 stability and coactivator peptide stabilization in response to agonist binding
    • Costantino, G.; Entrena-Gaudix, A.; Macchiarlo, A.; Gioiello, A.; Pellicciari, R. Molecular dynamics simulation of the ligand binding domain of farnesoid X receptor. Insight into helix-12 stability and coactivator peptide stabilization in response to agonist binding. J. Med. Chem. 2005, 48, 3251-3259.
    • (2005) J. Med. Chem. , vol.48 , pp. 3251-3259
    • Costantino, G.1    Entrena-Gaudix, A.2    Macchiarlo, A.3    Gioiello, A.4    Pellicciari, R.5
  • 28
    • 0004301669 scopus 로고
    • Tripos Inc. S. Hanley Rd, St. Louis, MO 63144-2913
    • Sybyl Molecular Modeling Software; Tripos Inc. (1699 S. Hanley Rd, St. Louis, MO 63144-2913); http://www.tripos.com.
    • (1699) Sybyl Molecular Modeling Software
  • 29
    • 49149147973 scopus 로고
    • Iterative partial equalization of orbital electronegativity. A rapid access to atomic charges
    • (a) Gasteiger, J.; Marsili, M. Iterative partial equalization of orbital electronegativity. A rapid access to atomic charges. Tetrahedron, 1980, 36, 3219-3228.
    • (1980) Tetrahedron , vol.36 , pp. 3219-3228
    • Gasteiger, J.1    Marsili, M.2
  • 30
    • 0000939786 scopus 로고
    • Charge distributions from molecular topology and pi-orbital electronegativity
    • (b) Marsili, M.; Gasteiger, J. Charge distributions from molecular topology and pi-orbital electronegativity. Croat. Chem. Acta 1980, 53, 601-614.
    • (1980) Croat. Chem. Acta , vol.53 , pp. 601-614
    • Marsili, M.1    Gasteiger, J.2
  • 31
    • 84986870156 scopus 로고
    • Prediction of proton magnetic resonance shifts: The dependence on hydrogen charges obtained by iterative partial equalization of orbital electronegativity
    • Gasteiger, J.; Marsili, M. Prediction of proton magnetic resonance shifts: the dependence on hydrogen charges obtained by iterative partial equalization of orbital electronegativity. Org. Magn. Reson. 1981, 15, 353-360.
    • (1981) Org. Magn. Reson. , vol.15 , pp. 353-360
    • Gasteiger, J.1    Marsili, M.2
  • 32
    • 11644261806 scopus 로고    scopus 로고
    • Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function
    • Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J. Comput. Chem. 1998, 19, 1639-1662.
    • (1998) J. Comput. Chem. , vol.19 , pp. 1639-1662
    • Morris, G.M.1    Goodsell, D.S.2    Halliday, R.S.3    Huey, R.4    Hart, W.E.5    Belew, R.K.6    Olson, A.J.7
  • 33
    • 33745843838 scopus 로고    scopus 로고
    • program is available from the Molecular Graphics Laboratory, at The Scripps Research Institute
    • AutoDock Tools (ADT) program is available from the Molecular Graphics Laboratory, at The Scripps Research Institute; http://www.scripps.edu/inb/olson/ index.html.
    • AutoDock Tools (ADT)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.