메뉴 건너뛰기




Volumn 52, Issue 19, 2009, Pages 5950-5966

Modeling, synthesis and biological evaluation of potential Retinoid X Receptor (RXR) selective agonists: Novel analogues of 4-[1-(3,5,5,8,8- pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (bexarotene)

Author keywords

[No Author keywords available]

Indexed keywords

BEXAROTENE; RETINOID X RECEPTOR;

EID: 70349645985     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900496b     Document Type: Article
Times cited : (62)

References (46)
  • 1
    • 0000530241 scopus 로고
    • The Retinoid Receptors
    • Academic Press: Orlando, FL
    • (a) Mangelsdorf, D. J.; Umesono, K.; Evans, R. M. The Retinoid Receptors. In The Retinoids; Academic Press: Orlando, FL, 1994; pp. 319-349.
    • (1994) The Retinoids , pp. 319-349
    • Mangelsdorf, D.J.1    Umesono, K.2    Evans, R.M.3
  • 2
    • 0026742534 scopus 로고
    • Multiplicity Generates Diversity in the Retinoic Acid Signaling Pathways
    • (b) Leid, M.; Kastner, P.; Chambon, P. Multiplicity Generates Diversity in the Retinoic Acid Signaling Pathways. Trends Biochem. Sci. 1992, 17, 427-433.
    • (1992) Trends Biochem. Sci. , vol.17 , pp. 427-433
    • Leid, M.1    Kastner, P.2    Chambon, P.3
  • 3
    • 0035813186 scopus 로고    scopus 로고
    • Nuclear Receptor Minireview Series
    • Olefsky, J. M. Nuclear Receptor Minireview Series. J. Biol. Chem. 2001, 276 (40), 36863-36864.
    • (2001) J. Biol. Chem. , vol.276 , Issue.40 , pp. 36863-36864
    • Olefsky, J.M.1
  • 4
    • 0024457916 scopus 로고
    • A domain containing leucin-zipper-like motifs mediates novel in vitro interactions between the thyroid hormone and retinoic acid receptors
    • Forman, B. M.; Yang, C.-R.; Au, M.; Casanova, J.; Ghysdael, J.; Samuels, H. H. A domain containing leucin-zipper-like motifs mediates novel in vitro interactions between the thyroid hormone and retinoic acid receptors. Mol. Endocrinol. 1989, 3, 1610-1626.
    • (1989) Mol. Endocrinol. , vol.3 , pp. 1610-1626
    • Forman, B.M.1    Yang, C.-R.2    Au, M.3    Casanova, J.4    Ghysdael, J.5    Samuels, H.H.6
  • 5
    • 0029562554 scopus 로고
    • The RXR heterodimers and orphan receptors
    • Mangelsdorf, D. J.; Evans, R. M. The RXR heterodimers and orphan receptors. Cell 1995, 83, 841-850.
    • (1995) Cell , vol.83 , pp. 841-850
    • Mangelsdorf, D.J.1    Evans, R.M.2
  • 11
    • 0027483915 scopus 로고
    • Conformational effects on retinoid receptor selectivity. 1. Effect of 9-double bond geometry on retinoid X receptor activity
    • (a) Jong, L.; Lehmann, J. M.; Hobbs, P. D.; Harlev, E.; Huffman, J. C.; Pfahl, M.; Dawson, M. I. Conformational effects on retinoid receptor selectivity. 1. Effect of 9-double bond geometry on retinoid X receptor activity. J. Med. Chem. 1993, 36, 2605-2613.
    • (1993) J. Med. Chem. , vol.36 , pp. 2605-2613
    • Jong, L.1    Lehmann, J.M.2    Hobbs, P.D.3    Harlev, E.4    Huffman, J.C.5    Pfahl, M.6    Dawson, M.I.7
  • 12
    • 0029102106 scopus 로고
    • Conformational Effects on Retinoid Receptor Selectivity. 2. Effects of Retinoid Bridging Group on Retinoid X Receptor Activity and Selectivity
    • (b) Dawson, M. I.; Jong, L.; Hobbs, P. D.; Cameron, J. F.; Chao, W.-R.; Pfahl, M.; Lee, M.-O.; Shroot, B.; Pfahl, M. Conformational Effects on Retinoid Receptor Selectivity. 2. Effects of Retinoid Bridging Group on Retinoid X Receptor Activity and Selectivity. J. Med. Chem. 1995, 38, 3368-3383.
    • (1995) J. Med. Chem. , Issue.38 , pp. 3368-3383
    • Dawson, M.I.1    Jong, L.2    Hobbs, P.D.3    Cameron, J.F.4    Chao, W.-R.5    Pfahl, M.6    Lee, M.-O.7    Shroot, B.8    Pfahl, M.9
  • 13
    • 23144441588 scopus 로고    scopus 로고
    • Synthesis, Crystal Structure Analysis, and Pharmacological Characterization of Disila-bexarotene, a Disila-Analogue of the RXR-Selective Retinoid Agonist Bexarotene
    • Daiss, J. O.; Burschka, C.; Mills, J. S.; Montana, J. G.; Showell, G. A.; Fleming, I.; Gaudon, C.; Ivanova, D.; Gronemeyer, H.; Tacke, R. Synthesis, Crystal Structure Analysis, and Pharmacological Characterization of Disila-bexarotene, a Disila-Analogue of the RXR-Selective Retinoid Agonist Bexarotene. Organometallics 2005, 24, 3192-3199.
    • (2005) Organometallics , vol.24 , pp. 3192-3199
    • Daiss, J.O.1    Burschka, C.2    Mills, J.S.3    Montana, J.G.4    Showell, G.A.5    Fleming, I.6    Gaudon, C.7    Ivanova, D.8    Gronemeyer, H.9    Tacke, R.10
  • 14
    • 9644295744 scopus 로고    scopus 로고
    • Synergistic effect of a retinoid X receptor-selective ligand bexarotene (LGD1069, Targretin) and paclitaxel (Taxol) in mammary carcinoma
    • Yen, W. -C.; Prudente, R. Y.; Lamph, W. W. Synergistic effect of a retinoid X receptor-selective ligand bexarotene (LGD1069, Targretin) and paclitaxel (Taxol) in mammary carcinoma. Breast Cancer Res. Treat. 2004, 88, 141-148.
    • (2004) Breast Cancer Res. Treat. , vol.88 , pp. 141-148
    • Yen, W.C.1    Prudente, R.Y.2    Lamph, W.W.3
  • 15
    • 11144239921 scopus 로고    scopus 로고
    • A Selective Retinoid X Receptor Agonist Bexarotene (Targretin) Prevents and Overcomes Acquired Paclitaxel (Taxol) Resistance in Human Non-Small Cell Lung Cancer
    • Yen, W.-C.; Corpuz, M. R.; Prudente, R. Y.; Cooke, T. A.; Bissonnette, R. P.; Negro-Vilar, A.; Lamph, W. W. A Selective Retinoid X Receptor Agonist Bexarotene (Targretin) Prevents and Overcomes Acquired Paclitaxel (Taxol) Resistance in Human Non-Small Cell Lung Cancer. Clin. Cancer Res. 2004, 10, 8656-8664.
    • (2004) Clin. Cancer Res. , vol.10 , pp. 8656-8664
    • Yen, W.-C.1    Corpuz, M.R.2    Prudente, R.Y.3    Cooke, T.A.4    Bissonnette, R.P.5    Negro-Vilar, A.6    Lamph, W.W.7
  • 16
    • 33746218695 scopus 로고    scopus 로고
    • Differentiation and growth inhibition mediated via the RXR:PPARγ heterodimer in colon cancer
    • Cesario, R. M.; Stone, J.; Yen, W.-C.; Bissonnette, R. P.; Lamph, W. W. Differentiation and growth inhibition mediated via the RXR:PPARγ heterodimer in colon cancer. Cancer Lett. 2006, 240, 225-233.
    • (2006) Cancer Lett. , vol.240 , pp. 225-233
    • Cesario, R.M.1    Stone, J.2    Yen, W.-C.3    Bissonnette, R.P.4    Lamph, W.W.5
  • 19
    • 0036318975 scopus 로고    scopus 로고
    • Functional Evidence for Retinoid X Receptor (RXR) as a Nonsilent Partner in the Thyroid Hormone Receptor/RXR Heterodimer
    • Li, D.; Li, T.; Wang, F.; Tian, H.; Samuels, H. H. Functional Evidence for Retinoid X Receptor (RXR) as a Nonsilent Partner in the Thyroid Hormone Receptor/RXR Heterodimer. Mol. Cell. Biol. 2002, 22, 5782-5792.
    • (2002) Mol. Cell. Biol. , vol.22 , pp. 5782-5792
    • Li, D.1    Li, T.2    Wang, F.3    Tian, H.4    Samuels, H.H.5
  • 20
    • 0030756037 scopus 로고    scopus 로고
    • A Suzuki coupling approach to the trifluoromethyl derivative of Targretin (LGD 1069)
    • Qing, F.-L.; Fan, J. A Suzuki coupling approach to the trifluoromethyl derivative of Targretin (LGD 1069). Bioorg. Med. Chem. Lett. 1997, 7, 2117-2120.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 2117-2120
    • Qing, F.-L.1    Fan, J.2
  • 21
    • 0035811459 scopus 로고    scopus 로고
    • Enantio-selective Synthesis of Potent Retinoid X Receptor Ligands: Differential Biological Activities of Individual Antipodes
    • Vuligonda, V.; Thacher, S. M.; Chandraratna, R. A. S. Enantio-selective Synthesis of Potent Retinoid X Receptor Ligands: Differential Biological Activities of Individual Antipodes. J. Med. Chem. 2001, 44, 2298-2303.
    • (2001) J. Med. Chem. , vol.44 , pp. 2298-2303
    • Vuligonda, V.1    Thacher, S.M.2    Chandraratna, R.A.S.3
  • 23
    • 0023709173 scopus 로고
    • Retinobenzoic Acids. 1. Structure-Activitiy Relationships of Aromatic Amides with Retinoidal Activity
    • Kagechika, H.; Kawachi, E.; Hashimoto, Y.; Himi, T.; Shudo, K. Retinobenzoic Acids. 1. Structure-Activitiy Relationships of Aromatic Amides with Retinoidal Activity. J. Med. Chem. 1988, 31, 2182-2192.
    • (1988) J. Med. Chem. , Issue.31 , pp. 2182-2192
    • Kagechika, H.1    Kawachi, E.2    Hashimoto, Y.3    Himi, T.4    Shudo, K.5
  • 37
    • 0036096774 scopus 로고    scopus 로고
    • Induction of Apoptosis by Bexarotene in Cutaneous T-Cell Lymphoma Cells
    • Zhang, C.; Hazarika, P.; Ni, X.; Weidner, D. A.; Duvic, M. Induction of Apoptosis by Bexarotene in Cutaneous T-Cell Lymphoma Cells. Clin. Cancer Res. 2002, 8, 1234-1240.
    • (2002) Clin. Cancer Res. , vol.8 , pp. 1234-1240
    • Zhang, C.1    Hazarika, P.2    Ni, X.3    Weidner, D.A.4    Duvic, M.5
  • 39
    • 33644839725 scopus 로고    scopus 로고
    • A selective retinoid X receptor agonist bexarotene (LGD1069, targretin) inhibits angiogenesis and metastasis in solid tumours
    • DOI 10.1038/sj.bjc.6602995, PII 6602995
    • Yen, W.-C.; Prudente, R. Y.; Corpuz, M. R.; Negro-Villar, A.; Lamph, W. W. A selective retinoid X receptor agonist bexarotene (LGD1069, targretin) inhibits angiogenesis and metastasis in solid tumours. Br. J. Cancer 2006, 94, 654-660. (Pubitemid 43361896)
    • (2006) British Journal of Cancer , vol.94 , Issue.5 , pp. 654-660
    • Yen, W.-C.1    Prudente, R.Y.2    Corpuz, M.R.3    Negro-Vilar, A.4    Lamph, W.W.5
  • 40
    • 0016605653 scopus 로고
    • Procedures used in the induction of mitotic recombination and mutation in the yeast Saccharomyces cerevisiae
    • (a) Zimmerman, F. K. Procedures used in the induction of mitotic recombination and mutation in the yeast Saccharomyces cerevisiae. Mutat. Res. 1975, 31, 71-86.
    • (1975) Mutat. Res. , vol.31 , pp. 71-86
    • Zimmerman, F.K.1
  • 41
    • 0016771744 scopus 로고
    • A yeast strain for simultaneous detection of mitotic crossing over, mitotic gene conversion, and reverse mutation
    • (b) Zimmermann, F. K.; Kern, R.; Rasenberger, H. A yeast strain for simultaneous detection of mitotic crossing over, mitotic gene conversion, and reverse mutation. Mutat. Res. 1975, 28, 381-388.
    • (1975) Mutat. Res. , vol.28 , pp. 381-388
    • Zimmermann, F.K.1    Kern, R.2    Rasenberger, H.3
  • 42
    • 38349097688 scopus 로고    scopus 로고
    • Using Saccharomyces cerevisiae to Test the Mutagenicity of Household Compounds: An Open Ended Hyothesis- Driven Teaching Lab
    • Marshall, P. A. Using Saccharomyces cerevisiae to Test the Mutagenicity of Household Compounds: An Open Ended Hyothesis- Driven Teaching Lab. CBE-LSE 2007, 6, 307-315.
    • (2007) CBE-LSE , vol.6 , pp. 307-315
    • Marshall, P.A.1
  • 43
    • 0036251738 scopus 로고    scopus 로고
    • Molecular Recognition of Agonist Ligands by RXRs
    • Egea, P. F.; Mitschler, A.; Moras, D. Molecular Recognition of Agonist Ligands by RXRs. Mol. Endocrinol. 2002, 16, 987-997.
    • (2002) Mol. Endocrinol. , vol.16 , pp. 987-997
    • Egea, P.F.1    Mitschler, A.2    Moras, D.3
  • 44
    • 0029002298 scopus 로고
    • Unique response pathways are established by allosteric interactions among nuclear hormone receptors
    • Forman, B. M.; Umesono, K.; Chen, J.; Evans, R. M. Unique response pathways are established by allosteric interactions among nuclear hormone receptors. Cell 1995, 81, 541-550.
    • (1995) Cell , vol.81 , pp. 541-550
    • Forman, B.M.1    Umesono, K.2    Chen, J.3    Evans, R.M.4
  • 46
    • 19644398887 scopus 로고
    • Aluminum Chloride-Catalyzed Formation of 2,5- Dichloro-2,5-dimethylhexane from tert-Butyl Chloride
    • Condon, F. E. Aluminum Chloride-Catalyzed Formation of 2,5- Dichloro-2,5-dimethylhexane from tert-Butyl Chloride. J. Org. Chem. 1956, 21, 761-763.
    • (1956) J. Org. Chem. , vol.21 , pp. 761-763
    • Condon, F.E.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.