메뉴 건너뛰기




Volumn 5, Issue 5, 2014, Pages 533-537

Dual RXR agonists and RAR antagonists based on the stilbene retinoid scaffold

Author keywords

agonists; antagonists; arotinoids; molecular modeling; Retinoid receptor subtypes; transactivation

Indexed keywords

ALITRETINOIN; AROTINOID; BENZYLPHOSPHONATE; LIGAND; NAPHTHALDEHYDE; NAPHTHALENE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; RETINOIC ACID; RETINOIC ACID DERIVATIVE; RETINOIC ACID RECEPTOR AGONIST; RETINOID X RECEPTOR AGONIST; STILBENE; UNCLASSIFIED DRUG;

EID: 84900422658     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml400521f     Document Type: Article
Times cited : (8)

References (47)
  • 1
    • 84876294515 scopus 로고    scopus 로고
    • Visualization of an endogenous retinoic acid gradient across embryonic development
    • Shimozono, S.; Iimura, T.; Kitaguchi, T.; Higashijima, S.-I.; Miyawaki, A. Visualization of an endogenous retinoic acid gradient across embryonic development Nature 2013, 496, 363-366
    • (2013) Nature , vol.496 , pp. 363-366
    • Shimozono, S.1    Iimura, T.2    Kitaguchi, T.3    Higashijima, S.-I.4    Miyawaki, A.5
  • 2
    • 33144488245 scopus 로고    scopus 로고
    • Function of retinoid nuclear receptors: Lessons from genetic and pharmacological dissections of the retinoic acid signalling pathway during mouse embryogenesis
    • Mark, M.; Ghyselinck, N.; Chambon, P. Function of retinoid nuclear receptors: lessons from genetic and pharmacological dissections of the retinoic acid signalling pathway during mouse embryogenesis Annu. Rev. Pharmacol. Toxicol. 2006, 46, 451-480
    • (2006) Annu. Rev. Pharmacol. Toxicol. , vol.46 , pp. 451-480
    • Mark, M.1    Ghyselinck, N.2    Chambon, P.3
  • 4
    • 45549091674 scopus 로고    scopus 로고
    • Retinoic acid in development: Towards an integrated view
    • Niederreither, K.; Dolle, P. Retinoic acid in development: towards an integrated view Nat. Rev. Genet. 2008, 9, 541-553
    • (2008) Nat. Rev. Genet. , vol.9 , pp. 541-553
    • Niederreither, K.1    Dolle, P.2
  • 7
    • 0034306499 scopus 로고    scopus 로고
    • Nuclear receptor ligand-binding domains: Three-dimensional structures, molecular interactions and pharmacological implications
    • Bourguet, W.; Germain, P.; Gronemeyer, H. Nuclear receptor ligand-binding domains: three-dimensional structures, molecular interactions and pharmacological implications Trends Pharmacol. Sci. 2000, 21, 381-388
    • (2000) Trends Pharmacol. Sci. , vol.21 , pp. 381-388
    • Bourguet, W.1    Germain, P.2    Gronemeyer, H.3
  • 8
    • 0035749803 scopus 로고    scopus 로고
    • The promise of retinoids to fight against cancer
    • Altucci, L.; Gronemeyer, H. The promise of retinoids to fight against cancer Nat. Rev. Cancer 2001, 1, 181-193
    • (2001) Nat. Rev. Cancer , vol.1 , pp. 181-193
    • Altucci, L.1    Gronemeyer, H.2
  • 9
    • 0036142502 scopus 로고    scopus 로고
    • Retinoids and their receptors in cancer development and chemoprevention
    • Sun, S. Y.; Lotan, R. Retinoids and their receptors in cancer development and chemoprevention Crit. Rev. Oncol. Hematol. 2002, 41, 41-55
    • (2002) Crit. Rev. Oncol. Hematol. , vol.41 , pp. 41-55
    • Sun, S.Y.1    Lotan, R.2
  • 12
    • 0037050017 scopus 로고    scopus 로고
    • Co-regulator recruitment and the mechanism of retinoic acid receptor synergy
    • Germain, P.; Iyer, J.; Zechel, C.; Gronemeyer, H. Co-regulator recruitment and the mechanism of retinoic acid receptor synergy Nature 2002, 415, 187-192
    • (2002) Nature , vol.415 , pp. 187-192
    • Germain, P.1    Iyer, J.2    Zechel, C.3    Gronemeyer, H.4
  • 13
    • 1642304065 scopus 로고    scopus 로고
    • Structural determinants of allosteric ligand activation in RXR heterodimers
    • Shulman, A. I.; Larson, C.; Mangelsdorf, D. J.; Ranganathan, R. Structural determinants of allosteric ligand activation in RXR heterodimers Cell 2004, 116, 417-429
    • (2004) Cell , vol.116 , pp. 417-429
    • Shulman, A.I.1    Larson, C.2    Mangelsdorf, D.J.3    Ranganathan, R.4
  • 14
    • 0023483399 scopus 로고
    • A human retinoic acid receptor which belongs to the family of nuclear receptors
    • Petkovich, M.; Brand, N. J.; Kurst, A.; Chambon, P. A human retinoic acid receptor which belongs to the family of nuclear receptors Nature 1987, 330, 444-450
    • (1987) Nature , vol.330 , pp. 444-450
    • Petkovich, M.1    Brand, N.J.2    Kurst, A.3    Chambon, P.4
  • 17
    • 78049491490 scopus 로고    scopus 로고
    • Inverse Agonists and Antagonists of Retinoid Receptors
    • In; Conn, P. M. Academic Press: New York, Vol. - 195
    • Bourguet, W.; de Lera, A. R.; Gronemeyer, H. Inverse Agonists and Antagonists of Retinoid Receptors. In Methods in Enzymology; Conn, P. M., Ed.; Academic Press: New York, 2010; Vol. 485, pp 161-195.
    • (2010) Methods in Enzymology , vol.485 , pp. 161
    • Bourguet, W.1    De Lera, A.R.2    Gronemeyer, H.3
  • 18
  • 20
    • 0029643780 scopus 로고
    • Crystal structure of the RARγ ligand-binding domain bound to all- trans -retinoic acid
    • Renaud, J.-P.; Rochel, N.; Ruff, M.; Vivat, V.; Chambon, P.; Gronemeyer, H.; Moras, D. Crystal structure of the RARγ ligand-binding domain bound to all- trans -retinoic acid Nature 1995, 378, 681-689
    • (1995) Nature , vol.378 , pp. 681-689
    • Renaud, J.-P.1    Rochel, N.2    Ruff, M.3    Vivat, V.4    Chambon, P.5    Gronemeyer, H.6    Moras, D.7
  • 23
    • 0029012163 scopus 로고
    • Crystal structure of the ligand-binding domain of the human nuclear receptor RXRα
    • Bourguet, W.; Ruff, M.; Chambon, P.; Gronemeyer, H.; Moras, D. Crystal structure of the ligand-binding domain of the human nuclear receptor RXRα Nature 1995, 375, 377-382
    • (1995) Nature , vol.375 , pp. 377-382
    • Bourguet, W.1    Ruff, M.2    Chambon, P.3    Gronemeyer, H.4    Moras, D.5
  • 24
    • 0033868825 scopus 로고    scopus 로고
    • Crystal structure of a heterodimeric complex of RAR and RXR ligand-binding domains
    • Bourguet, W.; Vivat, V.; Wurtz, J.-M.; Chambon, P.; Gronemeyer, H.; Moras, D. Crystal structure of a heterodimeric complex of RAR and RXR ligand-binding domains Mol. Cell 2000, 5, 289-298
    • (2000) Mol. Cell , vol.5 , pp. 289-298
    • Bourguet, W.1    Vivat, V.2    Wurtz, J.-M.3    Chambon, P.4    Gronemeyer, H.5    Moras, D.6
  • 26
    • 0019189707 scopus 로고
    • Arotinoids: A new class of highly active retinoids
    • Loeliger, P.; Bollag, W.; Mayer, H. Arotinoids: a new class of highly active retinoids Eur. J. Med. Chem. 1980, 15, 9-15
    • (1980) Eur. J. Med. Chem. , vol.15 , pp. 9-15
    • Loeliger, P.1    Bollag, W.2    Mayer, H.3
  • 28
    • 0028967616 scopus 로고
    • RAR-specific agonist/antagonists which dissociate transactivation and AP1 transrepression inhibit anchorage-independent cell proliferation
    • Chen, J. Y.; Penco, S.; Ostrowski, J.; Balaguer, P.; Pons, M.; Starrett, J. E.; Reczek, P.; Chambon, P.; Gronemeyer, H. RAR-specific agonist/antagonists which dissociate transactivation and AP1 transrepression inhibit anchorage-independent cell proliferation EMBO J. 1995, 14, 1187-1197
    • (1995) EMBO J. , vol.14 , pp. 1187-1197
    • Chen, J.Y.1    Penco, S.2    Ostrowski, J.3    Balaguer, P.4    Pons, M.5    Starrett, J.E.6    Reczek, P.7    Chambon, P.8    Gronemeyer, H.9
  • 29
    • 0023709173 scopus 로고
    • Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity
    • Kagechika, H.; Kawachi, E.; Hashimoto, Y.; Himi, T.; Shudo, K. Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity J. Med. Chem. 1988, 31, 2182-2192
    • (1988) J. Med. Chem. , vol.31 , pp. 2182-2192
    • Kagechika, H.1    Kawachi, E.2    Hashimoto, Y.3    Himi, T.4    Shudo, K.5
  • 32
    • 0034612290 scopus 로고    scopus 로고
    • Enantiomer discrimination illustrated by high-resolution crystal structures of the human nuclear receptor hRARγ
    • Klaholz, B. P.; Mitschler, A.; Belema, M.; Zusi, C.; Moras, D. Enantiomer discrimination illustrated by high-resolution crystal structures of the human nuclear receptor hRARγ Proc. Natl. Acad. Sci. 2000, 97, 6322-6327
    • (2000) Proc. Natl. Acad. Sci. , vol.97 , pp. 6322-6327
    • Klaholz, B.P.1    Mitschler, A.2    Belema, M.3    Zusi, C.4    Moras, D.5
  • 33
    • 0001592343 scopus 로고
    • Electrophilic additions of positive iodine to alkynes through an iodonium mechanism
    • Barluenga, J.; Rodriguez, M. A.; Campos, P. J. Electrophilic additions of positive iodine to alkynes through an iodonium mechanism J. Org. Chem. 1990, 55, 3104-3106
    • (1990) J. Org. Chem. , vol.55 , pp. 3104-3106
    • Barluenga, J.1    Rodriguez, M.A.2    Campos, P.J.3
  • 34
    • 0037175592 scopus 로고    scopus 로고
    • Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis
    • Kotha, S.; Lahiri, K.; Kashinath, D. Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis Tetrahedron 2002, 58, 9633-9695
    • (2002) Tetrahedron , vol.58 , pp. 9633-9695
    • Kotha, S.1    Lahiri, K.2    Kashinath, D.3
  • 35
    • 52149114261 scopus 로고    scopus 로고
    • Carbon-heteroatom bond formation catalysed by organometallic complexes
    • Hartwig, J. F. Carbon-heteroatom bond formation catalysed by organometallic complexes Nature 2008, 455, 314-322
    • (2008) Nature , vol.455 , pp. 314-322
    • Hartwig, J.F.1
  • 36
    • 51049095122 scopus 로고    scopus 로고
    • Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis
    • Evano, G.; Blanchard, N.; Toumi, M. Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis Chem. Rev. 2008, 108, 3054-3131
    • (2008) Chem. Rev. , vol.108 , pp. 3054-3131
    • Evano, G.1    Blanchard, N.2    Toumi, M.3
  • 37
    • 1342302805 scopus 로고    scopus 로고
    • Recent development of peptide coupling reagents in organic synthesis
    • Han, S.-Y.; Kim, Y.-A. Recent development of peptide coupling reagents in organic synthesis Tetrahedron 2004, 60, 2447-2467
    • (2004) Tetrahedron , vol.60 , pp. 2447-2467
    • Han, S.-Y.1    Kim, Y.-A.2
  • 38
    • 0034794463 scopus 로고    scopus 로고
    • A general and efficient copper catalyst for the amidation of aryl halides and the N -arylation of nitrogen heterocycles
    • Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. A general and efficient copper catalyst for the amidation of aryl halides and the N -arylation of nitrogen heterocycles J. Am. Chem. Soc. 2001, 123, 7727-7729
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7727-7729
    • Klapars, A.1    Antilla, J.C.2    Huang, X.3    Buchwald, S.L.4
  • 39
    • 0035891639 scopus 로고    scopus 로고
    • Synthesis of N -aryl hydrazides by copper-catalyzed coupling of hydrazides with aryl iodides
    • Wolter, M.; Klapars, A.; Buchwald, S. L. Synthesis of N -aryl hydrazides by copper-catalyzed coupling of hydrazides with aryl iodides Org. Lett. 2001, 3, 3803-3805
    • (2001) Org. Lett. , vol.3 , pp. 3803-3805
    • Wolter, M.1    Klapars, A.2    Buchwald, S.L.3
  • 40
    • 0037178121 scopus 로고    scopus 로고
    • A general and efficient copper catalyst for the amidation of aryl halides
    • Klapars, A.; Huang, X.; Buchwald, S. L. A general and efficient copper catalyst for the amidation of aryl halides J. Am. Chem. Soc. 2002, 124, 7421-7428
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 7421-7428
    • Klapars, A.1    Huang, X.2    Buchwald, S.L.3
  • 41
    • 0037149057 scopus 로고    scopus 로고
    • Copper-catalyzed coupling of alkylamines and aryl iodides: An efficient system even in an air atmosphere
    • Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Copper-catalyzed coupling of alkylamines and aryl iodides: an efficient system even in an air atmosphere Org. Lett. 2002, 4, 581-584
    • (2002) Org. Lett. , vol.4 , pp. 581-584
    • Kwong, F.Y.1    Klapars, A.2    Buchwald, S.L.3
  • 42
    • 0030865548 scopus 로고    scopus 로고
    • A mutation mimicking ligand-induced conformational change yields a constitutive RXR that senses allosteric effects in heterodimers
    • Vivat, V.; Zechel, C.; Wurtz, J.-M.; Bourguet, W.; Kagechika, H.; Umemiya, H.; Shudo, K.; Moras, D.; Gronemeyer, H.; Chambon, P. A mutation mimicking ligand-induced conformational change yields a constitutive RXR that senses allosteric effects in heterodimers EMBO J. 1997, 16, 5697-5709
    • (1997) EMBO J. , vol.16 , pp. 5697-5709
    • Vivat, V.1    Zechel, C.2    Wurtz, J.-M.3    Bourguet, W.4    Kagechika, H.5    Umemiya, H.6    Shudo, K.7    Moras, D.8    Gronemeyer, H.9    Chambon, P.10
  • 43
    • 0034622982 scopus 로고    scopus 로고
    • Structural basis for isotype selectivity of the human retinoic acid nuclear receptor
    • Klaholz, B. P.; Mitschler, A.; Moras, D. Structural basis for isotype selectivity of the human retinoic acid nuclear receptor J. Mol. Biol. 2000, 302, 155-170
    • (2000) J. Mol. Biol. , vol.302 , pp. 155-170
    • Klaholz, B.P.1    Mitschler, A.2    Moras, D.3
  • 44
    • 0036711448 scopus 로고    scopus 로고
    • C-H···O hydrogen bonds in the nuclear receptor RARγ. A potential tool for drug discovery
    • Klaholz, B. P.; Moras, D. C-H···O hydrogen bonds in the nuclear receptor RARγ. A potential tool for drug discovery Structure 2002, 10, 1197-1204
    • (2002) Structure , vol.10 , pp. 1197-1204
    • Klaholz, B.P.1    Moras, D.2
  • 45
    • 0021871375 scopus 로고
    • A computational procedure for determining energetically favorable binding sites on biologically important macromolecules
    • Goodford, P. J. A computational procedure for determining energetically favorable binding sites on biologically important macromolecules J. Med. Chem. 1985, 28, 849-857
    • (1985) J. Med. Chem. , vol.28 , pp. 849-857
    • Goodford, P.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.