메뉴 건너뛰기




Volumn 58, Issue 2, 2015, Pages 912-926

RXR partial agonist produced by side chain repositioning of alkoxy RXR full agonist retains antitype 2 diabetes activity without the adverse effects

Author keywords

[No Author keywords available]

Indexed keywords

6 [ETHYL (3 ISOBUTOXY 4 ISOPROPYLPHENYL)AMINO]PYRIDINE 3 CARBOXYLIC ACID; 6 [ETHYL (4 ISOBUTOXY 3 ISOPROPYLPHENYL)AMINO]PYRIDINE 3 CARBOXYLIC ACID; ALKYL GROUP; ANTIDIABETIC AGENT; GLUCOSE; HETERODIMER; LIVER X RECEPTOR; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR; PIOGLITAZONE; RETINOID X RECEPTOR; RETINOID X RECEPTOR PARTIAL AGONIST; TRIACYLGLYCEROL; UNCLASSIFIED DRUG;

EID: 84921449420     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm501863r     Document Type: Article
Times cited : (27)

References (51)
  • 1
    • 84896462023 scopus 로고    scopus 로고
    • Retinoid X receptor ligands: A patent review (2007-2013)
    • Yamada, S.; Kakuta, H. Retinoid X receptor ligands: a patent review (2007-2013) Expert Opin. Ther. Pat. 2014, 24, 443-452
    • (2014) Expert Opin. Ther. Pat. , vol.24 , pp. 443-452
    • Yamada, S.1    Kakuta, H.2
  • 4
    • 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
  • 5
    • 84897147399 scopus 로고    scopus 로고
    • Nuclear receptors, RXR, and the big bang
    • Ronald, M.; Evans, D.; Mangelsdorf, D. J. Nuclear receptors, RXR, and the big bang Cell 2014, 157, 255-266
    • (2014) Cell , vol.157 , pp. 255-266
    • Ronald, M.1    Evans, D.2    Mangelsdorf, D.J.3
  • 6
    • 84871490319 scopus 로고    scopus 로고
    • Examining the safety of PPAR agonists-current trends and future prospects
    • Bortolini, M.; Wright, M. B.; Bopst, M.; Balas, B. Examining the safety of PPAR agonists-current trends and future prospects Expert Opin. Drug Saf. 2013, 12, 65-79
    • (2013) Expert Opin. Drug Saf. , vol.12 , pp. 65-79
    • Bortolini, M.1    Wright, M.B.2    Bopst, M.3    Balas, B.4
  • 9
    • 0037432165 scopus 로고    scopus 로고
    • T-0901317, a synthetic liver X receptor ligand, inhibits development of atherosclerosis in LDL receptor-deficient mice
    • Terasaka, N.; Hiroshima, A.; Koieyama, T.; Ubukata, N.; Morikawa, Y.; Nakai, D.; Inaba, T. T-0901317, a synthetic liver X receptor ligand, inhibits development of atherosclerosis in LDL receptor-deficient mice FEBS Lett. 2003, 536, 6-11
    • (2003) FEBS Lett. , vol.536 , pp. 6-11
    • Terasaka, N.1    Hiroshima, A.2    Koieyama, T.3    Ubukata, N.4    Morikawa, Y.5    Nakai, D.6    Inaba, T.7
  • 10
    • 0031813879 scopus 로고    scopus 로고
    • Transactivation by retinoid X receptor-peroxisome proliferator-activated receptor gamma (PPARgamma) heterodimers: Intermolecular synergy requires only the PPARgamma hormone-dependent activation function
    • Schulman, I. G.; Shao, G.; Heyman, R. A. Transactivation by retinoid X receptor-peroxisome proliferator-activated receptor gamma (PPARgamma) heterodimers: intermolecular synergy requires only the PPARgamma hormone-dependent activation function Mol. Cell. Biol. 1998, 18, 3483-3494
    • (1998) Mol. Cell. Biol. , vol.18 , pp. 3483-3494
    • Schulman, I.G.1    Shao, G.2    Heyman, R.A.3
  • 12
    • 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
  • 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
  • 15
    • 84875952050 scopus 로고    scopus 로고
    • Role of bexarotene in the treatment of cutaneous T-cell lymphoma: The clinical and immunological sides
    • Pileri, A.; Delfino, C.; Grandi, V.; Pimpinelli, N. Role of bexarotene in the treatment of cutaneous T-cell lymphoma: the clinical and immunological sides Immunotherapy 2013, 5, 427-433
    • (2013) Immunotherapy , vol.5 , pp. 427-433
    • Pileri, A.1    Delfino, C.2    Grandi, V.3    Pimpinelli, N.4
  • 18
    • 84888380533 scopus 로고    scopus 로고
    • Low dose bexarotene treatment rescues dopamine neurons and restores behavioral function in models of Parkinsons disease
    • McFarland, K.; Spalding, T. A.; Hubbard, D.; Ma, J. N.; Olsson, R.; Burstein, E. S. Low dose bexarotene treatment rescues dopamine neurons and restores behavioral function in models of Parkinsons disease ACS Chem. Neurosci. 2013, 4, 1430-1438
    • (2013) ACS Chem. Neurosci. , vol.4 , pp. 1430-1438
    • McFarland, K.1    Spalding, T.A.2    Hubbard, D.3    Ma, J.N.4    Olsson, R.5    Burstein, E.S.6
  • 21
    • 0035581103 scopus 로고    scopus 로고
    • Retinoid X receptor agonist elevation of serum triglycerides in rats by potentiation of retinoic acid receptor agonist induction or by action as single agents
    • Standeven, A. M.; Thacher, S. M.; Yuan, Y. D.; Escobar, M.; Vuligonda, V.; Beard, R. L.; Chandraratna, R. A. Retinoid X receptor agonist elevation of serum triglycerides in rats by potentiation of retinoic acid receptor agonist induction or by action as single agents Biochem. Pharmacol. 2001, 62, 1501-1509
    • (2001) Biochem. Pharmacol. , vol.62 , pp. 1501-1509
    • Standeven, A.M.1    Thacher, S.M.2    Yuan, Y.D.3    Escobar, M.4    Vuligonda, V.5    Beard, R.L.6    Chandraratna, R.A.7
  • 23
    • 0032966295 scopus 로고    scopus 로고
    • The RXR agonist LG100268 causes hepatomegaly, improves glycaemic control and decreases cardiovascular risk and cachexia in diabetic mice suffering from pancreatic beta-cell dysfunction
    • Lenhard, J. M.; Lancaster, M. E.; Paulik, M. A.; Weiel, J. E.; Binz, J. G.; Sundseth, S. S.; Gaskill, B. A.; Lightfoot, R. M.; Brown, H. R. The RXR agonist LG100268 causes hepatomegaly, improves glycaemic control and decreases cardiovascular risk and cachexia in diabetic mice suffering from pancreatic beta-cell dysfunction Diabetologia 1999, 42, 545-554
    • (1999) Diabetologia , vol.42 , pp. 545-554
    • Lenhard, J.M.1    Lancaster, M.E.2    Paulik, M.A.3    Weiel, J.E.4    Binz, J.G.5    Sundseth, S.S.6    Gaskill, B.A.7    Lightfoot, R.M.8    Brown, H.R.9
  • 25
    • 0037357829 scopus 로고    scopus 로고
    • Etiology, diagnosis, and treatment recommendations for central hypothyroidism associated with bexarotene therapy for cutaneous T-cell lymphoma
    • Sherman, S. I. Etiology, diagnosis, and treatment recommendations for central hypothyroidism associated with bexarotene therapy for cutaneous T-cell lymphoma Clin. Lymphoma 2003, 3, 249-252
    • (2003) Clin. Lymphoma , vol.3 , pp. 249-252
    • Sherman, S.I.1
  • 27
    • 0029795523 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of retinoid X receptor selective diaryl sulfide analogs of retinoic acid
    • Beard, R. L.; Colon, D. F.; Song, T. K.; Davies, P. J.; Kochhar, D. M.; Chandraratna, R. A. Synthesis and structure-activity relationships of retinoid X receptor selective diaryl sulfide analogs of retinoic acid J. Med. Chem. 1996, 39, 3556-3563
    • (1996) J. Med. Chem. , vol.39 , pp. 3556-3563
    • Beard, R.L.1    Colon, D.F.2    Song, T.K.3    Davies, P.J.4    Kochhar, D.M.5    Chandraratna, R.A.6
  • 32
    • 78650207455 scopus 로고    scopus 로고
    • Modification at the lipophilic domain of RXR agonists differentially influences activation of RXR heterodimers
    • Ohsawa, F.; Morishita, K.; Yamada, S.; Makishima, M.; Kakuta, H. Modification at the lipophilic domain of RXR agonists differentially influences activation of RXR heterodimers ACS Med. Chem. Lett. 2010, 1, 521-525
    • (2010) ACS Med. Chem. Lett. , vol.1 , pp. 521-525
    • Ohsawa, F.1    Morishita, K.2    Yamada, S.3    Makishima, M.4    Kakuta, H.5
  • 33
    • 47649097615 scopus 로고    scopus 로고
    • The first potent subtype-selective retinoid X receptor (RXR) agonist possessing a 3-isopropoxy-4-isopropylphenylamino moiety, NEt-3IP (RXRalpha/beta-dual agonist)
    • Takamatsu, K.; Takano, A.; Yakushiji, N.; Morohashi, K.; Morishita, K.; Matsuura, N.; Makishima, M.; Tai, A.; Sasaki, K.; Kakuta, H. The first potent subtype-selective retinoid X receptor (RXR) agonist possessing a 3-isopropoxy-4-isopropylphenylamino moiety, NEt-3IP (RXRalpha/beta-dual agonist) ChemMedChem 2008, 3, 780-787
    • (2008) ChemMedChem , vol.3 , pp. 780-787
    • Takamatsu, K.1    Takano, A.2    Yakushiji, N.3    Morohashi, K.4    Morishita, K.5    Matsuura, N.6    Makishima, M.7    Tai, A.8    Sasaki, K.9    Kakuta, H.10
  • 35
    • 0036682057 scopus 로고    scopus 로고
    • Novel retinoid X receptor antagonists: Specific inhibition of retinoid synergism in RXR-RAR heterodimer actions
    • Takahashi, B.; Ohta, K.; Kawachi, E.; Fukasawa, H.; Hashimoto, Y.; Kagechika, H. Novel retinoid X receptor antagonists: Specific inhibition of retinoid synergism in RXR-RAR heterodimer actions J. Med. Chem. 2002, 45, 3327-3330
    • (2002) J. Med. Chem. , vol.45 , pp. 3327-3330
    • Takahashi, B.1    Ohta, K.2    Kawachi, E.3    Fukasawa, H.4    Hashimoto, Y.5    Kagechika, H.6
  • 36
    • 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
  • 38
    • 48649098099 scopus 로고    scopus 로고
    • Improvement of the transactivation activity of phenylpropanoic acid-type peroxisome proliferator-activated receptor pan agonists: Effect of introduction of fluorine at the linker part
    • Kasuga, J.; Oyama, T.; Hirakawa, Y.; Makishima, M.; Morikawa, K.; Hashimoto, Y.; Miyachi, H. Improvement of the transactivation activity of phenylpropanoic acid-type peroxisome proliferator-activated receptor pan agonists: effect of introduction of fluorine at the linker part Bioorg. Med. Chem. Lett. 2008, 18, 4525-4528
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 4525-4528
    • Kasuga, J.1    Oyama, T.2    Hirakawa, Y.3    Makishima, M.4    Morikawa, K.5    Hashimoto, Y.6    Miyachi, H.7
  • 39
    • 75849160939 scopus 로고    scopus 로고
    • LXR antagonists with a 5-substituted phenanthridin-6-one skeleton: Synthesis and LXR transrepression activities of conformationally restricted carba-T0901317 analogs
    • Aoyama, A.; Aoyama, H.; Dodo, K.; Makishima, M.; Hashimoto, Y.; Miyachi, H. LXR antagonists with a 5-substituted phenanthridin-6-one skeleton: synthesis and LXR transrepression activities of conformationally restricted carba-T0901317 analogs Heterocycles 2008, 76, 137-142
    • (2008) Heterocycles , vol.76 , pp. 137-142
    • Aoyama, A.1    Aoyama, H.2    Dodo, K.3    Makishima, M.4    Hashimoto, Y.5    Miyachi, H.6
  • 42
    • 0031712627 scopus 로고    scopus 로고
    • Actions of novel antidiabetic thiazolidinedione, T-174, in animal models of non-insulin-dependent diabetes mellitus (NIDDM) and in cultured muscle cells
    • Arakawa, K.; Ishihara, T.; Aoto, M.; Inamasu, M.; Saito, A.; Ikezawa, K. Actions of novel antidiabetic thiazolidinedione, T-174, in animal models of non-insulin-dependent diabetes mellitus (NIDDM) and in cultured muscle cells Br. J. Pharmacol. 1998, 125, 429-436
    • (1998) Br. J. Pharmacol. , vol.125 , pp. 429-436
    • Arakawa, K.1    Ishihara, T.2    Aoto, M.3    Inamasu, M.4    Saito, A.5    Ikezawa, K.6
  • 44
    • 0030633591 scopus 로고    scopus 로고
    • Use of secreted alkaline phosphatase as a reporter of gene expression in mammalian cells
    • Kain, S. R. Use of secreted alkaline phosphatase as a reporter of gene expression in mammalian cells Methods Mol. Biol. 1997, 63, 49-60
    • (1997) Methods Mol. Biol. , vol.63 , pp. 49-60
    • Kain, S.R.1
  • 45
    • 0024386798 scopus 로고
    • Dynamic, structural, and regulatory aspects of lambda site-specific recombination
    • Landy, A. Dynamic, structural, and regulatory aspects of lambda site-specific recombination Annu. Rev. Biochem. 1989, 58, 913-949
    • (1989) Annu. Rev. Biochem. , vol.58 , pp. 913-949
    • Landy, A.1
  • 48
    • 0029035842 scopus 로고
    • Purification of His-Tag fusion proteins from Escherichia coli
    • Hengen, P. Purification of His-Tag fusion proteins from Escherichia coli Trends Biochem. Sci. 1995, 20, 285-286
    • (1995) Trends Biochem. Sci. , vol.20 , pp. 285-286
    • Hengen, P.1
  • 49
    • 0028103275 scopus 로고
    • Number 4. The CCP4 suite: Programs for protein crystallography
    • Collaborative Computational Project
    • Collaborative Computational Project Number 4. The CCP4 suite: programs for protein crystallography Acta. Crystallogr.; Sect. D: Biol. Crystallogr. 1994, 50, 760-763
    • (1994) Acta. Crystallogr.; Sect. D: Biol. Crystallogr. , vol.50 , pp. 760-763
  • 50
    • 0020533372 scopus 로고
    • Revised methods for the Salmonella mutagenicity test
    • Maron, D. M.; Ames, B. N. Revised methods for the Salmonella mutagenicity test Mutat. Res. 1983, 113, 173-215
    • (1983) Mutat. Res. , vol.113 , pp. 173-215
    • Maron, D.M.1    Ames, B.N.2
  • 51
    • 84921521132 scopus 로고    scopus 로고
    • International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use (ICH): Geneva
    • Safety Guidelines; International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use (ICH): Geneva, 2014; http://www.ich.org/products/guidelines/safety/article/safety-guidelines.html.
    • (2014) Safety Guidelines


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.