A consideration of PPAR-γ ligands with respect to lipophilicity: current trends and perspectives

Bibliography

• NOLTE RT, WISELY GB, WESTIN S et al.: Ligand binding and co-activator assembly of the peroxisome proliferators activated receptor-γ. Nature (1998) 395:137-143.
   PubMed Web of Science ®Google Scholar
• WILLSON TM, BROWN PJ, STRENBACH DD, HENKE BR: The PPARs: from orphan receptors to drug discovery. J. Med. Chem. (2000) 43:527-550.
   PubMed Web of Science ®Google Scholar
• BRAISSANT O, FOUFELLE F, SCOTTO C, DAUÇA M, WAHLI W: Differential expression of peroxisome proliferator-activated receptors (PPARs): tissue distribution of PPAR-α, β- and -γ in the adult rat. Endocrinology (1996) 137:354-366.
   PubMed Web of Science ®Google Scholar
• LEMBERGER T, BRAISSANT O, JUGE-AUBRY C et al.: PPAR tissue distribution and interactions with other hormone-signaling pathways. Ann. NY Acad. Sci. (1996) 804:231-251.
   PubMed Web of Science ®Google Scholar
• RIZZO G, FIORUCCI S: PPARs and other nuclear receptors in inflammation. Curr. Opin. Pharm. (2006) 6:1-7.
   Web of Science ®Google Scholar
• THEOCHARIS S, MARGELI A, VIELH P, KOURAKLIS G: Peroxisome proliferator activated receptor-γ as cell cycle modulators. Cancer Treat. Rev. (2004) 30:545-554.
   PubMed Web of Science ®Google Scholar
• PATEL CB, DE LEMOS JA, WYNE KL, MCGUIRE DK: Thiazolidinediones and risk for atherosclerosis: pleiotropic effects of PPAR γ agonism. Diab. Vasc. Dis. Res. (2006) 3:65-71.
   PubMedGoogle Scholar
• WILLSON TM, LAMBERT MH, KLIEWER SA: Peroxisome proliferator-activated receptor γ and metabolic disease. Ann. Rev. Biochem. (2001) 70:341-367.
   PubMed Web of Science ®Google Scholar
• OGUCHI M, WADA K, HONNA H et al.: Molecular design, synthesis, and hypoglycemic activity of a series of thiazolidine-2,4-diones. J. Med. Chem. (2000) 43:3052-3066.
   PubMed Web of Science ®Google Scholar
• SCHOPFER GJ, LIN Y, BAKER PRS et al.: Nitrolinoleic acid: an endogenous peroxisome proliferator-activated receptor γ ligand. Proc. Natl. Acad. Sci. USA (2005) 102:2340-2345.
   PubMed Web of Science ®Google Scholar
• LEHMANN JM, MOORE LB, SMITH-OLIVER TA et al.: An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome-proliferator-activated receptor γ (PPARγ). J.Biol. Chem. (1995) 270:12953-12956.
   PubMed Web of Science ®Google Scholar
• HENKE B. BLANCHARD SB, BRACKEEN MF et al.: N-(2-benzoylphenyl)-l-tyrosine PPARγ agonists. 1. Discovery of a novel series of potent antihyperglycemic and antihyperlipidemic agents. J. Med. Chem. (1998) 41:5020-5036.
   PubMed Web of Science ®Google Scholar
• COLLINS JL, BLANCHARD SB, BOSWELL EG et al.: N-(2-benzoylphenyl)-l-tyrosine PPARγ agonists. 2. Structure–activity relationship and optimization of the phenyl alkyl ether moiety. J. Med. Chem. (1998) 41:5037-5054.
   PubMed Web of Science ®Google Scholar
• LEHMANN JM, LENHARD JM, OLIVER BB, RINGOLD GM, KLIEWER SA: Peroxisome proliferator-activated receptors α and γ are activated by indomethacin and other non-steroidal anti-inflammatory drugs. J. Biol. Chem. (1997) 272:3406-3410.
   PubMed Web of Science ®Google Scholar
• WYSOWSKI DK, ARMSTRONG G, GOVERNALE L: Rapid increase in the use of oral antidiabetic drugs in the United States, 1990 – 2001. Diabetes Care (2003) 26:1852-1855.
   PubMed Web of Science ®Google Scholar
• WILLSON TM, COBB JE, COWAN DJ et al.: The structure–activity relationship between peroxisome proliferator-activated receptor γ. Agonism and the anti-hyperglycemic activity of thiazolidinediones. J. Med. Chem. (1996) 39:665-668.
   PubMed Web of Science ®Google Scholar
• FEINSTEIN DL, SPANGOLO A, AKAR C et al.: Receptor-independent action of PPAR thiazolidinedione agonists: is mitochondrial function the key? Biochem. Pharmacol. (2005) 70:177-188.
   PubMed Web of Science ®Google Scholar
• KULKARNI SS, GEDIYA LK, KULKARNI VM: Three dimensional quantitative structure–activity relationships (3-D QSAR) of antihyperglycemic agents. Bioorg. Med. Chem. (1999) 7:1475-1485.
   PubMed Web of Science ®Google Scholar
• IWATA Y, MIYAMOTO S, TAKAMURA M, YANAGISAWA H, KASUYA A: Interaction between peroxisome proliferator-activated receptor γ and its agonists: docking study of oximes having 5-benzyl-2,4-thiazolidinedione. J. Mol. Graph. Model. (2001) 19:536-542.
   PubMed Web of Science ®Google Scholar
• PAGLIARA A, CARRUPT P-A, CARON G, GAILLARD P, TESTA B: Lipophilicity profiles of ampholytes. Chem. Rev. (1997) 97:3385-3400.
   PubMed Web of Science ®Google Scholar
• TAKACS-NOVAK K, JÓZAN M, SZÁS G: Lipophilicity of amphoteric molecules expressed by the true partition coefficient. Int. J. Pharm (1995) 113:47-55.
   Google Scholar
• PISTOS C, TSANTILI-KAKOULIDOU A, KOUPPARIS M: Investigation of the retention/pH profile of zwitterionic fluoroquinolones by means of reversed phase and ion-pair high performance liquid chromatography. J. Pharm. Biomed. Anal. (2005) 39:438-443.
   PubMed Web of Science ®Google Scholar
• PAGLIARA A, TESTA B, CARRUPT PA et al.: Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist. J. Med. Chem. (1998) 41:853-863.
   PubMed Web of Science ®Google Scholar
• PLISKA V, TESTA B, VAN DE WATERBEEMD H: Lipophilicity in drug action and toxicology. In: Methods and Principles in Medicinal Chemistry. (Volume 4). Mannhold R, Kubinyi H, Timmerman H (Eds), Wiley VCH, Weinheim, Germany (1996).
   Google Scholar
• HANSCH C, BJORKROTH JP, LEO A: Hydrophobicity and central nervous system agents: on the principle of minimal hydrophobicity in drug design. J. Pharm. Sci. (1987) 76:663-687.
   PubMed Web of Science ®Google Scholar
• LIPINSKI CA, LOMBARDO F, DOMINY BW, FEENEY PJ: Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug. Deliv. Rev. (1997) 23:3-25.
   Web of Science ®Google Scholar
• MANNHOLD R: Calculation of lipophilicity. A classification of method. In: Pharmacokinetic Profiling in Drug Research: Biological, Physicochemical, and Computational Strategies. Testa B, Krämer SD, Wunderli-Allenspach H, Folkers G (Eds), Verlag Helvetica Chimica Acta, Wiley VCH, Zürich, Switzerland (2006):333-352.
   Google Scholar
• VRAKAS D, TSANTILI-KAKOULIDOU A, HADJIPAVLOU-LITINA D: Exploring the consistency of logP estimation for substituted coumarins, Quant. Struct. – Act. Relat. (2003) 22:622-629.
   Google Scholar
• DELLIS D, GIAGINIS C, TSANTILI-KAKOULIDOU A: Physicochemical profile of nimesulide. Exploring the interplay of lipophilicity, solubility and ionization. J. Pharm. Biomed. Anal. (In Press).
   Google Scholar
• LIAO C, XIE A, ZHOU J, SHI L, LI Z, LU XP: 3D QSAR studies on peroxisome proliferator-activated receptor γ agonists using CoMFA and CoMSIA. J. Mol. Model. (2004) 10:165-177.
   PubMed Web of Science ®Google Scholar
• KUROGI Y: Three-dimensional quantitative structure–activity relationship (3D-QSAR) of antidiabetic thiazolidinediones. Drug Des. Discov. (1999) 16:109-118.
   Web of Science ®Google Scholar
• RATHI L, KASHAW SK, DIXIT A, PANDEY G, SAXENA AK: Pharmacophore identification and 3D-QSAR studies in N-(2-benzoyl phenyl)-l-tyrosines as PPAR agonists. Bioorg. Med. Chem. (2004) 12:63-69.
   PubMed Web of Science ®Google Scholar
• RUCKER C, SCARSI M, MERINGER M: 2D QSAR of PPARγ agonist binding and transactivation. Bioorg. Med. Chem. (2006) 14:5178-5195.
   PubMed Web of Science ®Google Scholar
• OPREA TI: Property distribution of drug-related chemical databases. J. Comput-Aided Mol. Des. (2000) 14:251-264.
   PubMed Web of Science ®Google Scholar
• GIAGINIS C, THEOCHARIS S, TSANTILI-KAKOULIDOU A: Investigation of the lipophilic behavior of the PPARγ ligands thiazolidinediones as an important issue for their action. Drugs Fut. (2006) 31:A44.
   Google Scholar