Molecular Modelling Study of the PPARγ Receptor in Relation to the Mode of Action/Adverse Outcome Pathway Framework for Liver Steatosis
Tóm tắt
Từ khóa
Tài liệu tham khảo
Gocht, 2012, Mode of action working group: Use of mode of action related to repeated dose systemic toxicity—A framework for capturing Information, Towards the Replacement of in Vivo Repeated Dose Systemic Toxicity Testing, 2, 284
(2013). Series on Testing and Assessment No. 184, OECD.
Fioravanzo, 2013, Molecular modelling of LXR binding to evaluate the potential for liver steatosis, Toxicol. Lett, 221, S83, 10.1016/j.toxlet.2013.05.092
Alov, 2013, Toward better understanding of liver steatosis MoA: Molecular modelling study of PPAR gamma receptor, Toxicol. Lett, 221, S85, 10.1016/j.toxlet.2013.05.099
Alov, 2014, Modes-of-action related to repeated dose toxicity: Tissue-specific biological roles of PPARγ ligand-dependent dysregulation in nonalcoholic fatty liver disease, PPAR Res, 2014, 432647:1
Landesmann, B., Goumenou, M., Munn, S., and Whelan, M. Description of Prototype Modes-Of-Action Related to Repeated dose Toxicity. 40 Pages, EUR 25631 EN. Available online: http://publications.jrc.ec.europa.eu.
Costa, 2010, PPARG: Gene expression regulation and next-generation sequencing for unsolved issues, PPAR Res, 2010, 409168:1, 10.1155/2010/409168
Kouskoumvekaki, 2013, Discovery of a Novel Selective PPARγ Ligand with Partial Agonist Binding Properties by Integrated in Silico/in Vitro Work Flow, J. Chem. Inf. Model, 53, 923, 10.1021/ci3006148
Day, 1999, Thiazolidinediones: A new class of antidiabetic drugs, Diabet. Med, 16, 179, 10.1046/j.1464-5491.1999.00023.x
Moya, 2010, Enhanced steatosis by nuclear receptor ligands: A study in cultured human hepatocytes and hepatoma cells with a characterized nuclear receptor expression profile, Chem. Biol. Interact, 184, 376, 10.1016/j.cbi.2010.01.008
Pan, 2006, Adverse hepatic and cardiac responses to rosiglitazone in a new mouse model of type 2 diabetes: Relation to dysregulated phosphatidylcholine metabolism, Vascul. Pharmacol, 45, 65, 10.1016/j.vph.2005.11.011
Bruning, 2007, Partial agonists activate PPARgamma using a helix 12 independent mechanism, Structure, 15, 1258, 10.1016/j.str.2007.07.014
Guasch, 2012, Identification of PPARgamma partial agonists of natural origin (I): Development of a virtual screening procedure and in vitro validation, PLoS One, 7, e50816, 10.1371/journal.pone.0050816
Waku, 2010, The nuclear receptor PPARγ individually responds to serotonin- and fatty acid- metabolites, EMBO J, 29, 3395, 10.1038/emboj.2010.197
Itoh, 2008, Structural basis for the activation of PPARγ by oxidized fatty acids, Nat. Struct. Mol. Biol, 15, 924, 10.1038/nsmb.1474
Li, 2008, Molecular recognition of nitrated fatty acids by PPARγ, Nat. Struct. Mol. Biol, 15, 865, 10.1038/nsmb.1447
Gampe, 2000, Asymmetry in the PPARgamma/RXRalpha crystal structure reveals the molecular basis of heterodimerization among nuclear receptors, Mol Cell, 5, 545, 10.1016/S1097-2765(00)80448-7
Liberato, 2012, Medium chain fatty acids are selective peroxisome proliferator activated receptor (PPAR)γ activators and pan-PPAR partial agonists, PLoS One, 7, e36297, 10.1371/journal.pone.0036297
Chandra, 2008, Structure of the intact PPAR-γ-RXR-nuclear receptor complex on DNA, Nature, 456, 350, 10.1038/nature07413
Nolte, 1998, Ligand binding and co-activator assembly of the peroxisome proliferator-activated receptor-gamma, Nature, 395, 137, 10.1038/25931
Li, 2008, Structural and biochemical basis for the binding selectivity of peroxisome proliferator-activated receptor gamma to PGC-1α, J. Biol. Chem, 283, 19132, 10.1074/jbc.M802040200
Li, 2005, Structural and biochemical basis for selective repression of the orphan nuclear receptor liver receptor homolog 1 by small heterodimer partner, Proc. Natl. Acad. Sci. USA, 102, 9505, 10.1073/pnas.0501204102
Pencheva, 2012, Post-docking optimization and analysis of protein-ligand interactions of estrogen receptor alpha using ammos software, Curr. Comput. Aided Drug Des, 9, 83, 10.2174/1573409911309010008
Xu, 2001, Structural determinants of ligand binding selectivity between the peroxisome proliferator-activated receptors, Proc. Natl. Acad. Sci. USA, 98, 13919, 10.1073/pnas.241410198
Ohashi, 2011, Design, synthesis, and structural analysis of phenylpropanoic acid-type PPARγ-selective agonists: Discovery of reversed stereochemistry-activity relationship, J. Med. Chem, 54, 331, 10.1021/jm101233f
Zhang, 2009, Design, synthesis and structure-activity relationships of azole acids as novel, potent dual PPAR alpha/gamma agonists, Bioorg. Med. Chem. Lett, 19, 1451, 10.1016/j.bmcl.2009.01.030
Bigge, 2009, Synthesis and evaluation of novel α-heteroaryl-phenylpropanoic acid derivatives as PPARalpha/gamma dual agonists, Bioorg. Med Chem, 17, 7113, 10.1016/j.bmc.2009.09.001
Cronet, 2001, Structure of the PPARalpha and -gamma ligand binding domain in complex with AZ 242; ligand selectivity and agonist activation in the PPAR family, Structure, 9, 699, 10.1016/S0969-2126(01)00634-7
Benz, 2009, Aleglitazar, a new, potent, and balanced dual PPARα/γ agonist for the treatment of type II diabetes, Bioorg. Med. Chem. Lett, 19, 2468, 10.1016/j.bmcl.2009.03.036
Oyama, 2009, Adaptability and selectivity of human peroxisome proliferator-activated receptor (PPAR) pan agonists revealed from crystal structures, Acta. Crystallogr. D Biol. Crystallogr, 65, 786, 10.1107/S0907444909015935
Lin, 2009, Design an d structural analysis of novel pharmacophores for potent and selective peroxisome proliferator-activated receptor gamma agonists, J. Med. Chem, 52, 2618, 10.1021/jm801594x
Kuwabara, 2012, Peroxisome proliferator-activated receptors (PPARs) have multiple binding points that accommodate ligands in various conformations: Phenylpropanoic acid-type PPAR ligands bind to PPAR in different conformations, depending on the subtype, J. Med. Chem, 55, 893, 10.1021/jm2014293
Mahindroo, 2006, Indol-1-yl acetic acids as peroxisome proliferator-activated receptor agonists: Design, synthesis, structural biology, and molecular docking studies, J. Med. Chem, 49, 1212, 10.1021/jm0510373
Bigge, 2008, Effects of modifications of the linker in a series of phenylpropanoic acid derivatives: Synthesis, evaluation as PPARα/γ dual agonists, and X-ray crystallographic studies, Bioorg. Med. Chem, 16, 4883, 10.1016/j.bmc.2008.03.043
Sauerberg, 2002, Novel tricyclic-alpha-alkyloxyphenylpropionic acids: Dual PPARα/γ agonists with hypolipidemic and antidiabetic activity, J. Med. Chem, 45, 789, 10.1021/jm010964g
Grether, 2009, Design and biological evaluation of novel, balanced dual PPARα/γ agonists, ChemMedChem, 4, 951, 10.1002/cmdc.200800425
Mahindroo, 2006, Structural basis for the structure-activity relationships of peroxisome proliferator-activated receptor agonists, J. Med. Chem, 49, 6421, 10.1021/jm060663c
Mahindroo, 2005, Novel indole-based peroxisome proliferator-activated receptor agonists: Design, SAR, structural biology, and biological activities, J. Med. Chem, 48, 8194, 10.1021/jm0506930
Mueller, J.J., Schupp, M., Unger, T., Kintscher, U., and Heinemann, U. (2011). Binding Diversity of Pioglitazone by Peroxisome Proliferator-Activated Receptor-Gamma, Unpublished work.
Ebdrup, 2003, Synthesis and biological and structural characterization of the dual-acting peroxisome proliferator-activated receptor alpha/gamma agonist ragaglitazar, J. Med. Chem, 46, 1306, 10.1021/jm021027r
Kuhn, 2006, Structure-based design of indole propionic acids as novel PPARalpha/gamma co-agonists, Bioorg. Med. Chem. Lett, 16, 4016, 10.1016/j.bmcl.2006.05.007
(2013). MOE (Molecular Operating Environment) Version 2013.08, Chemical Computing Group Inc.