212
Views
10
CrossRef citations to date
0
Altmetric
Original Research

Synthesis and Biological Activity of Piperine Derivatives as Potential PPARγ Agonists

ORCID Icon, , , , , & show all
Pages 2069-2078 | Published online: 26 May 2020

References

  • BergerJ, MollerDE. The mechanisms of action of PPARs. Annu Rev Med. 2002;53:409–435. doi:10.1146/annurev.med.53.082901.10401811818483
  • NettlesKW, GreeneGL. Ligand control of coregulator recruitment to nuclear receptors. Annu Rev Physiol. 2005;67:309–333. doi:10.1146/annurev.physiol.66.032802.15471015709961
  • PerissiV, RosenfeldMG. Controlling nuclear receptors: the circular logic of cofactor cycles. Nat Rev Mol Cell Biol. 2005;6:542.15957004
  • Vanden BergheW, VermeulenL, DeleriveP, De BosscherK, StaelsB, HaegemanG. A paradigm for gene regulation: inflammation, NF-kappaB and PPAR. Adv Exp Med Biol. 2003;544:181–196.14713228
  • VargaT, CzimmererZ, NagyL. PPARs are a unique set of fatty acid regulated transcription factors controlling both lipid metabolism and inflammation. BBA. 1812;2011:1007–1022.
  • WahliW, MichalikL. PPARs at the crossroads of lipid signaling and inflammation. Trends Endocrinol Metab. 2012;23:351–363. doi:10.1016/j.tem.2012.05.00122704720
  • KreyG, BraissantO, L HorsetF, et al. Fatty acids, eicosanoids, and hypolipidemic agents identified as ligands of peroxisome proliferator-activated receptors by coactivator-dependent receptor ligand assay. Mol Endocrinol. 1997;11:779–791. doi:10.1210/mend.11.6.00079171241
  • Marion-LetellierR, SavoyeG, GhoshS. Fatty acids, eicosanoids and PPAR gamma. Eur J Pharmacol. 2016;785:44–49.26632493
  • AhmadianM, SuhJM, HahN, et al. PPARγ signaling and metabolism: the good, the bad and the future. Nat Med. 2013;99:557–566. doi:10.1038/nm.3159
  • TripathiAC, GuptaSJ, FatimaGN, SonarPK, VermaA, SarafSK. 4-thiazolidinones: the advances continue. Eur J Med Chem. 2014;72:52–77. doi:10.1016/j.ejmech.2013.11.01724355348
  • da SilvaFMC, Dos SantosJC, CamposJLO, et al. Structure-based identification of novel PPAR gamma ligands. Bioorg Med Chem Lett. 2013;23:5795–5802. doi:10.1016/j.bmcl.2013.09.01024075729
  • OhashiM, GamoK, OyamaT, MiyachiH. Peroxisome proliferator-activated receptor gamma (PPARγ) has multiple binding points that accommodate ligands in various conformations: structurally similar PPARγ partial agonists bind to PPARγ LBD in different conformations. Bioorg Med Chem Lett. 2015;25:2758–2762. doi:10.1016/j.bmcl.2015.05.02526025876
  • OhashiM, OyamaT, MiyachiH. Different structures of the two peroxisome proliferator-activated receptor gamma (PPARγ) ligand-binding domains in homodimeric complex with partial agonist, but not full agonist. Bioorg Med Chem Lett. 2015;25:2639–2644. doi:10.1016/j.bmcl.2015.04.07625987371
  • KimKJ, LeeMS, JoK, HwangJK. Piperidine alkaloids from piper retrofractum Vahl. protect against high-fat diet-induced obesity by regulating lipid metabolism and activating AMP-activated protein kinase. Biochem Biophys Res Commun. 2011;411:219–225. doi:10.1016/j.bbrc.2011.06.15321741367
  • ParkU-H, JeongH-S, JoE-Y, et al. Piperine, a component of black pepper, inhibits adipogenesis by antagonizing PPARc activity in 3T3-L1 cells. J Agric Food Chem. 2012;60:3853–3860. doi:10.1021/jf204514a22463744
  • AtalCK, DubeyRK, SinghJ. Biochemical basis of enhanced drug bioavailability by piperine: evidence that piperine is a potent inhibitor of drug metabolism. J Pharmacol Exp Ther. 1985;232:258–262.3917507
  • PatilUK, SinghA, ChakrabortyAK. Role of piperine as a bioavailability enhancer. Int J Rec Adv Pharma Res. 2011;4:416–423.
  • PawineeP, GlinsukonT, ToskulkaoC. Acute and subacute toxicity of piperine in mice, rats and hamsters. Toxicol Lett. 1983;16:351–359.6857729
  • SinghIP, JainSK, KaurA, et al. Synthesis and antileishmanial activity of piperoyl-amino acid conjugates. Eur J Med Chem. 2010;45:3439–3445. doi:10.1016/j.ejmech.2010.04.03320546981
  • FerreP. The biology of peroxisome proliferator– activated receptors relationship with lipid metabolism and insulin sensitivity. Diabetes. 2004;53:S43–S50. doi:10.2337/diabetes.53.2007.S4314749265
  • Vidal-PuigA, Jimenez-LiñanM, LowellBB, et al. Regulation of PPAR gamma gene expression by nutrition and obesity in rodents. J Clin Invest. 1996;97:2553. doi:10.1172/JCI1187038647948
  • YaoY, FanL, ShiY, OdsbuI. Morigen. A spatial control for correct timing of gene expression during the Escherichia coli cell cycle. Genes. 2016;8:1. doi:10.3390/genes8010001
  • FleigeS, PfafflMW. RNA integrity and the effect on the real-time qRT-PCR performance. Mol Aspects Med. 2006;27:126–139. doi:10.1016/j.mam.2005.12.00316469371
  • MihaelaŠ, VeronikaO, ŠpelaJ, et al. Improved determination of plasmid copy number using quantitative real-time PCR for monitoring fermentation processes. Microb Cell Fact. 2008;7:1–12.18211716
  • UsuiS, SuzukiT, HattoriY, et al. Design, synthesis, and biological activity of novel PPARγ ligands based on rosiglitazone and 15d-PGJ2. Bioorg Med Chem Lett. 2005;15:1547–1551. doi:10.1016/j.bmcl.2005.01.07415745794
  • FangM, WebsterTF, FergusonPL, StapletonHM. Characterizing the peroxisome proliferator-activated receptor (PPARγ) ligand binding potential of several major flame retardants, their metabolites, and chemical mixtures in house dust. Environ Health Perspect. 2015;123:166–172. doi:10.1289/ehp.140852225314719
  • RossiAM, TaylorCW. Analysis of protein-ligand interactions by fluorescence polarization. Nat Protoc. 2011;6(3):365–387. doi:10.1038/nprot.2011.30521372817