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Xenobiotica
the fate of foreign compounds in biological systems
Volume 43, 2013 - Issue 8
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Molecular Toxicology

Chemical reactivity and biological activity of chalcones and other α,β-unsaturated carbonyl compounds

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Pages 711-718 | Received 20 Sep 2012, Accepted 26 Nov 2012, Published online: 23 Jan 2013

References

  • Adibi H, Mojarrad JS, Asgharloo H, Zarrini G. (2011). Synthesis, in vitro antimicrobial and antioxidant activities of chalcone and flavone derivatives holding allylic substitutions. Med Chem Res 20:1318–24
  • Bandgar BP, Hote BS, Dhole NA, Gacche R. (2012). Synthesis and biological evaluation of novel series of chalcone derivatives as inhibitors of cyclooxygenase and LPS-induced TNF-α with potent antioxidant properties. Med Chem Res. 21:2292--9
  • Beyer TA, auf dem Keller U, Braun S, et al. (2007). Roles and mechanisms of action of the Nrf2 transcription factor in skin morphogenesis, wound repair and skin cancer. Cell Death Differ 14:1250–4
  • Braun RU, Ansorge M, Müller TJJ. (2006). The coupling-isomerization synthesis of chalcones. Chem Eur J 12:9081–94
  • Copple IM, Goldring CE, Kitteringham R, Park BE. (2008). The Nrf2-Keap 1 defence pathway: role in protection against drug-induced toxicity. Toxicology 246:24–33
  • Cox RJ, Ritson DJ, Dane TA, et al. (2005). Room temperature palladium catalysed coupling of acyl chlorides with terminal alkynes. Chem Commun 1037–39 . DOI: 10.1039/B414826F
  • Dinkova-Kostova AT, Massiah MA, Bozak RE, et al. (2011). Potency of Michael reaction acceptors as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups. PNAS 98:3404–9
  • Eggler AL, Gay KA, Mesecar AD. (2008). Molecular mechanisms of natural products in chemoprevention: induction of cytoprotective enzymes by Nrf2. Mol Nut Food Res 52:84–94
  • Ernst IMS, Wagner AE, Schuemann C, et al. (2011). Allyl-, butyl- and phenylethyl-isothiocyanate activate Nrf2 in cultured fibroblasts. Pharmacol Res 63:233–40
  • Foresti R, Hoque M, Monti D, et al. (2004). Differential activation of heme oxygenase-1 by chalcones and rosolic acid in endothelial cells. J Pharmacol Exp Ther 312:686–93
  • Go ML, Wu X, Liu XL. (2005). Chalcones: an update on cytotoxic and chemoprotective properties. Curr Med Chem 12:483–99
  • Hansch C, Leo A, Taft RW. (1991). A survey of Hammett substituent constants and resonance and field parameters. Chem Rev 91:165–95
  • Holland R, Fishbein JC. (2010). Chemistry of the cysteine sensors in Kelch-Like ECH-associated protein 1. Antioxid Redox Signal 13:1749–61
  • Jin C, Liang YJ, He H, Fu L. (2010). Synthesis and antitumor activity of novel chalcone derivatives. Biomed Pharmacother (in press). doi: 10.1016/j.biopha.2010.12.010
  • Kimura Y. (2005). New anticancer agents: in vitro and in vivo evaluation of the antitumor and antimetastatic actions of various compounds isolated from medicinal plants. In vivo 19:37–60
  • Kobayashi A, Kang MI, Watai Y, et al. (2006). Oxidative and electrophilic stresses activate Nrf2 through inhibition of ubiquitination activity of Keap1. Mol Cell Biol 26:221–9
  • Kumar V, Kumar S, Hassan M, et al. (2011). Novel chalcone derivatives as potent Nrf2 activators in mice and human epithelial cells. J Med Chem 54:4147–59
  • Linnewiel K, Ernst H, Caris-Veyrat C, et al. (2009). Structure activity relationship of carotenoid derivates in activation of the electrophile/antioxidant response element transcription system. Free Radic Biol Med 47:659–67
  • Liu X, Testa B, Fahr A. (2011). Lipophilicity and its relationship with passive drug permeation. Pharm Res 28:962–77
  • Martin HD, Kock S, Scherrers R, et al. (2009). 3,3′-Dihydroxyisorenieratene: a natural carotenoid with superior antioxidant and photoprotective properties. Angew Chem Int Ed 48:400–3
  • Natsch A. (2009). The Nrf2-Keap1-ARE toxicity pathway as a cellular sensor for skin sensitizers-functional relevance and a hypothesis on innate reactions to skin sensitizers. Toxicol Sci 113:284–92
  • Nguyen T, Nioi P, Pickett C. (2009). The Nrf2-antioxidant response element signaling pathway and its activation by oxidative stress. Biol Chem 284:13291–5
  • Ryter S, Choi AMK. (2005). Heme oxygenase-1: redox regulation of a stress protein in lung and cell culture models. Antioxid Redox Signal 7:80–91
  • Sawle P, Moulton BE, Jarzykowska M, et al. (2008). Structure-activity relationships of methoxychalcones as inducers of heme oxygenase-1. Chem Res Toxicol 21:1484–94
  • Schramm OG, Dediu N, Müller TJJ. (2006). Microwave-accelerated coupling-isomerization reaction (MACIR): a general coupling- isomerization synthesis of 1,3-Diarylprop-2-en-1-ones. Adv Synth Cat 348:2565–70
  • Sivakumar PM, Prabhakar PK, Doble M. (2011). Synthesis, antioxidant evaluation, and quantitative structure-activity relationship studies of chalcones. Med Chem Res 20:482–92
  • Skehan P, Storeng R, Scudiero D, et al. (1990). New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 82:1107–12
  • Smith DA, Barry CJ, Walker DK. (1996). Design of drugs involving the concepts and theories of drug metabolism and pharmacokinetics. Med Res Rev 16:243–66
  • Solomon VR, Lee H. (2012). Anti-breast cancer activity of heteroaryl chalcone derivatives. Biomed Pharmacother 66:213–20
  • Tkachev VO, Menshchikova EB, Zenkov NK. (2011). Mechanism of the Nrf2/Keap1/ARE signaling system. Biochemistry (Moscow), 76:407–22
  • Vogel S, Ohmayer S, Brunner G, Heilmann J. (2008). Natural and non-natural prenylated chalcones: synthesis, cytotoxicity and antioxidative activity. Bioorg Med Chem 16:4286–93

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