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Research Article

Design, synthesis and preliminary evaluation of the anti-inflammatory of the specific selective targeting druggable enzymome cyclooxygenase-2 (COX-2) small molecule

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Pages 2505-2514 | Received 23 Oct 2015, Accepted 28 Feb 2016, Published online: 21 Apr 2016

References

  • Akao T, Kobashi K, Aburada M. 1994. Enzymic studies on the animal and intestinal bacterial metabolism of geniposide. Biol Pharm Bull. 17:1573–1576.
  • Bansal S, Bala M, Suthar SK, Choudharyd S, Bhattacharyaa S, Bhardwaje V, Singlaf S, Josephc A. 2014. Design and synthesis of novel 2-phenyl-5-(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazoles as selective COX-2 inhibitors with potent anti-inflammatory activity. Eur J Med Chem. 80:167–174.
  • Cai J, Duan Y, Yu J, Chen J, Chao M, Ji M. 2012. Bone-targeting glycol and NSAIDS ester prodrugs of rhein: synthesis, hydroxyapatite affinity, stability, anti-inflammatory, ulcerogenicity index and pharmacokinetics studies. Eur J Med Chem. 188:409–419.
  • Chang WL, Wang HY, Shian L, Lai JH, Lin HC. 2005. Immunosuppressive iridoids from the fruits of Gardenia jasminoides. J Nat Prod. 68:1683–1685.
  • Dai MM, Wu H, Li H, Chen J, Chen JY, Hu SL, Shen C. 2014. Effects and mechanisms of geniposide on rats with adjuvant arthritis. Int Immunopharmacol. 20:46–53.
  • Daniel LS, Regina MB, Timothy H. 2004. Cyclooxygenase isozymes: the biology of prostaglandin synthesis and inhibition. Pharmacol Rev. 56:387–437.
  • Fuhrmann J, Rurainski A, Lenhof HP, Neumann D. 2010. A new Lamarckian genetic algorithm for flexible ligand-receptor docking. J Comput Chem. 31:1911–1918.
  • Koo HJ, Lim KH, Jung HJ, Park EH. 2006. Anti-inflammatory evaluation of gardenia extract, geniposide and genipin. J Ethnopharmacol. 103:496–500.
  • Koo HJ, Song YS, Kim HJ. 2004. Anti-inflammatory effects of genipin, an active principle of Gardenia. Eur J Pharmacol. 495:201–208.
  • Kurumbail RG, Stevens AM, Gierse JK, McDonald JJ, Stegeman RA, Pak JY, Gildehaus D, Miyashiro JM, Penning TD, Seibert K, et al. 1996. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature. 384:644–648.
  • Li A, Sun H, Du L, Wu X, Cao J, You Q, Li Y. 2014. Discovery of novel covalent proteasome inhibitors through a combination of pharmacophore screening, covalent docking, and molecular dynamics simulations. J Mol Model. 20:2515–2528.
  • Moon SH, Chol HJ, Lee SJ, Chung JU, Kim JH, Chung DH, Park MS, Cho IK, Chol KH. 1998. Novel genipin derivative having anti hepatitis B virus activity. World Intellectual Property Organization Patent No. 17663. 04, 30.
  • Moon SH, Choi HJ, Lee SJ, Chung JU, Ha JR, Lee KJ, Oh SW, Jeong KW. 2001. Genipin derivative having liver protection activity. United State Patent No. 6262083. 07, 17.
  • National Toxicology Program. 2010. Toxicology and carcinogenesis studies of isoeugenol (CAS No. 97-54-1) in F344/N rats and B6C3F1 mice (gavage studies). Natl Toxicol Program Tech Rep Ser. 551:1–178.
  • Ozaki A, Kitano M, Furusawa N, Yamaguchi H, Kuroda K. 2002. Genotoxicity of gardenia yellow and its components. Food Chem. Toxicol. 40:1603–1610.
  • Phatak RS. 2015. Phytochemistry, pharmacological activities and intellectual property landscape of Gardenia jasminoides Ellis. Pharmacognosy J. 7:254–265.
  • Sasieni PD, Winnett A. 2003. Martingale difference residuals as a diagnostic tool for the Cox model. Biometrika. 90:899–912.
  • Shanbhag VR, Crider AM. 1992. Ester and amide prodrugs of ibuprofen and naproxen: synthesis, anti-inflammatory activity, and gastrointestinal toxicity. J Pharm Sci. 81:149–154.
  • Shi Q, Cao J, Fang L, Zhao H, Liu Z, Ran J, Zheng X, Li X, Zhou Y, Ge D, et al. 2014. Geniposide suppresses LPS-induced nitric oxide, PGE2 and inflammatory cytokine by downregulating NF-κB, MAPK and AP-1 signaling pathways in macrophages. Int Immunopharmacol. 20:298–306.
  • Song X, Zhang W, Wang T, Jiang H, Zhang Z, Fu Y, Yang Z, Cao Y, Zhang N. 2014. Geniposide plays an anti-inflammatory role via regulating TLR4 and downstream signaling pathways in lipopolysaccharide-induced mastitis in mice. Inflammation. 37:1588–1598.
  • Vanegas H, Schaible HG. 2001. Prostaglandins and cyclooxygenases [correction of cyclooxygenases] in the spinal cord. Prog Neurobiol. 64:327–363.
  • Wang QS, Xiang YZ, Cui YL, Lin KM, Zhang XF. 2012. Dietary blue pigments derived from genipin, attenuate inflammation by inhibiting LPS-Induced iNOS and COX-2 expression via the NF-κB Inactivation. PLoS ONE. 7:e34122.
  • Xu F, Li YH, Li S, Ma Y, Zhao N, Liu Y, Qian N, Zhao H, Li Y. 2014. Complete Freund’s adjuvant-induced acute inflammatory pain could be attenuated by triptolide via inhibiting spinal glia activation in rats. J Surg Res. 188:174–182.
  • Yamano T, Tsujimoto Y, Noda T. 1988. Hepatotoxicity of gardenia yellow color in rats. Toxicol Lett. 44:177–182.
  • Yamano T, Tsujimoto Y, Noda T, Shimizu M, Ohmori M, Morita S, Yamada A. 1990. Hepatotoxicity of geniposide in rats. Food Chem Toxicol. 28:515–519.
  • Zhang HY, Liu H, Yang M, Wei SF. 2013. Antithrombotic activities of aqueous extract from Gardenia jasminoides and its main constituent. Pharm Biol. 51:221–225.
  • Zhao M, Du L, Tao J, Qian D, Guo J, Jiang S, Shang E, Duan J, Wu C. 2015. Ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry for rapid analysis of the metabolites of morroniside produced by human intestinal bacteria. Chromatogr B Analyt Technol Biomed Life Sci. 976–977:61–67.
  • Zheng YY, Wang DC, Feng HT. 2010. Study on molecular docking of constituents of Sinomenium acutum with cyclooxygenase. Chem Res. 21:43–47.

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