Structure-based design, synthesis and preliminary anti-inflammatory activity of bolinaquinone analogues - PubMed (original) (raw)
Structure-based design, synthesis and preliminary anti-inflammatory activity of bolinaquinone analogues
Carmen Petronzi et al. Eur J Med Chem. 2011 Feb.
Abstract
As a part of our drug discovery efforts we developed a series of simplified derivatives of bolinaquinone (BLQ), a hydroxyquinone marine metabolite, showing potent anti-inflammatory activity. Thirteen new hydroxyquinone derivatives closely related to BLQ were synthesized and tested on mouse macrophage-like RAW 264.7 cell line in order to investigate their ability to modulate the production of Prostaglandin E2 (PGE2). This optimization process led to the identification of three strictly correlated compounds with comparable and higher inhibitory potency than BLQ on PGE2 production. To evaluate the affinity of BLQ and its analogues for hsPLA2, surface plasmon resonance (SPR) experiments were performed.
Copyright © 2010 Elsevier Masson SAS. All rights reserved.
Similar articles
- Anti-inflammatory activity of the synthetic C-C biflavonoids.
Park H, Kim YH, Chang HW, Kim HP. Park H, et al. J Pharm Pharmacol. 2006 Dec;58(12):1661-7. doi: 10.1211/jpp.58.12.0014. J Pharm Pharmacol. 2006. PMID: 17331331 - Synthesis and anti-inflammatory evaluation of novel mono-carbonyl analogues of curcumin in LPS-stimulated RAW 264.7 macrophages.
Zhao C, Cai Y, He X, Li J, Zhang L, Wu J, Zhao Y, Yang S, Li X, Li W, Liang G. Zhao C, et al. Eur J Med Chem. 2010 Dec;45(12):5773-80. doi: 10.1016/j.ejmech.2010.09.037. Epub 2010 Oct 8. Eur J Med Chem. 2010. PMID: 20934787 - Synthesis of mono-carbonyl analogues of curcumin and their effects on inhibition of cytokine release in LPS-stimulated RAW 264.7 macrophages.
Zhao C, Yang J, Wang Y, Liang D, Yang X, Li X, Wu J, Wu X, Yang S, Li X, Liang G. Zhao C, et al. Bioorg Med Chem. 2010 Apr 1;18(7):2388-93. doi: 10.1016/j.bmc.2010.03.001. Epub 2010 Mar 6. Bioorg Med Chem. 2010. PMID: 20338767 - Psilostachyin, acetylated pseudoguaianolides and their analogues: preparation and evaluation of their anti-inflammatory potential.
Chib R, Shah BA, Anand N, Pandey A, Kapoor K, Bani S, Gupta VK, Rajnikant, Sethi VK, Taneja SC. Chib R, et al. Bioorg Med Chem Lett. 2011 Aug 15;21(16):4847-51. doi: 10.1016/j.bmcl.2011.06.037. Epub 2011 Jun 22. Bioorg Med Chem Lett. 2011. PMID: 21752638 - Enantioselective pharmacodynamics and pharmacokinetics of chiral non-steroidal anti-inflammatory drugs.
Evans AM. Evans AM. Eur J Clin Pharmacol. 1992;42(3):237-56. doi: 10.1007/BF00266343. Eur J Clin Pharmacol. 1992. PMID: 1577041 Review. No abstract available.
Cited by
- Replacing conventional carbon nucleophiles with electrophiles: nickel-catalyzed reductive alkylation of aryl bromides and chlorides.
Everson DA, Jones BA, Weix DJ. Everson DA, et al. J Am Chem Soc. 2012 Apr 11;134(14):6146-59. doi: 10.1021/ja301769r. Epub 2012 Mar 30. J Am Chem Soc. 2012. PMID: 22463689 Free PMC article. - Anti-Inflammatory Drugs as Anticancer Agents.
Zappavigna S, Cossu AM, Grimaldi A, Bocchetti M, Ferraro GA, Nicoletti GF, Filosa R, Caraglia M. Zappavigna S, et al. Int J Mol Sci. 2020 Apr 9;21(7):2605. doi: 10.3390/ijms21072605. Int J Mol Sci. 2020. PMID: 32283655 Free PMC article. Review. - The 1,4 benzoquinone-featured 5-lipoxygenase inhibitor RF-Id induces apoptotic death through downregulation of IAPs in human glioblastoma cells.
Zappavigna S, Scuotto M, Cossu AM, Ingrosso D, De Rosa M, Schiraldi C, Filosa R, Caraglia M. Zappavigna S, et al. J Exp Clin Cancer Res. 2016 Oct 22;35(1):167. doi: 10.1186/s13046-016-0440-x. J Exp Clin Cancer Res. 2016. PMID: 27770821 Free PMC article. - Bioactive Prenyl- and Terpenyl-Quinones/Hydroquinones of Marine Origin †.
García PA, Hernández ÁP, San Feliciano A, Castro MÁ. García PA, et al. Mar Drugs. 2018 Aug 21;16(9):292. doi: 10.3390/md16090292. Mar Drugs. 2018. PMID: 30134616 Free PMC article. Review. - Ethnobotany and phytochemistry of plants used to treat musculoskeletal disorders among Skaw Karen, Thailand.
Kantasrila R, Pandith H, Balslev H, Wangpakapattanawong P, Panyadee P, Inta A. Kantasrila R, et al. Pharm Biol. 2024 Dec;62(1):62-104. doi: 10.1080/13880209.2023.2292261. Epub 2023 Dec 22. Pharm Biol. 2024. PMID: 38131672 Free PMC article.
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
Research Materials