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Discovery of Quinoline-Derived Trifluoromethyl Alcohols, Determination of Their in vivo Toxicity and Anticancer Activity in a Zebrafish Embryo Model
ChemMedchem
  • Vinoth Sittaramane, Georgia Southern University
  • Jihan Padgett, Georgia Southern University
  • Philip Salter, Georgia Southern University
  • Ashley Williams, Georgia Southern University
  • Shauntelle Luke, Georgia Southern University
  • Rebecca McCall, Georgia Southern University
  • Jonathan Arambula, Georgia Southern University
  • Vincent B. Graves, Georgia Southern University
  • Mark Blocker, Georgia Southern University
  • David Van Leuven, Georgia Southern University
  • Keturah Bowe, Georgia Southern University
  • Julia Heimberger, Georgia Southern University
  • Hannah C. Cade, Georgia Southern University
  • Supriya Immaneni, Georgia Southern University
  • Abid Shaikh, Georgia Southern University
Document Type
Article
Publication Date
11-1-2015
DOI
10.1002/cmdc.201500341
Disciplines
Abstract
In this study the rational design, synthesis, and anticancer activity of quinoline-derived trifluoromethyl alcohols were evaluated. Members of this novel class of trifluoromethyl alcohols were identified as potent growth inhibitors in a zebrafish embryo model. Synthesis of these compounds was carried out with an sp3-C−H functionalization strategy of methyl quinolines with trifluoromethyl ketones. A zebrafish embryo model was also used to explore the toxicity of ethyl 4,4,4-trifluoro-3-hydroxy-3-(quinolin-2-ylmethyl)butanoate (1), 2-benzyl-1,1,1-trifluoro-3-(quinolin-2-yl)propan-2-ol (2), and trifluoro-3-(isoquinolin-1-yl)-2-(thiophen-2-yl)propan-2-ol (3). Compounds 2 and 3 were found to be more toxic than compound 1; apoptotic staining assays indicated that compound 3 causes increased cell death. In vitro cell proliferation assays showed that compound 2, with an LC50 value of 14.14 μm, has more potent anticancer activity than cisplatin. This novel class of inhibitors provides a new direction in the discovery of effective anticancer agents.
Citation Information
Vinoth Sittaramane, Jihan Padgett, Philip Salter, Ashley Williams, et al.. "Discovery of Quinoline-Derived Trifluoromethyl Alcohols, Determination of Their in vivo Toxicity and Anticancer Activity in a Zebrafish Embryo Model" ChemMedchem Vol. 10 Iss. 11 (2015) p. 1802 - 1807
Available at: http://works.bepress.com/jonathan-arambula/18/