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A profile of the in vitro anti-tumor activity of imidazolium-based ionic liquids.

Abstract
The anti-cancer activity and cytotoxicity of imidazolium-based ionic liquids has been determined for the first time via NCI's in vitro 60 human tumor cell lines. The preliminary SAR showed that the chain length of alkyl substitution at N-3 position of imidazole ring plays crucial role towards anti-tumor activity and cytotoxicity of these ionic liquids. The ionic liquids with alkyl substitution of C-12 chain length were found to be effective against all 60 tumor cell lines and show very low cytotoxicity in most of the cases. Further increase in chain length resulted in enhanced growth inhibition of tumor cell lines as well as high cytotoxicity. Interestingly, active compounds 1-dodecyl-3-methylimidazolium chloride (8), 1-dodecyl-3-methylimidazolium tetrafluoroborate (9), 1-hexadecyl-3-methylimidazoium chloride (10), 1-octadecyl-3-methylimidazolium chloride (11), 1-octadecyl-3-methylimidazolium hexafluorophosphate (12), 1-octadecyl-3-methylimidazolium bis(triflic)imide (13) and 1-octadecyl-3-methylimidazolium tris(pentafluoroethyl)trifluorophosphate (14) were highly active against leukemia cell lines, especially compounds 13 and 14 where the cytotoxicity was also very low as given by LC(50) >100microM in all six leukemia cell lines.
AuthorsSanjay V Malhotra, Vineet Kumar
JournalBioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 20 Issue 2 Pg. 581-5 (Jan 15 2010) ISSN: 1464-3405 [Electronic] England
PMID20006501 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)
CopyrightCopyright 2009 Elsevier Ltd. All rights reserved.
Chemical References
  • 1-octadecyl-3-methylimidazolium
  • Antineoplastic Agents
  • Imidazoles
  • Ionic Liquids
Topics
  • Antineoplastic Agents (chemical synthesis, chemistry, toxicity)
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Imidazoles (chemical synthesis, chemistry, toxicity)
  • Ionic Liquids (chemical synthesis, chemistry, toxicity)
  • Structure-Activity Relationship

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