Synthesis and biological evaluation of (-)-16-normethyldictyostatin : A potent analogue of (-)-dictyostatin

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journal

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Author(s)

  • Youseung Shin
  • Jean-Hugues Fournier
  • Raghavan Balachandran
  • Charitha Madiraju
  • Brianne S. Raccor
  • Michael C. Edler
  • Ernest Hamel
  • Billy W. Day
  • Dennis P. Curran

Detail(s)

Original languageEnglish
Pages (from-to)2873-2876
Journal / PublicationOrganic Letters
Volume7
Issue number14
Publication statusPublished - 7 Jul 2005
Externally publishedYes

Abstract

(Chemical Equation Presented) (-)-16-Normethyldictyostatin has been made by total synthesis and is a potent antitumor agent in cells expressing wild-type tubulin and in one mutant cell line that is resistant to paclitaxel, but it is much less active than dictyostatin in another paclitaxel-resistant cell line where Val is substituted for Phe270. This provides strong evidence that the C16 methyl group of the dictyostatins is oriented toward Phe270 in the paclitaxel-binding site on β-tubulin. © 2005 American Chemical Society.

Citation Format(s)

Synthesis and biological evaluation of (-)-16-normethyldictyostatin : A potent analogue of (-)-dictyostatin. / Shin, Youseung; Fournier, Jean-Hugues; Balachandran, Raghavan; Madiraju, Charitha; Raccor, Brianne S.; Zhu, Guangyu; Edler, Michael C.; Hamel, Ernest; Day, Billy W.; Curran, Dennis P.

In: Organic Letters, Vol. 7, No. 14, 07.07.2005, p. 2873-2876.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journal