Biologically active fluorescent farnesol analogs

Roman Shchepin, Raluca Dumitru, Kenneth W. Nickerson, Miranda Lund, Patrick H. Dussault

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

We describe ten polyene analogs of farnesol, typified by 3,7,11-trimethyl-2,4,6,8,10-dodecapentenaldehyde oxime, which preserve the length, cross-section, and approximate hydrophobicity of farnesol. Four of the ten display strong quorum-sensing activity in the human pathogen Candida albicans, with IC50 values for inhibition of germ-tube formation as low as 10 μM. The polyenes display absorption maxima between 320 and 380 nm, with the extinction coefficients for the oximes approaching 100,000. All but two of the analogs are fluorescent, with excitation maxima varying over the range of 320-370 nm. Oxime anti-4, which can undergo fluorescence excitation at wavelengths beyond 400 nm, is demonstrated to be useful for confocal fluorescence microscopic imaging of fungal cells. The farnesol analogs are also expected to be useful for detection of farnesol binding proteins and in determination of farnesol pharmacokinetics.

Original languageEnglish (US)
Pages (from-to)639-641
Number of pages3
JournalChemistry and Biology
Volume12
Issue number6
DOIs
Publication statusPublished - Jan 1 2005

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ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmacology
  • Drug Discovery
  • Clinical Biochemistry

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