Biologically Active Fluorescent Farnesol Analogs

Authors

Roman Shchepin, University of Nebraska - Lincoln
Razvan Dumitru, University of Nebraska - LincolnFollow
Kenneth W. Nickerson, University of Nebraska-LincolnFollow
Miranda Lund, University of Nebraska - Lincoln
Patrick Dussault, University of Nebraska-LincolnFollow

Date of this Version

6-1-2005

Comments

Published in Chemistry & Biology 12:6 (June 2005), pp. 639-641. Copyright © 2005 Elsevier Ltd. Used by permission. http://www.sciencedirect.com/science/journal/10745521

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.

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