Shchepin Roman, Dumitru Raluca, Nickerson Kenneth W, Lund Miranda, Dussault Patrick H
Department of Chemistry, University of Nebraska, Lincoln, NE 68588, USA.
Chem Biol. 2005 Jun;12(6):639-41. doi: 10.1016/j.chembiol.2005.04.008.
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 IC(50) values for inhibition of germ-tube formation as low as 10 microM. 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.
我们描述了法尼醇的十种多烯类似物，以3,7,11 - 三甲基 - 2,4,6,8,10 - 十二碳五烯醛肟为代表，它们保留了法尼醇的长度、横截面和近似疏水性。这十种类似物中的四种在人类病原体白色念珠菌中表现出强烈的群体感应活性，抑制芽管形成的IC(50)值低至10微摩尔。这些多烯在320至380纳米之间有最大吸收峰，肟的消光系数接近100,000。除了两种类似物外，其余均有荧光，最大激发波长在320 - 370纳米范围内变化。肟抗 - 4可在波长超过400纳米处进行荧光激发，已证明其可用于真菌细胞的共聚焦荧光显微镜成像。法尼醇类似物预计也可用于检测法尼醇结合蛋白以及测定法尼醇的药代动力学。
