A NEW METHOD FOR THE SYNTHESIS OF HEPTAMETHINE CYANINE DYES - SYNTHESIS OF NEW NEAR-INFRARED FLUORESCENT LABELS
A NEW METHOD FOR THE SYNTHESIS OF HEPTAMETHINE CYANINE DYES - SYNTHESIS OF NEW NEAR-INFRARED FLUORESCENT LABELS
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DOI：
10.1021/jo00113a018
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发表时间：
1995-04-21
影响因子：
3.6
通讯作者：
PATONAY, G
中科院分区：
文献类型：
--
作者：
NARAYANAN, N;PATONAY, G
描述了一种新的七次甲基花青染料的非催化合成方法。该反应涉及将衍生自2,3,3-三甲基吲哚或2,3,3-三甲基联苯吲哚和2-氯-1-甲酰基-3-(羟基亚甲基)环己-1-烯的N-烷基取代季盐混合物在1-丁醇和苯(7:3)的混合物作为溶剂中加热回流。不使用催化剂，并且水作为共沸物被除去。所得氯化合物在近红外区域具有强吸收和荧光特性，并转化为带有反应性官能团（例如羟基和异硫氰酸酯基团）的染料，可用作核酸和蛋白质的荧光标签。几种对称和非对称染料已被高产率合成。
A new uncatalyzed synthesis of heptamethine cyanine dyes is described. The reaction involves heating a mixture of N-alkyl-substituted quaternary salts derived from 2,3,3-trimethylindole or 2,3,3-trimethylbenzindole and 2-chloro-1-formyl-3-(hydroxymethylene)cyclohex-1-ene to reflux in a mixture of 1-butanol and benzene (7:3) as solvent. No catalyst is used, and water is removed as an azeotrope. The resulting chloro compounds possess strong absorption and fluorescence properties in the near-infrared region and are converted to dyes bearing reactive functionalities such as hydroxy and isothiocyanate groups useful as fluorescent tags for nucleic acids and proteins. Several symmetric and nonsymmetric dyes have been synthesized in high yields.