发射长波长荧光的荧光素衍生物的设计与合成

Design and Synthesis of Long Wavelength Fluorescein Derivative

荧光团的光谱性能决定了荧光探针的性能,发射长波长的荧光团在生物化学、分子生物学领域具有特殊应用优势,文章以间苯二酚、邻苯二甲酸酐和环己酮为原料,通过傅克酰基化反应、浓硫酸催化下的缩合反应,制备类荧光素母体,以DMF与三氯氧磷制备Vilsmeier试剂。通过Vilsmeier试剂的甲酰化反应在类荧光素母体双键上引入一个醛基,邻氨基苯硫酚再与之发生亲核反应得到荧光素衍生物(化合物4),对该化合物做了结构鉴定,测定了其紫外可见吸收与荧光光谱,与荧光素相比,其荧光激发与发射波长均红移,是个性能优良的荧光团。

Spectral properties of the fluorophore determine the performance of fluorescent probe, fluorophore with long wavelength emission has a special advantage in the application of biochemistry and molecular biology. In this paper, using resorcinol, phthalie anhydride and cyclohexanone as raw material, by Friedel-Crafts acylation reaction and concentrated sulfuric acid catalyzed condensation reaction, fluorescein analogue was gained. Using DMF and POCl3, Vilsmeier reagent was prepared, by using Vilsmeier reagent formylation reaction, an dldehyde group was introduced in fluorescein analogue. Then, O-aminothiophenol had a nucleophilic reaction with it, fluorescein derivative （compound 4） was systhesized. Structure of compound 4 was identified; UV-visible absorption and fluorescent spectra of compound 4 were measured. Compared with fluorescein, its fluorescent excitation and emission wavelengths are all red-shifted; it can be an excellent fluorophore.