甲川链修饰菁染料的合成研究进展

doi:10.6023/cjoc202304019

摘要/Abstract

在小分子荧光探针中, 菁染料由于其良好的光学特性, 在成像及生物传感等领域具有广泛应用. 甲川链的功能化可以显著提高染料的稳定性并改变其光物理性能和生物选择性, 已成为近年来菁染料结构修饰的热点. 总结了甲川链修饰菁染料的合成方法, 根据甲川链取代基的不同来源, 按照甲川链不同长度对甲川链修饰菁染料的研究进展分别进行综述.

关键词: 菁染料, 甲川链修饰, 合成方法

Among small molecule fluorescent probes, cyanine dyes have been widely used in imaging and biosensing fields due to their good optical properties. Functionalization of the polymethine chain, which can significantly improve the stability of dyes and alter their photophysical properties and biological selectivity, has become a hotspot for structural modification of cyanine dyes in recent years. The synthesis methods of polymethine chain modified cyanine dyes are summarized and the progress of polymethine chain modified cyanine dyes is reviewed according to different lengths of polymethine chain, based on different sources of polymethine chain substituents.

Key words: cyanine dyes, polymethine chain modification, synthetic methods

引用此文

关丽, 周艳艳, 毛永爆, 付恺森, 关文惠, 付义乐. 甲川链修饰菁染料的合成研究进展[J]. 有机化学, 2023, 43(8): 2682-2698.

Li Guan, Yanyan Zhou, Yongbao Mao, Kaisen Fu, Wenhui Guan, Yile Fu. Research Progress in the Synthesis of Polymethine Chain Modified Cyanine Dyes[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2682-2698.

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图/表 30

图式1. 菁染料的可修饰位点分类

Scheme 1. Classification of modification sites of cyanine dyes

图式2. 单菁传统合成方法衍生的中位修饰合成路线

Scheme 2. Synthetic routes for the meso-modification derived from traditional synthetic methods of monomethine cyanines

图式3. Abd El-Aal课题组提出的不对称单菁中位修饰方法

Scheme 3. Asymmetric monomethine cyanines meso-modification method proposed by Abd El-Aal’s group

图式4. Voitenko课题组提出的通过酰氯引入中位取代基的方法

Scheme 4. Method to introduce meso-substituents via acid chloride proposed by Voitenko?s group

图式5. Grahn课题组提出的引入中位卤素的方法

Scheme 5. Method of introducing meso-halogens proposed by Grahn?s group

图式6. 通过甲川链与亲电试剂反应直接官能化噻唑橙的次甲基链

Scheme 6. Direct functionalization of the methine chain of thiazole orange by reaction of the polymethine chain with electrophiles

图式7. 由传统合成方法衍生的甲川链修饰三甲川菁合成路线

Scheme 7. Synthetic route of polymethine chain modified trimethine cyanines derived from traditional synthetic methods

图式8. 由中位脂肪烃基的反应引入大体积取代基的方法

Scheme 8. Methods for introducing bulky substituents from the reaction of median aliphatic hydrocarbon groups

图式9. 中位胺基取代三甲川菁染料的合成

Scheme 9. Synthesis of meso-amine groups substituted trimethine cyanines

图式10. 甲川链双取代三甲川菁的合成方法

Scheme 10. Synthetic method of polymethine chain bisubstitu- ted trimethine cyanines

图式11. 三甲川菁偏位引入氰基的合成方法

Scheme 11. Synthetic method of introducing cyano group into side position of trimethine cyanines

图式12. 三甲川菁中位引入TPE的合成方法

Scheme 12. Synthetic method of introducing TPE into meso-position of trimethine cyanines

图式13. 染料甲川链直接发生反应引入取代基的方法

Scheme 13. Direct reaction of cyanine dye polymethine chain to introduce substituents

图式14. 五甲川菁的传统合成方法和中位卤素取代的合成方法

Scheme 14. Traditional synthetic method and synthetic method of meso-halogen substitution of pentamethine cyanines

图式15. 利用中位氯的亲核性进一步修饰甲川链

Scheme 15. Further modification of polymethine chain using the nucleophilicity of the meso-chlorine

图式16. 利用中位溴经Suzuki偶联进一步修饰甲川链

Scheme 16. Further modification of polymethine chain using the meso-bromine by Suzuki coupling

图式17. 以新型苯胺缩合剂合成甲川链取代的五甲川菁

Scheme 17. Synthesis of meso-substituted pentamethine cyanines using novel aniline condensing agents

图式18. 由二醛类似物缩合剂合成中位氯代的五甲川菁

Scheme 18. Synthesis of meso-chlorine substituted pentamethine cyanines by dialdehyde analogue condensing agent

图式19. 由三甲酰基甲烷缩合剂合成中位醛基及进一步取代的五甲川菁

Scheme 19. Synthesis of meso-aldehyde and further substituted pentamethine cyanines using triformylmethane condensing agent

图式20. 以功能化的二醛类似物缩合剂合成甲川链修饰的五甲川菁

Scheme 20. Synthesis of meso-modified pentamethine cyanines by functionalized dialdehyde analogue condensing agents

图式21. 由七甲川菁染料经典合成方法衍生的甲川链嵌入刚性环的合成路线

Scheme 21. Synthetic route of embedding rigid rings into polymethine chain derived from the classical synthetic method of heptamethine cyanine dyes

图式22. 通过中位氯与亲核试剂的反应进一步对甲川链进行修饰

Scheme 22. Further modification of polymethine chain by reaction of the meso-chlorine with nucleophiles

图式23. 基于中位氯的进一步Suzuki和Sonogashira偶联反应

Scheme 23. Further Suzuki and Sonogashira coupling reaction based on meso-chlorine

图式24. 基于中位氯用巴比妥酸进一步取代修饰甲川链

Scheme 24. Further substitution of polymethine chain with barbituric acid based on meso-chlorine

图式25. 经Vilsmeier-Haack 反应将取代基引入二苯胺盐酸盐缩合剂

Scheme 25. Introducing substituents into diphenylamine hydrochloride condensing agents through Vilsmeier-Haack reaction

图式26. Zincke盐开环法合成甲川链C3'~C5'取代的七甲川菁

Scheme 26. Synthesis of polymethine chain C3'~C5' substituted heptamethine cyanines by the ring opening of Zincke salts

图式27. 由绿色原料糠醛及其衍生物合成甲川链C5'位置酰氧基类取代的七甲川菁

Scheme 27. Synthesis of polymethine chain C5' position acyloxy substituted heptamethine cyanines by green raw furfural and its derivatives

图式28. 以二醛衍生物为缩合剂合成甲川链修饰的七甲川菁染料

Scheme 28. Synthesis of polymethine chain modified heptamethine cyanines using dialdehyde derivatives as condensing agents

图式29. 以间苯二甲醛衍生物为缩合剂合成甲川链修饰的“turn-on”探针

Scheme 29. Synthesis of polymethine chain modified “turn on” probes using metaphthalaldehyde derivatives as condensing agents

图式30. 以哌啶环二醛衍生物为缩合剂合成甲川链修饰的七甲川菁染料

Scheme 30. Synthesis of polymethine chain modified heptamethine cyanines using piperidine cyclic dialdehyde derivative as condensation agents

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