Research Progress in the Synthesis of Polymethine Chain Modified Cyanine Dyes

doi:10.6023/cjoc202304019

Abstract

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

Cite this article

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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Fig. & Tab. 30

Scheme 1. Classification of modification sites of cyanine dyes

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

References 72

[1]	Ehrlich, S. H. J. Photochem. 1974, 75, 403.
[2]	Ma, X.-M.; Hua, J.-L.; Wu, W.-J.; Jin, Y.-H.; Meng, F.-H.; Zhan, W.-H.; Tian, H. Tetrahedron 2008, 64, 345. doi: 10.1016/j.tet.2007.10.094
[3]	Peng, B.-X.; Li, Q. Photogr. Sci. Photochem. 1994, 12, 150. (in Chinese)
	( 彭必先, 李群, 感光科学与光化学, 1994, 12, 150.)
[4]	Sakamoto, T.; Yu, Z.-H.; Otani, Y. Anal. Chem. 2022, 94, 4269. doi: 10.1021/acs.analchem.1c04804 pmid: 35234461
[5]	(a) Guan, L.; Zhao, J.-L.; Sun, W.; Deng, W.-T.; Wang, L.-Y. ACS Omega 2020, 5, 26056. doi: 10.1021/acsomega.0c03556 pmid: 33073132
	(b) Guan, L.; Mao, Y.-B.; Zhou, Y.-Y.; Feng, X.-W.; Fu, Y.-L. Chin. J. Org. Chem. 2022, 42, 2406. (in Chinese) doi: 10.6023/cjoc202203025 pmid: 33073132
	( 关丽, 毛永爆, 周艳艳, 冯潇雯, 付义乐, 有机化学, 2022, 42, 2406.) doi: 10.6023/cjoc202203025 pmid: 33073132
[6]	Yi, M.-W.; Liu, X.-J.; Liu, J.; Li, S.-N.; Li, D.-D.; Zhang, X.-R.; Zhang, N.; Wei, Y.-B.; Shangguan, D.-H. Spectrochim. Acta, Part A 2022, 278, 121305. doi: 10.1016/j.saa.2022.121305
[7]	Zhao, X.-J.; Zhao, H.-J.; Wang, S.; Fan, Z.-W.; Ma, Y.; Yin, Y.-M.; Wang, W.; Xi, R.-M.; Meng, M. J. Am. Chem. Soc. 2021, 143, 20828. doi: 10.1021/jacs.1c09155
[8]	Nödling, A. R.; Mills, E. M.; Li, X.-F.; Cardella, D.; Sayers, E. J.; Wu, S. H.; Jones, A. T.; Luk, L. Y. P.; Tsai, Y. H. Chem. Commun. (Cambridge, U. K.) 2020, 56, 4672. doi: 10.1039/C9CC07931A
[9]	Shindy, H. A. Dyes Pigm. 2017, 145, 505. doi: 10.1016/j.dyepig.2017.06.029
[10]	Panigrahi, M.; Dash, S.; Patel, S.; Mishra, B. K. Tetrahedron 2012, 68, 781. doi: 10.1016/j.tet.2011.10.069
[11]	(a) Tan, X.-H.; Constantin, T. P.; Sloane, K. L.; Waggoner, A. S.; Bruchez, M. P.; Armitage, B. A. J. Am. Chem. Soc. 2017, 139, 9001. doi: 10.1021/jacs.7b04211
	(b) Yadav, Y.; Owens, E.; Nomura, S.; Fukuda, T.; Baek, Y.; Kashiwagi, S.; Choi, H. S.; Henary, M. J. Med. Chem. 2020, 63, 9436. doi: 10.1021/acs.jmedchem.0c00617
[12]	Zhao, X.-Z.; Yao, Q.-C.; Long, S.; Chi, W.-J.; Yang, Y.-X.; Tan, D.; Liu, X.-G.; Huang, H.-Q.; Sun, W.; Du, J.-J.; Fan, J.-L.; Peng, X.-J. J. Am. Chem. Soc. 2021, 143, 12345. doi: 10.1021/jacs.1c06275
[13]	(a) Soriano, E.; Holder, C.; Levitz, A.; Henary, M. Molecules 2015, 21, 23. doi: 10.3390/molecules21010023
	(b) Levitz, A.; Holder, C.; Soriano, E.; Henary, M. Dyes Pigm. 2017, 145, 202. doi: 10.1016/j.dyepig.2017.05.051
	(c) Fabijanić, I.; Kurutos, A.; Paić, A. T.; Tadić, V.; Kamounah, F. S.; Horvat, L.; Brozovic, A.; Crnolatac, I.; Stojkovic, M. R. Biomolecules 2023, 13, 128. doi: 10.3390/biom13010128
[14]	(a) Levitz, A.; Holder, C.; Soriano, E.; Henary, M. Dyes Pigm. 2017, 145, 202. doi: 10.1016/j.dyepig.2017.05.051
	(b) Vasilev, A. A.; Kandinska, M. I.; Stoyanov, S. S.; Yordanova, S. B.; Sucunza, D.; Vaquero, J. J.; Castaño, O. D.; Baluschev, S.; Angelova, S. E. Beilstein J. Org. Chem. 2017, 13, 2902. doi: 10.3762/bjoc.13.283
[15]	Hamer, F. M.; Rathbone, R. J.; Winton, B. S. J. Chem. Soc. 1947, 954.
[16]	(a) Hamer, F. M. J. Chem. Soc. 1956, 1480.
	(b) Fry, D. J.; Kendall, J. D. J. Chem. Soc. 1951, 1723.
	(c) Hamer, F. M. J. Chem. Soc. 1939, 1008.
[17]	Seto, Y.; Sakazume, K.; Yamaguchi, H. US 3245874, 1966
[18]	(a) Davidson, A. W. GB 1027104, 1966.
	(b) Noboru, F.; Shigemasa, I.; Takeo, K. DE 2613377A1, 1976.
[19]	Nygren, J.; Svanvik, N.; Kubista, M. Biopolymers 1998, 46, 39 pmid: 9612138
[20]	Shank, N. I.; Pham, H. H.; Waggoner, A. S.; Armitage, B. A. J. Am. Chem. Soc. 2013, 135, 242. doi: 10.1021/ja308629w
[21]	Abd El-Aal, R. M. Dyes Pigm. 2004, 61, 251. doi: 10.1016/j.dyepig.2003.10.014
[22]	Voitenko, Z. V.; Kysil, A. I.; Wolf, J. G. Dyes Pigm. 2007, 74, 477. doi: 10.1016/j.dyepig.2006.03.017
[23]	Grahn, W.; Johannes, H.; H. ; Rheinheimer, J.; Knieriem, B.; Wurthwein, E. U. Liebigs Ann. 1995, 6, 1003.
[24]	Guan, L.; Li, A.-Y.; Song, Y.-Y.; Yan, M.-Q.; Gao, D.-F.; Zhang, X.-H.; Li, B.; Wang, L.-Y. J. Org. Chem. 2016, 81, 6303. doi: 10.1021/acs.joc.6b00928 pmid: 27379526
[25]	Wang, L.-Y.; Lin, W.-X.; Sun, W.; Yan, M.-Q.; Zhao, J.-L.; Guan, L.; Deng, W.-T.; Zhang, Y.-Q. J. Org. Chem. 2019, 84, 3960. doi: 10.1021/acs.joc.8b03122
[26]	Zeng, W.-X.; Chen, P.; Zheng, D.-S. Photogr. Sci. Photochem. 1995, 13, 136. (in Chinese)
	( 曾万学, 陈萍, 郑德水, 感光科学与光化学, 1995, 13, 136.)
[27]	Pronkin, P. G.; Tatikolov, A. S. Molecules 2022, 27, 6367. doi: 10.3390/molecules27196367
[28]	(a) Tang, K.; Zhang, P.-C.; Wang, S.; Qiu, N.; Zhang, F. L. Chin. J. Org. Chem. 2016, 36, 1700. (in Chinese) doi: 10.6023/cjoc201511020
	( 汤昆, 张鹏超, 王升, 邱娜, 张付利, 有机化学, 2016, 36, 1700.) doi: 10.6023/cjoc201511020
	(b) Gu, J.-M.; Anumala, U. R.; Heyny-von Haussen, R.; Holzer, J.; Goetschy-Meyer, V.; Mall, G.; Hilger, I.; Czech, C.; Schmidt, B. ChemMedChem 2013, 8, 891. doi: 10.1002/cmdc.201300090
[29]	Volkova, K. D.; Kovalska, V. B.; Losytskyy, M. Y.; Fal, K. O.; Derevyanko, N. O.; Slominskii, Y. L.; Tolmachov, O. I.; Yarmoluk, S. M. J. Fluoresc. 2011, 21, 775. doi: 10.1007/s10895-010-0770-6
[30]	Mitekura, H.; No, T.; Suzuki, K.; Satake, K.; Kimura, M. Dyes Pigm. 2002, 54, 113. doi: 10.1016/S0143-7208(02)00023-2
[31]	Hu, H.; Owens, E. A.; Su, H.; Yan, L.-L.; Levitz, A.; Zhao, X.-Y.; Henary, M.; Zheng, Y. G. J. Med. Chem. 2015, 58, 1228. doi: 10.1021/jm501452j
[32]	Chen, G.-W.; Song, F.-L.; Wang, X.; Sun, S.-G.; Fan, J.-L.; Peng, X.-J. Dyes Pigm. 2012, 93, 1532. doi: 10.1016/j.dyepig.2011.09.002
[33]	Abd El-Aal, R. M.; Younis, M. Bioorg. Chem. 2004, 32, 193. pmid: 15210335
[34]	Shank, N. I.; Zanotti, K. J.; Lanni, F.; Berget, P. B.; Armitage, B. A. J. Am. Chem. Soc. 2009, 131, 12960. doi: 10.1021/ja9016864
[35]	Bohländer, P. R.; Wagenknecht, H.-A. Eur. J. Org. Chem. 2014, 2014, 7547. doi: 10.1002/ejoc.v2014.34
[36]	Zhang, X.-H.; Wang, B.; Xia, Y.-Q.; Zhao, S.-M.; Tian, Z.-H.; Ning, P.-B.; Wang, Z.-L. ACS Appl. Mater. Interfaces 2018, 10, 25146. doi: 10.1021/acsami.8b07727
[37]	Wang, L.-Y.; Wang, Y.-Y.; Sun, W.; Zhao, J.-L.; Wang, Y.-X. Dyes Pigm. 2021, 192, 109459. doi: 10.1016/j.dyepig.2021.109459
[38]	Wang, L.-Y.; Yan, M.-Q.; Zhang, B.-R.; Zhao, J.-L.; Deng, W.-T.; Lin, W.-X.; Guan, L. Org. Lett. 2018, 20, 60. doi: 10.1021/acs.orglett.7b03345
[39]	(a) Oushiki, D.; Kojima, H.; Terai, T.; Arita, M.; Hanaoka, K.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2010, 132, 2795. doi: 10.1021/ja910090v pmid: 24845528
	(b) Ge, J.-F.; Zhang, Q.-Q.; Lu, J.-M.; Kaiser, M.; Wittlin, S.; Brunb, R.; Ihara, M. Med. Chem. Commun. 2012, 3, 1435. doi: 10.1039/c2md20136d pmid: 24845528
	(c) Pisoni, D. S.; Todeschini, L.; A. Borges, A. C.; Petzhold, C. L.; Rodembusch, F. S.; Campo, L. F. J. Org. Chem. 2014, 79, 5511. doi: 10.1021/jo500657s pmid: 24845528
[40]	(a) Dai, Z.-F.; Peng, B.-X. Dyes Pigm. 1998, 36, 169. doi: 10.1016/S0143-7208(97)00002-8 pmid: 27100476
	(b) Owens, E. A.; Hyun, H.; Dost, T. L.; Lee, J. H.; Park, G.; Pham, D. H.; Park, M. H.; Choi, H. S.; Henary, M. J. Med. Chem. 2016, 59, 5311. doi: 10.1021/acs.jmedchem.6b00038 pmid: 27100476
[41]	Xin, J.; Zhang, X.-H.; Liang, J.-M.; Xia, L.-M.; Yin, J.-P.; Nie, Y.-Z.; Wu, K.-C.; Tian, J. Bioconjugate Chem. 2013, 24, 1134. doi: 10.1021/bc3006539
[42]	Wycisk, V.; Pauli, J.; Welker, P.; Justies, A.; Resch-Genger, U.; Haag, R.; Licha, K. Bioconjugate Chem. 2015, 26, 773. doi: 10.1021/acs.bioconjchem.5b00097
[43]	Savicheva, E. A.; Bossi, M. L.; Belov, V. N.; Hell, S. W. Chem- PhotoChem 2022, 7, e202200222.
[44]	Lee, H.; Mason, C. M.; Achilefu, S. J. Org. Chem. 2008, 73, 723. doi: 10.1021/jo701793h
[45]	Shao, F.-W.; Weissleder, R.; Hilderbrand, S. A. Bioconjugate Chem. 2008, 19, 2487. doi: 10.1021/bc800417b
[46]	Hilderbrand, S. A.; Kelly, K. A.; Niedre, M.; Weissleder, R. Bioconjugate Chem. 2008, 19, 1635. doi: 10.1021/bc800188p pmid: 18666791
[47]	Peng, X.-J.; Yang, Z.-G.; Wang, J.-Y.; Fan, J.-L.; He, Y.-X.; Song, F.-L.; Wang, B.-S.; Sun, S.-G.; Qu, J.; Qi, J.; Yan, M. J. Am. Chem. Soc. 2011, 133, 6626. doi: 10.1021/ja1104014
[48]	Ma, H.; Long, S.; Cao, J.-F.; Xu, F.; Zhou, P.-W.; Zeng, G.; Zhou, X.; Shi, C.; Sun, W.; Du, J.-J.; Han, K.; Fan, J.-L.; Peng, X.-J. Chem. Sci. 2021, 12, 13809. doi: 10.1039/D1SC04570A
[49]	Yu, H.; Sun, M.-T.; Zhang, K.; Zhu, H.-J.; Liu, Z.-J.; Zhang, Y.-J.; Zhao, J.; Wu, L.-J.; Zhang, Z.-P.; Wang, S.-H. Sens. Actuators, B 2015, 219, 294. doi: 10.1016/j.snb.2015.05.029
[50]	Hou, T.-X.; Zhang, K.; Kang, X.-X.; Guo, X.-L.; Du, L.-B.; Chen, X.-F.; Yu, L.; Yue, J.; Ge, H.-W.; Liu, Y.; Asiri, A. M.; Alamry, K. A.; Yu, H.; Wang, S.-H. Talanta 2019, 196, 345. doi: 10.1016/j.talanta.2018.12.083
[51]	Lovett, W. R.; Al Hamd, A.; Casa, S.; Henary, M. Dyes Pigm. 2021, 190, 109268. doi: 10.1016/j.dyepig.2021.109268
[52]	Ma, H.; Lu, Y.; Huang, Z.-B.; Long, S.; Cao, J.-F.; Zhang, Z.; Zhou, X.; Shi, C.; Sun, W.; Du, J.-J.; Fan, J.-L.; Peng, X.-J. J. Am. Chem. Soc. 2022, 144, 3477. doi: 10.1021/jacs.1c11886
[53]	Zhao, X.; Zhang, F.; Lei, Z.-H. Chem. Sci. 2022, 13, 11280. doi: 10.1039/D2SC03136A
[54]	Exner, R. M.; Cortezon-Tamarit, F.; Pascu, S. I. Angew. Chem. Int. Ed. 2021, 60, 6230. doi: 10.1002/anie.v60.12
[55]	(a) Lindsey, J. S.; Brown, P. A.; Siesel, D. A. Tetrahedron 1989, 45, 4845. doi: 10.1016/S0040-4020(01)85156-5 pmid: 11985468
	(b) Achilefu, S.; Jimenez, H. N.; Dorshow, R. B.; Bugaj, J. E.; Webb, E. G.; Wilhelm, R. R.; Rajagopalan, R.; Johler, J. Erion, J. L. J. Med. Chem. 2002, 45, 2003. doi: 10.1021/jm010519l pmid: 11985468
	(c) Jansen-van Vuuren, R. D.; Deakin, P. C.; Olsen, S.; Burn, P. L. Dyes Pigm. 2014, 101, 1. doi: 10.1016/j.dyepig.2013.09.003 pmid: 11985468
[56]	(a) Flanagan, J. H.; Khan, S. H.; Menchen, S.; Soper, S. A.; Hammer, R. P. Bioconjugate Chem. 1997, 8, 751. pmid: 9327141
	(b) Nagao, Y.; Sakai, T.; Kozawa, K.; Urano, T. Dyes Pigm. 2007, 73, 344. doi: 10.1016/j.dyepig.2006.01.039 pmid: 9327141
[57]	Pham, W.; Cassell, L.; Gillman, A.; Koktysh, D.; Gore, J. C. Chem. Commun. (Cambridge, U. K.). 2008, 16, 1895.
[58]	Hyun, H.; Wada, H.; Bao, K.; Gravier, J.; Yadav, Y.; Laramie, M.; Henary, M.; Frangioni, J. V.; Choi, H. S. Angew. Chem. Int. Ed. 2014, 53, 10668. doi: 10.1002/anie.201404930
[59]	Ma, X.-Z.; Laramie, M.; Henary, M. Bioorg. Med. Chem. Lett. 2018, 28, 509. doi: 10.1016/j.bmcl.2017.12.001
[60]	Lee, H.; Mason, C.; Achilefu, S. J. Org. Chem. 2008, 73, 723. doi: 10.1021/jo701793h
[61]	Konig, S. G.; Krämer, R. Chemistry 2017, 23, 9306.
[62]	Levitz, A.; Marmarchi, F.; Henary, M. Photochem. Photobiol. Sci. 2018, 17, 1409. doi: 10.1039/c8pp00218e
[63]	Štacková, L.; Štacko, P.; Klán, P. J. Am. Chem. Soc. 2019, 141, 7155. doi: 10.1021/jacs.9b02537 pmid: 31017409
[64]	Li, D.-H.; Schreiber, C. L.; Smith, B. D. Angew. Chem. Int. Ed. 2020, 59, 12154. doi: 10.1002/anie.v59.29
[65]	Yang, Y.; Fan, Z.-W.; Dong, Q.-Y.; Sun, W.; Zhang, X.-H.; Guan, L.; Wang, L.-Y. ACS Sustainable Chem. Eng. 2022, 10, 2282. doi: 10.1021/acssuschemeng.1c08048
[66]	Hao, Z.-M.; Hu, L.-M.; Wang, X.-N.; Liu, Y.-J.; Mo, S.-Y. Org. Lett. 2023, 25, 1078. doi: 10.1021/acs.orglett.2c04289
[67]	Narayanan, N.; Patonay, G. J. Org. Chem. 1995, 60, 2391. doi: 10.1021/jo00113a018
[68]	Han, X.-Y.; Yu, F.-B.; Song, X.-Y.; Chen, L.-X. Chem. Sci. 2016, 7, 5098. doi: 10.1039/C6SC00838K
[69]	Karton-Lifshin, N.; Segal, E.; Omer, L.; Portnoy, M.; Satchi- Fainaro, R.; Shabat, D. J. Am. Chem. Soc. 2011, 133, 10960. doi: 10.1021/ja203145v pmid: 21631116
[70]	Li, P.; Wang, J.-J.; Wang, X.; Ding, Q.; Bai, X.-Y.; Zhang, Y.-D.; Su, D.; Zhang, W.; Zhang, W.; Tang, B. Chem. Sci. 2019, 10, 2805. doi: 10.1039/C8SC04891F
[71]	Gao, Z.-W.; Sun, J.-Y.; Gao, M.; Yu, F.-B.; Chen, L.-X.; Chen, Q.-G. Sens. Actuators, B 2018, 265, 565. doi: 10.1016/j.snb.2018.03.078
[72]	Ma, X.-X.; Huang, Y.-R.; Chen, W.-J.; Liu, J.; Liu, S.-H.; Yin, J.; Yang, G.-F. Angew. Chem. Int. Ed. 2023, 62, e202216109. doi: 10.1002/anie.v62.3

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