甲川链修饰菁染料的合成研究进展
收稿日期: 2023-04-16
修回日期: 2023-05-25
网络出版日期: 2023-06-07
基金资助
国家自然科学基金(21807086); 陕西省自然科学基础研究计划(2022JM-096); 陕西省教育厅科学研究计划(12JK0639); 2022年西安建筑科技大学“大创计划”(X2022159)
Research Progress in the Synthesis of Polymethine Chain Modified Cyanine Dyes
Received date: 2023-04-16
Revised date: 2023-05-25
Online published: 2023-06-07
Supported by
The National Natural Science Foundation of China(21807086); The Natural Science Basic Research Program of Shaanxi Province(2022JM-096); The Natural Science Foundation of Shaanxi Provincial Department of Education(12JK0639); The Xi'an University of Architecture and Technology “Great Innovation Plan” Project in 2022(X2022159)
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 . DOI: 10.6023/cjoc202304019
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
| [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. |
| [3] | Peng, B.-X.; Li, Q. Photogr. Sci. Photochem. 1994, 12, 150. (in Chinese) |
| [3] | ( 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. |
| [5] | (a) Guan, L.; Zhao, J.-L.; Sun, W.; Deng, W.-T.; Wang, L.-Y. ACS Omega 2020, 5, 26056. |
| [5] | (b) Guan, L.; Mao, Y.-B.; Zhou, Y.-Y.; Feng, X.-W.; Fu, Y.-L. Chin. J. Org. Chem. 2022, 42, 2406. (in Chinese) |
| [5] | ( 关丽, 毛永爆, 周艳艳, 冯潇雯, 付义乐, 有机化学, 2022, 42, 2406.) |
| [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. |
| [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. |
| [8] | N?dling, 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. |
| [9] | Shindy, H. A. Dyes Pigm. 2017, 145, 505. |
| [10] | Panigrahi, M.; Dash, S.; Patel, S.; Mishra, B. K. Tetrahedron 2012, 68, 781. |
| [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. |
| [11] | (b) Yadav, Y.; Owens, E.; Nomura, S.; Fukuda, T.; Baek, Y.; Kashiwagi, S.; Choi, H. S.; Henary, M. J. Med. Chem. 2020, 63, 9436. |
| [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. |
| [13] | (a) Soriano, E.; Holder, C.; Levitz, A.; Henary, M. Molecules 2015, 21, 23. |
| [13] | (b) Levitz, A.; Holder, C.; Soriano, E.; Henary, M. Dyes Pigm. 2017, 145, 202. |
| [13] | (c) Fabijani?, I.; Kurutos, A.; Pai?, A. T.; Tadi?, V.; Kamounah, F. S.; Horvat, L.; Brozovic, A.; Crnolatac, I.; Stojkovic, M. R. Biomolecules 2023, 13, 128. |
| [14] | (a) Levitz, A.; Holder, C.; Soriano, E.; Henary, M. Dyes Pigm. 2017, 145, 202. |
| [14] | (b) Vasilev, A. A.; Kandinska, M. I.; Stoyanov, S. S.; Yordanova, S. B.; Sucunza, D.; Vaquero, J. J.; Casta?o, O. D.; Baluschev, S.; Angelova, S. E. Beilstein J. Org. Chem. 2017, 13, 2902. |
| [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. |
| [16] | (b) Fry, D. J.; Kendall, J. D. J. Chem. Soc. 1951, 1723. |
| [16] | (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. |
| [18] | (b) Noboru, F.; Shigemasa, I.; Takeo, K. DE 2613377A1, 1976. |
| [19] | Nygren, J.; Svanvik, N.; Kubista, M. Biopolymers 1998, 46, 39 |
| [20] | Shank, N. I.; Pham, H. H.; Waggoner, A. S.; Armitage, B. A. J. Am. Chem. Soc. 2013, 135, 242. |
| [21] | Abd El-Aal, R. M. Dyes Pigm. 2004, 61, 251. |
| [22] | Voitenko, Z. V.; Kysil, A. I.; Wolf, J. G. Dyes Pigm. 2007, 74, 477. |
| [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. |
| [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. |
| [26] | Zeng, W.-X.; Chen, P.; Zheng, D.-S. Photogr. Sci. Photochem. 1995, 13, 136. (in Chinese) |
| [26] | ( 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. |
| [28] | (a) Tang, K.; Zhang, P.-C.; Wang, S.; Qiu, N.; Zhang, F. L. Chin. J. Org. Chem. 2016, 36, 1700. (in Chinese) |
| [28] | ( 汤昆, 张鹏超, 王升, 邱娜, 张付利, 有机化学, 2016, 36, 1700.) |
| [28] | (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. |
| [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. |
| [30] | Mitekura, H.; No, T.; Suzuki, K.; Satake, K.; Kimura, M. Dyes Pigm. 2002, 54, 113. |
| [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. |
| [32] | Chen, G.-W.; Song, F.-L.; Wang, X.; Sun, S.-G.; Fan, J.-L.; Peng, X.-J. Dyes Pigm. 2012, 93, 1532. |
| [33] | Abd El-Aal, R. M.; Younis, M. Bioorg. Chem. 2004, 32, 193. |
| [34] | Shank, N. I.; Zanotti, K. J.; Lanni, F.; Berget, P. B.; Armitage, B. A. J. Am. Chem. Soc. 2009, 131, 12960. |
| [35] | Bohl?nder, P. R.; Wagenknecht, H.-A. Eur. J. Org. Chem. 2014, 2014, 7547. |
| [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. |
| [37] | Wang, L.-Y.; Wang, Y.-Y.; Sun, W.; Zhao, J.-L.; Wang, Y.-X. Dyes Pigm. 2021, 192, 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. |
| [39] | (a) Oushiki, D.; Kojima, H.; Terai, T.; Arita, M.; Hanaoka, K.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2010, 132, 2795. |
| [39] | (b) Ge, J.-F.; Zhang, Q.-Q.; Lu, J.-M.; Kaiser, M.; Wittlin, S.; Brunb, R.; Ihara, M. Med. Chem. Commun. 2012, 3, 1435. |
| [39] | (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. |
| [40] | (a) Dai, Z.-F.; Peng, B.-X. Dyes Pigm. 1998, 36, 169. |
| [40] | (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. |
| [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. |
| [42] | Wycisk, V.; Pauli, J.; Welker, P.; Justies, A.; Resch-Genger, U.; Haag, R.; Licha, K. Bioconjugate Chem. 2015, 26, 773. |
| [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. |
| [45] | Shao, F.-W.; Weissleder, R.; Hilderbrand, S. A. Bioconjugate Chem. 2008, 19, 2487. |
| [46] | Hilderbrand, S. A.; Kelly, K. A.; Niedre, M.; Weissleder, R. Bioconjugate Chem. 2008, 19, 1635. |
| [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. |
| [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. |
| [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. |
| [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. |
| [51] | Lovett, W. R.; Al Hamd, A.; Casa, S.; Henary, M. Dyes Pigm. 2021, 190, 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. |
| [53] | Zhao, X.; Zhang, F.; Lei, Z.-H. Chem. Sci. 2022, 13, 11280. |
| [54] | Exner, R. M.; Cortezon-Tamarit, F.; Pascu, S. I. Angew. Chem. Int. Ed. 2021, 60, 6230. |
| [55] | (a) Lindsey, J. S.; Brown, P. A.; Siesel, D. A. Tetrahedron 1989, 45, 4845. |
| [55] | (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. |
| [55] | (c) Jansen-van Vuuren, R. D.; Deakin, P. C.; Olsen, S.; Burn, P. L. Dyes Pigm. 2014, 101, 1. |
| [56] | (a) Flanagan, J. H.; Khan, S. H.; Menchen, S.; Soper, S. A.; Hammer, R. P. Bioconjugate Chem. 1997, 8, 751. |
| [56] | (b) Nagao, Y.; Sakai, T.; Kozawa, K.; Urano, T. Dyes Pigm. 2007, 73, 344. |
| [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. |
| [59] | Ma, X.-Z.; Laramie, M.; Henary, M. Bioorg. Med. Chem. Lett. 2018, 28, 509. |
| [60] | Lee, H.; Mason, C.; Achilefu, S. J. Org. Chem. 2008, 73, 723. |
| [61] | Konig, S. G.; Kr?mer, R. Chemistry 2017, 23, 9306. |
| [62] | Levitz, A.; Marmarchi, F.; Henary, M. Photochem. Photobiol. Sci. 2018, 17, 1409. |
| [63] | ?tacková, L.; ?tacko, P.; Klán, P. J. Am. Chem. Soc. 2019, 141, 7155. |
| [64] | Li, D.-H.; Schreiber, C. L.; Smith, B. D. Angew. Chem. Int. Ed. 2020, 59, 12154. |
| [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. |
| [66] | Hao, Z.-M.; Hu, L.-M.; Wang, X.-N.; Liu, Y.-J.; Mo, S.-Y. Org. Lett. 2023, 25, 1078. |
| [67] | Narayanan, N.; Patonay, G. J. Org. Chem. 1995, 60, 2391. |
| [68] | Han, X.-Y.; Yu, F.-B.; Song, X.-Y.; Chen, L.-X. Chem. Sci. 2016, 7, 5098. |
| [69] | Karton-Lifshin, N.; Segal, E.; Omer, L.; Portnoy, M.; Satchi- Fainaro, R.; Shabat, D. J. Am. Chem. Soc. 2011, 133, 10960. |
| [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. |
| [71] | Gao, Z.-W.; Sun, J.-Y.; Gao, M.; Yu, F.-B.; Chen, L.-X.; Chen, Q.-G. Sens. Actuators, B 2018, 265, 565. |
| [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. |
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