Photophysical Features of Protolytic Equilibria of Fluorescein Bifluorophores
Abstract
The photophysical properties of these two carboxyfluorescein bifluorophores were investigated in more depth, including the effects of pH and different solution media on the photophysical properties, as well as comparing the fluorescence effect of bifluorophores with monomers carboxyfluoresceins (5-FAM and 6-FAM) in conjugates with protein molecules. The results showed that both bifluorophores fluoresced perfectly in alkaline medium, but the fluorescence intensity decreased at pH values of 6–7, and almost disappeared in acidic medium. The fluorescence of (6-FAM)2 is very sensitive to the solution composition, while (5-FAM)2 is more stable and almost independent of the solution medium. When bifluorophore-protein conjugate is formed, the quantum yield of bifluorophore fluorescence decreases more strongly compared to monomers carboxyfluoresceins, but the overall fluorescence intensity of the bifluorophore was not inferior to that of the two carboxyfluorescein monomer-protein conjugates due to the high extinction coefficient of the bifluorophore (~140,000 M–1 . cm–1).
About the Authors
F. FanBelarus
Minsk
V. A. Povedailo
Belarus
Minsk
I. L. Lysenko
Belarus
Minsk
O. L. Sharko
Belarus
Minsk
I. O. Mazunin
Russian Federation
Moscow
S. A. Tikhomirov
Belarus
Minsk
V. V. Shmanai
Belarus
Minsk
References
1. V. A. Povedailo, I. L. Lysenko, S. A. Tikhomirov, D. L. Yakovlev, D. A Tsybulsky, A. S. Kruhlik, F. Fan, Y. V. Martynenko-Makaev, O. L. Sharko, P. V. Duong, P. H. Minh, V. V. Shmanai. J. Fluores., 30 (2020) 629—635
2. J. R. Unruh, G. Gokulrangan, G. S. Wilson, C. K. Johnson. Photochem. and Photobiol., 81, N 3 (2005) 682-690
3. M. Götz, S. Hess, G. Beste, A. Skerra, M. E. Michel-Beyerle. Biochemistry, 41, N 12 (2002) 4156—4164
4. O. K. Abou-Zied, S. A. Sulaiman. Dyes and Pigments, 110 (2014) 89—96
5. T. Wang, T. Hong, Y. Huang, H. Su, F. Wu, Y. Chen, L. Wei, W. Huang, X. Hua, Y. Xia, J. Xu, J. Gan, B. Yuan, Y. Feng, X. Zhang, C. Yang, X. Zhou. J. Am. Chem. Soc., 137, N 43 (2015) 13736—13739
6. G. Li, B. Zhang, X. Song, Y. Xia, H. Yu, X. Zhang, Y. Xiao, Y. Song. Sensors and Actuators B: Chem., 253 (2017) 58—68
7. K. L. Bandamwar, E. B. Papas, Q. Garrett. Contact Lens and Anterior Eye, 37, N 3 (2014) 213—223
8. D. Y. Ryazantsev, D. A. Tsybulsky, I. A. Prokhorenko, M. V. Kvach, Y. V. Martynenko, P. M. Philipchenko, V. V. Shmanai, V. A. Korshun, S. K. Zavriev. Analyt. and Bioanalyt. Chem., 404 (2012) 59—68
9. D. A. Tsybulsky, M. V. Kvach, D. Y. Ryazantsev, I. O. Aparin, A. A. Stakheev, I. A. Prokhorenko, Y. V. Martynenko, S. V. Gontarev, A. A. Formanovsky, T. S. Zatsepin, V. V. Shmanai, V. A. Korshun, S. K. Zavriev. Mol. and Cell. Probes, 30, N 5 (2016) 285—290
10. N. Wanichacheva, O. Hanmeng, S. Kraithong, K. Sukrat. J. Photochem. and Photobiol. A: Chem., 278 (2014) 75—81
11. S. Wang, B. S. Gaylord, G. C. Bazan. J. Am. Chem. Soc., 126, N 17 (2004) 5446—5451
12. J. Saha, A. D. Roy, D. Dey, D. Bhattacharjee, P. K. Paul, R. Das, S. A. Hussain. Spectrochim. Acta Part A: Mol. and Biomolec. Spectrosc., 175 (2017) 110—116
13. A. J. Hickey, P. R. Byron. J. Pharm. Sci., 75, N 8 (1986) 756—759
14. H. Komatsu, N. Iwasawa, D. Citterio, Y. Suzuki, T. Kubota, K. Tokuno, Y. Kitamura, K. Oka, K. Suzuki. J. Am. Chem. Soc., 126, N 50 (2004) 16353—16360
15. E. Lanz, M. Gregor, J.Slavík, A. Kotyk. J. Fluores., 7 (1997) 317—319
16. E. Ralston, L. M. Hjelmeland, R. D. Klausner, J. N. Weinstein, R. Blumenthal. Biochim. Biophys. Acta (BBA) – Biomembranes, 649, N 1 (1981) 133—137
17. M. V. Kvach, D. A. Tsybulsky, A. V. Ustinov, I. A. Stepanova, S. L. Bondarev, S. V. Gontarev, V. A. Korshun, V. V. Shmanai. Bioconjugate Chem., 18, N 5 (2007) 1691—1696
18. M. M. Martin, L. Lindqvist. J. Lumin., 10, N 6 (1975) 381—390
19. N. Klonis, W. H. Sawyer. J. Fluores., 6 (1996) 147—157
20. D. P. Surzhikova, M. A. Gerasimova, E. A. Slyusareva. Russ. Phys. J., 64, N 11 (2022) 2102—2109
21. E. A. Slyusareva, M. A. Gerasimova. Russ. Phys. J., 56 (2014) 1370—1377
22. N. S. Castro, I. Moura, M. S. Carepo, C. A. Laia. J. Photochem. and Photobiol. A: Chem., 372 (2019) 59—62
23. F. Le Guern, V. Mussard, A. Gaucher, M. Rottman, D. Prim. Int. J. Mol. Sci., 21, N 23 (2020) 9217
24. P. A. Grimes, R. A. Stone, A. M. Laties, W. Li. Arch. Ophthalmology, 100, N 4 (1982) 635—639
25. M. H. Lee, J. H. Han, J. H. Lee, N. Park, R. Kumar, C. Kang, J. S. Kim. Angew. Chem. Int. Ed., 52, N 24 (2013) 6206—6209
26. Y. X. Wu, X. B. Zhang, J. B. Li, C. C. Zhang, H. Liang, G. J. Mao, L. Y. Zhou, W. Tan, R. Q. Yu. Analyt. Chem., 86, N 20 (2014) 10389—10396
27. V. V. Martin, I. S. Alferiev, A. L. Weis. Tetrahedron Lett., 40, N 2 (1999) 223—226
28. F. Fan, V. A. Povedailo, I. L. Lysenko, T. P. Seviarynchyk, O. L. Sharko, I. O. Mazunin, V. V. Shmanai. J. Fluores., 34, N 2 (2024) 925—933
29. R. G. Mayer, R. S. Drago. Inorg. Chem., 15, N 8 (1976) 2010—2011
30. T. Nowicka-Jankowska. J. Inorg. and Nuclear Chem., 33, N 7 (1971) 2043—2050
31. R. F. Chen, J. R. Knutson. Analyt. Biochem., 172, N 1 (1988) 61—77
32. S. Fery-Forgues, D. Lavabre. J. Chem. Ed., 76, N 9 (1999) 1260
33. T. Mineno, T. Ueno, Y. Urano, H. Kojima, T. Nagano. Org. Lett., 8, N 26 (2006) 5963—5966
34. N. Marmé, J. P. Knemeyer, M. Sauer, J. Wolfrum. Bioconjugate Chem., 14, N 6 (2003) 1133—1139
35. G. Vidarsson, G. Dekkers, T. Rispens. Front. Immun., 5 (2014) 520
36. A. Bujacz. Acta Crystallogr. D: Biol. Crystallography, 68, N 10 (2012) 1278—1289
Review
For citations:
Fan F., Povedailo V.A., Lysenko I.L., Sharko O.L., Mazunin I.O., Tikhomirov S.A., Shmanai V.V. Photophysical Features of Protolytic Equilibria of Fluorescein Bifluorophores. Zhurnal Prikladnoii Spektroskopii. 2024;91(5):723-732. (In Russ.)