Funct. Mater. 2020; 27 4: 836-845.
Comparison of water-soluble squaraine and norsquaraine as fluorescent material for biomedical applications
1SSI Institute for Single Crystals, STC Institute for Single Crystals, National Academy of Sciences of Ukraine, 60 Nauky Ave., 61072 Kharkiv, Ukraine
2Department of Chemical Sciences, The Faculty of Natural Sciences, Ariel University, 40700 Ariel, Israel
Spectral and photophysical properties of norsquaraine dye Nor-Sq were investigated and compared with those for 3-carboxypentyl substituted squaraine Sq in aqueous buffer solutions, organic solvents and under interactions with proteins in order to obtain fluorescent labels for proteins with improved properties. Both dyes absorb and fluoresce in the same spectral region, but Sq has higher the molar absorptivity and is much more sensitive to polarity and viscosity of the medium, as well as to the presence of proteins. The absence of a substituent at the nitrogen atom in norsquaraine molecule provides the pH-sensitivity of Nor-Sq in the range of 9.0-11.4. As a result, Sq is more preferable for using in the most of biomedical applications, where interaction with proteins increases the brightness of the dye due to changes of polarity and/or viscosity of environment, while Nor-Sq is applicable for pH monitoring and in assays, where signal should not depend on changes in dye molecule environment.
1. R.G.Haugland, The Molecular Probes Handbook: A Guide to Fluorescent Probes and Labeling Technologies, Life Technologies Corporation (2010). | ||||
2. A.Brahme, Comprehensive Biomedical Physics, Elsevier Science (2014). | ||||
3. J.O.Escobedo, O.Rusin, S.Lim, R.M.Strongin, Curr. Opin. Chem. Biol., 14, 64 (2010). https://doi.org/10.1016/j.cbpa.2009.10.022 |
||||
4. L.Patsenker, A.Tatarets, O.Kolosova et al., Ann. NY Acad. Sci., 1130, 179 (2008). https://doi.org/10.1196/annals.1430.035 |
||||
5. Z.Zheng, Development of Far-Red/Near-Infrared Luminescent Chromophores and Nanoparticles for in vivo Biphotonic Applications, Universite de Lyon (2016). | ||||
6. M.Sameiro, T.Goncalves, Chem. Rev., 109, 190 (2009). https://doi.org/10.1021/cr0783840 |
||||
7. T.D.Martins, M.L.Pacheco, R.E.Boto et al., Dyes and Pigments, 147, 120 (2017). https://doi.org/10.1016/j.dyepig.2017.07.070 |
||||
8. G.Xia, H.Wang, J. Photochem. Photobiol. C: Photochem. Rev., 31, 84 (2017). | ||||
9. I.V.Hovor, O.S.Kolosova, E.V.Sanin et al., Dyes and Pigments, 170, 107567 (2019). https://doi.org/10.1016/j.dyepig.2019.107567 |
||||
10. O.S.Kolosova, S.V.Shishkina, V.Marks et al., Dyes and Pigments, 163, 318 (2019). https://doi.org/10.1016/j.dyepig.2018.12.007 |
||||
11. W.-Y.Leung, Ch.-Y.Cheung, S.Yue, U.S. Patent US9423323B2 (2016). | ||||
12. J.E.Berlier, A.Rothe, G.Buller et al., J. Histochem. Cytochem., 51, 1699 (2003). https://doi.org/10.1177/002215540305101214 |
||||
13. L.D.Patsenker, A.L.Tatarets, Ye.A.Povrozin et al., Bioanal. Rev., 3, 115 (2011). https://doi.org/10.1007/s12566-011-0025-2 |
||||
14. B.Oswald, L.Patsenker, J.Duschl et al., Bioconj. Chem., 10, 925 (1999). https://doi.org/10.1021/bc9801023 |
||||
15. C.A.Parker, Photoluminescence of Solutions, Elsevier Publishing Company, Amsterdam, London and New York, (1968). | ||||
16. R.B.Mujumdar, L.A.Ernst, S.R.Mujumdar et al., Bioconj. Chem., 4, 105 (1993). https://doi.org/10.1021/bc00020a001 |
||||
17. S.R.Mujumdar et al., Bioconj. Chem., 7, 356 (1996). https://doi.org/10.1021/bc960021b |
||||
18. J.T.Peters, in: All about Albumin: Biochemistry, Genetics, and Medical Applications, Academic Press, New York (1975). | ||||
19. A guide to Understanding Extinction Coefficients, with Emphasis on Spectrophotometric Determination of Protein Concentration, https://tools.thermofisher.com/content/sfs/brochures/TR0006-Extinction-c... (2013). | ||||
20. M.V.Reddington, Bioconj. Chem., 18, 2178 (2007). https://doi.org/10.1021/bc070090y |
||||
21. C.Reichardt, Solvents and Solvent Effects in Organic Chemistry, 3rd ed, Wiley-VCH, Weinheim (2003). https://doi.org/10.1002/3527601791 |
||||
22. R.Weissleder, Nature Biotechnology, 19, 316 (2001). https://doi.org/10.1038/86684 |
||||
23. H.Mustroph, K.Reiner, J.Mistol et al., Chem. Phys. Chem., 10, 835, (2009). https://doi.org/10.1002/cphc.200800755 |
||||
24. K.-Y.Law, J. Phys. Chem., 99, 981, (1995). | ||||
25. A.A Ishchenko, Structure and Spectral-luminescent Properties of Polymethine Dyes, Naukova Dumka, Kiev (1994). | ||||
26. A.Mishra, R.K.Behera, P.K.Behera et al., Chem. Rev., 100, 1973 (2000). https://doi.org/10.1021/cr990402t |
||||
27. J.Park, C.Barolo, F.Sauvage et al., Chem. Commun., 48, 2782 (2012). https://doi.org/10.1039/c2cc17187b |
||||
28. A.L.Tatarets, I.A.Fedyunyayeva, T.S.Dyubko et al., Anal. Chim. Acta, 570, 214 (2006). https://doi.org/10.1016/j.aca.2006.04.019 |
||||
29. N.Barbero et al., Chem. Asian. J., 14, 896 (2019). https://doi.org/10.1002/asia.201900055 |
||||
30. Y.Xu, Z.Li, A.Malkovskiy et al., J. Phys. Chem. B, 114, 8574 (2010). https://doi.org/10.1021/jp1029536 |
||||
31. K.D.Volkova, V.B.Kovalska, A.L.Tatarets et al., Dyes and Pigments, 72, 285 (2007). https://doi.org/10.1016/j.dyepig.2005.09.007 |
||||
32. Y.Chang-Ying, L.Yi, Zh.Dan et al., J. Photochem. and Photobiol. A: Chem., 188, 51 (2007). | ||||
33. A.Hawe, M.Sutter, W.Jiskoot, Pharmaceut. Res., 25, 1487 (2008). https://doi.org/10.1007/s11095-007-9516-9 |
||||
34. D.V.Nicolau Jr., E.Paszek, F.Fulga, D.V.Nicolau, PLOS ONE, 9, e114042 (2014). https://doi.org/10.1371/journal.pone.0114042 |
||||
35. L.I.Markova, E.A.Terpetschnig, L.D.Patsenker, Dyes and Pigments, 99, 561 (2013). https://doi.org/10.1016/j.dyepig.2013.06.022 |