Novel squarylium dyes for detection of amyloid fibrils in vitro
Keywords:
amyloid fibrils of insulin/lysozyme, binding model, quantum yield, squarylium dyes
Abstract
A series of novel symmetrical and asymmetrical squarylium dyes with the different substituents in the donor moieties have been tested for their ability to detect and characterize insulin and lysozyme amyloid fibrils prepared in acidic buffer at elevated temperature. The dye-protein binding parameters were estimated in terms of the one-site Langmuir adsorption model using the data of direct and reverse fluorimetric titrations. By comparing the dye quantum yields, binding affinities, and extents of the fluorescence enhancement in the protein-bound state, G6 and G7 were selected as the most prospective amyloid tracers. Furthermore, these probes provided evidence for the lower polarity of the lysozyme fibrillar grooves compared to insulin aggregates. The novel dyes G6 and G7 were recommended for amyloid fibril detection and characterization in the near-infrared region.
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References
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4. Lindgren M. Detection and characterization of aggregates, prefibrillar amyloidogenic oligomers, and protofibrils using fluorescence spectroscopy / M. Lindgren, K. Sörgjerd, P. Hammarström. // Biophys. J. – 2005. – V. 88. – P. 4200–4212.
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11. Merritt V. Y. Organic solar cells of hydroxy squarylium / V. Y. Merritt, H. J. Hovel // Appl. Phys. Lett. – 1976. – V. 29. – P. 414.
12. Halogenated squaraine dyes as potential photochemotherapeutic agents. Synthesis and study of photophysical properties and quantum efficiencies of singlet oxygen generation / D. Ramaiah, A. Joy, N. Chandrasekhar [et.al.] // Photochem. Photobiol. – 1997. – V. 65. – P. 783–790.
13. Bis(3,5-diiodo-2,4,6-trihydroxyphenyl)squaraine: a novel candidate in photodynamic therapy for skin cancer models in vivo / D. Gayathri Devi, T. R. Cibin, D. Ramaiah [et al.] // J. Photochem. Photobiol. B. – 2008. – V. 92. – P. 153–159.
14. Singlet oxygen generation ability of squarylium cyanine dyes / P. F. Santos, L. V. Reis, P. Almeida [et.al.] // J. Photochem. Photobiol. A: Chemistry. – 2003. – V. 160. – P. 159–161.
15. Fluorescence study of protein-lipid complexes with a new symmetric squarylium probe / V. M. Ioffe, G. P. Gorbenko, T. Deligeorgiev [et al.] // Biophys. Chem. – 2007. – V. 128. – P. 75–86.
16. Bonnett R. Chemical aspects of photodynamic therapy / R. Bonnett. – Amsterdam: Gordon and Breach, 2000. – 305 p.
17. Mustroph H. Current developments in optical data storage with organic dyes / H. Mustroph, M. Stollenwerk, V. Bressau // Angew. Chem. Int. Ed. Engl. – 2006. – V. 45. – P. 2016–2035.
18. Examining protein-lipid interactions in model systems with a new squarylium fluorescent dye / V. M. Ioffe, G. P. Gorbenko, A. L. Tatarets [et al.] // J. Fluoresc. – 2006. – V. 16. – P. 547–554.
19. Aza-substituted squaraines for the fluorescent detection of albumins / K. D. Volkova, V. B. Kovalska, M. Y. Losytskyy [et.al.] // Dyes and Pigments. – 2011. – V. 90 – P. 41–47.
20. Fluorescent detection of a partially unfolded conformation of beta-lactoglobulin using squaraine dyes / V. B. Kovalska, M. Y. Losytskyy, L. V. Reis [et al.] // Macromolecular Symposia. – 2014. – V. 335. – P. 43–50.
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22. Synthesis of water-soluble, ring-substituted squaraine dyes and their evaluation as fluorescent probes and labels / A. L. Tatarets, I. A. Fedyunyayeva, T. S. Dyubko [et al.] // Anal. Chim. Acta. – 2006. – V. 570. – P. 214–223.
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24. Fluorescence investigation of interactions between novel benzanthrone dyes and lysozyme amyloid fibrils / K. Vus, V. Trusova, G. Gorbenko [et al.] // J. Fluorescence. – 2014. – V. 24. – P. 493–504.
25. The synthesis and characterization of novel, aza-substituted squarylium cyanine dyes / L. V. Reis, J. P. Serrano, Paulo Almeid [et al.] // Dyes and Pigments – 2009. – V. 81. – P. 197–202.
26. Law K. Y. Squaraine chemistry. Effects of structural changes on the absorption and multiple fluorescence emission of bis[4-(dimethylamino)phenyl]squaraine and its derivatives / K. Y. Law // J. Phys. Chem. – 1987. – V. 91. – P. 5184–5193.
27. Fluorescence study of protein–lipid complexes with a new symmetric squarylium probe / V. M. Ioffe, G. P. Gorbenko, T. Deligeorgiev [et al.] // Biophys. Chem. – 2007. – V. 128. – P. 75–86.
28. Studies of benzothiazole and benzoselenazole squaraines as fluorescent probes for albumins detection / K. D. Volkova, V. B. Kovalska, M. Y. Losytskyy [et al.] // J. Fluoresc. – 2008. – V. 18. – P. 877–882.
29. Awasthi K., Nishimura G. Modification of near-infrared cyanine dyes by serum albumin protein / K. Awasthi, G. Nishimura // Photochem. Photobiol. Sci. – 2011. – V. 10. – P. 461–463.
30. Squaraines as reporter units: insights into their photophysics, protonation, and metal-ion coordination behavior / J. V. Ros-Lis, R. Martínez-Máñez, F. Sancenón [et al.] // Chemistry. – 2008. – V. 14. – P. 10101–10114.
31. Tatikolov A. S., Costa S. M. Complexation of polymethine dyes with human serum albumin: a spectroscopic study / A. S. Tatikolov, S. M. Costa // Biophys. Chem. – 2004. – V. 107. – P. 33–49.
Cited
How to Cite
Vus, K. O., Trusova, V. M., Gorbenko, G. P., Sood, R., & Kinnunen, P. (1). Novel squarylium dyes for detection of amyloid fibrils in vitro. Biophysical Bulletin, 2(32), 61-68. Retrieved from https://periodicals.karazin.ua/biophysvisnyk/article/view/1592
Section
Methods of biophysical investigations
Copyright (c) 2014 K.O. Vus, V.M. Trusova, G.P. Gorbenko, R. Sood, P. Kinnunen
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