Regularities of complexation of indotricarbocyanine dyes with human blood serum proteins
Abstract
The interaction of indotricarbocyanine dyes with human blood serum proteins was studied. The spectral and fluorescent properties of dyes in butanol, Dulbecco’s sodium and potassium phosphate buffer (0.14 mol/L) with pH 7.4, and human blood serum solutions were determined. It was shown that the spectral properties of dyes in butanol differ significantly from the spectral properties in solutions of Dulbecco’s sodium and potassium phosphate buffer and human blood serum, and that butanol effectively extracts the molecules of the studied dyes that do not form covalently bound complexes with blood serum components. By analysing the extraction products, the proportion of covalent complexes of dyes with protein molecules was determined. It has been established that indotricarbocyanine dyes with a chlorine-substituted orthophenylene bridge in the conjugation chain are partially passes into butanol, the degree of extraction depends on the ratio of dye and protein concentrations. Thus, at a concentration of 10 mmol/L in 5 % human serum, the degree of extraction of these dyes is ~50 – 60 % respectively, the proportion of dye molecules in strong covalently bound complexes with blood serum components is ~ 40 –50 %. On the contrary, the dye with a free polymethine chain is extracted almost completely (91.4 % extraction rate). The indotricarbocyanine dyes are promising for use as a photosensitisers for photodynamic therapy.
References
- Gunaydin G, Gedik ME, Ayan S. Photodynamic therapy for the treatment and diagnosis of cancer – a review of the current clinical status. Frontiers in Chemistry. 2021;9:686303. DOI: 10.3389/fchem.2021.686303.
- Agostinis P, Berg K, Cengel KA, Foster TH, Girotti AW, Gollnick SO, et al. Photodynamic therapy of cancer: an update. CA: a Cancer Journal for Clinicians. 2011;61(4):250–281. DOI: 10.3322/caac.20114.
- Chilakamarthi U, Giribabu L. Photodynamic therapy: past, present and future. The Chemical Record. 2017;17(8):775–802. DOI: 10.1002/tcr.201600121.
- Kudinova NV, Berezov TT. Photodynamic therapy of cancer: search for ideal photosensitiser. Biochemistry (Moscow) Supplement Series B: Biomedical Chemistry. 2010;4(1):95–103. DOI: 10.1134/S1990750810010129.
- Dereje DM, Pontremoli C, Moran Plata MJ, Visentin S, Barbero N. Polymethine dyes for PDT: recent advances and perspectives to drive future applications. Photochemical & Photobiological Sciences. 2022;21(3):397–419. DOI: 10.1007/s43630-022-00175-6.
- Lugovski AА, Samtsov MP, Kaplevsky KN, Tarasau DS, Voropay ES, Petrov PT, et al. Novel indotricarbocyanine dyes covalently bonded to polyethylene glycol for theranostics. Journal of Photochemistry and Photobiology A: Chemistry. 2016;316(3):31–36. DOI: 10.1016/j.jphotochem.2015.10.008.
- Zhu C, Xia Y. Biomimetics: reconstitution of low-density lipoprotein for targeted drug delivery and related theranostic applications. Chemical Society Reviews. 2017;46(24):7668–7682. DOI: 10.1039/C7CS00492C.
- Bhushan B, Khanadeev V, Khlebtsov B, Khlebtsov N, Gopinath P. Impact of albumin based approaches in nanomedicine: imaging, targeting and drug delivery. Advances in Colloid and Interface Science. 2017;246:13–39. DOI: 10.1016/j.cis.2017.06.012.
- Belko NV, Khludeev II, Zorin VP, Samtsov MP. Influence of complex formation with blood plasma proteins on the spectral characteristics of tricarbocyanine dyes. Vesci BDPU. Seryja 3. Fizika. Matjematyka. Infarmatyka. Bijalogija. Geagrafija. 2018;1:14–20. Russian.
- Samtsov MP, Tarasov DS, Maliushkova EV, Khludeyev II, Lugovski AP, Semak IV. Analysis of the properties of polymethine dyes complexes with blood serum proteins by gel electrophoresis. Russian Journal of Biological Physics and Chemistry. 2021;6(3): 499–504. Russian.
- Gordon AJ, Ford RA. The chemist’s companion: a handbook of practical data, techniques and references. New York: Wiley; 1973. 560 p.
- Poole CF, editor. Liquid-phase extraction. 1st edition. Amsterdam: Elsevier; 2019. 816 p. (Handbooks in separation science).
- Simpson NJK, editor. Solid-phase extraction: principles, techniques and applications. 1st edition. Boca Raton: CRC Press; 2000. 528 p. DOI: 10.1201/9780367802653.
- Belko NV, Samtsov MP, Lugovski AP. Controlling H* - and J-aggregation of an indotricarbocyanine dye in aqueous solutions of inorganic salts. Journal of the Belarusian State University. Physics. 2020;2:19–27. Russian. DOI: 10.33581/2520-2243-2020-2-19-27.
- Tarasov DS, Kaplevsky KN, Samtsov MP, Voropay ES. Analysis of spectral properties of multicomponent solutions of new indotricarbocyanine dye. Vestnik BGU. Seriya 1. Fizika. Matematika. Informatika. 2015;2:8–12. Russian.
- Samtsov MP, Tikhomirov SA, Lyashenka LS, Tarasau DS, Buganov OV, Galievsky VA, et al. Photophysical and photochemical properties of HITC indotricarbocyanine dye molecules in solutions. Journal of Applied Spectroscopy. 2013;80(2):170–175. DOI: 10.1007/s10812-013-9741-4.
- Chibisov AK, Zakharova GV, Görner H. Photoprocesses in dimers of thiacarbocyanines. Physical Chemistry Chemical Physics. 1999;1:1455–1460. DOI: 10.1039/A809354G.
- Samtsov MP, Tarasau DS, Stasheuski AS, Kaplevsky KN, Voropay ES. Concentration increase of the singlet-oxygen generation quantum yield by an indotricarbocyanine dye. Journal of Applied Spectroscopy. 2014;81(2):214–221. DOI: 10.1007/s10812-014-9912-y.
- Tatikolov AS, Costa SMB. Complexation of polymethine dyes with human serum albumin: a spectroscopic study. Biophysical Chemistry. 2004;107(1):33–49. DOI: 10.1016/S0301-4622(03)00218-7.
- Soper SA, Mattingly QL. Steady-state and picosecond laser fluorescence studies of nonradiative pathways in tricarbocyanine dyes: implications to the design of near-IR fluorochromes with high fluorescence efficiencies. Journal of the American Chemical Society. 1994;116(9):3744–3752. DOI: 10.1021/ja00088a010.
- Berezin MY, Lee H, Akers W, Achilefu S. Near infrared dyes as lifetime solvatochromic probes for micropolarity measurements of biological systems. Biophysical Journal. 2007;93(8):2892–2899. DOI: 10.1529/biophysj.107.111609.
- Parray ZA, Hassan MI, Ahmad F, Islam A. Amphiphilic nature of polyethylene glycols and their role in medical research. Polymer Testing. 2020;82:106316. DOI: 10.1016/j.polymertesting.2019.106316.
- Farruggia B, Nerli B, Di Nuci H, Rigatusso R, Picó G. Thermal features of the bovine serum albumin unfolding by polyethylene glycols. International Journal of Biological Macromolecules. 1999;26(1):23–33. DOI: 10.1016/S0141-8130(99)00061-6.
- Arakawa T, Timasheff SN. Mechanism of poly(ethylene glycol) interaction with proteins. Biochemistry. 1985;24(24):6756–6762. DOI: 10.1021/bi00345a005.
- Bhat R, Timasheff SN. Steric exclusion is the principal source of the preferential hydration of proteins in the presence of polyethylene glycols. Protein Science. 1992;1(9):1133–1143. DOI: 10.1002/pro.5560010907.
- Atha DH, Ingham KC. Mechanism of precipitation of proteins by polyethylene glycols. Analysis in terms of excluded volume. Journal of Biological Chemistry. 1981;256(23):12108–12117. DOI: 10.1016/S0021-9258(18)43240-1.
- Farruggia B, Nerli B, Picó G. Study of the serum albumin-polyethyleneglycol interaction to predict the protein partitioning in aqueous two-phase systems. Journal of Chromatography B. Analytical Technologies in the Biomedical and Life Sciences. 2003;798(1):25–33. DOI: 10.1016/j.jchromb.2003.08.044.
Copyright (c) 2022 Journal of the Belarusian State University. Physics

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
The authors who are published in this journal agree to the following:
- The authors retain copyright on the work and provide the journal with the right of first publication of the work on condition of license Creative Commons Attribution-NonCommercial. 4.0 International (CC BY-NC 4.0).
- The authors retain the right to enter into certain contractual agreements relating to the non-exclusive distribution of the published version of the work (e.g. post it on the institutional repository, publication in the book), with the reference to its original publication in this journal.
- The authors have the right to post their work on the Internet (e.g. on the institutional store or personal website) prior to and during the review process, conducted by the journal, as this may lead to a productive discussion and a large number of references to this work. (See The Effect of Open Access.)