Crown-Containing Phthalocyanines are Potential Sensibilizers for Photodynamic Therapy. Synthesis, Properties and Role of Non-Covalent Interactions

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Published: Oct 1, 2018
DOI: https://doi.org/10.18097/BMCRM00042
Keywords:
phthalocyanines photodynamic therapy microheterogeneous environments spectroscopy

Main Article Content

V.E. Baulin
Institute of Physiologically Active Compounds of the Russian Academy of Sciences, 1 Severny proezd, Moscow region, Chernogolovka, 142432 Russia
N.F. Goldshleger
Institute of Problems of Chemical Physics of Russian Academy of Sciences, 1 Acad. Semenova av., Chernogolovka, Moscow region, 142432 Russia
D.V. Baulin
Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31 Leninsky av., Moscow, 119071 Russia
I.P. Kalashnikova
Institute of Physiologically Active Compounds of the Russian Academy of Sciences, 1 Severny proezd, Moscow region, Chernogolovka, 142432 Russia

Abstract

Phthalocyanines (Pc) and their supramolecular aggregates are widely used in molecular electronics, chemical sensors, and catalysis, as well as in biology and medicine, including photodynamic therapy (PDT). One of the possibilities of preventing Pc aggregation in an aqueous medium is using surfactants: with their molecules are self-organized various supramolecular complexes. This results in formation of the required microheterogeneous Pc environment compatible with the biological medium. The monomolecular state of Pc in an aqueous medium is especially important for their use as sensitizers in fluorescence diagnostics and PDT. We have summarized here the results of investigations of distinctive features of the supramolecular aggregation of octa-[(4′-benzo-15-crown-5)oxy]phthalocyaninates (Mcr8Pc) and tetra-[(4′-benzo-15-crown-5)oxy]phthalocyaninates (Mcr4Pc) in electrolytic solutions and solutions of synthetic cetyltrimethylammonium bromide (CTAB), sodium dodecyl sulfate (SDS), sodium dodecylbenzenesulfonate (SDBS). Biocompatible surfactants such as carboxymethylcellulose sodium salt (Na-CMC) and sodium deoxycholate (SDC) were also studied. Using the electron absorption spectra it has been shown that formation of Mсr8Pc monomers in micellar solutions of SDC is affected by both increased surfactant concentration and by changes in the ionic strength of solution after sodium chloride is added. The effect of the chemical structure of the biocompatible anionic surfactant on monomerization of crown_containing phthalocyanines has been identified; this fact opens new possibilities for using this family of compounds for fluorescent diagnosis and PDT.

Article Details

How to Cite
Baulin, V., Goldshleger, N., Baulin, D., & Kalashnikova, I. (2018). Crown-Containing Phthalocyanines are Potential Sensibilizers for Photodynamic Therapy. Synthesis, Properties and Role of Non-Covalent Interactions. Biomedical Chemistry: Research and Methods, 1(3), e00042. https://doi.org/10.18097/BMCRM00042
Issue
Vol. 1 No. 3 (2018)
Section
REVIEWS

References

  1. Rechtman, E., Ciulla, T. A., Criswell, M. H., Pollack A., Harris, A. (2002). An update on photodynamic therapy in age-related macular degeneration. Expert Opin. Pharmacother, 3(7), 931-938. DOI
  2. Lukyanets, E. A. (1999). Phthalocyanines as Photosensitizers in the Photodynamic Therapy of Cancer. J. Porphyrins Phthalocyanines, 3(6), 424-433. DOI
  3. Wang, S., Gao, R., Zhou, F., Selke, M. (2004). Nanomaterials and singlet oxygen photosensitizers: potential applications in photodynamic therapy. J. Mater. Chem., 14(4), 487-493. DOI
  4. Zhang, X.F., Xi, Q., Zhao, J. (2010). Fluorescent and triplet state photoactive J-type phthalocyanine nano assemblies: controlled formation and photosensitizing properties. J. Mater. Chem., 20(32), 6726-6733. DOI
  5. Lang, K., Kubat, P., Mosinger, J., Wagnerova, D.M. (1998). Photochemical consequences of porphyrin and phthalocyanine aggregation on nucleoprotein histone. J. Photochem. Photobiol. A: Chem. 119(1), 47-52. DOI
  6. Tsivadze, A. Yu (2004). Supramolecular metal complex systems based on crown-substituted tetrapyrroles. Russ Chem. Rev., 73 (1), 6-25 DOI
  7. Logacheva, N. M., Baulin, V. E., Tsivadze, A. Yu., Basova, T. V., Sheludyakova, L. A. (2008). Synthesis and spectroscopic study of the d-metal complexes with new octa(benzo-15-crown-5)substituted phthalocyanine. Izvestiya Akademii Nauk. Seriya Khimicheskaya, (7), 1439–1447.
  8. Hamuryudan, E. (2006). Synthesis and solution properties of phthalocyanines substituted with four crown ethers. Dyes and Pigments. 68 (2–3), 151-157. DOI
  9. Gordon, A.J., Ford, R.A. (1972). A Handbook of practical data, technique, references. N.Y., London, Sydney, Toronto: Wiley & Sons
  10. Gol’dshleger, N. F. , Kalashnikova, I. P. Baulin, V. E. , Tsivadze, A. Yu. (2011). Octa- and tetra-(benzo-15-crown-5)phthalocyanines in surfactant-containing solutions. Protection of Metals and Physical Chemistry of Surfaces. 47(4), 471–477. DOI
  11. Gol’dshleger N.F., Lobach, A.S., Gak, V.Yu., Kalashnikova, I.P. Baulin, V.E., Tsivadze, A.Yu. (2014) Magnesium Octa[(4'-Benzo-15-crown_5)oxy]phthalocyaninate in Water Micellar Solutions of Sodium Deoxycholate. Protection of Metals and Physical Chemistry of Surfaces. 50 (5), 496–505. DOI
  12. Ovsyannikova, E. V., Goldshleger N. F., Kurochkina N.M., Baulin, ., V. E. Tsivadze, A. Yu. and Alpatova N. M. (2010). Behavior of Octa(benzo-15-crown-5)substituted Metal Phthalocyanines in Polar Media and their Immobilization on Solid Supports. Macroheterocycles, 3 (2-3), 125-133. DOI
  13. Rosen, M. J.( 2004). Surfactants and Interfacial Phenomena. 3rd ed. Wiley_Int., 444. DOI:10.1002/0471670561.
  14. Goldshleger, N.F., Chernyak, A.V., Kalashnikova, I.P., Baulin, V.E., Tsivadze (2012 ) A.Yu Magnesium Octa(benzo-15-crown-5)phthalocyaninate in the sodium dodecyl sulfate solutions: A study using electron and 1H NMR spectroscopy. Russian Journal of General Chemistry. 82(5), 927-935. DOI
  15. Lastovoy A. P., Avramenko G.V. (2013). Spectral-Luminescent Properties of the Substituted Tetraazachlorins Solubilized in Solutions of Nonionic Surfactants. Macroheterocycles.6 (2), 137-143. DOI
  16. Slota, R., Dyrda, G. (2003). UV Photostability of Metal Phthalocyanines in Organic Solvents // Inorg. Chem., 42 (18), 5743-5750. DOI
  17. Lapkina, L.A., Gorbunova, Y.G., Gil, D.O., Ivanov, V.K., Konstantinov, N.Yu., Tsivadze A.Yu. (2013). Synthesis, spectral properties, cation-induced dimerization and photochemical stability of tetra-(15-crown-5)-phthalocyaninato indium(III). J. Porphyrins Phthalocyanines, 17 (6-7), 564-572. DOI
  18. Komissarov, A. N., Makarov, D. A., Yuzhakova, O. A., Savvina, L. P., Kuznetsova, N. A., Kaliya, O. L., Lukyanets, E. А., Negrimovsky V. M. (2012). Synthesis and Some Properties of Phosphonomethyl Substituted Phthalocyanines. Macroheterocycles, 5 (2) 169-174. DOI