Abstract
Electronic absorption spectroscopy and fluorescence spectroscopy were used to study conditions for the formation of associates of amphiphilic phorbins and chlorins in an ethanol–water system. The conditions and degree of disaggregation in the presence of solubilizing additives of nonionic surfactants (Tween 80) and biocompatible polymers (polyethylene glycol and polyvinylpyrrolidone) were also investigated. The propensity of the macroheterocycles based on chlorophyll a to association in water-alcoholic solutions decreases on going from covalently bound dimeric structures to monomeric ones, on going from phorbins to chlorins and on accumulating hydrophilic glycol or positively charged alkylammonium fragments in the molecule. Among the considered solubilizers, the nonionic surfactant Tween 80 emerged as the most efficient means for destroying chlorin associates in water–alcohol solutions with a high content of water.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
R. Bonnett, Chemical Aspects of Photodynamic Therapy, VHC Publ., London, 2000, 285 pp.
A. S. Brandis, Y. Salomon, A. Schetz, in Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions, and Application, Eds B. Grimm, R. J. Porra, W. Rüdiger, H. Scheer, Springer, Berlin, 2006, p.461.
M. A. Grin, A. F. Mironov, Russ. Chem. Bull., 2016, 65,333.
A. V. Kustov, D. V. Belykh, N. L. Smirnova, E. A. Venediktov, T. V. Kudayarova, S. O. Kruchin, D. B. Berezin, Dyes Pigm., 2018, 149,553.
A. A. Krasnovskii, in Uspekhi khimii porfirinov [Success in the Chemistry of Porphyrins], Ed. O. A. Golubchkov, SPbGU, St. Petersburg, 2004, Vol. 4, p. 191 (in Russian).
L. A. Martinez, C. G. Marti´nez, B. B. Klopotek, J. Lang, A. Neuner, A. M. Braun, E. Oliveros, Photochem. Photobiol. B: Biol., 2000, 58,94.
O. V. Shukhto, T. N. Solodukhin, O. M. Startseva, I. S. Khudyaeva, D. V. Belykh, A. V. Kustov, Yu. V. Romanenko, D. B. Berezin, Vestn. Tadzhikskogo Natsional´nogo Un-ta. Ser. Estestv. Nauk [Bulletin of Tadjik National University], 2016, 216, 127 (in Russian).
M. Hädener, I. Gjuroski, J. Furrer, M. Vermathen, J. Phys. Chem. B, 2015, 119, 12117.
M. Vermathen, M. Marzorati, P. Bigler, J. Phys. Chem. B, 2013, 117, 6990.
A. P. Gerola, T. N. Tsubone, A. Santana, H. P. M. de Oliveira, N. Hioka, W. Caetano, J. Phys. Chem. B, 2011, 115, 7364.
T. M. Zhientaev, N. S. Melik-Nubarov, E. A. Litmanovich, N. A. Aksenova, N. N. Glagolev, A. B. Solovieva, Polym. Sci. Ser. B, 2009, 51, 5,502.
A. P. Lastovoi, G. V. Avramenko, Makrogeterotsikly [Macrohetero cycles], 2013, 6, 137 (in Russian).
A. Vashurin, A. Filippova, S. Znoyko, A. Voronina, O. Lefedova, I. Kuzmin, V. Maizlish, O. Koifman, J. Porph. Phthaloc., 2015, 19,983.
D. W. Dixon, V. Steullet, J. Inorg. Biochem., 1998, 69,25.
M. A. Gradova, V. N. Kuryakov, A. V. Lobanov, Macro heterocycles, 2013, 8,244.
D. V. Belykh, Doct. Sci. (Chem.) Thesis, Ivanovo State University of Chemical Technology, Ivanovo, 2012, 320 pp. (in Russian).
D. V. Belykh, O. M. Startseva, S. A. Patov, Macroheterocycles, 2014, 7,401.
O. I. Gushchina, E. A. Larkina, A. F. Mironov, Macroheterocycles, 2014, 7,414.
A. V. Kustov, D. V. Belykh, N. L. Smirnova, I. S. Khudyaeva, D. B. Berezin, J. Chem. Thermodyn., 2017, 115,302.
I. S. Tarabukina, O. M. Startseva, S. A. Patov, D. V. Belykh, Macroheterocycles, 2015, 8,168.
K. Burger, Solvation, Ionic and Complex Formation Reactions in Non-Aqueous Solvents, Vol. 6, 1st ed., Elsevier, Amsterdam, 1983, 268 pp.
R. Giovannetti, in Nanotechnology and Nanomaterials. Micro to Nano Spectroscopy, Ed. J. Uddin, In Tech, Shanghai, 2012, p.87.
M. Kano, K. Fukuda, H. Wakami, R. Nishiyabu, R. F. Pasternack, J. Am. Chem. Soc., 2000, 122, 7494.
O. Ohmo, Y. Kaizu, H. Kobayashi, J. Chem. Phys., 1993, 99, 4128.
D. A. Smith, H. van de Waterbeemd, D. K. Walker, R. Mannhold, H. Kubinyi, H. Timmerman, Methods and Principles in Medicinal Chemistry, Eds R. Mannhold, H. Kubinyi, H. Timmerman, Wiley–VCH Verlag, Weinheim, 2001, p.1.
D. B. Berezin, A. V. Kustov, D. V. Belykh, E. A. Venediktov, O. V. Shukhto, E. V. Garas´ko, Tez. Dokl. III Mezhdunar. Simp. po meditsinskoi, organicheskoi, biologicheskoi khimii i farmatsevtike (MOBI-KhimFarma 2017) [Proc. III Intern. Symp. on Medicinal, Organic, and Biological Chemistry and Pharmaceutics (MOBI-ChemPharma] (May 28–31, 2017, Sevastopol, Russia), MGU, Moscow, 2017, p. 6 (in Russian).
B. K. Paul, S. P. Moulik, Curr. Sci., 2001, 80,990.
Kh. Surabhi, O. R. Katare, N. Atul, G. Arun, Res. J. Pharm. Biol. Chem. Sci., 2010, 1,683.
N. D. Zadymova, N. I. Ivanova, Vestn. MGU. Ser. 2. Khimiya [Moscow State University Bulletin. Ser. 2, Chem.], 2013, 54, 112 (in Russian).
Author information
Authors and Affiliations
Corresponding author
Additional information
Based on the materials of the V International Conference "Supramolecular systems at the interface" (September 11–15, 2017; Tuapse, Russia).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1273–1279, July, 2018.
Rights and permissions
About this article
Cite this article
Berezin, D.B., Solodukhin, T.N., Shukhto, O.V. et al. Association of hydrophilic derivatives of chlorophyll a in ethanol–water and ethanol–water–solubilizer systems. Russ Chem Bull 67, 1273–1279 (2018). https://doi.org/10.1007/s11172-018-2212-6
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-018-2212-6