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Chitosan impregnation with biologically active tryaryl imidazoles in supercritical carbon dioxide

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Abstract

The presented paper is focused on impregnation of chitosan and its derivatives with a biologically active triaryl imidazole model compound ((2-2-hydroxyphenyl)-4.5-diphenyl-1H-imidazole) in the supercritical carbon dioxide medium. Since initial chitosan represents a polycation-exchange resin and does not swell in supercritical carbon dioxide, the impregnation was carried out in the presence of water (0.15–3.0 vol%). The maximum 2-2-hydroxyphenyl)-4.5-diphenyl-1H-imidazole concentration in a chitosan film was achieved at the ~5 × 10−3 g/cm3 water content in the reactor. We also used hydroxy carboxylic acid derivatives of chitosan and its copolymer with polylactide as matrices for introduction of hydrophobic 2-2-hydroxyphenyl)-4.5-diphenyl-1H-imidazole. We have shown that unmodified chitosan contains the greatest amount of 2-2-hydroxyphenyl)-4.5-diphenyl-1H-imidazole, as compared with its hydrophobic derivatives. The kinetics of 2-2-hydroxyphenyl)-4.5-diphenyl-1H-imidazole diffusion from a chitosan matrix was studied in acidified water with pH 1.6. We found that the complete release of 2-2-hydroxyphenyl)-4.5-diphenyl-1H-imidazole into the aqueous phase from unmodified chitosan films occurred in 48 h, while its complete release from chitosan modified with hydroxy carboxylic acids occurred in 5 min or less.

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Acknowledgments

This study was funded by the Russian Science Foundation, Grant No. 14-13-01422 (supercritical modification of chitosan) and the Russian Foundation for Basic Research, Grant No. 15-02-06826a (kinetics of supercritical impregnation).

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Authors and Affiliations

  1. N.N.Semenov Institute of Chemical Physics, Department of Polymers and Composites, 4 Kosygin St., Moscow, 119991, Russia

    Anastasia V. Cherkasova, Nikolay N. Glagolev, Andrey I. Shienok, Svetlana L. Kotova, Natalia L. Zaichenko & Anna B. Solovieva

  2. N.S. Enikolopov Institute of Synthetic Polymeric Materials, 70 Profsoyuznaya St., Moscow, 117393, Russia

    Tatiana S. Demina & Tatiana A. Akopova

  3. Institute of Photonic Technologies, Research Center of Crystallography and Photonics, 2 Pionerskaia St., Troitsk, Moscow, 142190, Russia

    Peter S. Timashev & Victor N. Bagratashvili

  4. Sechenov First Moscow State Medical University, Institute for Regenerative Medicine, 2-4 Bolshaya Pirogovskaya St., Moscow, 119991, Russia

    Peter S. Timashev

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  1. Anastasia V. Cherkasova
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  2. Nikolay N. Glagolev
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Correspondence to Svetlana L. Kotova.

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Cherkasova, A.V., Glagolev, N.N., Shienok, A.I. et al. Chitosan impregnation with biologically active tryaryl imidazoles in supercritical carbon dioxide. J Mater Sci: Mater Med 27, 141 (2016). https://doi.org/10.1007/s10856-016-5753-y

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