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Synthesis and supramolecular self-assembly of phenothiazine functionalized by carboxyphenyl fragments

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Abstract

Dispersions of non-toxic compounds characterized by an intense absorbance in the near-IR range find use in photodynamic therapy as effcient antibacterial and anticancer agents. An approach to the preparation of aqueous dispersions of nanoparticles with controlled morphology is described. 3,7-Bis(arylamino)phenothiazin-5-ium derivatives containing the ester and carboxylic groups were synthesized for the first time by the oxidative addition of methyl anthranilate to phenothiazin-5-ium tetraiodide with subsequent hydrolysis of the ester groups. The association with 3-phenylimino-7-phenylaminophenothiazine was studied for the synthesized bis(carboxyl)phenothiazinium derivative. The obtained 1: 1 associate is characterized by the bathochromic shift. The nanoprecipitation of the obtained nanoassociate in a methanol-water system was studied, and the morphology of the prepared dispersions was characterized: 3-phenylimino-7-phenylaminophenothiazine forms nanofiber structures, bis(carboxyl) derivative forms spherical particles, and the two-component associate forms facet-shaped particles

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Authors and Affiliations

  1. Alexander Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    A. I. Khadieva, V. V. Gorbachuk & I. I. Stoikov

Authors
  1. A. I. Khadieva
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  2. V. V. Gorbachuk
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  3. I. I. Stoikov
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Correspondence to I. I. Stoikov.

Additional information

Based on the materials of the Markovnikov Congress on Organic Chemistry (June 21–28, 2019, Moscow—Kazan, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0333—0338, February, 2020.

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Khadieva, A.I., Gorbachuk, V.V. & Stoikov, I.I. Synthesis and supramolecular self-assembly of phenothiazine functionalized by carboxyphenyl fragments. Russ Chem Bull 69, 333–338 (2020). https://doi.org/10.1007/s11172-020-2765-z

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  • DOI: https://doi.org/10.1007/s11172-020-2765-z

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