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

Abstract

© 2020, Springer Science+Business Media LLC. 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