Effect of meso-substituents and medium properties on the photo- and pH-stability, penetration efficiency into bacterial and microscopic fungi cells of terpene-BODIPY conjugates.

Autor: Guseva GB; G.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences, 153045 Ivanovo, Russia. Electronic address: gbg@isc-ras.ru., Eremeeva YV; G.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences, 153045 Ivanovo, Russia. Electronic address: yulya.khrushkova.99@mail.ru., Antina EV; G.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences, 153045 Ivanovo, Russia. Electronic address: eva@isc-ras.ru., Gilfanov IR; Institute of Fundamental Medicine and Biology, Kazan Federal University, 420008 Kazan, Russia. Electronic address: ilmir.gilfanov@gmail.com., Lisovskaya SA; Kazan State Medical University, Faculty of Medicine and Biology, 420012 Kazan, Russia; Institute of Fundamental Medicine and Biology, Kazan Federal University, 420008 Kazan, Russia; Scientific Research Institute of Epidemiology and Microbiology, 420015 Kazan, Russia. Electronic address: s_lisovskaya@mail.ru., Ostolopovskaya OV; Kazan State Medical University, Faculty of Medicine and Biology, 420012 Kazan, Russia; Institute of Fundamental Medicine and Biology, Kazan Federal University, 420008 Kazan, Russia. Electronic address: olga-ov.kirill@mail.ru., Trizna EY; Institute of Fundamental Medicine and Biology, Kazan Federal University, 420008 Kazan, Russia. Electronic address: trizna91@mail.ru., Kayumov AR; Institute of Fundamental Medicine and Biology, Kazan Federal University, 420008 Kazan, Russia. Electronic address: kairatr@yandex.ru., Nikitina LE; Kazan State Medical University, Faculty of Medicine and Biology, 420012 Kazan, Russia; Institute of Fundamental Medicine and Biology, Kazan Federal University, 420008 Kazan, Russia. Electronic address: nikitl@mail.ru.
Jazyk: angličtina
Zdroj: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy [Spectrochim Acta A Mol Biomol Spectrosc] 2024 Mar 05; Vol. 308, pp. 123701. Date of Electronic Publication: 2023 Dec 07.
DOI: 10.1016/j.saa.2023.123701
Abstrakt: In order to expand the arsenal of tools and areas for practical use of BODIPY dyes as bifunctional fluorescent theranostics, we studied the effect of the meso-substituents nature and medium properties on photo- and pH-stability, efficiency of singlet oxygen generation, and affinity to biostructures of terpene-BODIPY conjugates. The BODIPYs fused with myrtenol or thiotherpenoid via carboxylic acid residues exhibit high stability over a wide pH range and the presence of a bulky substituent at the meso-position of BODIPY conjugates increases their photostability two-fold compared to structurally related meso-unsubstituted analogues. Furthermore, the photodegradation rate of the conjugates directly depends on their ability to generate singlet oxygen and the course probability of the corresponding red-ox reactions involving reactive oxygen species. The conjugate of BODIPY with a thiotherpenoid demonstrated high ability to penetrate the membranes of filamentous and yeast-like fungi and bind to membrane of organelles in the fungal cell. At the same time, this compound also had a high ability to penetrate into biofilms of Staphylococcus aureus and Klebsiella pneumoniae and into bacterial cells within the matrix, which makes this compound promising for staining intracellular structures of eukaryotic cells and bacteria embedded into biofilms.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2023 Elsevier B.V. All rights reserved.)
Databáze: MEDLINE
Externí odkaz: