Molecular design and synthesis of methoxy-substitued spiropyrans with photomodulated NIR-fluorescence.

Autor: Pugachev AD; Institute of Physical and Organic Chemistry, Southern Federal University, 344090 Stachki prosp., 194/2, Rostov-On-Don, Russian Federation. apugachev@sfedu.ru., Kozlenko AS; Institute of Physical and Organic Chemistry, Southern Federal University, 344090 Stachki prosp., 194/2, Rostov-On-Don, Russian Federation., Makarova NI; Institute of Physical and Organic Chemistry, Southern Federal University, 344090 Stachki prosp., 194/2, Rostov-On-Don, Russian Federation., Rostovtseva IA; Institute of Physical and Organic Chemistry, Southern Federal University, 344090 Stachki prosp., 194/2, Rostov-On-Don, Russian Federation., Ozhogin IV; Institute of Physical and Organic Chemistry, Southern Federal University, 344090 Stachki prosp., 194/2, Rostov-On-Don, Russian Federation., Dmitriev VS; Institute of Physical and Organic Chemistry, Southern Federal University, 344090 Stachki prosp., 194/2, Rostov-On-Don, Russian Federation., Borodkin GS; Institute of Physical and Organic Chemistry, Southern Federal University, 344090 Stachki prosp., 194/2, Rostov-On-Don, Russian Federation., Tkachev VV; Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry RAS, 142432 Ac. Semenov Avenue, 1, Moscow Region, Chernogolovka, Russian Federation., Utenyshev AN; Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry RAS, 142432 Ac. Semenov Avenue, 1, Moscow Region, Chernogolovka, Russian Federation., Sazykina MA; Academy of Biology and Biotechnologies, Southern Federal University, 344090 Stachki prosp., 194/1, Rostov-On-Don, Russian Federation., Sazykin IS; Academy of Biology and Biotechnologies, Southern Federal University, 344090 Stachki prosp., 194/1, Rostov-On-Don, Russian Federation., Azhogina TN; Academy of Biology and Biotechnologies, Southern Federal University, 344090 Stachki prosp., 194/1, Rostov-On-Don, Russian Federation., Karchava SK; Academy of Biology and Biotechnologies, Southern Federal University, 344090 Stachki prosp., 194/1, Rostov-On-Don, Russian Federation., Klimova MV; Academy of Biology and Biotechnologies, Southern Federal University, 344090 Stachki prosp., 194/1, Rostov-On-Don, Russian Federation., Metelitsa AV; Institute of Physical and Organic Chemistry, Southern Federal University, 344090 Stachki prosp., 194/2, Rostov-On-Don, Russian Federation., Lukyanov BS; Institute of Physical and Organic Chemistry, Southern Federal University, 344090 Stachki prosp., 194/2, Rostov-On-Don, Russian Federation.
Jazyk: angličtina
Zdroj: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology [Photochem Photobiol Sci] 2023 Nov; Vol. 22 (11), pp. 2651-2673. Date of Electronic Publication: 2023 Sep 21.
DOI: 10.1007/s43630-023-00479-1
Abstrakt: This study focuses on the molecular design and synthesis of salt spiropyrans with near-IR fluorescence. The structure of the obtained compounds was confirmed by NMR, IR and mass spectroscopy. In the course of studying the spectral and photoluminescent characteristics, it was possible to reveal the effect of some substituents in various positions on the properties of spiropyran dyes. Due to the structural similarity of one of the isomers to cyanine dyes, the obtained compounds are of interest as potential fluorescent probes for bioimagimg, in particular, for DNA studies. To reveal their ability of binding to DNA molecules molecular docking was carried out. Toxic effects of compounds demonstrating NIR fluorescence were studied on biofilms, as well as using bacterial lux-biosensors.
(© 2023. The Author(s), under exclusive licence to European Photochemistry Association, European Society for Photobiology.)
Databáze: MEDLINE
Externí odkaz: