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

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Abstract

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.

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Acknowledgements

The study was financially supported by the Russian Science Foundation Grant No. 22-73-00330, https://rscf.ru/project/22-73-00330/, and carried out in Southern Federal University. SCXRD studies were performed in accordance with the state task, state registration Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry RAS No.AAAA-A19-119092390076-7.

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  1. Institute of Physical and Organic Chemistry, Southern Federal University, 344090 Stachki prosp., 194/2, Rostov-On-Don, Russian Federation

    Artem D. Pugachev, Anastasia S. Kozlenko, Nadezhda I. Makarova, Irina A. Rostovtseva, Ilya V. Ozhogin, Vitaly S. Dmitriev, Gennady S. Borodkin, Anatoly V. Metelitsa & Boris S. Lukyanov

  2. Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry RAS, 142432 Ac. Semenov Avenue, 1, Moscow Region, Chernogolovka, Russian Federation

    Valery V. Tkachev & Andrey N. Utenyshev

  3. Academy of Biology and Biotechnologies, Southern Federal University, 344090 Stachki prosp., 194/1, Rostov-On-Don, Russian Federation

    Marina A. Sazykina, Ivan S. Sazykin, Tatiana N. Azhogina, Shorena K. Karchava & Maria V. Klimova

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Pugachev, A.D., Kozlenko, A.S., Makarova, N.I. et al. Molecular design and synthesis of methoxy-substitued spiropyrans with photomodulated NIR-fluorescence. Photochem Photobiol Sci 22, 2651–2673 (2023). https://doi.org/10.1007/s43630-023-00479-1

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