Low‐symmetry <scp>A<sub>3</sub>B</scp>‐type <scp>6</scp><i>H</i>‐1,4‐diazepinoporphyrazines with anti‐Kasha effect as promising photosensitizers

Tarakanov, P.A.; Neganova, M.E.; Mishchenko, D.V.; Bondarenko, S.D.; Sergeeva, I.A.; Krot, A.R.; Goryachev, N.S.; Simakov, A.O.; Kukharsky, M.S.; Pukhov, S.A.; Pushkarev, V.E.

Авторы: Tarakanov Pavel A., Neganova Margarita E., Mishchenko Denis V., Bondarenko Sergey D., Sergeeva Irina A., Krot Aleksey R., Goryachev Nikolay S., Simakov Anton O., Kukharsky Michail S., Pukhov Sergey A., Pushkarev Victor E.
Журнал: Photochemistry and Photobiology
Номер: 1
Год издания: 2024
Издательство: American Society for Photobiology
Местоположение издательства: United States
Первая страница: 1
Последняя страница: 13
DOI: 10.1111/php.13898
Аннотация: A series of tribenzo[g,l,q]- 6H- 1,4- diazepino[2,3- b]porphyrazines has been synthesized. A temperature- dependent steric effect was applied in the mixed Linstead macrocyclization of phthalonitrile and 5,7- bis(2′- arylethenyl)- 6- propyl- 6H- 1,4- diazepine- 2,3- dicarbonitrile to achieve high yield of low- symmetry A3B- type Mg(II) tribenzo[g,l,q]- 6H- 1,4- diazepino[2,3- b]porphyrazinate. The analysis of photophysical and photochemical properties of the obtained complexes showed the anti- Kasha effect: the ultrafast spin changes success-fully compete with the IC. TD- DFT calculations showed that the presence of 1,4- diazepine heterocycle in the porphyrazine structure leads to the formation of additional charge- transfer triplet state T2. We propose, it could participate in the pumping of T1x state alongside with T1y state (these states are degener-ate in D4h symmetry) and, therefore, increase singlet oxygen (1Δg) generation. Stable micellar nanoparticles have been obtained based on the tribenzo[g,l,q]- 6H- 1,4- diazepino[2,3- b]porphyrazine Mg(II) and Zn(II) complexes using poly-vinylpyrrolidone. The nanoparticles effectively interact with model biological structures (FBS and brain homogenate), leading to disaggregation of the mac-rocycles. They also exhibit pronounced phototoxic effects in MCF- 7 cells upon red light irradiation. We propose that enhancement in PDT activity could be explained by their increased resistance to aggregation due to the presence of n- propyl substituent directly attached to the C6 position of the 1,4- diazepine
Добавил в систему: Сергеева Ирина Александровна

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Low‐symmetry <scp>A<sub>3</sub>B</scp>‐type <scp>6</scp><i>H</i>‐1,4‐diazepinoporphyrazines with anti‐Kasha effect as promising photosensitizersстатья

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