Effect of the spacer length and nitroxide sterical shielding upon photostability of spin-labeled kynurenines

Effect of the spacer length and nitroxide sterical shielding upon photostability of spin-labeled kynurenines Full article

Journal

Journal of Photochemistry and Photobiology A: Chemistry
ISSN: 1010-6030

Output data

Year: 2016, Volume: 322, Pages: 76-84 Pages count : 9 DOI: 10.1016/j.jphotochem.2016.03.007

Tags

Nitroxide; Kynurenine; Photolysis; Photostability; Spin exchange

Authors

Polienko Yuliya F. ^1,3 , Snytnikova Olga A. ^2,3 , Yanshole Vadim V. ^2,3 , Chernyak Elena I. ¹ , Morozov Sergey V. ^1,3 , Grigor'ev Igor A. ^1,4 , Tsentalovich Yuri P. ^2,3

Affiliations

1	(Данные Web of science) Novosibirsk Inst Organ Chem SB RAS, Acad Lavrentjev Ave 9, Novosibirsk, Russia
2	(Данные Web of science) Int Tomog Ctr SB RAS, Inst Skaya 3A, Novosibirsk, Russia
3	(Данные Web of science) Novosibirsk State Univ, Pirogova St 2, Novosibirsk 630090, Russia
4	(Данные Web of science) Academician EN Meshalkin State Res Inst Circulat, Rechkunovskaya 15, Novosibirsk, Russia

The synthesis of the natural molecular UV filters - kynurenines (KN) - covalently bound to nitroxides has recently been proposed as an alternative for traditional combination of antioxidants and UV-filters in sunscreen formulations. Due to the spin-exchange interaction between KN and nitroxide moieties, the triplet lifetimes in such conjugates are much shorter than in KN molecule, but the triplet quantum yields are significantly higher. The reaction of intramolecular electron transfer between photoexcited KN and nitroxide moieties is the main factor determining the quantum yield of KN-RNO center dot conjugates photodecomposition. Searching for a method to suppress this side process we synthesized analogues of previously prepared conjugates with the enlarged spacer between the nitroxide and kynurenine parts and with the sterically hindered access to the nitroxide group. The new spin-labeled kynurenines showed at least three-fold higher photostability compared to the previously synthesized compounds of this type. (C) 2016 Elsevier B.V. All rights reserved.

Polienko Y.F. , Snytnikova O.A. , Yanshole V.V. , Chernyak E.I. , Morozov S.V. , Grigor'ev I.A. , Tsentalovich Y.P.
Effect of the spacer length and nitroxide sterical shielding upon photostability of spin-labeled kynurenines
Journal of Photochemistry and Photobiology A: Chemistry. 2016. V.322. P.76-84. DOI: 10.1016/j.jphotochem.2016.03.007 WOS Scopus РИНЦ

Published print:

May 1, 2016

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