UV filter decomposition. A study of reactions of 4-(2-aminophenyl)-4-oxocrotonic acid with amino acids and antioxidants present in the human lens

UV filter decomposition. A study of reactions of 4-(2-aminophenyl)-4-oxocrotonic acid with amino acids and antioxidants present in the human lens Научная публикация

Журнал

Experimental Eye Research
ISSN: 0014-4835 , E-ISSN: 1096-0007

Вых. Данные

Год: 2007, Том: 85, Номер: 2, Страницы: 242-249 Страниц : 8 DOI: 10.1016/j.exer.2007.04.008

Ключевые слова

kynurenine; UV filter compounds; cataract; deamination; lens protein modification

Авторы

Kopylova Lyudmila V. ¹ , Snytnikova Olga A. ^1,2 , Chernyak Elena I. ³ , Morozov Sergey V. ³ , Tsentalovich Yuri P. ¹

Организации

1	(Данные Web of science) Int Tomog Ctr, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

Deamination of UV filters, such as kynurenine (KN), in the human lens results in protein modification. Thermal reactions of the product of kynurenine deamination, 4-(2-aminophenyl)-4-oxocrotonic acid (CKA), with amino acids (histidine, lysine, methionine, tryptophan, tyrosine, cysteine) and antioxidants (ascorbate, NADH, glutathione reduced) were studied. The rate constants of the reactions under physiological conditions were measured. The rate constants of CKA addition to cysteine k(Cys) = 36 +/- 4 M-1 s(-1) and to glutathione k(GSH) = 2.1 +/- 0.2 M-1 s(-1) are 4-5 orders of magnitude higher than the rate constants of CKA reactions with the other amino acids and antioxidants. The Arrhenius parameters for k(Cys) and k(GSH) were determined: A(GSH) = (1.8 +/- 0.7) x 10(5) M-1 s(-1), E-GSH = 29.2 +/- 5.6 kJ mol(-1) A(Cys) = (2.7 +/- 0.9) x 10(8) M-1 s(-1), E-Cys = 40.4 +/- 5.7 kJ mol(-1). The large difference in frequency factors for k(Cys) and k(GSH) is attributed to steric hindrance, peculiar to the bulky GSH molecule. (c) 2007 Elsevier Ltd. All rights reserved.

Kopylova L.V. , Snytnikova O.A. , Chernyak E.I. , Morozov S.V. , Tsentalovich Y.P.
UV filter decomposition. A study of reactions of 4-(2-aminophenyl)-4-oxocrotonic acid with amino acids and antioxidants present in the human lens
Experimental Eye Research. 2007. V.85. N2. P.242-249. DOI: 10.1016/j.exer.2007.04.008 WOS Scopus РИНЦ

Опубликована в печати:

1 авг. 2007 г.

Web of science	WOS:000248807400009
Scopus	2-s2.0-34447646160
РИНЦ	13535306
OpenAlex	W2037607507