Antioxidant properties of thio-caffeine derivatives: Identification of the newly synthesized 8-[(pyrrolidin-1-ylcarbonothioyl)sulfanyl] caffeine as antioxidant and highly potent cytoprotective agent

被引：21

作者：

Jasiewicz, Beata ^{[1
]}

Sierakowska, Arleta ^{[1
]}

Wandyszewska, Natalia ^{[2
]}

Warzajtis, Beata ^{[1
]}

Rychlewska, Urszula ^{[1
]}

Wawrzyniak, Rafal ^{[1
]}

Mrowczynska, Lucyna ^{[2
]}

机构：

[1] Adam Mickiewicz Univ, Fac Chem, Umultowska 89B, PL-61614 Poznan, Poland

[2] Adam Mickiewicz Univ, Fac Biol, Dept Cell Biol, Umultowska 89, PL-61614 Poznan, Poland

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2016年 / 26卷 / 16期

关键词：

Caffeine thioderivatives; Antioxidant activity; Haemolysis; Human erythrocytes; Trolox; X-ray structure; ADENOSINE RECEPTOR ANTAGONISTS; MONOAMINE-OXIDASE; KAPPA-B; PYRROLIDINE DITHIOCARBAMATE; ILEX-PARAGUARIENSIS; PARKINSONS-DISEASE; HUMAN ERYTHROCYTES; RADIATION-DAMAGE; IN-VITRO; INHIBITORS;

D O I：

10.1016/j.bmcl.2016.06.091

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of nine thio-caffeine analogues were synthesized and characterised by NMR, FT-IR and MS spectroscopic methods. Molecular structures of four of them were determined using single crystal X-ray diffraction methods. The antioxidant properties of all compounds, at concentration ranges from 0.025 to 0.1 mg/mL, were evaluated by various chemical-and cell-based antioxidant assays. Human erythrocytes were used to examine in vitro haemolytic activity of all compounds and their protective effect against oxidative haemolysis induced by AAPH, one of the commonly used free radical generator. All compounds studied showed no effect on the human erythrocytes membrane structure and permeability with the exception of 8-(phenylsulfanyl)caffeine. Among the nine caffeine thio-analogues tested, the newly synthesized 8-[(pyrrolidin-1-ylcarbonothioyl)sulfanyl]caffeine possessed exceptionally high antioxidant properties. Moreover, it protects human erythrocytes against AAPH-induced oxidative damage as efficiently as the standard antioxidant Trolox. Therefore, 8-[(pyrrolidin-1-ylcarbonothioyl)sulfanyl] caffeine may have a significant cytoprotective potential caused by its antioxidant activity. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：3994 / 3998

页数：5

共 44 条

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