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首页> 外文期刊>The Journal of toxicological sciences >Structure-activity relationship of a series of 17 parabens and related compounds for histamine release in rat peritoneal mast cells and skin allergic reaction in guinea pigs
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Structure-activity relationship of a series of 17 parabens and related compounds for histamine release in rat peritoneal mast cells and skin allergic reaction in guinea pigs

机译：一系列17种对羟基苯甲酸酯和相关化合物对大鼠腹膜肥大细胞中组胺释放和豚鼠皮肤过敏反应的构效关系

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Parabens, which are a homologous series of esters of p-hydroxybenzoic acid, have been used as preservatives in cosmetics, medicines and foods because of their antimicrobial activity. However, parabens in cosmetics have been suspected to cause allergic contact dermatitis. In this study, we examined paraben-induced histamine release from rat peritoneal mast cells and skin reaction in guinea pigs using a series of 17 parabens with different alcohol side chains, ranging from methylparaben to dodecylparaben. Octylparaben showed the greatest histamine release-inducing activity from mast cells, and the activity was decreased in shorter-and longer-side-chain parabens. Octyl benzoate, octyl o-hydroxybenzoate and phenyloctane caused no significant degranulation of mast cells, whereas octyl m-hydroxybenzoate, octyl p-hydroxybenzoate and octyl phenol induced concentration-related degranulation. Metabolites of these parabens (p-hydroxybenzoic acid and alcohols) did not show histamine release-inducing activity. In the guinea pig skin reaction test, heptylparaben induced a typical strong skin reaction, while butylparaben induced a typical weak skin reaction, and methylparaben and dodecylparaben were inactive. Metabolites of parabens (p-hydroxybenzoic acid and alcohols) were also inactive. These results indicate that interaction of parabens with rat mast cells requires a minimum length and adequate lipophilicity of the alkyl side chain. Since metabolites of parabens were inactive, parabens appear to be direct-acting allergens.
机译：对羟基苯甲酸酯是对羟基苯甲酸的同系酯系列，由于其抗菌活性，已被用作化妆品，药​​品和食品中的防腐剂。然而，怀疑化妆品中的对羟基苯甲酸酯会引起过敏性接触性皮炎。在这项研究中，我们使用一系列17种具有不同醇侧链的对羟基苯甲酸酯，范围从对羟基苯甲酸甲酯到对羟基苯甲酸十二烷基酯，检查了对羟基苯甲酸酯引起的组胺从大鼠腹膜肥大细胞中的释放以及豚鼠的皮肤反应。对羟基苯甲酸酯显示出肥大细胞中最大的组胺释放诱导活性，而在较短和较长侧链的对羟基苯甲酸酯中活性降低。苯甲酸辛酯，邻羟基苯甲酸辛酯和苯辛烷不会引起肥大细胞的明显脱粒，而间羟基苯甲酸辛酯，对羟基苯甲酸辛酯和辛基苯酚则引起浓度相关的脱粒。这些对羟基苯甲酸酯的代谢产物（对羟基苯甲酸和醇类）不显示诱导组胺释放的活性。在豚鼠的皮肤反应测试中，对羟基苯甲酸庚酯引起典型的强烈皮肤反应，而对羟基苯甲酸丁酯引起典型的弱皮肤反应，而对羟基苯甲酸甲酯和十二烷基对羟基苯甲酸没有活性。对羟基苯甲酸酯的代谢物（对羟基苯甲酸和醇类）也没有活性。这些结果表明对羟基苯甲酸酯与大鼠肥大细胞的相互作用需要最短的长度和烷基侧链的足够的亲脂性。由于对羟基苯甲酸酯的代谢产物没有活性，所以对羟基苯甲酸酯似乎是直接作用的过敏原。

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