Disconnecting the Estrogen Receptor Binding Properties and Antimicrobial Properties of Parabens through 3,5-Substitution,ACS Medicinal Chemistry Letters

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Disconnecting the Estrogen Receptor Binding Properties and Antimicrobial Properties of Parabens through 3,5-Substitution
ACS Medicinal Chemistry Letters ( IF 3.5 ) Pub Date : 2017-12-19 00:00:00 , DOI: 10.1021/acsmedchemlett.7b00431
Bridget L. Bergquist ₁ , Kaelyn G. Jefferson ₁ , Hailey N. Kintz ₁ , Amorette E. Barber ₁ , Andrew A. Yeagley ₁

Affiliation

Commercially utilized parabens are employed for their antimicrobial properties, but a weak binding to the estrogen receptor alpha (ER_α) may lead to breast cancer in some applications. Modification of the paraben scaffold should allow for a disconnection of these observed properties. Toward this goal, various 3,5-substituted parabens were synthesized and assessed for antimicrobial properties against S. aureus as well as competitive binding to the ER_α. The minimum inhibitory concentration assay confirmed retention of antimicrobial activity in many of these derivatives, while all compounds exhibited decreased xenoestrogen activity as determined by a combination of competitive enzyme linked immunosorbent assay (ELISA), proliferation, and estrogen receptor binding assay. Thus, these changes to the paraben scaffold have led to a multitude of paraben derivatives with antimicrobial properties up to 16 times more active than the parent paraben and that are devoid or significantly diminished of potential breast cancer causing properties.

中文翻译：

通过3,5-取代断开对羟基苯甲酸酯的雌激素受体结合特性和抗菌特性

在商业上用来对羟基苯甲酸酯被用于它们的抗微生物性质，但是弱的结合雌激素受体α（ER _α）可以导致乳腺癌在一些应用中。对羟基苯甲酸酯支架的修饰应允许断开这些观察到的特性。为了实现这一目标，各种3,5-取代的对羟基苯甲酸酯的合成和评价了针对抗微生物性质的金黄色葡萄球菌以及竞争性结合至ER _α。最小抑菌浓度测定法证实了许多这些衍生物中都保留了抗菌活性，而所有化合物均表现出降低的异雌激素活性，这是通过竞争性酶联免疫吸附测定（ELISA），增殖和雌激素受体结合测定法的组合确定的。因此，对羟基苯甲酸酯支架的这些变化已导致具有对羟基苯甲酸酯衍生物的抗微生物特性的许多对羟基苯甲酸酯衍生物的活性高达母对羟基苯甲酸酯的十六倍，并且没有或显着降低了潜在的引起乳腺癌的特性。

更新日期：2017-12-19

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