Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133, Milano, Italy.
Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133, Milano, Italy.
J Pharm Biomed Anal. 2018 Sep 10;159:224-228. doi: 10.1016/j.jpba.2018.06.055. Epub 2018 Jun 30.
Nowadays, parabens have been replaced by domiphen bromide, which is widely used in pharmaceutical and cosmetic products. The main aim of this study was to investigate stressed degradation products of domiphen bromide by mean of a rapid, specific and reliable LC-ESI MS/MS since phenyl bromination may occur due to the oxidation of bromide counter ion under oxidative conditions. LC-ESI-MS/MS have characterized a new compound, p-bromodomiphen, as the only degradation product and structure elucidation was also confirmed by the synthesis of the standard. Notably, the resulting p-bromodomiphen bromide is more stable then domiphen bromide in oxidizing conditions since no di-bromoderivatives were detected by MS studies; both domiphen and its p-bromo derivative were tested for antibacterial activity and were more effective on Gram positive (Staphylococcus aureus ATCC25923 and Bacillus cereus DSM31) compared to Gram negative bacteria (Escherichia coli ATCC25922 and Pseudomonas aeruginosa DSM22644). In conclusion, stressed degradation studies by LC-ESI-MS/MS have characterized a new compound that comprises an alternative to domiphen bromide since its antimicrobial activity is comparable to, if not better than, the parental compound.
如今，已将对羟基苯甲酸酯类物质替换为二溴丁二酸二甲酯，后者广泛应用于医药和化妆品产品中。本研究的主要目的是通过快速、特异且可靠的 LC-ESI-MS/MS 研究二溴丁二酸二甲酯的应激降解产物，因为在氧化条件下溴化物反离子可能由于氧化而发生苯溴化。LC-ESI-MS/MS 鉴定出一种新的化合物 p-溴代二苯甲酮，这是唯一的降解产物，并且通过标准品的合成也得到了结构确证。值得注意的是，在氧化条件下生成的 p-溴代二苯甲酮溴化物比二溴丁二酸二甲酯更稳定，因为 MS 研究未检测到二溴衍生物；对二苯甲酮及其 p-溴代衍生物进行了抗菌活性测试，与革兰氏阴性菌（大肠杆菌 ATCC25922 和铜绿假单胞菌 DSM22644）相比，它们对革兰氏阳性菌（金黄色葡萄球菌 ATCC25923 和蜡状芽孢杆菌 DSM31）的作用更有效。总之，通过 LC-ESI-MS/MS 的应激降解研究鉴定出一种新的化合物，它构成了二溴丁二酸二甲酯的替代品，因为其抗菌活性与母体化合物相当，如果不是更好的话。
