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Novel quaternary ammonium compounds derived from aromatic and cyclic amino acids: Synthesis, physicochemical studies and biological evaluation
Chemistry and Physics of Lipids ( IF 3.4 ) Pub Date : 2021-01-15 , DOI: 10.1016/j.chemphyslip.2021.105051
Nausheen Joondan 1 , Prakashanand Caumul 1 , Graham Jackson 2 , Sabina Jhaumeer Laulloo 1
Affiliation  

Novel quaternary ammonium surfactants (QUATs) derived from phenylalaninyl-proline dipeptide with chain length C12 and C14 were synthesised as potential active ingredients to be used in body cleansing formulations. The physicochemical properties and biological activities of the QUATs were determined in both single and in mixed surfactant system with either the conventional anionic surfactant sodium dodecyl sulphate (SDS) or sodium N-dodecyl prolinate. The C12 QUAT derivative showed antagonistic behaviour in both SDS and sodium N-dodecyl prolinate mixed surfactant system. Comparing the mixed system of the C12 QUAT with SDS and sodium N-dodecyl prolinate, it was found that the latter displayed better antibacterial activity together with the lower ocular irritation. The C12 QUAT-sodium N-dodecyl prolinate mixture were non cytotoxic at a concentration corresponding to its MIC value, showing that the mixture was selective towards bacterial cells rather than mammalian cell lines. Diffusion measurements showed that the sodium N-dodecyl prolinate surfactant consisted of 26 molecules per micelle in water but only 3 molecules per micelle in DMSO/water (1:1). On the other hand, C12 QUAT did not form a micelle in DMSO/Water. Membrane permeability studies of the C12 QUAT and sodium N-dodecyl prolinate showed that these surfactants are capable to penetrate into deeper skin layers to exert their antibacterial and cleansing action and hence can be used as a promising candidate as active ingredients in body wash formulations.



中文翻译:

源自芳香族和环状氨基酸的新型季铵化合物:合成、理化研究和生物学评价

合成了链长为 C 12和 C 14 的苯丙氨酰脯氨酸二肽的新型季铵表面活性剂 (QUAT) ,作为用于身体清洁配方的潜在活性成分。QUAT 的理化性质和生物活性在单一和混合表面活性剂体系中与常规阴离子表面活性剂十二烷基硫酸钠 (SDS) 或N-十二烷基脯氨酸钠一起测定。C 12 QUAT 衍生物在SDS 和N-十二烷基脯氨酸钠混合表面活性剂体系中均表现出拮抗行为。比较 C 12季铵盐与 SDS 和N钠的混合体系-十二烷基脯氨酸,发现后者表现出更好的抗菌活性以及较低的眼部刺激。的C 12 QUAT-钠Ñ十二烷基脯氨酸混合物是非细胞毒性的,在对应于它的MIC值的浓度,显示出该混合物是朝着细菌细胞而不是哺乳动物细胞系的选择性。扩散测量表明,N-十二烷基脯氨酸钠表面活性剂在水中每个胶束由 26 个分子组成,但在 DMSO/水 (1:1) 中每个胶束只有 3 个分子。另一方面,C 12 QUAT 在 DMSO/水中不形成胶束。C 12季铵盐和钠N 的膜渗透性研究-十二烷基脯氨酸表明这些表面活性剂能够渗透到更深的皮肤层以发挥其抗菌和清洁作用,因此可作为沐浴露配方中的活性成分的有希望的候选物。

更新日期:2021-01-24
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