A Novel Surfactant with Short Hydrophobic Head and Long Hydrophilic Tail Generates Vesicles with Unique Structural Feature,Small

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A Novel Surfactant with Short Hydrophobic Head and Long Hydrophilic Tail Generates Vesicles with Unique Structural Feature
Small ( IF 13.0 ) Pub Date : 2023-02-17 , DOI: 10.1002/smll.202206906
Smriti Mukherjee _{1,

2} , Ganesh Shanmugam _{1,

2}

Affiliation

Surfactant molecules typically have a long hydrophobic tail and a short hydrophilic head group. It remains unexplored if surfactants can have a short hydrophobic head group and a long hydrophilic tail. Designing such surfactants is a challenge as a lengthy hydrophilic tail would completely solubilize the molecules. In this context, herein, the Fmoc-functionalized Gly-Pro-Hyp (GPO) tripeptide repeat-based molecule (Fm-GPO) with fluorenyl moiety as a short hydrophobic head and peptide as a long hydrophilic tail is demonstrated as a reverse surfactant at physiological pH, for the first time. π–π stacking of the fluorenyl moieties and intermolecular hydrogen bonding between the peptide chains with extended polyproline-II structure promoted the self-assembly into spherical vesicles with a unique feature of a large hydrophilic area in the interior and exterior of the bilayer. The current Fm-GPO system offers a new class of surfactants with unique features that can aid in the design of drug-loaded vehicles, which can be target-specific as the peptide chain can be manipulated with different functional ultra-short peptide sequences.

中文翻译：

一种具有短疏水头和长亲水尾的新型表面活性剂可生成具有独特结构特征的囊泡

表面活性剂分子通常具有长的疏水性尾部和短的亲水性头部基团。表面活性剂是否可以具有短的疏水性头基和长的亲水性尾部，目前仍未得到探索。设计这样的表面活性剂是一项挑战，因为长的亲水性尾巴会完全溶解分子。在本文中，Fmoc 功能化的 Gly-Pro-Hyp (GPO) 三肽重复基分子 (Fm-GPO) 以芴基部分作为短疏水头和肽作为长亲水尾被证明为反向表面活性剂生理 pH 值，第一次。芴基的 π-π 堆叠和具有扩展的聚脯氨酸-II 结构的肽链之间的分子间氢键促进了自组装成球形囊泡，其独特的特点是在双层的内部和外部具有大的亲水区域。目前的 Fm-GPO 系统提供了一类具有独特功能的新型表面活性剂，可以帮助设计载药载体，它可以是目标特异性的，因为肽链可以用不同功能的超短肽序列进行操作。

更新日期：2023-02-17

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