Synthesis of Mannosylerythritol Lipid Analogues and their Self‐Assembling Properties, Recovery Effects on Damaged Skin Cells, and Antibacterial Activity
Synthesis of Mannosylerythritol Lipid Analogues and their Self‐Assembling Properties, Recovery Effects on Damaged Skin Cells, and Antibacterial Activity
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甘露赤藓糖醇脂质类似物的合成及其自组装特性、对受损皮肤细胞的恢复作用和抗菌活性
DOI：
10.1002/chem.202201733
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发表时间：
2022
期刊：
影响因子：
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通讯作者：
Toshima Kazunobu
中科院分区：
文献类型：
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作者：
Kondo Takanori;Yasui Chihiro;Miyajima Ikkei;Banno Taisuke;Asakura Kouichi;Fukuoka Tokuma;Ushimaru Kazunori;Koga Maito;Saika Azusa;Morita Tomotake;Takahashi Yoshiaki;Hayashi Chigusa;Igarashi Masayuki;Takahashi Daisuke;Toshima Kazunobu
利用我们的硼介导的糖苷配基递送（BMAD）方法完成了三种类型的具有癸酰基的专门设计的甘露糖基化脂质（MEL）-D类似物β-GlcEL-D、α-GlcEL-D和α-MEL-D的合成。评估了它们的自组装特性、对受损皮肤细胞的恢复效果和抗菌活性。首次发现，α-GlcEL-D和α-MEL-D仅产生巨大的囊泡，表明α-GlcEL-D和脂肪酰基链的空间构型的微小差异影响形成囊泡的能力。Anasthenia α-MEL-D对受损皮肤细胞具有显著的恢复作用。此外，α-MEL-D表现出与MEL-D一样高的抗菌活性，表明α-MEL-D是一种有前途的用于增强角质层屏障功能的人造糖基材料候选物，上级已知的化妆品成分，并且具有抗菌活性。
Synthesis of three types of purpose‐designed mannosylerythritol lipid (MEL)‐D analogues with decanoyl groups, β‐GlcEL‐D, α‐GlcEL‐D, and α‐MEL‐D, was accomplished utilizing our boron‐mediated aglycon delivery (BMAD) methods. Their self‐assembling properties, recovery effects on damaged skin cells, and antibacterial activity were evaluated. It was revealed, for the first time, that α‐GlcEL‐D and α‐MEL‐D only generated giant vesicles, indicating that slight differences in the steric configuration of an erythritol moiety and fatty acyl chains affect the ability to form vesicles. Analogue α‐MEL‐D exhibited significant recovery effects on damaged skin cells. Furthermore, α‐MEL‐D exhibited antibacterial activity as high as that for MEL‐D, indicating that α‐MEL‐D is a promising artificial sugar‐based material candidate for enhancing the barrier function of the stratum corneum, superior to a known cosmetic ingredient, and possesses antibacterial activity.