Lipid-Based Catalysis Demonstrated by Bilayer-Enabled Ester Hydrolysis.

IF 3.3 4区 工程技术 Q2 CHEMISTRY, PHYSICAL Membranes Pub Date : 2024-07-30 DOI:10.3390/membranes14080168
Shu Liu, Kiran Kumar, Tracey Bell, Ayyalusamy Ramamoorthy, David Van Winkle, Steven Lenhert
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Abstract

Lipids have not traditionally been considered likely candidates for catalyzing reactions in biological systems. However, there is significant evidence that aggregates of amphiphilic compounds are capable of catalyzing reactions in synthetic organic chemistry. Here, we demonstrate the potential for the hydrophobic region of a lipid bilayer to provide an environment suitable for catalysis by means of a lipid aggregate capable of speeding up a chemical reaction. By bringing organic molecules into the nonpolar or hydrophobic region of a lipid bilayer, reactions can be catalyzed by individual or collections of small, nonpolar, or amphiphilic molecules. We demonstrate this concept by the ester hydrolysis of calcein-AM to produce a fluorescent product, which is a widely used assay for esterase activity in cells. The reaction was first carried out in a two-phase octanol-water system, with the organic phase containing the cationic amphiphiles cetyltrimethylammonium bromide (CTAB) or octadecylamine. The octanol phase was then replaced with phospholipid vesicles in water, where the reaction was also found to be carried out. The reaction was monitored using quantitative fluorescence, which revealed catalytic turnover numbers on a scale of 10-7 to 10-8 s-1 for each system, which is much slower than enzymatic catalysis. The reaction product was characterized by 1H-NMR measurements, which were consistent with ester hydrolysis. The implications of thinking about lipids and lipid aggregates as catalytic entities are discussed in the context of biochemistry, pharmacology, and synthetic biology.

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双分子层催化酯类水解所展示的脂基催化作用
传统上,人们认为脂质不可能催化生物系统中的反应。然而,有大量证据表明,两亲化合物的聚集体能够催化合成有机化学中的反应。在这里,我们证明了脂质双分子层的疏水区域有可能通过能够加速化学反应的脂质聚集体提供适合催化反应的环境。通过将有机分子带入脂质双分子层的非极性或疏水区域,可以由单个或集合的小分子、非极性分子或两性分子催化反应。我们通过钙黄绿素-AM 的酯水解产生荧光产物来证明这一概念,这是细胞中酯酶活性的一种广泛应用的检测方法。反应首先在正辛醇-水两相体系中进行,有机相中含有阳离子两性化合物十六烷基三甲基溴化铵(CTAB)或十八胺。然后用水中的磷脂囊泡取代正辛醇相,发现反应也在水中进行。利用定量荧光对反应进行了监测,结果显示每个体系的催化周转次数为 10-7 至 10-8 s-1,比酶催化反应慢得多。反应产物通过 1H-NMR 测量进行表征,结果与酯水解一致。本文从生物化学、药理学和合成生物学的角度讨论了将脂质和脂质聚集体视为催化实体的意义。
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来源期刊
Membranes
Membranes Chemical Engineering-Filtration and Separation
CiteScore
6.10
自引率
16.70%
发文量
1071
审稿时长
11 weeks
期刊介绍: Membranes (ISSN 2077-0375) is an international, peer-reviewed open access journal of separation science and technology. It publishes reviews, research articles, communications and technical notes. Our aim is to encourage scientists to publish their experimental and theoretical results in as much detail as possible. There is no restriction on the length of the papers. Full experimental and/or methodical details must be provided.
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