Cyclopentane rings in hydrophobic chains of a phospholipid enhance the bilayer stability to electric breakdown,Soft Matter

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Cyclopentane rings in hydrophobic chains of a phospholipid enhance the bilayer stability to electric breakdown
Soft Matter ( IF 2.9 ) Pub Date : 2020/03/03 , DOI: 10.1039/c9sm02001b
Oleg V. Batishchev _{1,

2,

3,

4} , Anna S. Alekseeva _{2,

3,

4,

5} , Daria S. Tretiakova _{2,

3,

4,

5} , Timur R. Galimzyanov _{1,

2,

3,

4,

6} , Andrey Yu. Chernyadyev _{1,

2,

3,

4} , Natalia R. Onishchenko _{2,

3,

4,

5} , Pavel E. Volynsky _{2,

3,

4,

5} , Ivan A. Boldyrev _{2,

3,

4,

5}

Affiliation

Archaeal lipids ensure unprecedented stability of archaea membranes in extreme environments. Here, we incorporate a characteristic structural feature of an archaeal lipid, the cyclopentane ring, into hydrocarbon chains of a short-chain (C12) phosphatidylcholine to explore whether the insertion would allow such a lipid (1,2-di-(3-(3-hexylcyclopentyl)-propanoate)-sn-glycero-3-phosphatidylcholine, diC12cp-PC) to form stable bilayers at room temperature. According to fluorescence-based assays, in water diC12cp-PC formed liquid-crystalline bilayers at room temperature. Liposomes produced from diC12cp-PC retained calcein for over a week when stored at +4 °C. diC12cp-PC could also form model bilayer lipid membranes that were by an order of magnitude more stable to electrical breakdown than egg PC membranes. Molecular dynamics simulation showed that the cyclopentane fragment fixes five carbon atoms (or four C–C bonds), which is compensated by the higher mobility of the rest of the chain. This was found to be the reason for the remarkable stability of the diC12cp-PC bilayer: restricted conformational mobility of a chain segment increases the membrane bending modulus (compared to a normal hydrocarbon chain of the same length). Here, higher stiffness practically does not affect the line tension of a membrane pore edge. Rather it makes it more difficult for diC12cp-PC to rearrange in order to line the edge of a hydrophilic pore; therefore, fewer pores are formed.

中文翻译：

磷脂疏水链中的环戊烷环可增强双层稳定性以防止电击穿

古细菌脂质可确保在极端环境中古细菌膜具有前所未有的稳定性。在这里，我们将古细菌脂质的特征结构特征，环戊烷环，纳入短链（C12）磷脂酰胆碱的烃链中，探索插入是否会允许这种脂质（1,2-di-（3-（ 3-己基环戊基）-丙酸酯）-sn-甘油-3-磷脂酰胆碱（diC12cp-PC）在室温下形成稳定的双层。根据基于荧光的分析，diC12cp-PC在水中在室温下形成液晶双层。当储存在+4°C下时，由diC12cp-PC产生的脂质体将钙黄绿素保留一周以上。diC12cp-PC还可以形成模型双层脂质膜，其对电击穿的稳定性比鸡蛋PC膜高一个数量级。分子动力学模拟表明，环戊烷片段固定了5个碳原子（或4个C–C键），这被链中其余部分的较高迁移率所补偿。发现这是diC12cp-PC双层显着稳定性的原因：链段的受限构象迁移率增加了膜的弯曲模量（与相同长度的正常烃链相比）。此处，较高的刚度实际上不影响膜孔边缘的线张力。而是使diC12cp-PC更加困难重新排列以便使亲水孔的边缘排成一行；因此，形成的孔较少。

更新日期：2020-04-01

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