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How 1,n-Bis(3-alkylimidazolium-1-yl) Alkane Interacts with the Phospholipid Membrane and Impacts the Toxicity of Dicationic Ionic Liquids
Langmuir ( IF 3.7 ) Pub Date : 2022-11-02 , DOI: 10.1021/acs.langmuir.2c01956
Navleen Kaur 1 , Markus Fischer 2 , Prashant Hitaishi 3 , Sandeep Kumar 1 , Veerendra Kumar Sharma 4, 5 , Sajal Kumar Ghosh 3 , Gagandeep Kaur Gahlay 6 , Holger A Scheidt 2 , Venus Singh Mithu 1, 7
Langmuir ( IF 3.7 ) Pub Date : 2022-11-02 , DOI: 10.1021/acs.langmuir.2c01956
Navleen Kaur 1 , Markus Fischer 2 , Prashant Hitaishi 3 , Sandeep Kumar 1 , Veerendra Kumar Sharma 4, 5 , Sajal Kumar Ghosh 3 , Gagandeep Kaur Gahlay 6 , Holger A Scheidt 2 , Venus Singh Mithu 1, 7
Affiliation
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Ionic liquids based on doubly charged cations, often termed dicationic ionic liquids (DILs), offer robust physicochemical properties and low toxicity than conventional monocationic ionic liquids. In this design-based study, we used solid-state NMR spectroscopy to provide the interaction mechanism of two DILs, 1,n-bis(3-alkylimidazolium-1-yl) alkane dibromide ([C2n(C7–nIM)2]2+·2Br–, n = 1, 6), with 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) and 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (POPG) phospholipid membranes, to explain the low toxicity of DILs toward HeLa, Escherichia coli, Bacillus subtilis, and Saccharomyces cerevisiae cell lines. Dications with a short linker and long terminal chains cause substantial perturbation to the bilayer structure, making them more membrane permeabilizing, as shown by fluorescence-based dye leakage assays. The structural perturbation is even higher than [C12(MIM)]+ monocations, which carry a single 12-carbon long chain and exhibit a much higher membrane affinity, permeability, and cytotoxicity. These structural details are a crucial contribution to the design strategies aimed at harnessing the biological activity of ionic liquids.
中文翻译:
1,n-Bis(3-alkylimidazolium-1-yl) Alkane 如何与磷脂膜相互作用并影响双阳离子液体的毒性
基于双电荷阳离子的离子液体,通常称为双阳离子离子液体 (DIL),与传统的单阳离子离子液体相比,具有稳健的物理化学性质和低毒性。在这项基于设计的研究中,我们使用固态 NMR 光谱提供了两种 DIL 的相互作用机制,1, n -bis (3-alkylimidazolium-1-yl) alkane dibromide ([C 2 n (C 7– n IM ) 2 ] 2+ ·2Br – , n = 1, 6), 与 1-palmitoyl-2-oleoyl- sn -glycero-3-phosphocholine (POPC) 和 1-palmitoyl-2-oleoyl- sn -glycero-3-磷酸-(1'- rac-甘油) (POPG) 磷脂膜,以解释 DIL 对 HeLa、大肠杆菌、枯草芽孢杆菌和酿酒酵母细胞系的低毒性。如基于荧光的染料渗漏测定所示,具有短接头和长末端链的双离子化会对双层结构造成显着扰动,使它们更具膜渗透性。结构扰动甚至高于 [C 12 (MIM)] +单阳离子,其携带单个 12 碳长链并表现出更高的膜亲和力、渗透性和细胞毒性。这些结构细节对旨在利用离子液体的生物活性的设计策略做出了重要贡献。
更新日期:2022-11-02
中文翻译:
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1,n-Bis(3-alkylimidazolium-1-yl) Alkane 如何与磷脂膜相互作用并影响双阳离子液体的毒性
基于双电荷阳离子的离子液体,通常称为双阳离子离子液体 (DIL),与传统的单阳离子离子液体相比,具有稳健的物理化学性质和低毒性。在这项基于设计的研究中,我们使用固态 NMR 光谱提供了两种 DIL 的相互作用机制,1, n -bis (3-alkylimidazolium-1-yl) alkane dibromide ([C 2 n (C 7– n IM ) 2 ] 2+ ·2Br – , n = 1, 6), 与 1-palmitoyl-2-oleoyl- sn -glycero-3-phosphocholine (POPC) 和 1-palmitoyl-2-oleoyl- sn -glycero-3-磷酸-(1'- rac-甘油) (POPG) 磷脂膜,以解释 DIL 对 HeLa、大肠杆菌、枯草芽孢杆菌和酿酒酵母细胞系的低毒性。如基于荧光的染料渗漏测定所示,具有短接头和长末端链的双离子化会对双层结构造成显着扰动,使它们更具膜渗透性。结构扰动甚至高于 [C 12 (MIM)] +单阳离子,其携带单个 12 碳长链并表现出更高的膜亲和力、渗透性和细胞毒性。这些结构细节对旨在利用离子液体的生物活性的设计策略做出了重要贡献。