Micelles and vesicles from thio-lipids as models for the prebiotic evolution of membranes

• Research unit: COST
• Project number: C04.0268

Key words (English)

lipids; surfactants; micelles; vesicles; bilayers; membranes; origin of life; prebiotic; self-organisation; self.-assembly; disulfide; thioether; compartments; evolution

Research programs (English)

COST-Action D27 - Prebiotic Chemistry and Early Evolution

Short description (English)

The aim of the project is (a) to synthesize disulfide- and thioether-linked double-chain lipids with one or two carboxylate head groups and to characterize the respective vesicles; (b) to investigate the synthesis of above double-chain lipids from reactive mono-chain lipids in aqueous buffer as a model for the prebiotic evolution of membrane compartments; and (c) to characterize morphological changes occuring during the transformation of mono- to double-tail lipids (micelle-to-vesicle transition).

Partners and International Organizations (English)

AT, BE, BG, HR, FR, DE, EL, HU, IL, IT, LT, NL, PL, SI, ES, SE, CH, UK

Abstract (English)

Two new zwitterionic gemini lipids, (N-[2-[[(dodecyloxy)hydroxyphosphinyl]thio] ethyl]-N,N-dimethyl-1-dodecanaminium, inner salt) and (N-[2-[[(tetradecyloxy)hydroxyphosphinyl]thio] ethyl]-N,N-dimethyl-1-tetradecanaminium, inner salt) have been synthesized from the corresponding oppositely charged single chain surfactants, (i) the O-monododecylester or monotetradecylester of phosphorothioate, and (ii) N-(2-bromoethyl)-N,N-dimethyl-1-dodecanaminium bromide or N-(2-bromoethyl)-N,N-dimethyl-1-tetardecanaminium bromide). The single chain surfactants formed micelles in aqueous buffer at pH 8 above their respective cmc (critical micellization concentration) but no vesicles formation was observed. When aqueous solutions of the two surfactants were slowly mixed they reacted to form the zwitterionic gemini lipid which self-assembled into vesicles. During vesicle formation water soluble molecules were captured by the vesicles, as demonstrated by using fluorescently labelled dextran.

References in databases (English)

Swiss Database: COST-DB of the State Secretariat for Education and Research Hallwylstrasse 4 CH-3003 Berne, Switzerland Tel. [phone] Swiss Project-Number: C04.0268