Synthesis and aggregation behaviour of single-chain, 1,32-alkyl-branched bis(phosphocholines) – part 2: lateral chain length triggers self-assembling from sheets to fibres to vesicles

Abstract

The synthesis of six single-chain, alkyl-branched bolalipids and first investigations of the lyotropic behaviour of these lipids are reported.

Investigation of Self‐Assembly of Symmetric and Asymmetric Peptide Bolaamphiphiles by COSMO‐RS and Atomistic Simulations and Their Interactions with POPC Bilayers

“…Overall, PbAs 1, 3 and 4 stabilized in the range of 2.3 nm to 2.5 nm by the end of the simulation, while PbA 2 stabilized at 3.5 nm indicating that it is the most flexible out of PbAs 1-4 which only varied in the chain length and had the In previous work, it has been demonstrated that aggregation behavior of single-chain alkyl branched lipids was controlled by the alkyl chain length, wherein short and long lateral linkers led to lamellar structures, while medium length led to fibrous aggregates. [75] A similar phenomenon may be occurring in the case of PbAs 1 through 4, where PbA 2 is likely to form fibrous aggregates due to its intermediate chain length while PbAs 1, 3, and 4 form globular structures. PbAs 5 and 6 have an even number of alkyl carbons (six) separating hydrophilic, polar identical head groups (Thr-Thr) at both ends, the only difference being the presence of a double bond in the case of PbA 5.…”

The Phospholipid Research Center: Current Research in Phospholipids and Their Use in Drug Delivery

“…Here, the group of Simon Drescher (Martin Luther University Halle-Wittenberg, Halle/Saale, Germany) is trying to find an easy-to-synthesize bolalipid that can be used for the stabilization of orally administered liposomes. During this project, two novel classes of artificial bolalipids, the glycerol diether bolalipids [160,161] and alkyl-substituted single-chain bolalipids [162,163], were synthesized and characterized. Drescher and his group could show that these artificial bolalipids are miscible with unsaturated phospholipids [164,165], and that these mixed vesicles (bolasomes) show promising results regarding the stability of those bolasomes in artificial digestive media [166].…”