Synthesis and aggregation behaviour of single-chain, 1,32-alkyl branched bis(phosphocholines): effect of lateral chain length

Abstract

Three novel single-chain bis(phosphocholines) bearing two lateral alkyl chains of variable length next to the headgroup have been synthesized as model lipids for naturally occurring archaeal membrane lipids. The synthesis was realized using the Cu-catalyzed Grignard bis-coupling reaction of a primary bromide as a side part and a 1,ω-dibromide as a centre part. We could show that the aggregation behaviour of the resulting bolalipids strongly depends on the length of the lateral alkyl chain: the C3-branched bolalipid self-assembles into lamellar sheets, whereas the C6- and C9-analogues form nanofibres. The lamella-forming bolalipids could be used in the future to prepare stable and tailored liposomes for oral drug delivery.

Targeted Metabolomics Analysis on Obstructive Sleep Apnea Patients after Multilevel Sleep Surgery

“…Phospholipids, also called glycerophospholipids, are important structural components in the lipid bilayer of the plasma membrane. Phosphocholines are a class of phospholipids that are also part of the plasma membrane and play an important role as signaling molecules [ 56 , 57 , 58 ]. Interestingly, two PCs were increased following the surgical treatment of OSA.…”

Bolalipid-Doped Liposomes: Can Bolalipids Increase the Integrity of Liposomes Exposed to Gastrointestinal Fluids?

“…The bolalipids (1RS,32RS)-1,32-dihexyldotriacontane-1,32-diylbis [2-(trimethylammonio)ethyl phosphate] (PC-C32(1,32C6)-PC) and (1RS,32RS)-1,32-dinonyldotriacontane-1,32-diylbis [2-(trimethylammonio)ethyl phosphate] (PC-C32(1,32C9)-PC) were synthesized according to procedures described previously [52].…”

“…Pure soyPC showed no phase transition in the temperature range investigated (5-80 • C), which is due to the fact that the main transition temperature (T m ) of soyPC is below 0 • C. Depending on the fatty acid composition of natural phospholipids, T m can vary between −50 and −20 • C [60]. The bolalipid PC-C32(1,32C9)-PC shows a transition at T m = 20.8 • C and it self-assembles into fibers below and sheet-like aggregates above this T m [52]. In the 1/4 mixture of PC-C32(1,32C9)-PC and soyPC ( Figure 2, green line), no transition can be observed in the DSC heating curve.…”

“…Several attempts including, for example, the incorporation of a phenyl group into the alkyl chain of the bolalipid [47][48][49][50][51] have failed. Hence, we synthesized a set of single-chain bolalipids bearing a lateral alkyl chain of different length right next to the PC headgroups, the PC-C32(1,32Cn)-PC with n = 3, 6, 9 [52] (Figure 1). Figure 1.…”

“…The bolalipids PC-C32(1,32C6)-PC and PC-C32(1,32C9)-PC are used in this study. Chemical structure of single-chain, alkyl-branched bolalipids PC-C32(1,32Cn)-PC with n = 3, 6, 9 [52]. The bolalipids PC-C32(1,32C6)-PC and PC-C32(1,32C9)-PC are used in this study.…”