Mixing behaviour of bilayer-forming phosphatidylcholines with single-chain alkyl-branched bolalipids: effect of lateral chain length

Müller, Sindy; Kind, Maximilian; Gruhle, Kai; Hause, Gerd; Meister, Annette; Drescher, Simon

doi:10.1016/j.bpc.2018.10.003

Cited by 9 publications

(21 citation statements)

References 46 publications

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“…In a previous publication, we showed that the two single-chain alkyl-branched bolalipids PC-C32(1,32C6)-PC and PC-C32(1,32C9)-PC-bearing a lateral C6 or C9 alkyl chain right next to the PC headgroups (see Figure 1)-can be incorporated into lipid vesicles composed of unsaturated phos-pholipids, POPC and DOPC, respectively [53]. This leads to the formation of mixed bolalipid/ phospholipid vesicles (bolasomes).…”

Section: Resultsmentioning

confidence: 95%

“…In the case of lateral hexyl (C6) and nonyl (C9) alkyl chains, i.e., PC-C32(1,32C6)-PC and PC-C32(1,32C9)-PC, we could demonstrate that these groups are sufficient to fill the void volume in a mixed bolalipid/phospholipid membrane when unsaturated phospholipids, that is POPC or DOPC, are used [53]. As a result, we were able to produce for the first time storage-stable liposomes (bolasomes) composed of POPC and DOPC with 20 mol% of PC-C32(1,32C6)-PC and PC-C32(1,32C9)-PC, respectively.…”

Section: Introductionmentioning

confidence: 94%

“…As published previously [53,56], DSC measurements were carried out using a MicroCal VP-DSC differential scanning calorimeter (MicroCal Inc. Northampton, MA, USA). Before each measurement, the lipid dispersion (c = 3 mM) and the reference were degassed under vacuum while stirring.…”

Section: Differential Scanning Calorimetry (Dsc)mentioning

confidence: 99%

“…As published previously [53], the lipid samples (c = 6 mM) were cryo-fixed using a propane jet-freeze device JFD 030 (BAL-TEC, Balzers, Lichtenstein). Afterwards, the samples were freeze-fractured at −150 • C without etching, using a freeze fracture/freeze etching system BAF 060 (BAL-TEC, Balzers, Liechtenstein).…”

Section: Transmission Electron Microscopy Of Replica Of Freeze-fractumentioning

confidence: 99%

“…In the present work, we focused on stability studies of our bolasomes in different artificial digestion media, namely simulated gastric fluid (SGF) and simulated intestinal fluid (SIF). Besides PC-C32(1,32C6)-PC/DOPC (1/4, n/n) and PC-C32(1,32C9)-PC/DOPC (1/4, n/n) [53], we also used a natural phospholipid mixture, that is Phospholipon 90G ® , containing at least 95% of phosphatidyl-cholines from soy beans (soyPC), for our stability measurements, since natural phospholipids have been attracting more and more attention in the pharmaceutical industry [18,54].…”

Section: Introductionmentioning

confidence: 99%

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

Müller

Gruhle

Meister³

et al. 2019

Pharmaceutics

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The use of archaeal lipids and their artificial analogues, also known as bolalipids, represents a promising approach for the stabilization of classical lipid vesicles for oral application. In a previous study, we investigated the mixing behavior of three single-chain alkyl-branched bolalipids PC-C32(1,32Cn)-PC (n = 3, 6, 9) with either saturated or unsaturated phosphatidyl-cholines. We proved, that the bolalipids PC-C32(1,32C6)-PC and PC-C32(1,32C9)-PC show miscibility with 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) and 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC). In the present work, we extended our vesicle system to natural lipid mixtures using phosphatidylcholine from soy beans, and we investigated the effect of incorporated bolalipids on the integrity of these mixed liposomes (bolasomes) in different gastrointestinal fluids using a dithionite assay and a calcein release assay in combination with particle size measurements. Finally, we also studied the retention of calcein within the bolasomes during freeze-drying. As a main result, we could show that in particular PC-C32(1,32C6)-PC is able to increase the stability of bolasomes in simulated gastric fluid—a prerequisite for the further use of liposomes as oral drug delivery vehicles.

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Section: Resultsmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 94%

Section: Differential Scanning Calorimetry (Dsc)mentioning

confidence: 99%

Section: Transmission Electron Microscopy Of Replica Of Freeze-fractumentioning

confidence: 99%