ChemInform Abstract: SYNTHESIS AND BIOLOGICAL ACTIVITY OF SOME LYZING AND FUSOGENICALLY ACTIVE PHOSPHOCHOLINE DERIVATIVES

Nuhn, P.; Kertscher, P.; Dobner, Bodo; Braune, K.-D.; Kluge, Siegfried

doi:10.1002/chin.198308259

Cited by 2 publications

(3 citation statements)

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“…One the other hand, and if one would like to insert an ether instead of an ester bond, a total synthetic approach is the method of choice. For this, Arnold et al and later Nuhn et al described the use of a selectively blocked and alkylated glycerol derivative, namely rac -1- O -benzyl-2- O -hexadecyl- sn -glycero-3-phosphocholine ( 2 ), which could easily be synthesized in four steps from 1,3- O -dibenzylidene glycerol. After cleavage of the benzyl moiety, one can insert any desired fatty acid using for example the Steglich esterification reaction.…”

Section: Resultsmentioning

confidence: 99%

“…The total synthetic approach starts from rac -1- O -benzyl-2- O -hexadecyl- sn -glycero-3-phosphocholine ( 2 ). This precursor, which was synthesized according to Nuhn et al, already contained an alkyl chain in the 2 position of the glycerol. The benzyl protecting group was removed using a hydrogenation reaction under increased pressure and palladium on carbon as catalyst, yielding the rac -1-hydroxy-2- O -hexadecyl- sn -glycero-3-phosphocholine ( 3 ).…”

Section: Resultsmentioning

confidence: 99%

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Azide-Modified Membrane Lipids: Synthesis, Properties, and Reactivity

et al. 2017

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In the present work, we describe the synthesis and the temperature-dependent behavior of photoreactive membrane lipids as well as their capability to study peptide/lipid interactions. The modified phospholipids contain an azide group either in the middle part or at the end of an alkyl chain and also differ in the linkage (ester vs ether) of the second alkyl chain. The temperature-dependent aggregation behavior of the azidolipids was studied using differential scanning calorimetry (DSC), Fourier-transform infrared (FTIR) spectroscopy, and small-angle X-ray scattering (SAXS). Aggregate structures were visualized by stain and cryo transmission electron microscopy (TEM) and were further characterized by dynamic light scattering (DLS). We show that the position of the azide group and the type of linkage of the alkyl chain at the sn-2 position of the glycerol influences the type of aggregates formed as well as their long-term stability: P10AzSPC and r12AzSHPC show the formation of extrudable liposomes, which are stable in size during storage. In contrast, azidolipids that carry a terminal azido moiety either form extrudable liposomes, which show time-dependent vesicle fusion (P15AzPdPC), or self-assemble in large sheet-like, nonextrudable aggregates (r15AzPdHPC) where the lipid molecules are arranged in an interdigitated orientation at temperatures below T (LI phase). Finally, a P10AzSPC:DMPC mixture was used for photochemically induced cross-linking experiments with a transmembrane peptide (WAL-peptide) to demonstrate the applicability of the azidolipids for the analysis of peptide/lipid interactions. The efficiency of photo-cross-linking was monitored by attenuated total reflection infrared (ATR-IR) spectroscopy and mass spectrometry (MS).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Azide-Modified Membrane Lipids: Synthesis, Properties, and Reactivity

et al. 2017

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“…5 The synthesis of PHPC was performed according to the same protocol. 5 Briefly, after removing the benzyl protecting group from rac-1-O-benzyl-2-O-hexadecyl-sn-glycerophosphocholine, 13 the new fatty acid, which is palmitic acid in our case, was introduced using dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP) as coupling reagents. The resulting PHPC was purified using column chromatography.…”

Section: ■ Introductionmentioning

confidence: 99%

An Azidolipid Monolayer – Transitions, Miscibility, and UV Reactivity Studied by Infrared Reflection Absorption Spectroscopy

Hoffmann¹,

Drescher

Ihling

et al. 2020

Langmuir

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In this study, we characterized monolayers of an azide-modified lipid at the air−water interface, pure and in its mixtures with the model lipid DPPC, with the aim of proving its potential to be applied for photo-cross-linking with other molecules. We chose a phospholipid bearing a terminal azide group in one of its hydrophobic tails to study its monolayer characteristics with the Langmuir film balance technique. Furthermore, we performed infrared reflection absorption spectroscopy (IRRAS) to get detailed insights into the organization of those monolayers as well as high-resolution mass spectrometry (HRMS) to see the effects of UV-irradiation on the lipids' chemical structure and organization. Our results suggest that in expanded monolayers of pure azidemodified membrane lipids, the azido-terminated chain folds back toward the air−water interface. Above the LE/LC (liquidexpanded/liquid-condensed) phase transition, the chains stretched, and thus, the azide group detaches from the interface. From temperature-dependent monolayer compressions, we evaluated all relevant thermodynamic parameters of the monolayers, such as the phase transition pressure, the critical temperature, and the triple point, and compare them to those of model lipids. For future applications, we studied the miscibility of the azide-modified lipid with DPPC in monolayers and found at least a certain miscibility over all investigated mixing ratios ranging from 10 to 75% of the azidolipid. Finally, we irradiated the azidolipid monolayer with UV light at 305 nm and measured photodissociation of the azide, leading to chemical cross-linking with other lipids, which shows the potential to be used as a cross-linking agent within self-assembled lipid or lipid/protein layers.

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ChemInform Abstract: SYNTHESIS AND BIOLOGICAL ACTIVITY OF SOME LYZING AND FUSOGENICALLY ACTIVE PHOSPHOCHOLINE DERIVATIVES

Cited by 2 publications

References 0 publications

Azide-Modified Membrane Lipids: Synthesis, Properties, and Reactivity

Azide-Modified Membrane Lipids: Synthesis, Properties, and Reactivity

An Azidolipid Monolayer – Transitions, Miscibility, and UV Reactivity Studied by Infrared Reflection Absorption Spectroscopy

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