Phospholipid conjugates: formation of the intramolecular π-cation complex
Abstract Phospholipid conjugates consist of functionally different classes of molecules: phospholipid drug conjugates, fluorescent lipid probes and lipid molecular motors. All these conjugates are molecules that bear a functional group– a drug, a fluorophore or a molecular motor attached to the phos...
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| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
BMC
2025-05-01
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| Series: | BMC Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.1186/s13065-025-01526-x |
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| Summary: | Abstract Phospholipid conjugates consist of functionally different classes of molecules: phospholipid drug conjugates, fluorescent lipid probes and lipid molecular motors. All these conjugates are molecules that bear a functional group– a drug, a fluorophore or a molecular motor attached to the phospholipid. The conjugation is needed to incorporate a functional group into the lipid bilayer of liposome or lipid nanoparticle and thus, either modulate the effect of the drug or bring a new function to the liposome. Here, using NMR spectroscopy and quantum chemistry calculations, we show that phospholipid conjugates can form intramolecular π-cation complexes between quaternary ammonium group of the phosphatidylcholine and aromatic ring of the conjugated moiety. We also report on how to avoid the π-cation complex formation. If the linker between the aromatic moiety and the choline group is long enough the formation of π-cation complex is not observed. |
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| ISSN: | 2661-801X |