Aggregate formation in the intercalation of long-chain fatty acid esters into liposomes

Yael Cohen; Michal Afri; Aryeh A. Frimer

doi:10.1016/j.chemphyslip.2008.07.005

Aggregate formation in the intercalation of long-chain fatty acid esters into liposomes

Yael Cohen, Michal Afri, Aryeh A. Frimer

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

Various hydrophobic benzenediacetic esters, the corresponding benzenedipropionic esters, and branched alkyl esters were intercalated into DMPC liposomes, where the molar ratio (n/n) of ester:DMPC was 1:5. In the case of the very long-chain derivatives, double carbonyl peaks were observed in the ¹³C NMR spectrum. This doubling phenomenon was observed only for the carbonyl peaks, whose chemical shift is most sensitive to solvent polarity, and disappeared when the ester:DMPC molar ratio drops below 1:15. This doubling reflects the presence of two populations in these samples: one group includes those molecules which are intercalated within the liposome and feel the polarity corresponding to the liposomal microenvironment; the other consists of aggregates of these long-chain derivatives located in the extra-liposomal aqueous phase.

Original language	English
Pages (from-to)	120-125
Number of pages	6
Journal	Chemistry and Physics of Lipids
Volume	155
Issue number	2
DOIs	https://doi.org/10.1016/j.chemphyslip.2008.07.005
State	Published - Oct 2008

Bibliographical note

Funding Information:
We acknowledge the kind and generous support of the Israel Science Foundation (Grants Number 327/02 and 437/06) founded by The Israel Academy of Sciences and Humanities, and The Ethel and David Resnick Chair in Active Oxygen Chemistry.

Funding

We acknowledge the kind and generous support of the Israel Science Foundation (Grants Number 327/02 and 437/06) founded by The Israel Academy of Sciences and Humanities, and The Ethel and David Resnick Chair in Active Oxygen Chemistry.

Funders	Funder number
Israel Academy of Sciences and Humanities
Israel Science Foundation	327/02, 437/06

Keywords

Aggregate
C NMR
DMPC
E(30)
Liposome
Membrane

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10.1016/j.chemphyslip.2008.07.005

Cite this

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title = "Aggregate formation in the intercalation of long-chain fatty acid esters into liposomes",

abstract = "Various hydrophobic benzenediacetic esters, the corresponding benzenedipropionic esters, and branched alkyl esters were intercalated into DMPC liposomes, where the molar ratio (n/n) of ester:DMPC was 1:5. In the case of the very long-chain derivatives, double carbonyl peaks were observed in the 13C NMR spectrum. This doubling phenomenon was observed only for the carbonyl peaks, whose chemical shift is most sensitive to solvent polarity, and disappeared when the ester:DMPC molar ratio drops below 1:15. This doubling reflects the presence of two populations in these samples: one group includes those molecules which are intercalated within the liposome and feel the polarity corresponding to the liposomal microenvironment; the other consists of aggregates of these long-chain derivatives located in the extra-liposomal aqueous phase.",

keywords = "Aggregate, C NMR, DMPC, E(30), Liposome, Membrane",

author = "Yael Cohen and Michal Afri and Frimer, \{Aryeh A.\}",

note = "Funding Information: We acknowledge the kind and generous support of the Israel Science Foundation (Grants Number 327/02 and 437/06) founded by The Israel Academy of Sciences and Humanities, and The Ethel and David Resnick Chair in Active Oxygen Chemistry.",

year = "2008",

month = oct,

doi = "10.1016/j.chemphyslip.2008.07.005",

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AU - Cohen, Yael

AU - Afri, Michal

AU - Frimer, Aryeh A.

N1 - Funding Information: We acknowledge the kind and generous support of the Israel Science Foundation (Grants Number 327/02 and 437/06) founded by The Israel Academy of Sciences and Humanities, and The Ethel and David Resnick Chair in Active Oxygen Chemistry.

PY - 2008/10

Y1 - 2008/10

N2 - Various hydrophobic benzenediacetic esters, the corresponding benzenedipropionic esters, and branched alkyl esters were intercalated into DMPC liposomes, where the molar ratio (n/n) of ester:DMPC was 1:5. In the case of the very long-chain derivatives, double carbonyl peaks were observed in the 13C NMR spectrum. This doubling phenomenon was observed only for the carbonyl peaks, whose chemical shift is most sensitive to solvent polarity, and disappeared when the ester:DMPC molar ratio drops below 1:15. This doubling reflects the presence of two populations in these samples: one group includes those molecules which are intercalated within the liposome and feel the polarity corresponding to the liposomal microenvironment; the other consists of aggregates of these long-chain derivatives located in the extra-liposomal aqueous phase.

AB - Various hydrophobic benzenediacetic esters, the corresponding benzenedipropionic esters, and branched alkyl esters were intercalated into DMPC liposomes, where the molar ratio (n/n) of ester:DMPC was 1:5. In the case of the very long-chain derivatives, double carbonyl peaks were observed in the 13C NMR spectrum. This doubling phenomenon was observed only for the carbonyl peaks, whose chemical shift is most sensitive to solvent polarity, and disappeared when the ester:DMPC molar ratio drops below 1:15. This doubling reflects the presence of two populations in these samples: one group includes those molecules which are intercalated within the liposome and feel the polarity corresponding to the liposomal microenvironment; the other consists of aggregates of these long-chain derivatives located in the extra-liposomal aqueous phase.

KW - Aggregate

KW - C NMR

KW - DMPC

KW - E(30)

KW - Liposome

KW - Membrane

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U2 - 10.1016/j.chemphyslip.2008.07.005

DO - 10.1016/j.chemphyslip.2008.07.005

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AN - SCOPUS:53749100125

SN - 0009-3084

VL - 155

SP - 120

EP - 125

JO - Chemistry and Physics of Lipids

JF - Chemistry and Physics of Lipids

IS - 2

ER -

Aggregate formation in the intercalation of long-chain fatty acid esters into liposomes

Abstract

Bibliographical note

Funding

Keywords

Access to Document

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