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Cyclodextrin-Lipid Complexes: Cavity Size Matters

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Abstract

Lipids being hydrophobic or amphiphilic can be encapsulated by cyclodextrin complexation. Among the various groups of lipids cholesterol, fatty acids, phospholipids and sphingolipids are overviewed concerning the structural requirements for both the lipid and the cyclodextrin component of the complexes. The chain length and the number and position of the double bonds in the fatty acids, the polarity of the head-group in the phospholipids and sphingolipids are important factors. Concerning the cyclodextrins, in addition to the most crucial cavity size also the chemical microenvironment of cavity entrances determine the interaction with lipids. While fatty acids, phospholipids and sphingolipids prefer the alpha-cyclodextrin cavity, cholesterol is complexed first of all by the beta-cyclodextrin and its derivatives. Methylated beta-cyclodextrin has extreme affinity to all of these lipids, which are common constituents of cell membranes. Based on the knowledge on the specific cyclodextrin-lipid interactions, cyclodextrin derivatives are able to selectively remove certain lipid components from model and biological membranes and can be selected making possible to modulate the lipid profile in such membranes.

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Abbreviations

ACD:

Alpha-cyclodextrin

ALA:

Alpha-linolenic acid

BCD:

Beta-cyclodextrin

BCFA:

Branched chain fatty acid

CD:

Cyclodextrin

CMC:

Critical micelle concentration

DIMEB:

Dimethyl beta-cyclodextrin

DHA:

Docosahexaenoic acid

DLPC:

Dilauroyl phosphatidylcholine

DMPC:

Dimyristoyl phosphatidylcholine

DPPC:

Dipalmitoyl phosphatidylcholine

DS:

Degree of substitution

DSPC:

Distearoyl phosphatidylcholine

EPA:

Eicosapentaenoic acid

FA:

Fatty acid

HPBCD:

Hydroxypropyl beta-cyclodextrin

GCD:

Gamma-cyclodextrin

LBPA:

Lysobisphosphatidic acid

LUV:

Large unilamellar vesicle

PLPC:

Palmitoyl-l-α-lysophosphatidylcholine

POPC:

1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylcholine

PC:

Phosphatidylcholines

PE:

Phosphatidylethanolamines

PI:

Phosphoinositides

PS:

Phosphatidylserines

PUFA:

Polyunsaturated fatty acid

RAMEA:

Randomly methylated alpha-cyclodextrin

RAMEB:

Randomly methylated beta-cyclodextrin

RAMEG:

Random methylated gamma-cyclodextrin

SBEACD:

Sulfobutylether alpha-cyclodextrin

SBEBCD:

Sulfobutylated beta-cyclodextin

SBEGCD:

Sulfobutylated gamma-cyclodextrin

SPM:

Sphingomyelins

SUV:

Small unilamellar vesicle

TRIMEA:

Hexakis(2,3,6-tri-O-methyl) alpha-cyclodextrin

TRIMEB:

Heptakis(2,3,6-tri-O-methyl) beta-cyclodextrin

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Acknowledgment

The financial support of National Research Fund (Multidrug project, NKFP-1A-041/2004) and EU Framework 7 (Tornado project, EU FP7 KBBE-2007-2-2-07-222720) is greatly acknowledged. The authors thank Mr. Mihaly Balint for the graphical illustrations.

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  1. CycloLab Cyclodextrin Research and Development Lab. Ltd., Illatos út 7, Budapest, 1097, Hungary

    Lajos Szente & Éva Fenyvesi

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Correspondence to Éva Fenyvesi.

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Szente, L., Fenyvesi, É. Cyclodextrin-Lipid Complexes: Cavity Size Matters. Struct Chem 28, 479–492 (2017). https://doi.org/10.1007/s11224-016-0884-9

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  • DOI: https://doi.org/10.1007/s11224-016-0884-9

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