Synthesis and Application of Neoglycolipids for Liposome Modification

We synthesized various glycolipid derivatives and examined the in vivo behaviors of liposomes modified with these movel glycolipid derivatives. Gal-t-pas (1, {8-(2-hexadecyloctadecanoylamino)-3, 6-dioxaoctyl}-β-D-galactoside), Lac-t-psa (3, 8-(2-hexadecyloctadecanoylamino)-3, 6-dioxaoctyl β-D-lactos...

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Bibliographic Details
Published in:Biological & pharmaceutical bulletin 1997/06/15, Vol.20(6), pp.704-707
Main Authors: MURAHASHI, Naokazu, ISHIHARA, Hiroshi, SAKAGAMI, Masahiro, SASAKI, Atsushi
Format: Article
Language:English
Subjects:
Animals
Biological and medical sciences
Drug Stability
General pharmacology
glycolipid
Glycolipids - chemical synthesis
Glycolipids - chemistry
Ligands
liposome
Liposomes - chemistry
Liposomes - pharmacokinetics
Liver - metabolism
Male
Medical sciences
Pharmaceutical technology. Pharmaceutical industry
Pharmacokinetics. Pharmacogenetics. Drug-receptor interactions
Pharmacology. Drug treatments
rat
Rats
Rats, Sprague-Dawley
Structure-Activity Relationship
targeting
Tissue Distribution
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Summary:We synthesized various glycolipid derivatives and examined the in vivo behaviors of liposomes modified with these movel glycolipid derivatives. Gal-t-pas (1, {8-(2-hexadecyloctadecanoylamino)-3, 6-dioxaoctyl}-β-D-galactoside), Lac-t-psa (3, 8-(2-hexadecyloctadecanoylamino)-3, 6-dioxaoctyl β-D-lactoside) and GalNAc-t-psa (4, 8-(2-hexadecyloctadecanoylamino)-3, 6-dioxaoctyl 2-acetamido-β-D-galactopyranoside) modified liposomes were recognized by the liver. Lac-t-psa (3) modified liposome was accumulated to the highest degree, followed by GalNAc-t-psa (4) modified liposome and then Gal-t-psa (1) modified liposome. The intrahepatic distributions of Gal-t-psa (1), GalNAc-t-psa (4), Glc-t-psa (2, 8-(2-hexadecyloctadecanoylamido)-3, 6-dioxaoctylβ-D-glucopyranoside) and Lac-t-psa (3) modified liposomes were investigated. GalNAc-t-psa (4) and Lac-t-psa (3) modified liposome were accumulated to greater extents than Gal-t-psa (1) modified liposome in hepatic parenchymal cells. The intrahepatic distribution of these liposomes showed that Lac-t-psa (3) and GalNAc-t-psa (4) were preferable to Gal-t-psa (1) for the selective delivery of liposomes to hepatic parenchymal cells.
ISSN:0918-6158
1347-5215
DOI:10.1248/bpb.20.704