Anchorage of Synthetic Peptides onto Liposomes via Hydrazone and -Oxo Hydrazone Bonds. Preliminary Functional Investigations
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- 作者：Line Bourel-Bonnet ; Eve-Isabelle Pé ; cheur ; Cyrille Grandjean ; Annick Blanpain ; Thorsten Baust ; Oleg Melnyk ; Bernard Hoflack ; and Hé ; lè ; ne Gras-Masse
- 刊名：Bioconjugate Chemistry
- 出版年：2005
- 出版时间：March 2005
- 年：2005
- 卷：16
- 期：2
- 页码：450 - 457
- 全文大小：144K
- 年卷期：v.16,no.2(March 2005)
- ISSN：1520-4812
文摘
Synthetic peptidoliposomes have been designed and prepared according to a chemoselective ligation.Two aldehyde-functionalized lipidic anchors were synthesized and incorporated into the lipidic bilayersof unilamellar liposomes during their preparation. Complementary hydrazino acetyl peptides weresynthesized on the solid phase using N,N',N'-tri(tert-butyloxycarbonyl)-hydrazino acetic acid andfurther coupled to the aldehyde groups displayed at the surface of the vesicles. Coupling yields weremeasured by amino acid hydrolysis following total acid hydrolysis. The ligation methodology provedsuperior to the simple insertion of lipopeptides, which was performed for comparison in terms of yields,implementation, and reproducibility. To check whether the grafted-peptides were accessible andfunctional, cytoplasmic sequences of LAMP protein (lysosomal associated membrane protein), whichis involved in intracellular membrane trafficking, have been selected. Using this model, wedemonstrated in vitro the specific interaction of the synthetic LAMP-peptidoliposomes with thecytoplasmic adaptor protein AP-3, a result that contributes to the understanding of protein sorting incells. Thus, these results clearly indicate the usefulness of such peptidoliposomes, easily prepared byhydrazone chemoselective ligation, as a tool for biological investigation.