Lipopeptide conjugates: biomolecular building blocks for receptor activating membrane-mimetic structures

Biomaterials
T M WingerE L Chaikof

Abstract

A simple method for the derivatization of phospholipid subunits with short peptide sequences is presented. Amphiphilic conjugates of distearoylphosphatidylethanolamine (DSPE) and the minimal human thrombin-receptor peptide agonist SFLLRN were synthesized via coupling of the bromoacetyl derivative of DSPE (PEBr) with a thiol-terminated decapeptide of SFLLRN. Bromoderivatization of DSPE was performed by condensation of bromoacetic acid and DSPE, with an overall yield of 40%. Coupling of PEBr and the unprotected thiol-terminated decapeptide was performed in chloroform/methanol/water in the presence of triethylamine and afforded 25.5% of the lipopeptide. The compound was characterized by TLC, 1H-NMR (600 MHz) and mass spectrometry. Lipopeptide bioactivity was confirmed by a platelet aggregation assay. The EC50 of the all-L amino acid lipopeptide was 38 +/- 3 microM. The all-D conjugate was inactive. Model receptor-activating systems, including well-ordered assemblies of amphiphilic phospholipid-peptide conjugates, represent the first step in the construction of bioactive surfaces for tissue engineering based on a membrane-mimetic approach.

References

Oct 30, 1992·Biochemical and Biophysical Research Communications·T SaboE Elhanaty
Feb 1, 1992·American Journal of Respiratory Cell and Molecular Biology·R Bar-ShavitI Vlodavsky
Jun 1, 1989·Trends in Biochemical Sciences·R E Steele
Dec 30, 1983·Journal of Immunological Methods·S C KinskyA L Benson
Oct 1, 1981·Analytical Biochemistry·V K SarinR B Merrifield
May 1, 1959·Archives of Biochemistry and Biophysics·G L ELLMAN

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Citations

Mar 9, 2005·Chemistry and Physics of Lipids·Stephanie Tristram-NagleJames W Schneider
Nov 8, 2014·Soft Matter·Maria-Teodora PopescuConstantinos Tsitsilianis
Apr 13, 1999·Bioorganic & Medicinal Chemistry·G B Fields
May 11, 2004·Biomacromolecules·Anastasia Mardilovich, Efrosini Kokkoli
May 14, 2003·Biomacromolecules·Navdeep B MalkarGregg B Fields

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