Structural and thermodynamic aspects of the interaction between heparan sulfate and analogues of melittin

Biochemistry
Elisabete GonçalvesJoachim Seelig

Abstract

Melittin is an amphipathic cationic peptide derived from honeybee venom with well-known cytolytic and antimicrobial properties. When coupled to cationic polymers or lipid molecules, it forms conjugates with high transfection efficiency and low toxicity with promising applications in gene therapy. A first step in the internalization of melittin and its conjugates is their binding to the cell surface, a reaction likely to involve heparan sulfate proteoglycans (HSPG). In the present work, we characterize the binding equilibrium of heparan sulfate (HS) with two melittin analogues, [Cys(1)]melittin (mel-SH) and retro-inverso [Cys(1)]melittin (ri-mel-SH). The terminal cysteine found in these peptides replaces the N-terminal glycine present in native melittin and allows covalent binding to other molecules. Isothermal titration calorimetry (ITC) reveals a high affinity of each melittin analogue to HS. Association constants of 4.7 x 10(4) and 3.5 x 10(5) M(-)(1) are found at physiological ionic strength and 15 degrees C for ri-mel-SH and mel-SH, respectively. The reaction enthalpy measured under these conditions is DeltaH(degrees)pep= 4.2 kcal/mol for ri-mel-SH and DeltaH(degrees)pep= 1.1 kcal/mol for mel-SH. The peptide-to-HS stoichiom...Continue Reading

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Citations

Jul 26, 2007·Biochemistry·Christine O SallumAndrei T Alexandrescu
Aug 29, 2012·Journal of the American Chemical Society·Shih-Hui LeeKenneth J Shea
May 12, 2009·Peptides·Jiun-Ming WuHueih Min Chen
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Feb 20, 2014·Journal of Controlled Release : Official Journal of the Controlled Release Society·Marco E FavrettoRoland Brock
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Jan 18, 2008·Journal of Molecular Recognition : JMR·Oksana Okhrimenko, Ilian Jelesarov
May 29, 2014·Organic & Biomolecular Chemistry·Ji YangHisakazu Mihara
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Jan 29, 2008·Biochemistry·Gabriela Klocek, Joachim Seelig
Sep 11, 2013·The Journal of Physical Chemistry. B·Gabriela QuébatteJoachim Seelig

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