Synthesis, biophysical and functional studies of two BP100 analogues modified by a hydrophobic chain and a cyclic peptide

Biochimica Et Biophysica Acta. Biomembranes
Gustavo P B CarreteroIolanda M Cuccovia

Abstract

Antimicrobial peptides (AMPs) work as a primary defense against pathogenic microorganisms. BP100, (KKLFKKILKYL-NH2), a rationally designed short, highly cationic AMP, acts against many bacteria, displaying low toxicity to eukaryotic cells. Previously we found that its mechanism of action depends on membrane surface charge and on peptide-to-lipid ratio. Here we present the synthesis of two BP100 analogs: BP100‑alanyl‑hexadecyl‑1‑amine (BP100-Ala-NH-C16H33) and cyclo(1‑4)‑d‑Cys1, Ile2, Leu3, Cys4-BP100 (Cyclo(1‑4)‑cILC-BP100). We examined their binding to large unilamellar vesicles (LUV), conformational and functional properties, and compared with those of BP100. The analogs bound to membranes with higher affinity and a lesser dependence on electrostatic forces than BP100. In the presence of LUV, BP100 and BP100-Ala-NH-C16H33 acquired α-helical conformation, while Cyclo(1‑4)‑cILC-BP100) was partly α-helical and partly β-turn. Taking in conjunction: 1. particle sizes and zeta potential, 2. effects on lipid flip-flop, 3. leakage of LUVs internal contents, and 4. optical microscopy of giant unilamellar vesicles, we concluded that at high concentrations, all three peptides acted by a carpet mechanism, while at low concentrations the ...Continue Reading

Citations

Jun 5, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Andrea Díaz-RoaFelio J Bello
Jun 15, 2019·Scientific Reports·Peter ParkFilipe S Lima
Oct 17, 2018·Frontiers in Microbiology·Andrea Díaz-RoaPedro I Da Silva
Mar 31, 2019·Biochimica Et Biophysica Acta. Biomembranes·Isabel C M FensterseiferOctavio L Franco
May 1, 2021·Biomolecules·Gustavo Penteado Battesini CarreteroIolanda Midea Cuccovia
Jan 29, 2020·Biochimica Et Biophysica Acta. Biomembranes·N P SantistebanV Booth
Jul 3, 2021·International Journal of Molecular Sciences·Ruslan KashapovOleg Sinyashin
Oct 8, 2019·Langmuir : the ACS Journal of Surfaces and Colloids·Marcio M AlmeidaKarin A Riske

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