Membrane association and contact formation by a synthetic analogue of polymyxin B and its fluorescent derivatives

The Journal of Physical Chemistry. B
Adrià ClausellY Cajal

Abstract

sP-B is a synthetic analogue of the natural lipopeptide antibiotic polymyxin B (PxB) that maintains the ability of the parent compound to form vesicle-vesicle contacts and induce lipid exchange. Exchange is selective, and only monoanionic phospholipids such as 1-palmitoyl-2-oleoyl-glycero-sn-3-phosphoglycerol (POPG) are transferred, whereas dianionic phospholipids such as 1-palmitoyl-2-oleoyl-glycero-sn-3-phosphate (POPA) are not, as shown by fluorescence experiments based on the excimer/monomer ratio of pyrene-labeled phospholipids. Synthetic fluorescent analogues of sP-B are used to investigate the peptide position and orientation in the intermembrane contacts: sP-Bw, an analogue that contains D-tryptophan (D-Trp) instead of the naturally occurring D-phenylalanine, and sP-Bpy, incorporating a pyrene group at the N-terminus. Tryptophan fluorescence, anisotropy, and quenching measurements performed with sP-Bw indicate that the peptide binds and inserts in anionic vesicles of POPG and POPA. However, significant differences are seen depending on the lipid composition, as also demonstrated by fluorescence resonance energy transfer (FRET) experiments from Trp to 7-nitro-2-1,3-benzoxadiazol (NBD) groups at the interface. Intermolecu...Continue Reading

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Citations

Jun 6, 2013·Journal of Medicinal Chemistry·Thomas V MageeJinshan Michael Chen
Oct 31, 2009·Journal of Medicinal Chemistry·Tony VelkovJian Li
Dec 25, 2015·Colloids and Surfaces. B, Biointerfaces·Ernesto E AmbroggioGerardo D Fidelio
Aug 9, 2012·Burns : Journal of the International Society for Burn Injuries·Ernest A AzzopardiWilliam A Dickson
May 30, 2015·Scientific Reports·Francesc RabanalYolanda Cajal
Feb 11, 2015·BioMed Research International·Zhiliang YuJuanping Qiu
Sep 15, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Héctor RudillaMiguel Viñas
Jun 20, 2017·Natural Product Reports·Francesc Rabanal, Yolanda Cajal
Dec 9, 2017·Probiotics and Antimicrobial Proteins·Satya Eswari Jujjavarapu, Swasti Dhagat
Aug 11, 2021·The Journal of Biological Chemistry·Ernesto E AmbroggioAndrea V Gamarnik
Nov 9, 2017·Biophysical Journal·Adree KhondkerMaikel C Rheinstädter

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