Interaction of lipophilic peptides derived from mastoparan with phospholipid vesicles.
Various kinds of lipophilic peptides were prepared by acylation of an alpha-helical peptide, mastoparan, to investigate the effects of acyl groups on the interaction of peptides with phospholipid membranes. alpha-Helicity of the peptides was increased by introduction of long acyl groups. Acyl peptides showed different membrane-perturbation activities for neutral and acidic phospholipid vesicles, whereas a peptide with a dialkycarbamoyl group always exhibited a strong activity. High hemolytic activities were observed for the peptides with long acyls (single or double chain). These results indicate that lipophilic groups introduced to mastoparan contribute greatly to the interaction of the peptide with phospholipid membranes with lengthening of the acyl chain and that the structural character of the lipophilic group also influences the conformation of the peptide.
Niidome
T
T
Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, Japan. tanido@net.nagasaki-u.ac.jp
Kawakami
R
R
Okamoto
K
K
Ohmori
N
N
Mihara
H
H
Aoyagi
H
H
D015060:1,2-Dipalmitoylphosphatidylcholine / Q000378:metabolism; D000215:Acylation; D002942:Circular Dichroism; D015195:Drug Design; D006461:Hemolysis; D036341:Intercellular Signaling Peptides and Proteins; D008081:Liposomes / Q000378:metabolism*; D008563:Membrane Lipids / Q000378:metabolism; D010455:Peptides / Q000138:chemical synthesis* / Q000378:metabolism*; D010715:Phosphatidylglycerols / Q000378:metabolism; D010743:Phospholipids / Q000378:metabolism*; D017433:Protein Structure, Secondary; D013329:Structure-Activity Relationship; D014862:Wasp Venoms / Q000737:chemistry*
D036341:Intercellular Signaling Peptides and Proteins; D008081:Liposomes; D008563:Membrane Lipids; D010455:Peptides; D010715:Phosphatidylglycerols; D010743:Phospholipids; D014862:Wasp Venoms; D015060:1,2-Dipalmitoylphosphatidylcholine; C037500:mastoparan; C030345:1,2-dipalmitoylphosphatidylglycerol