NMR structural characterization of cecropin A(1-8) - magainin 2(1-12) and cecropin A (1-8) - melittin (1-12) hybrid peptides

J Pept Res. 1999 May;53(5):578-89. doi: 10.1034/j.1399-3011.1999.00067.x.

Abstract

In order to elucidate the structure-antibiotic activity relationships of the peptides, the three-dimensional structures of two hybrid peptides, CA(1-8) - MA(1-12) and CA(1-8) - ME(1-12) in trifluoroethanol-containing aqueous solution were investigated by NMR spectroscopy. Both CA(1-8) - MA(1-12) and CA(1-8) - ME(1-12) have strong antibacterial activity but only CA(1-8) - ME(1-12) has hemolytic activity against human erythrocytes. CA(1-8) - MA(1-12) has a hydrophobic 310-helix of only two turns combined with one short helix in the N-terminus with a flexible hinge section in between. CA(1-8) - MA(1-12) has a severely bent structure in the middle of the peptide. These structural features as well as the low hydrophobicity of CA(1-8) - MA(1-12) seem to be crucial for the selective lysis against the membrane of prokaryotic cells. CA(1-8) - ME(1-12) has an alpha-helical structure of about three turns in the melittin domain and a flexible structure with one turn in the cecropin domain connected with a flexible hinge section in between, and these might be the structural features required for membrane disruption against prokaryotic and eukaryotic cells. The central hinge region (Gly9-Ile10-Gly11) in an amphipathic antibacterial peptide is considered to play an important role in providing the conformational flexibility required for ion channel formation of the C-terminal hydrophobic alpha-helix on cell membrane.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Antimicrobial Cationic Peptides*
  • Carcinoma, Small Cell / pathology
  • Circular Dichroism
  • Erythrocytes / drug effects
  • Hemolysin Proteins / chemistry*
  • Hemolysin Proteins / pharmacology
  • Humans
  • Lung Neoplasms / pathology
  • Magnetic Resonance Spectroscopy*
  • Melitten / analogs & derivatives*
  • Melitten / chemistry
  • Melitten / pharmacology
  • Models, Molecular
  • Molecular Sequence Data
  • Peptides / chemistry*
  • Peptides / pharmacology
  • Protein Conformation
  • Structure-Activity Relationship
  • Tumor Cells, Cultured / drug effects

Substances

  • Anti-Bacterial Agents
  • Antimicrobial Cationic Peptides
  • Hemolysin Proteins
  • Peptides
  • cecropin A(1-8)magainin 2(1-12)
  • cecropin A(1-8)melittin(1-2)
  • Melitten