General Information
-
DRAMP ID
- DRAMP21478
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Peptide Name
- peptide 12 (derived from OH-CM6)
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Sequence
- KFFKKLKKAVKⓀGFKⓀFAKV
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Sequence Length
- 20
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Original Sequence
- KFFKKLKKAVKKGFKKFAKV
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Source
- Synthetic construct
Activity Information
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Biological Activity
- Antimicrobial, Antibacterial, Anti-Gram+, Anti-Gram-
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Comments
- Function: Antibacterial activity against Gram-positive and Gram-negative bacteria.
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Target Organism
-
- [Ref.32216308] Gram-positive bacteria: Staphylococcus aureus (MIC99.9= 4 μg/mL), methicillin-resistant Staphylococcus aureus (MIC99.9= 2 μg/mL), Listeria monocytogenes (MIC99.9= 4 μg/mL);
- Gram-negative bacteria: E.coli (MIC99.9= 4 μg/mL), Pseudomonas aeruginosa (MIC99.9= 8 μg/mL), clinically isolated drug-resistant E.coli (MIC99.9= 8 μg/mL)
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Hemolytic Activity
-
- [Ref.32216308] It has 8.7% hemolysis against red blood cells at peptide concentration of 320 μg/mL
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Cytotoxicity
-
- [Ref.32216308] The cell survial of HEK 293T cell line induced by peptide 12 is 102.9%, 101.8%, 101.5%, 66.4% and 62.8%.
Structure Information
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Linear/Cyclic
- Cyclic (Stapled)
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N-terminal Modification
- Free
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C-terminal Modification
- Amidation
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Special Amino Acid and Stapling Position
- ①The Ⓚ (position: 12 and 16) in sequence indicates Nε-o-Ns-Nα-Fmoc-lysine before stapling. ②Ⓚ (12) and Ⓚ (16) are cross-linked by a 1,2-baremethylenebenzene spacer employing the N-alkylation.
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Stereochemistry
- L
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Secondary Structure
- ①45% α-helical content in 30 mM SDS. ②Random coils in PBS.
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Structure Description
- ①All the peptides were random coils in PBS but displayed varied levels of α-helicity in the presence of 30 mM SDS. ②Stapled peptides 10 and 12 had a high content of α-helix of about 41 and 45%, respectively, respectively, which could partly explain their strong antibacterial activity and proteolytic resistance.
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Helical Wheel Diagram
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Predicted Structure
- Please click DRAMP21478 predicted structure to download. The green ribbons represent the stapling amino acids, and the green bonds are the bridge linking two residues of stapling amino acids.
Physicochemical Information
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Formula
- C₁₂₈H₂₁₁N₃₁O₂₀
Absent Amino Acids
- CDEHIMNPQRSTWY
Common Amino Acids
- K
Mass
- 2504.23
PI
- /
-
Basic Residues
- 8
Acidic Residues
- 0
Hydrophobic Residues
- 9
Hydrophobicity
- /
Polar Residues
- 1
DRAMP21478
Literature Information
- Literature 1
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Title
- Novel Stapling by Lysine Tethering Provides Stable and Low Hemolytic Cationic Antimicrobial Peptides
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Pubmed ID
- 32216308
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Reference
- J Med Chem. 2020 Apr 23;63(8):4081-4089. doi: 10.1021/acs.jmedchem.9b02025. Epub 2020 Apr 8.
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Author
- Hong Li, Yuchen Hu, Qi Pu, Tong He, Qianyu Zhang, Wen Wu, Xuefeng Xia and Jinqiang Zhang