General Information
-
DRAMP ID
- DRAMP21619
-
Peptide Name
- sWWSP
-
Sequence
- PLIⓀLRLⒹRGQF
-
Sequence Length
- 12
-
Original Sequence
- PLILLRLLRGQF
-
Source
- Synthetic construct
Activity Information
-
Biological Activity
- Antimicrobial, Antibacterial, Anti-Gram+, Anti-Gram-
-
Comments
- Function: Antibacterial activity against Gram-positive and Gram-negative bacteria.
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Target Organism
-
- [Ref.28921993] Gram-positive bacteria: Staphylococcus aureus (MIC > 256 μg/mL), Enterococcus faecalis (MIC > 256 μg/mL);
- Gram-negative bacteria: Escherichia coli (MIC > 256 μg/mL), Pseudomonas aeruginosa (MIC > 256 μg/mL)
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Hemolytic Activity
-
- [Ref.28921993] It has 4.0%, 4.8%, 4.6%, 4.2% and 7.0% hemolysis against human red blood cells at 15, 20, 25, 30 and 40 μg/ml.
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Cytotoxicity
-
- [Ref.28921993] The toxicity of sWWSP toward HEK293 and HeLa cells is much less than nonaarginine (R9) by use of flow cytometry and the peptide doesn't show any cytotoxicity at 2 μM.
Structure Information
-
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
- Ⓚ (4) and Ⓓ (8) are cross-linked by lactam stapling through the polar amide bond of a lactam bridge.
-
Stereochemistry
- L
-
Secondary Structure
- ①α-helix in aqueous solutions [pure water (H₂O), phosphate buffer (PB, 10 mM), and phosphate buffer with high salt (NaF, 100 mM)]. ②43% average α-helix content in various membranes environments [38% in POPC; 58% in POPC/POPG(3:1); 47% in POPC:lysoPC(9:1);
-
Structure Description
- On the other hand, sWWSP and sMAP-1 assumed an α-helical conformation in aqueous solution, in contrast to their unstructured linear countparts.
-
Helical Wheel Diagram
-
Predicted Structure
- There is no predicted structure for DRAMP21619.
Physicochemical Information
-
Formula
- C₆₉H₁₁₇N₁₉O₁₃
Absent Amino Acids
- ACEHMNSTVWY
Common Amino Acids
- L
Mass
- 1420.8
PI
- /
-
Basic Residues
- 3
Acidic Residues
- 1
Hydrophobic Residues
- 5
Hydrophobicity
- /
Polar Residues
- 1
DRAMP21619
Literature Information
- Literature 1
-
Title
- Lactam-Stapled Cell-Penetrating Peptides: Cell Uptake and Membrane Binding Properties.
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Pubmed ID
- 28921993
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Reference
- J Med Chem. 2017 Oct 12;60(19):8071-8082. doi: 10.1021/acs.jmedchem.7b00813. Epub 2017 Sep 26.
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Author
- Marco J Klein, Samuel Schmidt, Parvesh Wadhwani, Jochen Bürck, Johannes Reichert, Sergii Afonin, Marina Berditsch, Tim Schober, Roland Brock, Manfred Kansy, Anne S Ulrich