Peptide name : Esculentin-2CHa

Source/Organism : Chiricahua leopard frog

Linear/Cyclic : Not found

Chirality : Not found

Peptide length: 37

C-terminal modification: Not found

N-terminal modification : Free

Non-natural peptide information: None

Assay type : Cytotoxicity assay, Cell TiterGlo Luminescent cell viability assay

Assay time : 24h

Activity : LC50 : 10μM

Cell line : A549 cells

Cancer type : Lung adenocarcinoma

Other activity : Not found

Amino acid composition bar chart :

Molecular mass : 3843.5619 Dalton

Aliphatic index : 0.975

Instability index : 15.627

Hydrophobicity (GRAVY) : 0.373

Isoelectric point : 9.7873

Charge (pH 7) : 4.7365

Aromaticity : 0.081

Molar extinction coefficient (cysteine, cystine): (0, 125)

Hydrophobic/hydrophilic ratio : 1.64285714

hydrophobic moment : -0.043

Missing amino acid : W,H,T,P,M,E,Y,N

Most occurring amino acid : K

Most occurring amino acid frequency : 6

Least occurring amino acid : R

Least occurring amino acid frequency : 1

Secondary structure fraction (Helix, Turn, Sheet): (0.3, 0.3, 0.3)

SMILES Notation: CC[C@H](C)[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccccc1)NC(=O)CN)[C@@H](C)CC)C(C)C)C(C)C)C(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CS)C(=O)O

1 : Attoub S, et al. Esculentin-2CHa: a host-defense peptide with differential cytotoxicity against bacteria, erythrocytes and tumor cells. Peptides. 2013; 39:95-102. doi: 10.1016/j.peptides.2012.11.004

Paper title : Esculentin-2CHa: a host-defense peptide with differential cytotoxicity against bacteria, erythrocytes and tumor cells.

Doi : https://doi.org/10.1016/j.peptides.2012.11.004

Abstract : The host-defense peptide, esculentin-2CHa (GFSSIFRGVA(10)KFASKGLGK D(20)LAKLGVDLVA(30) CKISKQC) shows potent (MIC≤6 μM) growth inhibitory activity against clinical isolates of multidrug-resistant strains of Staphylococcus aureus, Acinetobacter baumannii, and Stenotrophomonas maltophilia and differential cytotoxic activity against human erythrocytes (LC(50)=150 μM) and human non-small cell lung adenocarcinoma A549 cells (LC(50)=10 μM). Esculentin-2CHa significantly (P<0.01) stimulates the release of the anti-inflammatory cytokine IL-10 by mouse lymphoid cells and elevates its production after stimulation with concanavalin A and significantly (P<0.05) stimulates TNF-α production by peritoneal macrophages. Effects on IL-6 and IL-1β production were not significant. Removal of the hydrophobic N-terminal hexapeptide (GFSSIF) from esculentin-2CHa results in abolition of growth inhibitory activity against S. aureus and cytotoxic activity against erythrocytes and A549 cells as well as a marked (≥16-fold) reduction in potency against A. baumannii and S. maltophilia. The primary structure of esculentin-2 has been poorly conserved between frog species but evolutionary pressure has acted to maintain the hydrophobic character of this N-terminal hexapeptide sequence. Removal of the cyclic C-terminal domain (CKISKQC) and replacement of the Cys(31) and Cys(37) residues by serine resulted in appreciable decreases in cytotoxicity against all microorganisms and against mammalian cells. The more cationic [D20K, D27K] analog showed a modest increase in potency against all microorganisms (up to 4-fold) but a marked increase in cytotoxicity against erythrocytes (LC(50)=11 μM) and A549 cells (LC(50)=3 μM).