dbacp08006
General Description
Peptide name : [G4,7a]SHa
Source/Organism : Synthetic analogue of Temporin-1SHa
Linear/Cyclic : Linear
Chirality : Mix
Sequence Information
Sequence : FLSaIVaMLGKLF
Peptide length: 13
C-terminal modification: Linear
N-terminal modification : Amidation
Non-natural peptide information:
Activity Information
Assay type : MTT assay
Assay time : 24-h
Activity : IC50 >100 µM
Cell line : HeLa
Cancer type : Cervical Cancer
Other activity : Antimicrobial
Physicochemical Properties
Amino acid composition bar chart :
Molecular mass : 1409.777 Dalton
Aliphatic index : 1.423
Instability index : -10.361
Hydrophobicity (GRAVY) : 2.0077
Isoelectric point : 8.7501
Charge (pH 7) : 0.7591
Aromaticity : 15.38
Molar extinction coefficient (cysteine, cystine): (0, 0)
Hydrophobic/hydrophilic ratio : 4.5
hydrophobic moment : 0.5739
Missing amino acid : A,C,D,E,H,N,P,Q,R,T,W,Y
Most occurring amino acid : L
Most occurring amino acid frequency : 3
Least occurring amino acid : S
Least occurring amino acid frequency : 1
Structural Information
3D structure :
Secondary structure fraction (Helix, Turn, Sheet): (53., 15., 53.)
SMILES Notation: CC[C@H](C)[C@H](NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)Cc1ccccc1)C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)O)C(C)C
Secondary Structure :
| Method | Prediction |
|---|---|
| GOR | HHHHHHHHHHHHH |
| Chou-Fasman (CF) | CEEEEHHHHHCCC |
| Neural Network (NN) | HHHHHHHHHHHHC |
| Joint/Consensus | HHHHHHHHHHHHC |
Molecular Descriptors and ADMET Properties
Molecular Descriptors: Click here to download
ADMET Properties: Click here to download
Cross Referencing databases
CancerPPD : Not available
ApIAPDB : Not available
CancerPPD2 ID: 5896
Reference
1 : Shaheen F, et al. Synthesis of breast cancer targeting conjugate of temporin-SHa analog and its effect on pro- and anti-apoptotic protein expression in MCF-7 cells. Peptides. 2018; 106:68-82. doi: 10.1016/j.peptides.2018.07.002
Literature
Paper title : Synthesis of breast cancer targeting conjugate of temporin-SHa analog and its effect on pro- and anti-apoptotic protein expression in MCF-7 cells.
Doi : https://doi.org/10.1016/j.peptides.2018.07.002
Abstract : The frog natural product temporin-SHa (FLSGIVGMLGKLF<sub>amide</sub>) is a potent antimicrobial peptide, as is the analog [S3K]SHa. By solid-phase synthesis, we prepared temporin-SHa and several temporin-SHa analogs with one or more D-alanine residues incorporated. The natural product and the analog [G10a]SHa were found to be cytotoxic in mammalian cell lines and induce cell death. To achieve selectivity, we conjugated the analog [G10a]SHa with a breast cancer targeting peptide (BCTP). The resulting peptide temporin [G10a]SHa-BCTP conjugate was selectively active against the MCF-7 breast cancer cell line with no cytotoxicity in NIH-3T3 fibroblasts. Unlike the natural product or [G10a]SHa, the conjugated peptide induced apoptosis, downregulating the expression of Bcl-2 and survivin and upregulating Bax and caspase-3.