dbacp07997
General Description
Peptide name : [G10a]SHa-BCTP
Source/Organism : Synthetic analogue of Temporin-1SHa
Linear/Cyclic : Linear
Chirality : Mix
Sequence Information
Sequence : FLSGIVGMLaKLFLFKQYAELW
Peptide length: 22
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 : 2575.1159 Dalton
Aliphatic index : 1.240
Instability index : 16.1227
Hydrophobicity (GRAVY) : 1.0455
Isoelectric point : 8.4976
Charge (pH 7) : 0.7599
Aromaticity : 22.72
Molar extinction coefficient (cysteine, cystine): (0, 0)
Hydrophobic/hydrophilic ratio : 2.5
hydrophobic moment : 0.2839
Missing amino acid : C,D,H,N,P,R,T
Most occurring amino acid : L
Most occurring amino acid frequency : 5
Least occurring amino acid : S
Least occurring amino acid frequency : 1
Structural Information
3D structure :
Secondary structure fraction (Helix, Turn, Sheet): (50., 13., 54.)
SMILES Notation: CC[C@H](C)[C@H](NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)Cc1ccccc1)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O)C(C)C
Secondary Structure :
| Method | Prediction |
|---|---|
| GOR | EETTHHHHHHHHHHHHHHHHHH |
| Chou-Fasman (CF) | EEEEEEHHHHHHHHCHHHHCCC |
| Neural Network (NN) | CCCHHHHHHHHHHHHHHHHHHH |
| Joint/Consensus | EECCHHHHHHHHHHHHHHHHHH |
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: 5884
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.