dbacp07421
General Description
Peptide name : Si15
Source/Organism : Synthetic
Linear/Cyclic : Linear
Chirality : L
Sequence Information
Sequence : KnLAKnLAK
Peptide length: 9
C-terminal modification: Linear
N-terminal modification : Amidation
Non-natural peptide information: nL = nor-Leu
Activity Information
Assay type : MTT assay
Assay time : 72-h
Activity : IC50 = 140.3 ± 7.12 µM
Cell line : MCF-7
Cancer type : Breast Cancer
Other activity : Antimicrobial and Anticancer
Physicochemical Properties
Amino acid composition bar chart :
Molecular mass : 999.2084 Dalton
Aliphatic index : 1.088
Instability index : 8.8889
Hydrophobicity (GRAVY) : -0.833
Isoelectric point : 10.302
Charge (pH 7) : 2.7571
Aromaticity : 0
Molar extinction coefficient (cysteine, cystine): (0, 0)
Hydrophobic/hydrophilic ratio : 1.3333
hydrophobic moment : -1.160
Missing amino acid : C,D,E,F,G,H,I,M,N,P,Q,R,S,T,V,W,Y
Most occurring amino acid : K
Most occurring amino acid frequency : 3
Least occurring amino acid : n
Least occurring amino acid frequency : 2
Structural Information
3D structure :
Secondary structure fraction (Helix, Turn, Sheet): (77., 22., 22.)
SMILES Notation: CC(C)C[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](N)CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)O
Secondary Structure :
| Method | Prediction |
|---|---|
| GOR | HHHHHHHHH |
| Chou-Fasman (CF) | HHHHHHCCC |
| Neural Network (NN) | HHHHHHHHH |
| Joint/Consensus | HHHHHHHHH |
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: 6853
Reference
1 : Jaber S, et al. Synthesis, Antitumor and Antibacterial Studies of New Shortened Analogues of (KLAKLAK)<sub>2</sub>-NH<sub>2</sub> and Their Conjugates Containing Unnatural Amino Acids. Molecules. 2021; 26:(unknown pages). doi: 10.3390/molecules26040898
Literature
Paper title : Synthesis, Antitumor and Antibacterial Studies of New Shortened Analogues of (KLAKLAK)<sub>2</sub>-NH<sub>2</sub> and Their Conjugates Containing Unnatural Amino Acids.
Doi : https://doi.org/10.3390/molecules26040898
Abstract : (1) Background: (KLAKLAK)<sub>2</sub> is a representative of the antimicrobial peptide group which also shows good anticancer properties. (2) Methods: Herein, we report synthesis using SPPS and characterization by HPLC/MS of a series of shortened analogues of (KLAKLAK)<sub>2</sub>. They contain single sequence KLAKLAK as C-terminal amides. In addition, substitution of some natural amino acids with unnatural β-Ala and nor-Leu is realized. In addition, these structures are conjugated with second pharmacophore with well proven anticancer properties 1,8-naphthalimide or caffeic acid. Cytotoxicity, antiproliferative effect and antimicrobial activity of newly synthesized structures were studied. (3) Results: The obtained experimental results reveal significant selective index for substances with common chemical structure KLβAKLβAK-NH<sub>2</sub>. The antibacterial properties of newly synthesized analogues at two different concentrations 10 μM and 20 μM, were tested against Gram-negative microorganisms Escherichia coli K12 407. Only two of the studied compounds KLAKLAK-NH<sub>2</sub> and the one conjugated with second pharmacophore 1,8-naphthalimide and unnatural amino acid nor-Leu showed moderate activity against tested strains at concentration of 20 μM. (4) Conclusions: The obtained results reveal that the introducing of 1,8-naphthalimideGly- and Caf- increase the cytotoxicity and antiproliferative activity of the peptides but not their selectivity. Only two compounds KLAKLAK-NH<sub>2</sub> and 1,8-naphthalimideGKnLAKnLAK-NH<sub>2</sub> show moderate activity against Escherichia coli K12 at low concentration of 20μM.