dbacp08054
General Description
Peptide name : CyO4
Source/Organism : Viola odorata
Linear/Cyclic : Cyclic
Chirality : L
Sequence Information
Sequence : GIPCGESCVWIPCISSAIGCSCKNKVCYRN
Peptide length: 30
C-terminal modification: Cyclic
N-terminal modification : Cyclized
Non-natural peptide information:
Activity Information
Assay type : MTS assay
Assay time : 24-h
Activity : IC50 = 9.8 μM
Cell line : MDA-MB-231
Cancer type : Breast Cancer
Other activity : Antimicrobial,Cytotoxic
Physicochemical Properties
Amino acid composition bar chart :
Molecular mass : 3191.7691 Dalton
Aliphatic index : 0.746
Instability index : 32.9767
Hydrophobicity (GRAVY) : 0.3533
Isoelectric point : 8.3338
Charge (pH 7) : 1.7005
Aromaticity : 6.666
Molar extinction coefficient (cysteine, cystine): (6, 3)
Hydrophobic/hydrophilic ratio : 1.7273
hydrophobic moment : 0.1281
Missing amino acid : D,F,H,L,M,Q,T
Most occurring amino acid : C
Most occurring amino acid frequency : 6
Least occurring amino acid : E
Least occurring amino acid frequency : 1
Structural Information
3D structure :
Secondary structure fraction (Helix, Turn, Sheet): (13., 36., 26.)
SMILES Notation: CC[C@H](C)[C@H](NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CS)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H](NC(=O)[C@H](CS)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(=O)O)NC(=O)CNC(=O)[C@H](CS)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)C(C)C)[C@@H](C)CC)[C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CS)C(=O)N[C@@H](CO)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(N)=O)C(=O)O)C(C)C
Secondary Structure :
| Method | Prediction |
|---|---|
| GOR | CCCTCCTEEECCECCCCCCCTTTTTTEETT |
| Chou-Fasman (CF) | EECCCEEEEEEEEEEEEECCCCCEEECCCC |
| Neural Network (NN) | CCCCCCCCCEEECCCCCCCCCCCCCCCCCC |
| Joint/Consensus | CCCCCCCEEEEEECCCCCCCCCCCCCCCCC |
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: 5974
Reference
1 : Pinto MEF, et al. Inhibition of Breast Cancer Cell Migration by Cyclotides Isolated from Pombalia calceolaria. J Nat Prod. 2018; 81:1203-1208. doi: 10.1021/acs.jnatprod.7b00969
Literature
Paper title : Inhibition of Breast Cancer Cell Migration by Cyclotides Isolated from Pombalia calceolaria.
Doi : https://doi.org/10.1021/acs.jnatprod.7b00969
Abstract : Two new bracelet cyclotides from roots of Pombalia calceolaria with potential anticancer activity have been characterized in this work. The cyclotides Poca A and B (1 and 2) and the previously known CyO4 (3) were de novo sequenced by MALDI-TOF/TOF mass spectrometry (MS). The MS2 spectra were examined and the amino acid sequences were determined. The purified peptides were tested for their cytotoxicity and effects on cell migration of MDA-MB-231, a triple-negative breast cancer cell line. The isolated cyclotides reduced the number of cancer cells by more than 80% at 20 μM, and the concentration-related cytotoxic responses were observed with IC<sub>50</sub> values of 1.8, 2.7, and 9.8 μM for Poca A (1), Poca B (2), and CyO4 (3), respectively. Additionally, the inhibition of cell migration (wound-healing assay) exhibited that CyO4 (3) presents an interesting activity profile, in being able to inhibit cell migration (50%) at a subtoxic concentration (2 μM). The distribution of these cyclotides in the roots was analyzed by MALDI imaging, demonstrating that all three compounds are present in the phloem and cortical parenchyma regions.