| Chemical Information | |
| Antiviral agent ID | DrugRepV_6380 | |
| Antiviral agent name | (2S)-6-amino-2-[(2S)-5-carbamimidamido-2-[(4-{[(5Z)-4-oxo-3-(prop-2-en-1-yl)-2-sulfanylidene-1,3-thiazolidin-5-ylidene]methyl}phenyl)formamido]pentanamido]-N-[(1S)-1-carbamoylpentyl]hexanamide | |
| IUPAC Name | (2S)-6-amino-2-[(2S)-5-carbamimidamido-2-[(4-{[(5Z)-4-oxo-3-(prop-2-en-1-yl)-2-sulfanylidene-1,3-thiazolidin-5-ylidene]methyl}phenyl)formamido]pentanamido]-N-[(1S)-1-carbamoylpentyl]hexanamide |  |
| SMILES (isomeric) | CCCC[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(N)=N)NC(=O)C1=CC=C(\C=C2/SC(=S)N(CC=C)C2=O)C=C1)C(N)=O | |
| Molecular Formula | C32H47N9O5S2 | |
| Molecular Weight (g/mol) | 701.91 | |
| InChl | InChI=1S/C32H47N9O5S2/c1-3-5-9-22(26(34)42)38-28(44)23(10-6-7-16-33)40-29(45)24(11-8-17-37-31(35)36)39-27(43)21-14-12-20(13-15-21)19-25-30(46)41(18-4-2)32(47)48-25/h4,12-15,19,22-24H,2-3,5-11,16-18,33H2,1H3,(H2,34,42)(H,38,44)(H,39,43)(H,40,45)(H4,35,36,37)/b25-19-/t22-,23-,24-/m0/s1 | |
| Structural Information | |
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| Clinical Information | |
| Biological Information | |
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Secondary Indication | Dengue virus (DENV) 2 NA |   |
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Secondary Indication (Approaches) | Experimental | |
| Secondary Indication (Methods) | In-vitro | |
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Secondary Indication (Model system) [cell lines/ animal models] | Huh-7
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Secondary Indication (Mode of viral infection) | Adsorption
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Secondary Indication (Mode of drug delivery) | Culture
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Secondary Indication (Drug concentration) | 31.3 ± 1.3 μM
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Secondary Indication (Cell based assay) | Renilla luciferase assay
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Secondary Indication (Change) | Decrease
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Secondary Indication (Type of Inhibition) | EC50 [ 50 % ] | |
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Reference | Nitsche C, Schreier VN, Behnam MA, Kumar A, Bartenschlager R, Klein CD..Thiazolidinone-peptide hybrids as dengue virus protease inhibitors with antiviral activity in cell culture..J Med Chem. 2013 Nov 14;56(21):8389-403. doi: 10.1021/jm400828u. Epub 2013 Oct 22. PMID:24083834
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Comment | The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with Ki values between 1.5 and 1.8 μM and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.
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