| Chemical Information | |
| Antiviral agent ID | DrugRepV_6398 | |
| Antiviral agent name | (2S)-N-[(5S,8S)-1-amino-11-carbamimidamido-8-(2-{3-[(4-methoxyphenyl)methyl]-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-yl}acetamido)-6,7-dioxoundecan-5-yl]-2-hydrazinylhexanamide | |
| IUPAC Name | (2S)-N-[(5S,8S)-1-amino-11-carbamimidamido-8-(2-{3-[(4-methoxyphenyl)methyl]-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-yl}acetamido)-6,7-dioxoundecan-5-yl]-2-hydrazinylhexanamide |  |
| SMILES (isomeric) | CCCC[C@H](NN)C(=O)N[C@@H](CCCCN)C(=O)C(=O)[C@H](CCCNC(N)=N)NC(=O)CC1SC(=S)N(CC2=CC=C(OC)C=C2)C1=O | |
| Molecular Formula | C31H49N9O6S2 | |
| Molecular Weight (g/mol) | 707.91 | |
| InChl | InChI=1/C31H49N9O6S2/c1-3-4-8-23(39-35)28(44)38-22(9-5-6-15-32)27(43)26(42)21(10-7-16-36-30(33)34)37-25(41)17-24-29(45)40(31(47)48-24)18-19-11-13-20(46-2)14-12-19/h11-14,21-24,39H,3-10,15-18,32,35H2,1-2H3,(H,37,41)(H,38,44)(H4,33,34,36)/t21-,22-,23-,24?/s2 | |
| 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) | 30.3 ± 1.2 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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