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Literature summary for 3.4.19.12 extracted from
- Structure-activity relationship, kinetic mechanism, and selectivity for a new class of ubiquitin C-terminal hydrolase-L1 (UCH-L1) inhibitors (2007), Bioorg. Med. Chem. Lett., 17, 3729-3732.
Application
| Application | Comment | Organism |
|---|---|---|
| medicine | class of 3-amino-2-keto-7H-thieno[2,3-b]pyridin-6-one derivatives as UCH-L1 inhibitors provide useful tools for investigating the role of UCH-L1 in normal cellular physiology, as well as in pathological conditions, such as Parkinsons disease and some forms of cancer | Mus musculus |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| 3-amino-2-(cyclohexylcarbonyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus |  |
| 3-amino-2-keto-7Hthieno[2,3-b]pyridin-6-one derivative | - |
Mus musculus | |
| 3-amino-2-[(2-methoxyphenyl)carbonyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
| 3-amino-2-[(4-chlorophenyl)carbonyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
| 3-amino-2-[(4-methylphenyl)carbonyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
| 3-amino-2-[(4-tert-butylphenyl)carbonyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
| 3-amino-2-[(naphthalen-1-yloxy)carbonyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
| 3-amino-2-[(naphthalen-2-yloxy)carbonyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
| 3-amino-6-oxo-2-[[4-(trifluoromethyl)phenyl]carbonyl]-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
| additional information | class of 3-amino-2-keto-7H-thieno[2,3-b]pyridin-6-one derivatives are moderately potent UCH-L1 inhibitors. Carboxylate at the 5-position and the 6-pyridinone ring are necessary for inhibitory activity. Inhibitory activity is dependent on the nature of the ketone substituent at the 2-position, with 4-Me-Ph and 2-naphthyl being best. Compounds are uncompetitive inhibitors of UCH-L1, binding only to the Michaelis-complex and not to free enzyme. Active compounds are selective for UCH-L1, exhibiting no inhibition of other cysteine hydrolases or cytotoxicity in serum starved N2A cells. Not inhibited by compound 9, 17, 19, 22, 24, 27, 28, 29, 30, 32 and 33 | Mus musculus |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Mus musculus | - |
- |
- |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| Neuro-2a cell | - |
Mus musculus | - |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| ubiquitin-7-amido-4-methylcoumarin + H2O | - |
Mus musculus | ubiquitin + 7-amino-4-methylcoumarin | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| ubiquitin C-terminal hydrolase-L1 | - |
Mus musculus |
| UCH-L1 | - |
Mus musculus |
Ki Value [mM]
| Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.00074 | - |
3-amino-2-[(naphthalen-2-yloxy)carbonyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
| 0.00091 | - |
3-amino-2-[(4-methylphenyl)carbonyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
| 0.0012 | - |
3-amino-2-[(4-chlorophenyl)carbonyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
| 0.0014 | - |
3-amino-2-[(4-tert-butylphenyl)carbonyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
| 0.0015 | - |
3-amino-2-[(naphthalen-1-yloxy)carbonyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
| 0.002 | - |
3-amino-2-(cyclohexylcarbonyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
| 0.0028 | - |
3-amino-2-keto-7Hthieno[2,3-b]pyridin-6-one derivative | - |
Mus musculus | |
| 0.0036 | - |
3-amino-6-oxo-2-[[4-(trifluoromethyl)phenyl]carbonyl]-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
| 0.0053 | - |
3-amino-2-[(2-methoxyphenyl)carbonyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid | - |
Mus musculus | |
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