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Literature summary for 1.6.5.2 extracted from
- Synthesis and evaluation of 3-aryloxymethyl-1,2-dimethylindole-4,7-diones as mechanism-based inhibitors of NAD(P)H:quinone oxidoreductase 1 (NQO1) activity (2007), J. Med. Chem., 50, 5780-5789.
Application
| Application | Comment | Organism |
|---|---|---|
| medicine | series of indolequinones are synthesized and tested as inhibitors for NQO1 in pancreatic tumor cells, NQO1 inhibition does not correlate with growth inhibitory activity in MiaPaCa-2 cells | Homo sapiens |
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| expressed in Escherichia coli | Homo sapiens |
| expression in Escherichia coli | Homo sapiens |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| 3-(2,4-difluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione | effective inhibitor of the growth of MiaPaCa-2 cells | Homo sapiens |  |
| 3-(2-fluoro-4-nitrophenoxymethyl)-5-methoxy-1,2-dimethylindole-4,7-dione | - |
Homo sapiens | |
| 3-(2-fluoro-4-nitrophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione | effective inhibitor of the growth of MiaPaCa-2 cells | Homo sapiens | |
| 3-(4-aminophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione | effective inhibitor of the growth of MiaPaCa-2 cells | Homo sapiens | |
| 3-(4-cyanophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione | effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 22, dose dependent inhibition of NQO1 activity in MiaPaCa-2 | Homo sapiens | |
| 3-(4-fluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione | indolequinone derivative 24, dose dependent inhibition of NQO1 activity in MiaPaCa-2 | Homo sapiens | |
| 3-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione | - |
Homo sapiens | |
| 5-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione | effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 10, mechanism based 80% inhibition | Homo sapiens | |
| 5-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione | effective inhibitor of the growth of MiaPaCa-2 cells | Homo sapiens | |
| 5-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione | effective inhibitor of the growth of MiaPaCaa-2 cells; indolequinone derivative 6, dose dependent inhibition of NQO1 activity in MiaPaCa-2 | Homo sapiens | |
| 5-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione | indolequinone derivative 12, dose dependent inhibition of NQO1 activity in MiaPaCa-2 | Homo sapiens | |
| 5-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione | effective inhibitor of the growth of MiaPaCa-2 cells | Homo sapiens | |
| 5-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione | - |
Homo sapiens | |
| 5-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione | indolequinone derivative 11, mechanism based 90% inhibition | Homo sapiens | |
| 5-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione | - |
Homo sapiens | |
| 5-methoxy-1,2-dimethyl-3-[1-(4-nitrophenoxy)ethyl]indole-4,7-dione | - |
Homo sapiens | |
| 6-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione | effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 26, mechanism based 90% inhibition | Homo sapiens | |
| 6-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione | effective inhibitor of the growth of MiaPaCaa-2 cells | Homo sapiens | |
| 6-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione | effective inhibitor of the growth of MiaPaCa-2 cells | Homo sapiens | |
| 6-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione | effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 15, mechanism based 85% inhibition | Homo sapiens | |
| 6-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione | - |
Homo sapiens | |
| 6-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione | indolequinone derivative 27, mechanism based 90% inhibition | Homo sapiens | |
| 6-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione | indolequinone derivative 29, mechanism based 95% inhibition | Homo sapiens | |
| 6-methoxy-1,2-dimethyl-3-[2-nitrophenoxymethyl]indole-4,7-dione | indolequinone derivative 19, mechanism based 95% inhibition, dose dependent inhibition of NQO1 activity in MiaPaCa-2 | Homo sapiens | |
| 6-methoxy-1,2-dimethyl-3-[4-(trifluoromethyl)phenoxymethyl]-indole-4,7-dione | effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 23, dose dependent inhibition of NQO1 activity in MiaPaCa-2 | Homo sapiens | |
| additional information | compounds 5-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(2,4-dinitrophenoxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(2,4-dinitrophenoxymethyl)indole-4,7-dione, 3-(2-fluoro-4-nitrophenoxymethyl)-5-methoxy-1,2-dimethylindole-4,7-dione, 3-(4-fluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione, 3-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione, and 5-methoxy-1,2-dimethyl-3-[1-(4-nitrophenoxy)ethyl]indole-4,7-dione are relatively ineffective at inducing growth inhibition. Inhibition of recombinant NQO1 is related to the pKa of the leaving group: compounds with poorer phenolic leaving groups are poor inhibitors whereas those with more acidic leaving groups are more efficient inhibitors | Homo sapiens |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Homo sapiens | - |
- |
- |
| Homo sapiens | - |
recombinant protein | - |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| by affinity chromatography | Homo sapiens |
| of the recombinant protein by cibacron blue affinity chromatography | Homo sapiens |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| MiaPaCa-2 cell | - |
Homo sapiens | - |
| MiaPaCa-2 cell | human pancreatic carcinoma cells | Homo sapiens | - |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| NADPH + H+ + oxidized 2,6-dichlorophenolindophenol | - |
Homo sapiens | NADP+ + reduced 2,6-dichlorophenolindophenol | - |
? | |
| NADPH + H+ + quinone | - |
Homo sapiens | NADP+ + ? | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| EC 1.6.99.2 | formerly | Homo sapiens |
| NAD(P)H:quinone oxidoreductase 1 | - |
Homo sapiens |
| NADPH:quinone oxidoreductase 1 | - |
Homo sapiens |
| NQO1 | - |
Homo sapiens |
IC50 Value
| IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|
| 0.000255 | - |
- |
Homo sapiens | 3-(2,4-difluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione | |
| 0.000345 | - |
- |
Homo sapiens | 5-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione | |
| 0.000351 | - |
- |
Homo sapiens | 6-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione | |
| 0.000352 | - |
- |
Homo sapiens | 5-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione | |
| 0.000363 | - |
- |
Homo sapiens | 6-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione | |
| 0.000427 | - |
- |
Homo sapiens | 5-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione | |
| 0.000452 | - |
- |
Homo sapiens | 6-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione | |
| 0.000463 | - |
- |
Homo sapiens | 3-(4-cyanophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione | |
| 0.000496 | - |
- |
Homo sapiens | 6-methoxy-1,2-dimethyl-3-[4-(trifluoromethyl)phenoxymethyl]-indole-4,7-dione | |
| 0.000504 | - |
- |
Homo sapiens | 3-(4-aminophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione | |
| 0.000529 | - |
- |
Homo sapiens | 3-(2-fluoro-4-nitrophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione | |
| 0.000629 | - |
- |
Homo sapiens | 5-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione | |
| 0.000638 | - |
- |
Homo sapiens | 6-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione | |
| 0.000904 | - |
- |
Homo sapiens | 5-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione | |
| 0.000905 | - |
- |
Homo sapiens | 3-(4-fluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione | |
| 0.001385 | - |
- |
Homo sapiens | 5-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione | |
| 0.001829 | - |
- |
Homo sapiens | 5-methoxy-1,2-dimethyl-3-[1-(4-nitrophenoxy)ethyl]indole-4,7-dione | |
| 0.002007 | - |
- |
Homo sapiens | 5-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione | |
| 0.002475 | - |
- |
Homo sapiens | 3-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione | |
| 0.00256 | - |
- |
Homo sapiens | 6-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione | |
| 0.004563 | - |
- |
Homo sapiens | 6-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione | |
| 0.004654 | - |
- |
Homo sapiens | 3-(2-fluoro-4-nitrophenoxymethyl)-5-methoxy-1,2-dimethylindole-4,7-dione | |
| 0.009579 | - |
- |
Homo sapiens | 6-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione | |
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