Inhibitors | Comment | Organism | Structure |
---|---|---|---|
1,3-dimethyl-5-nitro-1H-indazole | - |
Homo sapiens | |
1-(4-chlorobutyl)-5-nitro-1H-indazol-3-ol | - |
Homo sapiens | |
1-benzyl-5-nitro-1H-indazol-3-ol | - |
Homo sapiens | |
1-methyl-5-nitro-1H-indazol-3-ol | inhibits MAO-B by 34% at 0.015 mM | Homo sapiens | |
3-(benzyloxy)-5-nitro-1H-indazole | - |
Homo sapiens | |
3-benzyl-5-nitro-1H-indazole | - |
Homo sapiens | |
3-methoxy-1-methyl-5-nitro-1H-indazole | inhibits MAO-B by 52% at 0.015 mM | Homo sapiens | |
3-methoxy-5-nitro-1H-indazole | - |
Homo sapiens | |
3-methyl-5-nitro-1H-indazole | - |
Homo sapiens | |
5-nitro-1-(pyridin-2-ylmethyl)-1H-indazol-3-ol | - |
Homo sapiens | |
5-nitroindazole | inhibits MAO-B by 98.5% at 0.015 mM | Homo sapiens | |
6-nitroindazole | inhibits MAO-B by 89% at 0.015 mM, also inhibits MAO-A | Homo sapiens | |
7-nitroindazole | inhibits MAO-B by 35% at 0.015 mM | Homo sapiens | |
Clorgyline | - |
Homo sapiens | |
additional information | nitroindazole isomers are good hydroxyl radical scavengers and inhibhit MPTP neurotoxin oxidation by MAO. Compounds 4, 5, 6, 7, 8, 9, 10, and 11 are poor inhibitors | Homo sapiens | |
R-deprenyl | - |
Homo sapiens |
Localization | Comment | Organism | GeneOntology No. | Textmining |
---|---|---|---|---|
mitochondrion | - |
Homo sapiens | 5739 | - |
Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
2 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + 2 H2O + 3 O2 | Homo sapiens | activation of the neurotoxin to neurotoxic pyridinium cations. MPTP easily crosses the blood-brain barrier and is preferentially metabolized by MAO-B present in glial cells to 1-methyl-4-phenyl-2,3-dihydropyridinium. This enzymatic metabolite is subsequently oxidized to 1-methyl-4-phenylpyridinium, which is selectively uptaken by dopaminergic cells, producing inhibition of complex I of mitochondria, energy depletion, oxidative stress and cell death | 1-methyl-4-phenyl-2,3-dihydropyridinium + 1-methyl-4-phenylpyridinium + 4 H2O2 | 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine is metabolically oxidized by alpha-carbon oxidation by MAO enzymes to give 1-methyl-4-phenyl-2,3-dihydropyridinium and hydrogen peroxide, which, in a further step, is readily oxidized to 1-methyl-4-phenylpyridinium, that is a directly-acting neurotoxic substance | ? |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Homo sapiens | - |
- |
- |
Source Tissue | Comment | Organism | Textmining |
---|---|---|---|
brain | - |
Homo sapiens | - |
glial cell | - |
Homo sapiens | - |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
2 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + 2 H2O + 3 O2 | activation of the neurotoxin to neurotoxic pyridinium cations. MPTP easily crosses the blood-brain barrier and is preferentially metabolized by MAO-B present in glial cells to 1-methyl-4-phenyl-2,3-dihydropyridinium. This enzymatic metabolite is subsequently oxidized to 1-methyl-4-phenylpyridinium, which is selectively uptaken by dopaminergic cells, producing inhibition of complex I of mitochondria, energy depletion, oxidative stress and cell death | Homo sapiens | 1-methyl-4-phenyl-2,3-dihydropyridinium + 1-methyl-4-phenylpyridinium + 4 H2O2 | 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine is metabolically oxidized by alpha-carbon oxidation by MAO enzymes to give 1-methyl-4-phenyl-2,3-dihydropyridinium and hydrogen peroxide, which, in a further step, is readily oxidized to 1-methyl-4-phenylpyridinium, that is a directly-acting neurotoxic substance | ? | |
2 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + 2 H2O + 3 O2 | activation of the neurotoxin to neurotoxic pyridinium cations | Homo sapiens | 1-methyl-4-phenyl-2,3-dihydropyridinium + 1-methyl-4-phenylpyridinium + 4 H2O2 | - |
? | |
kynuramine + O2 | - |
Homo sapiens | 4-hydroxyquinoline + NH3 + H2O2 | - |
? | |
additional information | ABTS assay is used to measure total antioxidant activity of nitroindazoles against the radical ABTS*+, overview | Homo sapiens | ? | - |
? |
Synonyms | Comment | Organism |
---|---|---|
MAO | - |
Homo sapiens |
Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|
37 | - |
assay at | Homo sapiens |
pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|
7.4 | - |
assay at | Homo sapiens |
Cofactor | Comment | Organism | Structure |
---|---|---|---|
FAD | - |
Homo sapiens |
Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
---|---|---|---|---|---|
0.000102 | - |
5-nitroindazole | pH 7.4, 37°C, MAO-B | Homo sapiens | |
0.00067 | - |
6-nitroindazole | pH 7.4, 37°C, MAO-B | Homo sapiens | |
0.0074 | - |
7-nitroindazole | pH 7.4, 37°C, MAO-B | Homo sapiens |
IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
---|---|---|---|---|---|
0.00099 | - |
pH 7.4, 37°C, MAO-B | Homo sapiens | 5-nitroindazole | |
0.00252 | - |
pH 7.4, 37°C, MAO-B | Homo sapiens | 6-nitroindazole | |
0.0278 | - |
pH 7.4, 37°C, MAO-B | Homo sapiens | 7-nitroindazole |