Application | Comment | Organism |
---|---|---|
drug development | the upregulation of heparanase expression increases tumor size, angiogenesis, and metastasis, represents a validated target in the anti-cancer field. 2-(4-(4-(bromo-methoxybenzamido)benzylamino)phenyl) benzazole derivatives act as anti-heparanase agents, proposing this scaffold for development of broadly effective heparanase inhibitors. Symmetrical 2-aminophenyl benzazolyl-5-acetate derivatives, proving that symmetrical compounds, are more effective than asymmetrical analogues | Homo sapiens |
Inhibitors | Comment | Organism | Structure |
---|---|---|---|
(((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis-(1H-benzo[d]imidazole-2,5-diyl))bis(acetyl))bis(azanediyl))bis-(methylene))diboronic acid | - |
Homo sapiens | |
(((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis-(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis(azanediyl))bis(3-methylbutane-1,1-diyl))diboronic acid | - |
Homo sapiens | |
(((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis-(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis(azanediyl))bis-(methylene))diboronic acid | - |
Homo sapiens | |
1,3-bis(1-(5,6-dimethylbenzo[d]oxazol-2-yl)piperidin-4-yl)urea | - |
Homo sapiens | |
1,3-bis(4-(5,6-dimethylbenzo[d]oxazol-2-yl)-2-fluorophenyl)urea | - |
Homo sapiens | |
1,3-bis(4-(5,6-dimethylbenzo[d]oxazol-2-yl)phenyl)urea | - |
Homo sapiens | |
1,3-bis[4-(5,6-dimethyl-1H-benzimidazol-2-yl)phenyl]urea | - |
Homo sapiens | |
2,2'-((((carbonylbis(azanediyl))bis(4,1-phenylenesulfonyl))bis-(azanediyl))bis(3,1-phenylene))diacetic acid | - |
Homo sapiens | |
2,2'-((((Iminomethylene)bis(azanediyl))bis(4,1-phenylene))bis-(benzo[d]oxazole-2,5-diyl))diacetic acid | - |
Homo sapiens | |
2,2'-(((4,4'-(2-hydroxypropane-1,3-diyl)bis(benzoyl))bis-(azanediyl))bis(3,1-phenylene))diacetic acid | - |
Homo sapiens | |
2,2'-(((4,4'-(2-oxopropane-1,3-diyl)bis(benzoyl))bis-(azanediyl))bis(3,1-phenylene))diacetic acid | - |
Homo sapiens | |
2,2'-(((4,4'-(carbonylbis(azanediyl))bis(benzoyl))bis(azanediyl))-bis(3,1-phenylene))diacetic acid | - |
Homo sapiens | |
2,2'-(((4,4'-(carbonylbis(azanediyl))bis(benzoyl))bis(azanediyl))-bis(4-hydroxy-3,1-phenylene))diacetic acid | - |
Homo sapiens | |
2,2'-(((4,4'-(thiocarbonylbis(azanediyl))bis(3-fluorobenzoyl))bis-(azanediyl))bis(3,1-phenylene))diacetic acid | - |
Homo sapiens | |
2,2'-(((carbonylbis(azanediyl))bis(3,1-phenylene))bis(benzo[d]-oxazole-2,5-diyl))diacetic acid | - |
Homo sapiens | |
2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis-(1H-benzo[d]imidazole-2,5-diyl))diacetic acid | - |
Homo sapiens | |
2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis-(benzo[d]oxazole-2,5-diyl))bis(N-isopentylacetamide) | - |
Homo sapiens | |
2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis-(benzo[d]oxazole-2,5-diyl))diacetic acid | causes inhibition of the proliferation of human CME-1 synovial sarcoma cells | Homo sapiens | |
2,2'-(((carbonylbis(azanediyl))bis(4,1-phenylene))bis(benzo[d]-oxazole-2,5-diyl))diacetic acid | - |
Homo sapiens | |
2,2'-(((carbonylbis(azanediyl))bis(piperidine-4,1-diyl))bis(benzo-[d]oxazole-2,5-diyl))diacetic acid | - |
Homo sapiens | |
2,2'-(((thiocarbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))-bis(1H-benzo[d]imidazole-2,5-diyl))diacetic acid | - |
Homo sapiens | |
2,2'-(((thiocarbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))-bis(benzo[d]oxazole-2,5-diyl))diacetic acid | - |
Homo sapiens | |
2,2'-(((thiocarbonylbis(azanediyl))bis(4,1-phenylene))bis(benzo-[d]oxazole-2,5-diyl))diacetic acid | - |
Homo sapiens | |
2,2'-((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis(1H-benzo[d]imidazole-2,5-diyl))bis(acetyl))bis-(azanediyl))bis(3-phenylpropanoic acid) | - |
Homo sapiens | |
2,2'-((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis-(azanediyl))bis(3-phenylpropanoic acid) | - |
Homo sapiens | |
2,2'-((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis-(azanediyl))diacetic acid | - |
Homo sapiens | |
2,2'-((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis-(azanediyl))dipropionic acid | - |
Homo sapiens | |
2,2'-((2,2'-(((thiocarbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis-(azanediyl))diacetic acid | - |
Homo sapiens | |
2-(3-(4-(3-(4-((5-(carboxymethyl)-2-hydroxyphenyl)carbamoyl)-phenyl)-2-hydroxypropyl)-3-hydroxybenzamido)phenyl)acetic acid | - |
Homo sapiens | |
3,3'-((4,4'-(carbonylbis(azanediyl))bis(benzoyl))bis(azanediyl))-dibenzoic acid | - |
Homo sapiens | |
5-[2-[4-([4-[(3-bromo-4-methoxybenzoyl)amino]benzyl]amino)-3-fluorophenyl]-1H-benzimidazol-5-yl]-4-oxopentanoic acid | i.e. SST0871AA1 | Homo sapiens | |
additional information | symmetrical benzazolyl derivatives show potent anti-heparanase activity, synthesis, and molecular docking studies, overview. The anti-metastatic potential of compounds 2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis-(benzo[d]oxazole-2,5-diyl))diacetic acid, 2,2'-((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis-(azanediyl))diacetic acid, and 2,2'-((2,2'-(((thiocarbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis-(azanediyl))diacetic acid, proves the inhibition of the expression of proangiogenic factors in tumor cells. Molecular modeling of inhibitor binding and mechanism | Homo sapiens | |
SST0001 | N-acetylated, glycol-split heparin | Homo sapiens | |
[2-(4-[[(2E)-3-(4-bromophenyl)prop-2-enoyl]amino]phenyl)-1,3-benzoxazol-5-yl]acetic acid | - |
Homo sapiens | |
[2-[4-([4-[(3-bromo-4-methoxybenzoyl)amino]benzyl]amino)-3-fluorophenyl]-1H-benzimidazol-5-yl]acetic acid | i.e. SST0867AA1 | Homo sapiens |
Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
heparan sulfate + H2O | Homo sapiens | - |
? | - |
? |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Homo sapiens | Q9Y251 | - |
- |
Source Tissue | Comment | Organism | Textmining |
---|---|---|---|
carcinoma cell | upregulation of heparanase expression | Homo sapiens | - |
CME-1 cell | - |
Homo sapiens | - |
fibrosarcoma cell | - |
Homo sapiens | - |
glioblastoma cell | - |
Homo sapiens | - |
HT-1080 cell | - |
Homo sapiens | - |
osteosarcoma cell | - |
Homo sapiens | - |
synovial sarcoma cell | - |
Homo sapiens | - |
U-87MG cell | - |
Homo sapiens | - |
U2-OS cell | - |
Homo sapiens | - |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
heparan sulfate + H2O | - |
Homo sapiens | ? | - |
? | |
additional information | fondaparinux assay method | Homo sapiens | ? | - |
? |
Synonyms | Comment | Organism |
---|---|---|
endo-beta-D-glucuronidase | - |
Homo sapiens |
HPSE | - |
Homo sapiens |
Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|
37 | - |
assay at | Homo sapiens |
pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|
5 | - |
assay at | Homo sapiens |
IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
---|---|---|---|---|---|
0.000005 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | SST0001 | |
0.00001 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | (((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis-(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis(azanediyl))bis-(methylene))diboronic acid | |
0.00008 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-((2,2'-(((thiocarbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis-(azanediyl))diacetic acid | |
0.00018 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis-(benzo[d]oxazole-2,5-diyl))diacetic acid | |
0.00037 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis-(azanediyl))dipropionic acid | |
0.00042 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | [2-(4-[[(2E)-3-(4-bromophenyl)prop-2-enoyl]amino]phenyl)-1,3-benzoxazol-5-yl]acetic acid | |
0.00045 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis-(azanediyl))diacetic acid | |
0.00056 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 1,3-bis[4-(5,6-dimethyl-1H-benzimidazol-2-yl)phenyl]urea | |
0.00064 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 5-[2-[4-([4-[(3-bromo-4-methoxybenzoyl)amino]benzyl]amino)-3-fluorophenyl]-1H-benzimidazol-5-yl]-4-oxopentanoic acid | |
0.00072 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis-(azanediyl))bis(3-phenylpropanoic acid) | |
0.00082 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis(1H-benzo[d]imidazole-2,5-diyl))bis(acetyl))bis-(azanediyl))bis(3-phenylpropanoic acid) | |
0.00098 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis-(1H-benzo[d]imidazole-2,5-diyl))diacetic acid | |
0.00099 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-(((thiocarbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))-bis(1H-benzo[d]imidazole-2,5-diyl))diacetic acid | |
0.0014 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-(((thiocarbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))-bis(benzo[d]oxazole-2,5-diyl))diacetic acid | |
0.00176 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-(((4,4'-(carbonylbis(azanediyl))bis(benzoyl))bis(azanediyl))-bis(3,1-phenylene))diacetic acid | |
0.00181 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-(((thiocarbonylbis(azanediyl))bis(4,1-phenylene))bis(benzo-[d]oxazole-2,5-diyl))diacetic acid | |
0.00261 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-(((4,4'-(thiocarbonylbis(azanediyl))bis(3-fluorobenzoyl))bis-(azanediyl))bis(3,1-phenylene))diacetic acid | |
0.00273 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-(((4,4'-(carbonylbis(azanediyl))bis(benzoyl))bis(azanediyl))-bis(4-hydroxy-3,1-phenylene))diacetic acid | |
0.00286 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | [2-[4-([4-[(3-bromo-4-methoxybenzoyl)amino]benzyl]amino)-3-fluorophenyl]-1H-benzimidazol-5-yl]acetic acid | |
0.0032 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-(((carbonylbis(azanediyl))bis(4,1-phenylene))bis(benzo[d]-oxazole-2,5-diyl))diacetic acid | |
0.00487 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | (((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis-(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis(azanediyl))bis(3-methylbutane-1,1-diyl))diboronic acid | |
0.00602 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-((((Iminomethylene)bis(azanediyl))bis(4,1-phenylene))bis-(benzo[d]oxazole-2,5-diyl))diacetic acid | |
0.00917 | - |
pH 5.0 37°C, recombinant enzyme | Homo sapiens | 3,3'-((4,4'-(carbonylbis(azanediyl))bis(benzoyl))bis(azanediyl))-dibenzoic acid | |
0.01 | - |
above, pH 5.0 37°C, recombinant enzyme | Homo sapiens | (((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis-(1H-benzo[d]imidazole-2,5-diyl))bis(acetyl))bis(azanediyl))bis-(methylene))diboronic acid | |
0.01 | - |
above, pH 5.0 37°C, recombinant enzyme | Homo sapiens | (((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis-(benzo[d]oxazole-2,5-diyl))bis(acetyl))bis(azanediyl))bis(3-methylbutane-1,1-diyl))diboronic acid | |
0.01 | - |
above, pH 5.0 37°C, recombinant enzyme | Homo sapiens | 1,3-bis(1-(5,6-dimethylbenzo[d]oxazol-2-yl)piperidin-4-yl)urea | |
0.01 | - |
above, pH 5.0 37°C, recombinant enzyme | Homo sapiens | 1,3-bis(4-(5,6-dimethylbenzo[d]oxazol-2-yl)-2-fluorophenyl)urea | |
0.01 | - |
above, pH 5.0 37°C, recombinant enzyme | Homo sapiens | 1,3-bis(4-(5,6-dimethylbenzo[d]oxazol-2-yl)phenyl)urea | |
0.01 | - |
above, pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-((((carbonylbis(azanediyl))bis(4,1-phenylenesulfonyl))bis-(azanediyl))bis(3,1-phenylene))diacetic acid | |
0.01 | - |
above, pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-(((4,4'-(2-hydroxypropane-1,3-diyl)bis(benzoyl))bis-(azanediyl))bis(3,1-phenylene))diacetic acid | |
0.01 | - |
above, pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-(((4,4'-(2-oxopropane-1,3-diyl)bis(benzoyl))bis-(azanediyl))bis(3,1-phenylene))diacetic acid | |
0.01 | - |
above, pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-(((carbonylbis(azanediyl))bis(3,1-phenylene))bis(benzo[d]-oxazole-2,5-diyl))diacetic acid | |
0.01 | - |
above, pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis-(benzo[d]oxazole-2,5-diyl))bis(N-isopentylacetamide) | |
0.01 | - |
above, pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-(((carbonylbis(azanediyl))bis(piperidine-4,1-diyl))bis(benzo-[d]oxazole-2,5-diyl))diacetic acid | |
0.01 | - |
above, pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2,2'-((2,2'-(((carbonylbis(azanediyl))bis(3-fluoro-4,1-phenylene))bis(1H-benzo[d]imidazole-2,5-diyl))bis(acetyl))bis-(azanediyl))bis(3-phenylpropanoic acid) | |
0.01 | - |
above, pH 5.0 37°C, recombinant enzyme | Homo sapiens | 2-(3-(4-(3-(4-((5-(carboxymethyl)-2-hydroxyphenyl)carbamoyl)-phenyl)-2-hydroxypropyl)-3-hydroxybenzamido)phenyl)acetic acid |
General Information | Comment | Organism |
---|---|---|
physiological function | the upregulation of heparanase expression increases tumor size, angiogenesis, and metastasis, represents a validated target in the anti-cancer field | Homo sapiens |