for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at 2-8°C,Desiccated Ships Wet ice Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Prinomastat hydrochloride (AG3340 hydrochloride) is a broad spectrum, potent, orally active metalloproteinase (MMP) inhibitor with IC 50 s of 79, 6.3 and 5.0 nM for MMP-1 , MMP-3 and MMP-9 , respectively. Prinomastat hydrochloride inhibits MMP-2 , MMP-3 and MMP-9 with K i s of 0.05 nM, 0.3 nM and 0.26 nM, respectively. Prinomastat hydrochloride can cross blood-brain barrier. Antitumor avtivity.
In Vitro
Prinomastat (AG3340; 0.1-1 µg/mL; 4 days; C57MG/Wnt1 cells) inhibits Wnt1-induced MMP-3 production. Reversal of Wnt1-induced EMT and β-catenin transcriptional activity by Prinomastat. Co-culture of L/Wnt3a cells and CT7 cells increases the Topflash activity in CT7 cells, and co-culturing both L/Wnt3a cells and MMP-3 overexpressing C57MG cells with CT7 cells increases the Topflash luciferase activity in CT7 cells beyond the level observed with L/Wnt3a cells, and these effects are all suppressed by Prinomastat (AG3340). Inhibition of entry of C57MG/Wnt1 cells into S phase by Prinomastat corresponds to a decrease in expression of cyclin D1 and Erk1/2 phosphorylation. The effect of Prinomastat on Wnt1-induced migration is then examined using an in vitro wound assay. As anticipated, the migration of C57MG/Wnt1 cells is increased by 1.8-fold when compared with C57MG cells.The effect of Wnt1 on the cellular distribution of vimentin is reversed by Prinomastat in C57MG/Wnt1 cells. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Western Blot AnalysisCell Line: C57MG/Wnt1 cells Concentration: 0.1 µg/mL, 1 µg/mL Incubation Time: 4 days Result: A significant decrease in MMP-3 promoter activity in C57MG/Wnt1 cells.
In Vivo
In a human fibrosarcoma mouse model (HT1080), the mice are treated therapeutically for 14-16 days with 50 mg/kg/day ip daily starting day 3 to 6 after tumour inoculation. Prinomastat is well tolerated by the animals, and there are no signs of weight loss or other adverse effects. Prinomastat has good tumour growth inhibition, with a short T 1/2 of 1.6 hours . MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
| Sonrisas canónicas | CC1(C(N(CCS1)S(=O)(=O)C2=CC=C(C=C2)OC3=CC=NC=C3)C(=O)NO)C.Cl |
|---|---|
| IUPAC Name | (3S)-N-hydroxy-2,2-dimethyl-4-(4-pyridin-4-yloxyphenyl)sulfonylthiomorpholine-3-carboxamide;hydrochloride |
| InChIKey | UQGWXXLNXBRNBU-NTISSMGPSA-N |
| INCHI | 1S/C18H21N3O5S2.ClH/c1-18(2)16(17(22)20-23)21(11-12-27-18)28(24,25)15-5-3-13(4-6-15)26-14-7-9-19-10-8-14;/h3-10,16,23H,11-12H2,1-2H3,(H,20,22);1H/t16-;/m0./s1 |
| Isómeros SMILES | CC1([C@@H](N(CCS1)S(=O)(=O)C2=CC=C(C=C2)OC3=CC=NC=C3)C(=O)NO)C.Cl |
| CAS alternativo | 1435779-45-5 |
| PubChem CID | 10321991 |
| Peso molecular | 459.97 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic oxygen compounds |
| Clase | Organooxygen compounds |
| Subclass | Ethers |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Diarylethers |
| Alternative Parents | Alpha amino acids and derivatives Benzenesulfonamides Benzenesulfonyl compounds Phenoxy compounds Phenol ethers Thiomorpholines Pyridines and derivatives Organosulfonamides Sulfonyls Heteroaromatic compounds Hydroxamic acids Dialkylthioethers Azacyclic compounds Hydrochlorides Carbonyl compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Diaryl ether - Alpha-amino acid or derivatives - Benzenesulfonamide - Benzenesulfonyl group - Phenoxy compound - Phenol ether - Monocyclic benzene moiety - Pyridine - Benzenoid - 1,4-thiazinane - Organosulfonic acid amide - Heteroaromatic compound - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Hydroxamic acid - Dialkylthioether - Organoheterocyclic compound - Azacycle - Carboxylic acid derivative - Thioether - Hydrochloride - Organosulfur compound - Organonitrogen compound - Organic nitrogen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Aromatic heteromonocyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. |
| External Descriptors | Not available |
| Solubilidad | DMSO : 100 mg/mL (217.41 mM; Need ultrasonic) H2O : 50 mg/mL (108.70 mM; Need ultrasonic) |
|---|---|
| Peso molecular | 460.000 g/mol |
| XLogP3 | |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 5 |
| Exact Mass | 459.069 Da |
| Monoisotopic Mass | 459.069 Da |
| Topological Polar Surface Area | 143.000 Ų |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Complexity | 638.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 2 |
