Introduction：Basic information about CAS 134-47-4|AMI-1 free acid, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | AMI-1 free acid |
|---|
| CAS Number | 134-47-4 | Molecular Weight | 504.49000 |
|---|
| Density | 1.798 g/cm3 | Boiling Point | / |
|---|
| Molecular Formula | C21H16N2O9S2 | Melting Point | 86-88 °C |
|---|
| MSDS | / | Flash Point | / |
|---|
Names
| Name | 7,7'-(Carbonylbis(azanediyl))bis(4-hydroxynaphthalene-2-sulfonic acid) |
|---|
| Synonym | More Synonyms |
|---|
AMI-1 free acid BiologicalActivity
| Description | AMI-1 free acid is a potent, cell-permeable and reversible inhibitor of protein arginine N-methyltransferases (PRMTs), with IC50s of 8.8 μM and 3.0 μM for human PRMT1 and yeast-Hmt1p, respectively. AMI-1 free acid exerts PRMTs inhibitory effects by blocking peptide-substrate binding[1]. |
|---|
| Related Catalog | Research Areas >>CancerSignaling Pathways >>Epigenetics >>Histone Methyltransferase |
|---|
| Target | IC50: 8.8 μM (PRMT1), 3.0 μM (yeast-Hmt1p)[1] |
|---|
| In Vitro | AMI-1 free acid can inhibit the in vitro methylation reactions performed by all five recombinantly active PRMTs (PRMT1, -3, -4, and -6 and Hmt1p)[2]. AMI-1 free acid not only inhibits type I PRMTs (PRMT1, 3, 4 and 6) but also type II PRMT5[2]. AMI-1 free acid specifically inhibits arginine, but not lysine, methyltransferase activity in vitro and does not compete for the AdoMet binding site[3]. AMI-1 free acid inhibits methylation of GFP-Npl3 and cellular proteins[3]. AMI-1 free acid (0.6-2.4 mM; 48-96 hours) inhibits the cell viability of sarcoma in S180 and U2OS cells in a time-dependent and dose-dependent manner in vitro[4]. AMI-1 free acid (1.2-2.4 mM; 48-72 hours) reduces S180 cell viability through the induction of cell apoptosis[4]. Cell Viability Assay[4] Cell Line: S180 cells, U2OS cells Concentration: 0.6 mM, 1.2 mM, 2.4 mM Incubation Time: 48 hours, 72 hours, 96 hours Result: Inhibited the cell viability. Apoptosis Analysis[4] Cell Line: S180 cells Concentration: 1.2 mM, 2.4 mM Incubation Time: 48 hours, 72 hours Result: Increased the percentages of cells undergoing apoptosis. |
|---|
| In Vivo | AMI-1 free acid (0.5 mg; intratumorally; daily; for 7 days) inhibits S180 viability in vivo[4]. AMI-1 free acid (0.5 mg; intratumorally; daily; for 7 days) downregulates PRMT5 but does not regulate the expression of PRMT7 in a tumor xenograft model[4]. AMI-1 free acid (0.5 mg; intratumorally; daily; for 7 days) decreases the levels of H4R3me2s and H3R8me2s in a tumor xenograft model[4]. Animal Model: 6-7 weeks old male Kunming mice (18-22 g), with S180 cells xenograft[4] Dosage: 0.5 mg Administration: Intratumorally, daily, for 7 days Result: Decreased tumor weight. |
|---|
| References | [1]. Donghang Cheng, et al. Small Molecule Regulators of Protein Arginine Methyltransferases. J Biol Chem. 2004 Jun 4;279(23):23892-9. [2]. Zhang, B., et al. Targeting protein arginine methyltransferase 5 inhibits colorectal cancer growth by decreasing arginine methylation of eIF4E and FGFR3. Oncotarget. 2015 Sep 8;6(26):22799-811. [3]. Donghang Cheng, et al. Small Molecule Regulators of Protein Arginine Methyltransferases. J Biol Chem. 2004 Jun 4;279(23):23892-9. [4]. Baolai Zhang, et al. Arginine Methyltransferase inhibitor-1 Inhibits Sarcoma Viability in vitro and in vivo. Oncol Lett. 2018 Aug;16(2):2161-2166. |
|---|
Chemical & Physical Properties
| Density | 1.798 g/cm3 |
|---|
| Melting Point | 86-88 °C |
|---|
| Molecular Formula | C21H16N2O9S2 |
|---|
| Molecular Weight | 504.49000 |
|---|
| Exact Mass | 504.03000 |
|---|
| PSA | 207.09000 |
|---|
| LogP | 5.84920 |
|---|
| Index of Refraction | -45 ° (C=1, AcOH) |
|---|
| InChIKey | PCGISRHGYLRXSR-UHFFFAOYSA-N |
|---|
| SMILES | O=C(Nc1ccc2c(O)cc(S(=O)(=O)O)cc2c1)Nc1ccc2c(O)cc(S(=O)(=O)O)cc2c1 |
|---|
Safety Information
| Hazard Codes | Xi |
|---|
| Safety Phrases | S22-S24/25 |
|---|
| WGK Germany | 3 |
|---|
| HS Code | 2922210000 |
|---|
Customs
| HS Code | 2934999090 |
|---|
| Summary | 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
|---|
Synonyms
| 6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid) |
| EINECS 205-142-9 |
