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Home > Products > Specialty & Industrial Chemicals > Specialty Chemicals > 6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid)
6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid) structure, CAS 134-47-4

6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid)

CAS Number134-47-4

Synonyms6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid); EINECS 205-142-9

Molecular FormulaC21H16O9N2S2

Molecular Weight504.5

Purity98.00%

Density1.798 g/cm3

Boiling Point

Melting Point86-88 °C

Flash Point

AppearanceDry gray-white powder

EINECS

MSDSChineseEnglish

Symbol

Signal Word

Cat. No.: 2A-9020727 Purity: 98.00%
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Quality Control of [ 134-47-4 ] Purity: 98.00% SDS Specification MoL

COA NMR CNMR HPLC LC-MS
Chemical & Physical Properties
CAS Number134-47-4
Catalog No.2A-9020727
Chinese Name腥红酸
Synonyms6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid); EINECS 205-142-9
Molecular FormulaC21H16O9N2S2
Molecular Weight504.5
Purity98.00
Density1.798 g/cm3
Melting Point86-88 °C
AppearanceDry gray-white powder
Storage ConditionRoom temperature, dry
ApplicationAMI-1 free acid is a potent, cell-permeable, reversible inhibitor of protein arginine N-methyltransferases (PRMTs) with IC50 values ​​of 8.8 μM and 3.0 μM for human PRMT1 and yeast Hmt1p, respectively
HTC2922210000
MDL NumberMFCD00035715
SMILESO=C(Nc1ccc2c(O)cc(S(=O)(=O)O)cc2c1)Nc1ccc2c(O)cc(S(=O)(=O)O)cc2c1
InChIInChI=1S/C21H16N2O9S2/c24-19-9-15(33(27,28)29)7-11-5-13(1-3-17(11)19)22-21(26)23-14-2-4-18-12(6-14)8-16(10-20(18)25)34(30,31)32/h1-10,24-25H,(H2,22,23,26)(H,27,28,29)(H,30,31,32)
InChI KeyPCGISRHGYLRXSR-UHFFFAOYSA-N
MSDSmsds/20727_1_134_47_4.pdf
BioactivityAMI-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 >> Cancer Signaling 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
Use ofAMI-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]. Properties Name 7,7'-(Carbonylbis(azanediyl))bis(4-hydroxynaphthalene-2-sulfonic acid) Synonym More Synonyms AMI-1 free acid Biological Activity 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 >> Cancer Signaling Pathways >> Epigenetics >> Histone Methyltransferase IC50: 8.8 μM (PRMT1), 3.0 μM (yeast-Hmt1p)[1] 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 Molecular Formula C21H16N2O9S2 Exact Mass 504.03000 PSA 207.09000 LogP 5.84920 InChIKey PCGISRHGYLRXSR-UHFFFAOYSA-N
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