猩红酸

中文名称:

猩红酸

中文同义词:

腥红酸;6,6-(1,3-亚脲基)双(1,1-萘酚)-3,3-磺酸;猩红酸;7,7-(羰基二亚氨基)二(4-羟基-2-萘磺酸)

英文名称:

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

英文同义词:

4,4-dihydroxy-7,7-ureylenedi(naphthalene-2-sulphonic acid);7,7-(Carbonyldiimino)bis[4-hydroxy-2-naphthalenesulfonic acid];6,6-ureylene-bis(1-naphthol-3-sulfonic acid);phosgenated;N,N-bis(4-hydroxy-2-sulfonaphthalene-7-yl)urea;7,7-Ureylenebis(4-hydroxy-2-naphthalenesulfonic acid);N,N-Bis[6-(1-naphthol-3-sulfonic acid)]urea;6,6-ureylenbis-1-naphthol-3-sulfonic acid

CAS号:

134-47-4

分子式:

C21H16N2O9S2

分子量:

504.49

EINECS号:

205-142-9

相关类别:

化工原料;染料中间体;Intermediates of Dyes and Pigments

Mol文件:

134-47-4.mol

密度 

1.798±0.06 g/cm3(Predicted)

酸度系数(pKa)

-0.17±0.40(Predicted)

CAS 数据库

134-47-4(CAS DataBase Reference)

EPA化学物质信息

7,7-(Carbonyldiimino)bis[4-hydroxy-2-naphthalenesulfonic acid] (134-47-4)

生物活性

AMI-1 free acid 是一种有效的，细胞渗透性的，可逆的蛋白精氨酸 N-甲基转移酶 (PRMTs) 抑制剂，对人 PRMT1 和酵母 Hmt1p 作用的 IC50 值分别为 8.8 μM 和 3.0 μM。AMI-1 free acid 通过阻断肽-底物结合对 PRMTs 发挥抑制作用。

靶点

Target Value HMT () human PRMT1 () yeast Hmt1p (Cell-free assay) 3.0 μM

Target

Value

HMT ()

human PRMT1 ()

yeast Hmt1p (Cell-free assay)

3.0 μM

体外研究

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). AMI-1 free acid not only inhibits type I PRMTs (PRMT1, 3, 4 and 6) but also type II PRMT5. AMI-1 free acid specifically inhibits arginine, but not lysine, methyltransferase activity in vitro and does not compete for the AdoMet binding site. AMI-1 free acid inhibits methylation of GFP-Npl3 and cellular proteins. 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. AMI-1 free acid (1.2-2.4 mM; 48-72 hours) reduces S180 cell viability through the induction of cell apoptosis. Cell Viability Assay 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 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.

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.

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.

体内研究

AMI-1 free acid (0.5 mg; intratumorally; daily; for 7 days) inhibits S180 viability in vivo. 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. AMI-1 free acid (0.5 mg; intratumorally; daily; for 7 days) decreases the levels of H4R3me2s and H3R8me2s in a tumor xenograft model. Animal Model: 6-7 weeks old male Kunming mice (18-22 g), with S180 cells xenograft Dosage: 0.5 mg Administration: Intratumorally, daily, for 7 days Result: Decreased tumor weight.

Animal Model:

6-7 weeks old male Kunming mice (18-22 g), with S180 cells xenograft

Dosage:

0.5 mg

Administration:

Intratumorally, daily, for 7 days

Result:

Decreased tumor weight.

用途 

为偶氮染料用的中间体，用于制造直接橙S、直接耐酸大红4BS等