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Merck
CN

654270

TNP-470

A cell-permeable Fumagillin analog that inhibits MetAP2, but not MetAP1, methionine aminopeptidase activity, without affecting the inhibitory activity of MetAP2 against HRI- catalyzed eIF-2α phosphorylation.

别名:

TNP-470, AGM-1470, O-(Chloroacetyl-carbamoyl)fumagillol, AGM1470, MetAP-2 Inhibitor II, MetAP2 Inhibitor II, Methionine Aminopeptidase 2 Inhibitor II, TNP470

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关于此项目

经验公式（希尔记法）:
C19H28ClNO6
化学文摘社编号:
129298-91-5
分子量:
401.88
MDL number:
MFCD00870281
UNSPSC Code:
12352200
NACRES:
NA.77

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产品名称

TNP-470, A cell-permeable Fumagillin analog that inhibits MetAP2, but not MetAP1, methionine aminopeptidase activity, without affecting the inhibitory activity of MetAP2 against HRI- catalyzed eIF-2α phosphorylation.

SMILES string

ClCC(=O)NC(=O)O[C@H]1[C@H]([C@@H]([C@]3(OC3)CC1)[C@]2(O[C@@H]2CC=C(C)C)C)OC

InChI

1S/C19H28ClNO6/c1-11(2)5-6-13-18(3,27-13)16-15(24-4)12(7-8-19(16)10-25-19)26-17(23)21-14(22)9-20/h5,12-13,15-16H,6-10H2,1-4H3,(H,21,22,23)/t12-,13-,15-,16-,18+,19+/m1/s1

InChI key

MSHZHSPISPJWHW-PVDLLORBSA-N

assay

≥97% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

white to light yellow

solubility

DMSO: 100 mg/mL

shipped in

ambient

storage temp.

−20°C

Quality Level

200

相关类别

Disclaimer

Toxicity: Irritant (B)

Other Notes

Zhang, Y., et al. 2000. Proc. Natl. Acad. Sci. USA97, 6427.
Sin, N., et al. Proc. Natl. Acad. Sci. USA94, 6099.
Yamaoka, M., et al. 1993. Cancer Res.53, 4262.
Kusaka, M., et al. 1991. Biochem. Biophys. Res. Commun.174, 1070.
Ingber, D., et al. 1990. Nature348, 555.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

General description

A cell-permeable Fumagillin (Cat. No. 344845) analog that inhibits MetAP2, but not MetAP1, methionine aminopeptidase activity (IC50 = 1 nM against human MetAP2) by covalently modifying MetAP2 active site histidine (aa 231 in human/mouse/rat; aa 174 in yeast) via its epoxide group, without affecting the inhibitory activity of MetAP2 against HRI- (heme-regulated inhibitor kinase) catalyzed eIF-2α phosphorylation. Cellular MetAP2 inhibition is particularly effective in inducing endothelial cytostasis (IC50 = 25 pM and 37 pM, respectively, against HUVEC and bovine BAEC proliferation by TNP-470), making TNP-470 a potent anti-angiogenesis agent in vivo (2 to 100 mg/kg in mice and rats; s.c.). Reported to be more potent and less toxic than Fumagillin.

存储类别

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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