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654270

TNP-470

Name: TNP-470
Brand: MM

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

Assay:

≥97% (HPLC)

Form:

solid

Quality level:

200

Storage condition:

OK to freeze

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属性

Quality Level

200

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

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

说明

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 (IC_{50 = 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.}

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

Disclaimer

Toxicity: Irritant (B)

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存储类别

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c