An inhibitor of angiogenesis
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TNP-470

Item No. 16449

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-chloroacetyl)-carbamic acid, (3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl]-1-oxaspiro[2.5]oct-6-yl ester
CAS Number
129298-91-5
Synonyms
  • AGM-1470
  • O-(Chloroacetyl-carbamoyl) Fumagillol
  • NSC 642492
Molecular Formula
C19H28ClNO6
Formula Weight
401.9
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/ml
SMILES
O=C(NC(CCl)=O)O[C@@H]1CC[C@@]2(OC2)[C@]([C@](O3)(C)[C@H]3C/C=C(C)/C)([H])[C@@H]1OC
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $101

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    10 mg

    $191

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    25 mg

    $451

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    Cayman Chemical
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    Product Description

    TNP-470 is a synthetic analog of fumagillin (Item No. 11332) that inhibits angiogenesis. It irreversibly inactivates methionine aminopeptidase-2 (MetAP2; IC50 = 2 µM), blocking endothelial cell proliferation in vitro and angiogenesis in vivo.1,2,3 It is without effect on MetAP1.1 TNP-470 has therapeutic potential in cancer and microsporidiosis.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chen, X., Xie, S., Bhat, S., et al. Fumagillin and fumarranol interact with P. falciparum methionine aminopeptidase 2 and inhibit malaria parasite growth in vitro and in vivo. Chem. Biol. 16(2), 193-202 (2009).

    2. Yanase, T., Tamura, M., Rujita, K., et al. Inhibitory effect of angiogenesis inhibitor TNP-470 on tumor growth and metastasis of human cell lines in vitro and in vivo. Cancer Res. 53(11), 2566-2570 (1993).

    3. Drahl, C., Cravatt, B.F., and Sorensen, E.J. Protein-reactive natural products. Angew. Chem. Int. Ed. Engl. 44(36), 5788-5809 (2005).

    4. Gervaz, P., and Fontolliet, C. Therapeutic potential of the anti-angiogenesis drug TNP-470. Int. J. Exp. Pathol. 79(6), 359-362 (1998).