An inhibitor of heparanase
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Heparastatin

Item No. 32899

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4S,5R-dihydroxy-6R-[(2,2,2-trifluoroacetyl)amino]-3S-piperidinecarboxylic acid
CAS Number
153758-25-9
Synonyms
  • SF4
Molecular Formula
C8H11F3N2O5
Formula Weight
272.2
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
FC(F)(F)C(N[C@@H]1[C@H]([C@H]([C@H](CN1)C(O)=O)O)O)=O
InChi Code
InChI=1S/C8H11F3N2O5/c9-8(10,11)7(18)13-5-4(15)3(14)2(1-12-5)6(16)17/h2-5,12,14-15H,1H2,(H,13,18)(H,16,17)/t2-,3-,4-,5+/m0/s1
InChi Key
UOPZEWVVILIZJY-NEEWWZBLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $623

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    Product Description

    Heparastatin is an inhibitor of heparanase, an enzyme that cleaves heparan sulfate into glucuronic acid (GlcUA) and N-acetylglucosamine (GlcNAc).1 It inhibits heparanase in A375-M human melanoma cells expressing the recombinant human enzyme (IC50 = 10.55 µM). Heparastatin also inhibits bovine liver β-glucuronidase and almond β-glucosidase (IC50s = 0.31 and 11 µM, respectively). It reduces air pouch neutrophil and monocyte infiltration and levels of chemokine (C-C motif) ligand 2 (CCL2) in a mouse model of dorsal air pouch inflammation induced by carrageenan.2 Heparastatin (100 mg/kg once per day) inhibits metastasis by 57.1% in a murine Lewis lung carcinoma model.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nishimura, Y., Shitara, E., Adachi, H., et al. Flexible synthesis and biological activity of uronic acid-type gem-diamine 1-N-iminosugars: A new family of glycosidase inhibitors. The Journal of Organic Chemistry 65(1), 2-11 (2000).

    2. Sue, M., Higashi, N., Shida, H., et al. An iminosugar-based heparanase inhibitor heparastatin (SF4) suppresses infiltration of neutrophils and monocytes into inflamed dorsal air pouches. Int. Immunopharmacol. 35, 15-21 (2016).

    3. Nishimura, Y., Satoh, T., Kondo, S., et al. Effect on spontaneous metastasis of mouse Lewis lung carcinoma by a trifluoroacetamide analogue of siastatin B. J. Antibiot. (Tokyo) 47(7), 840-842 (1994).