Heparanase Inhibitor Heparastatin (SF4) Hydrochloride

Heparastatin is an inhibitor of heparanase.

• Specification
• Application Notes
• References

Specification

CAS#	153758-26-0
Molecular Formula	C8H11F3N2O5 HCl
Molecular Weight	308.638
Source	Chemically synthesized from natural siastatin B
Purity	> 95%
Long Term Storage	at -20℃
Solubility	Soluble in MeOH, DMSO, H2O. Insoluble in CHCl3

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Application Notes

• Heparastatin(SF4) inhibits recombinant human heparanasefrom human melanoma A375M cells transfected with pBK-CMV expression vectors containing the heparanase cDNA (IC50=1.02μM) 3).
• Heparastatin(SF4) inhibits β-D-glucuronidase from bovine liver (IC50=6.5 x10-2μM) 3).
• In a in vitro HS degradation assay, 100μM Heparastatin(SF4) completely inhibits the enzyme activity of recombinant heparanase of murine mammary epitherialcells(NMuMG) transefected with a mouse heparanase expression vector pcDNA3.1(-)-Hygro-Hep at 0.15μg/mL 6).
• Heparastatin(SF4) inhibits heparansulfate(HS) chain degradation of HSPGs of Matrigel by heparanase of the LPS-treated microgliallysates from the forebrain cells of Wistar rats and the in vitro transmigration of microglia through the Matrigel-coated insert in a dose-dependent manner 5).
• Heparastatin(SF4) markedly inhibits degradation of HS by heparanasein the nucleus translocatedfrom the cytoplasm of the calcium-induced human esophageal keratinocyte cells and keratinocyte differentiation at 100μM 4).

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References

1. Effect on spontaneous metastasis of mouse Lewis lung carcinoma by a trifluoroacetamideanalogue of siastatin B. Nishimura Y, Satoh T, Kondo S, Takeuchi T, AzetakaM, FukuyasuH, IizukaY, Shibahara S, J. Antibiotics, 1994, 47, 840-842
2. Apracticalsynthesis of(3S,4S,5R,6R)-4,5-dihydroxy-6-(trifluoroacetamido)piperidine -3-carboxylic acid having antimetastaticactivity in mice from siastatinB. Satoh T., Nishimura Y., Kondo S., Takeuchi T. Carbohyd. Res., 1996,286, 173-178
   
3. Flexible synthesis and biological activity of uronicacid-type gem-diamine1-N-iminosugars: a new family of glycosidase inhibitors. Nishimura Y, ShitaraE, Adachi H, Toyoshima M, Nakajima M, OkamiY, Takeuchi T J. Org. Chem., 2000, 65, 2-11
4. Heparanaseregulates esophageal keratinocyte differentiation through nuclear translocation and heparin sulfate cleavage. Kobayashi M., NaomotoY., NobuhisaT., OkawaT., Takaoka M., ShirakawaY., YamatsujiT., Matsuoka J., MizushimaT., Matsuura H., Nakajima M., Nakagawa H., RustgiA., Tanaka N. Differentiation, 2006, 74, 235-243
5. Involvement of heparanasein migration of microglial cells. Takahashi H., Matsumoto H., SmirkinA., ItaiT., Nishimura Y., Tanaka J., Biochim. Biophys. Acta., 2008, 1780, 709-715
6. Heparanasedownmodulationin the process of epithelial-to-mesenchymaltransition of mouse mammary epithelial cells. KoganeY., Higashi N., Nishimura Y., Nakajima M., T.IrimuraT.,J. GlycomicsLipdomics,2013 (online publication), 3 (1), 1000107

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