SF-4 (Heparastatin), 1.0mg

SF-4 (Heparastatin)

Cat. No. FNK-11829
Size 1.0 mg
CAS# 153758-25-9
Molecular Formula C8H₁₁F₃N₂O₅.HCl
Molecular Weight 308.64 (hydrochloride)
Appearance white powder
Purity >95%
Long Term Storage at -20℃
Solubility Soluble in MeOH, DMSO, H2O Insoluble in CHCl3

Description

Heparastatin (SF4) Hydrochloride (Inhibitor for heparanase )
Heparastatin (SF4) inhibits recombinant human heparanase from human melanoma A375M cells transfected with pBK-CMV expression vectors containing the heparanase cDNA with IC50 1.02 µM. Heparastatin (SF4) inhibits beta-D-glucuronidase from bovine liver with IC50 6.5 x 10^-2 µM.

Application Notes

Heparastatin (SF4) inhibits recombinant human heparanase from human melanoma A375M cells transfected with pBK-CMV expression vectors containing the heparanase cDNA with IC50 1.02μM³). Heparastatin (SF4) inhibits β-D-glucuronidase from bovine liver with IC₅₀ 6.5 x 10^-2μM³). Heparastatin (SF4) (100μM) completely inhibits the enzyme activity of recombinant heparanase of murine mammary epitherial cells (NMuMG) transefected with a mouse heparanase expression vector pcDNA3.1(-)-Hygro-Hep at 0.15μg/mL in a in vitro HS degradation assay⁶).

Heparastatin (SF4) inhibits heparan sulfate (HS) chain degradation of HSPGs of Matrigel by heparanase of the LPS-treated microglial lysates from the forebrain cells of Wistar rats and the in vitro transmigration of microglia through the Matrigel-coated insert in a dosedependent manner5). Heparastatin (SF4) markedly inhibits degradation of HS by heparanase in the nucleus translocated from the cytoplasm of the calcium-induced human esophageal keratinocyte cells and keratinocyte differentiation at 100μM⁴). Heparastatin (SF4) markedly inhibits in a dose-dependent manner experimentally induced pulmonary metastasis of the B16BL6 in mice. Inhibitory ratio by ex vivo treatment with 50 μg/mL of Heparastatin (SF4) is 90.8%1). Heparastatin (SF4) shows 57% inhibition of lung metastasis of 3LL cells by s.c. inoculation in mice with i.v. administration of 100mg/kg/day for 5 days.

Specifications

1. Effect on spontaneous metastasis of mouse Lewis lung carcinoma by a trifluoroacetamide analogue of siastatin B. Nishimura Y, Satoh T, Kondo S, Takeuchi T, Azetaka M, Fukuyasu H, Iizuka Y, Shibahara S, J. Antibiotics, 1994, 47, 840-842.
2. A practical synthesis of (3S,4S,5R,6R)-4,5-dihydroxy-6-(trifluoroacetamido)piperidine -3-carboxylic acid having antimetastatic activity in mice from siastatin B. Satoh T., Nishimura Y., Kondo S., Takeuchi T. Carbohyd. Res., 1996,286, 173-178
3. Flexible synthesis and biological activity of uronic acid-type gem-diamine 1-N-iminosugars: a new family of glycosidase inhibitors. Nishimura Y, Shitara E, Adachi H, Toyoshima M, Nakajima M, Okami Y, Takeuchi T J. Org. Chem., 2000, 65, 2-11 
4. Heparanase regulates esophageal keratinocyte differentiation through nuclear translocation and heparin sulfate cleavage. Kobayashi M., Naomoto Y., Nobuhisa T., Okawa T., Takaoka M., Shirakawa Y., Yamatsuji T., Matsuoka J., Mizushima T.,  Matsuura H., Nakajima M., Nakagawa H., Rustgi A., Tanaka N. Differentiation, 2006, 74, 235-243 
5. Involvement of heparanase in migration of microglial cells. Takahashi H., Matsumoto H., Smirkin A., Itai T., Nishimura Y., Tanaka J., Biochim. Biophys. Acta., 2008, 1780, 709-715 
6. Heparanase downmodulation in the process of epithelial-to-mesenchymal transition of mouse mammary epithelial cells. Kogane Y., Higashi N., Nishimura Y., Nakajima M., T.Irimura T., J. Glycomics Lipdomics, 2013 (online publication), 3 (1), 1000107

Reference

1. Nishimura Y., et al., J. Antibiotics, 47, 840 - 842 (1994). 
2. Satoh T., et al., Carbohyd. Res., 286, 173 - 178 (1996). 
3. Nishimura Y., et al., J. Org. Chem., 65, 2 - 11 (2000). 
4. Kobayashi M., et al., Differentiation, 74, 235 - 243 (2006). 
5. Takahashi H., et al., Biochim. Biophys. Acta., 1780, 709 - 715 (2008). 
6. Kogane Y.,et al., J. Glycomics Lipdomics, 3 (1), 1000107 (2013).
7. Waxman, B., Salka, K., Timilsina, U., Umthong, S., Shukla, D., & Stavrou, S. (2025). Heparanase, a host gene that potently restricts retrovirus transcription. mBio, 16(4), e03252-24.
8. Noda, K., Atale, N., Al?Zahrani, A., Furukawa, M., Snyder, M. E., Ren, X., & Sanchez, P. G. (2024). Heparanase?induced endothelial glycocalyx degradation exacerbates lung ischemia/reperfusion injury in male mice. Physiological Reports, 12(20), e70113.

Enzyme Inhibitors	Name	Product Code	Link
Alkaline Phosphatase Inhibitor	Forphenicine	FNK-09636
NADH:Ubiquinone Oxidoreductase Inhibitor	Piericidin A1	FNK-14688
β-Galactosidase Inhibitor	Pyridindolol	FNK-00372
Glyoxylase Ⅰ (GloⅠ) Inhibitor	COTC	FNK-14675
α-Glucosidase Inhibitor	6-O-Methylreticulol	FNK-14693
Glutathione S-Transferase (GST) Inhibitor	Benastatin A	FNK-00379
	Benastatin B	FNK-14653
	Benastatin C	FNK-00380
Glutathione S-Transferase (GST) π Class Inhibitor	Bequinostatin A	FNK-14681
	Bequinostatin C	FNK-14654
GRP78 Up-regulation suppressor	Piericidin A1	FNK-14688
GMP synthase Inhibitor	Oxanosine	FNK-00762
Human Dipeptidyl Aminopeptidase Ⅱ Inhibitor	Dioctatin A (HCl)	FNK-14700
Dipeptidyl Peptidase Ⅲ (DPP-Ⅲ) Inhibitor	Fluostatin B	FNK-14683
Protein Phosphatase 2A (PP2A) Inhibitor	Cytostatin (Na Salt)	FNK-10664
	Rubratoxin A	FNK-10663
Thymidylate Synthase Inhibitor	Vanoxonin	FNK-10744
Receptor Tyrosine Kinase Inhibitor	Erbstatin	FNK-14697
DNA Helicase Inhibitor	Heliquinomycin	FNK-10665
Dopamine β-Hydroxylase Inhibitor	Dopastin	FNK-00381
Trehalase Resistant Trehalose Analogue	Lentztrehalose A	FNK-14678
	Lentztrehalose B	FNK-14679
	Lentztrehalose C	FNK-14680
Nucleoside Diphosphate Kinase (NDPK) Inhibitor	Cyclamidomycin	FNK-01541
Heparanase Inhibitor	Heparastatin<SF4>(HCl)	FNK-11829	Current Link