Heparastatin

    WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H530438

CAS#: 153758-25-9

Description: Heparastatin is an inhibitor of heparanase, an enzyme that cleaves heparan sulfate into glucuronic acid (GlcUA) and N-acetylglucosamine (GlcNAc). 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. Heparastatin (100 mg/kg once per day) inhibits metastasis by 57.1% in a murine Lewis lung carcinoma model.


Chemical Structure

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Heparastatin
CAS# 153758-25-9

Theoretical Analysis

Hodoodo Cat#: H530438
Name: Heparastatin
CAS#: 153758-25-9
Chemical Formula: C8H11F3N2O5
Exact Mass: 272.06
Molecular Weight: 272.180
Elemental Analysis: C, 35.30; H, 4.07; F, 20.94; N, 10.29; O, 29.39

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Heparastatin; SF4; SF-4; SF 4;

IUPAC/Chemical Name: (3S,4S,5R,6R)-4,5-dihydroxy-6-(2,2,2-trifluoroacetamido)piperidine-3-carboxylic acid

InChi Key: UOPZEWVVILIZJY-NEEWWZBLSA-N

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

SMILES Code: O=C([C@H]1CN[C@H](NC(C(F)(F)F)=O)[C@@H](O)[C@H]1O)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 272.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Sue M, Higashi N, Shida H, Kogane Y, Nishimura Y, Adachi H, Kolaczkowska E, Kepka M, Nakajima M, Irimura T. An iminosugar-based heparanase inhibitor heparastatin (SF4) suppresses infiltration of neutrophils and monocytes into inflamed dorsal air pouches. Int Immunopharmacol. 2016 Jun;35:15-21. doi: 10.1016/j.intimp.2016.03.017. Epub 2016 Mar 22. PMID: 27015605.

2: Tsunekawa N, Higashi N, Kogane Y, Waki M, Shida H, Nishimura Y, Adachi H, Nakajima M, Irimura T. Heparanase augments inflammatory chemokine production from colorectal carcinoma cell lines. Biochem Biophys Res Commun. 2016 Jan 22;469(4):878-83. doi: 10.1016/j.bbrc.2015.12.074. Epub 2015 Dec 20. PMID: 26713365.

3: Satoh T, Nishimura Y, Kondo S, Takeuchi T. A practical synthesis from siastatin B of (3S,4S,5R,6R)- 4,5-dihydroxy-6-(trifluoroacetamido)piperidine-3-carboxylic acid having antimetastatic activity in mice. Carbohydr Res. 1996 Jun 5;286:173-8. doi: 10.1016/0008-6215(96)00052-3. PMID: 8925513.

4: Satoh T, Nishimura Y, Kondo S, Takeuchi T, Azetaka M, Fukuyasu H, Iizuka Y, Ohuchi S, Shibahara S. Synthesis and antimetastatic activity of 6-trichloroacetamido and 6-guanidino analogues of siastatin B. J Antibiot (Tokyo). 1996 Mar;49(3):321-5. doi: 10.7164/antibiotics.49.321. PMID: 8626252.