Synonym
Heparastatin; 6-TFA-4,5-DHPC; SF-4; SF 4; SF4;
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
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
Biological target:
Heparastatin is a heparanase inhibitor.
In vitro activity:
To further test how heparastatin (SF4) influences transmigration of inflammatory neutrophils, its suppressive effect on migration and matrix degradation was examined in vitro.
Reference: Int Immunopharmacol. 2016 Jun;35:15-21. https://pubmed.ncbi.nlm.nih.gov/27015605/
In vivo activity:
In a carrageenan- or formyl peptide-induced dorsal air pouch inflammation model, the number of infiltrated neutrophils and monocytes was significantly lower in mice after topical administration of heparastatin (SF4).
Reference: Int Immunopharmacol. 2016 Jun;35:15-21. https://pubmed.ncbi.nlm.nih.gov/27015605/
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.
| 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:
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.
In vitro protocol:
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.
In vivo protocol:
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.
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.
