WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 407477
Description: SX-517 is a potent noncompetitive boronic acid CXCR1/2 antagonist. SX-517 inhibited CXCL1-induced Ca(2+) flux (IC50 = 38 nM) in human PMNs but had no effect on the Ca(2+) flux induced by C5a, fMLF, or PAF. SX-517 is the first reported boronic acid chemokine antagonist and represents a novel pharmacophore for CXCR1/2 antagonism.
MedKoo Cat#: 407477
Chemical Formula: C19H16BFN2O3S
Exact Mass: 382.0959
Molecular Weight: 382.2164
Elemental Analysis: C, 59.71; H, 4.22; B, 2.83; F, 4.97; N, 7.33; O, 12.56; S, 8.39
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Synonym: SX-517; SX 517; SX517.
IUPAC/Chemical Name: 2-[5-(4-Fluoro-phenylcarbamoyl)-pyridin-2-ylsulfanylmethyl]-phenylboronic acid
InChi Key: VZRIHFZJVIOJBE-UHFFFAOYSA-N
InChi Code: InChI=1S/C19H16BFN2O3S/c21-15-6-8-16(9-7-15)23-19(24)13-5-10-18(22-11-13)27-12-14-3-1-2-4-17(14)20(25)26/h1-11,25-26H,12H2,(H,23,24)
SMILES Code: OB(C1=CC=CC=C1CSC2=NC=C(C(NC3=CC=C(F)C=C3)=O)C=C2)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
The following data is based on the product molecular weight 382.2164 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|
1: Schuler AD, Engles CA, Maeda DY, Quinn MT, Kirpotina LN, Wicomb WN, Mason SN,
Auten RL, Zebala JA. Boronic acid-containing aminopyridine- and
aminopyrimidinecarboxamide CXCR1/2 antagonists: Optimization of aqueous
solubility and oral bioavailability. Bioorg Med Chem Lett. 2015 Sep
15;25(18):3793-7. doi: 10.1016/j.bmcl.2015.07.090. Epub 2015 Jul 30. PubMed PMID:
26248802; PubMed Central PMCID: PMC4564001.
2: Maeda DY, Peck AM, Schuler AD, Quinn MT, Kirpotina LN, Wicomb WN, Fan GH,
Zebala JA. Discovery of
(SX-517): Noncompetitive Boronic Acid Antagonist of CXCR1 and CXCR2. J Med Chem.
2014 Oct 23;57(20):8378-97. doi: 10.1021/jm500827t. Epub 2014 Oct 8. PubMed PMID:
25254640; PubMed Central PMCID: PMC4207547.
The G protein-coupled chemokine receptors CXCR1 and CXCR2 play key roles in inflammatory diseases and carcinogenesis. In inflammation, they activate and recruit polymorphonuclear cells (PMNs) through binding of the chemokines CXCL1 (CXCR1) and CXCL8 (CXCR1 and CXCR2).