WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 555427
CAS#: 1630288-74-2 (chloride)
Description: JAS239 is a novel carbocyanine dye that binds and competitively inhibits choline kinase (ChoK) intracellularly. JAS239 attenuated choline phosphorylation and viability in a panel of human breast cancer cell lines. Antibody blockade prevented cellular retention of JAS239 indicating direct interaction with ChoKα independent of the choline transporters and catabolic choline pathways. In mice bearing orthotopic MCF7 breast xenografts, optical imaging with JAS239 distinguished tumors overexpressing ChoKα from their empty vector counterparts and delineated tumor margins.
MedKoo Cat#: 555427
CAS#: 1630288-74-2 (chloride)
Chemical Formula: C31H37ClN2O2
Molecular Weight: 505.099
Elemental Analysis: C, 73.72; H, 7.38; Cl, 7.02; N, 5.55; O, 6.33
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Related CAS #: 95736-64-4 (cation) 1630288-74-2 (chloride)
Synonym: JAS239; JAS-239; JAS 239;
IUPAC/Chemical Name: 1-(2-hydroxyethyl)-2-((1E,3E,5E)-7-((Z/E)-1-(2-hydroxyethyl)-3,3-dimethylindolin-2-ylidene)hepta-1,3,5-trien-1-yl)-3,3-dimethyl-3H-indol-1-ium chloride
InChi Key: QSVUHZZKDVAPPZ-UHFFFAOYSA-M
InChi Code: InChI=1S/C31H37N2O2.ClH/c1-30(2)24-14-10-12-16-26(24)32(20-22-34)28(30)18-8-6-5-7-9-19-29-31(3,4)25-15-11-13-17-27(25)33(29)21-23-35;/h5-19,34-35H,20-23H2,1-4H3;1H/q+1;/p-1
SMILES Code: CC1(C)C(/C=C/C=C/C=C/C=C2N(CCO)C3=C(C=CC=C3)C/2(C)C)=[N+](CCO)C4=C1C=CC=C4.[Cl-]
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: >3 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 505.099 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: Arlauckas SP, Kumar M, Popov AV, Poptani H, Delikatny EJ. Near infrared
fluorescent imaging of choline kinase alpha expression and inhibition in breast
tumors. Oncotarget. 2017 Mar 7;8(10):16518-16530. doi: 10.18632/oncotarget.14965.
PubMed PMID: 28157707; PubMed Central PMCID: PMC5369982.
2: Arlauckas SP, Popov AV, Delikatny EJ. Direct inhibition of choline kinase by a
near-infrared fluorescent carbocyanine. Mol Cancer Ther. 2014 Sep;13(9):2149-58.
doi: 10.1158/1535-7163.MCT-14-0085. Epub 2014 Jul 15. PubMed PMID: 25028471;
PubMed Central PMCID: PMC4209917.
Pharmacological inhibition of ChoK by the established inhibitor MN58b led to a growth inhibition in 4175-Luc+ tumors that was accompanied by concomitant reduction in JAS239 uptake and decreased total choline metabolite levels as measured using magnetic resonance spectroscopy. At higher therapeutic doses, JAS239 was as effective as MN58b at arresting tumor growth and inducing apoptosis in MDA-MB-231 tumors, significantly reducing tumor choline below baseline levels without observable systemic toxicity. These data introduce a new method to monitor therapeutically effective inhibitors of choline metabolism in breast cancer using a small molecule companion diagnostic.