(±)-CPSI-1306 is an orally bioactive macrophage migratory factor (MIF) antagonist.

Physicochemical Properties

Molecular Formula	C15H16F2N2O3
Molecular Weight	310.3
Exact Mass	310.112
CAS #	1309793-47-2
PubChem CID	59723793
Appearance	White to off-white solid powder
Density	1.4±0.1 g/cm3
Boiling Point	453.3±55.0 °C at 760 mmHg
Flash Point	227.9±31.5 °C
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.591
LogP	1.27
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Heavy Atom Count	22
Complexity	441
Defined Atom Stereocenter Count	0
InChi Key	GUWOSEVHCSNYFK-UHFFFAOYSA-N
InChi Code	InChI=1S/C15H16F2N2O3/c16-10-1-2-12(13(17)7-10)14-8-11(22-18-14)9-15(20)19-3-5-21-6-4-19/h1-2,7,11H,3-6,8-9H2
Chemical Name	2-[3-(2,4-difluorophenyl)-4,5-dihydro-1,2-oxazol-5-yl]-1-morpholin-4-ylethanone
Synonyms	CPSI1306; CPSI 1306; CPSI-1306
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vivo

Blood glucose levels significantly dropped in mice given CPSI-1306, and this was correlated with lower levels of inflammatory cytokines in the serum. Anticipatedly, mice under vehicle treatment developed non-insulin-dependent diabetic macular disease (NIDDM), typified by elevated serum levels of glucose and inflammatory cytokines. Furthermore, they demonstrated the efficacious treatment of this illness by orally accessible CPSI-1306 [1]. One can witness CPSI-1306-induced keratinocyte death as early as half an hour following a single UVB exposure. At6,24, and 48 hours following UVB exposure, mice treated with CPSI-1306 had significantly higher expression of cleaved caspase-3 as compared to mice treated with vehicle. UVB-induced acute inflammation and keratinocyte DNA damage can both be reduced by CPSI-1306 [2].

References

[1]. Macrophage migration inhibitory factor is a therapeutic target in treatment of non-insulin-dependent diabetes mellitus. FASEB J. 2010 Jul;24(7):2583-90. [2]. MIF antagonist (CPSI-1306) protects against UVB-induced squamous cell carcinoma. Mol Cancer Res. 2014 Sep;12(9):1292-302.

Solubility Data

Solubility (In Vitro)

DMSO : ~6 mg/mL (~19.34 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 0.6 mg/mL (1.93 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 6.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 0.6 mg/mL (1.93 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 6.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 0.6 mg/mL (1.93 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 6.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.2227 mL	16.1134 mL	32.2269 mL
	5 mM	0.6445 mL	3.2227 mL	6.4454 mL
	10 mM	0.3223 mL	1.6113 mL	3.2227 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.