ML339 is a selective CXCR6 antagonist (inhibitor) with IC50 of 140 nM. ML339 has IC50 of >79 μM for CXCR5, CXCR4, CCR6 and Apelin receptor (APJ). ML339 may be used to advance the field of prostate cancer research.

Physicochemical Properties

Molecular Formula	C26H32CLN3O5
Molecular Weight	502.00
Exact Mass	501.2
Elemental Analysis	C, 62.21; H, 6.43; Cl, 7.06; N, 8.37; O, 15.94
CAS #	2579689-83-9
Related CAS #	2579689-83-9;2080300-49-6 (deleted);
PubChem CID	71768224
Appearance	White to off-white solid powder
LogP	4.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	8
Heavy Atom Count	35
Complexity	699
Defined Atom Stereocenter Count	2
SMILES	COC1=CC(=CC(=C1OC)OC)C(=O)NC2C[C@H]3CCC[C@@H](C2)N3CC(=O)NC4=CC=CC=C4Cl
InChi Key	SSPYAPRDKNCABY-LDLYASANSA-N
InChi Code	InChI=1S/C26H32ClN3O5/c1-33-22-11-16(12-23(34-2)25(22)35-3)26(32)28-17-13-18-7-6-8-19(14-17)30(18)15-24(31)29-21-10-5-4-9-20(21)27/h4-5,9-12,17-19H,6-8,13-15H2,1-3H3,(H,28,32)(H,29,31)/t17-,18-,19+
Chemical Name	N-((1R,3s,5S)-9-(2-((2-chlorophenyl)amino)-2-oxoethyl)-9-azabicyclo[3.3.1]nonan-3-yl)-3,4,5-trimethoxybenzamide
Synonyms	ML-339; ML 339; ML339.
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

References

1: Hershberger PM, Peddibhotla S, Sugarman E, Maloney P, Key D, Suyama E, Nguyen K, Vasile S, Kraft M, Stonich D, Mangravita-Novo A, Vicchiarelli M, Gosalia P, Milewski M, Li L, Hedrick M, Sun Q, Sergienko E, Cheltsov A, Salanawil S, Diwan J, Smith LH, Taichman RS, Chung TDY, Pinkerton AB, Malany S, Roth GP. Probing the CXCR6/CXCL16 Axis: Targeting Prevention of Prostate Cancer Metastasis. 2012 Dec 15 [updated 2014 May 13]. Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2010-. Available from http://www.ncbi.nlm.nih.gov/books/NBK158948/ PubMed PMID: 24049849.

Solubility Data

Solubility (In Vitro)

DMSO : ~75 mg/mL (~149.40 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 3.75 mg/mL (7.47 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 37.5 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	1.9920 mL	9.9602 mL	19.9203 mL
	5 mM	0.3984 mL	1.9920 mL	3.9841 mL
	10 mM	0.1992 mL	0.9960 mL	1.9920 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.