5-Amino-2-methoxypyridine

• CAT Number: R032085
• CAS Number: 6628-77-9
• Molecular Formula: C6H8N2O
• Molecular Weight: 124.143
• Purity: ≥95%
• Solubility: Solubility in water: slightly soluble in water. Other solubilities: soluble in methanol, ethanol
• Storage: Store at -20°C
• IUPAC Name: 6-methoxypyridin-3-amine
• InChI: InChI=1S/C6H8N2O/c1-9-6-3-2-5(7)4-8-6/h2-4H,7H2,1H3
• InChIKey: UUVDJIWRSIJEBS-UHFFFAOYSA-N
• SMILES: COC1=NC=C(C=C1)N

Reference

[1]. Anal Biochem. 2018 Apr 1;546:50-57. doi: 10.1016/j.ab.2018.01.026. Epub 2018 Jan 31.
Characterization of fatty acid amide hydrolase activity by a fluorescence-based assay.
Dato FM(1), Maaßen A(1), Goldfuß B(2), Pietsch M(3).
Author information: (1)Institute II of Pharmacology, Center of Pharmacology, Medical Faculty, University of Cologne, Gleueler Str. 24, D-50931 Cologne, Germany; Institute of Organic Chemistry, Department of Chemistry, University of Cologne, Greinstr. 4, D-50939 Cologne, Germany. (2)Institute of Organic Chemistry, Department of Chemistry, University of Cologne, Greinstr. 4, D-50939 Cologne, Germany. (3)Institute II of Pharmacology, Center of Pharmacology, Medical Faculty, University of Cologne, Gleueler Str. 24, D-50931 Cologne, Germany. Electronic address: .
Fatty acid amide hydrolase (FAAH) is involved in many human diseases, particularly cancer, pain and inflammation as well as neurological, metabolic and cardiovascular disorders. Therefore, FAAH is an attractive target for the development of low-molecular-weight inhibitors as therapeutics, which requires robust assays that can be used for high-throughput screening (HTS) of compound libraries. Here, we report the development of a fluorometric assay based on FAAH's ability to effectively hydrolyze medium-chain fatty acid amides, introducing N-decanoyl-substituted 5-amino-2-methoxypyridine (D-MAP) as new amide substrate. D-MAP is cleaved by FAAH with an 8-fold larger specificity constant than the previously reported octanoyl-analog Oc-MAP (Vmax/Km of 1.09 and 0.134 mL min-1 mg-1, respectively), with both MAP derivatives possessing superior substrate properties and much increased aqueous solubility compared to the respective p-nitroaniline compounds D-pNA and Oc-pNA. The new assay with D-MAP as substrate is highly sensitive using a lower enzyme concentration (1 μg mL-1) than literature-reported fluorimetric FAAH assays. In addition, D-MAP was validated in comparison to the substrate Oc-MAP for the characterization of FAAH inhibitors by means of the reference compounds URB597 and TC-F2 and was shown to be highly suitable for HTS in both kinetic and endpoint assays (Z' factors of 0.81 and 0.78, respectively).
DOI: 10.1016/j.ab.2018.01.026 PMID: 29408178 [Indexed for MEDLINE]