5.31492

12/15-Lipoxygenase Inhibitor, ML351

• Synonym(e): 12/15-Lipoxygenase Inhibitor, ML351, 5-(Methylamino)-2-(naphthalen-1-yl)oxazole-4-carbonitrile, 12/15-LOX Inhibitor, 15-Lipoxygenase-1 Inhibitor
• Empirische Formel (Hill-System): C₁₅H₁₁N₃O
• CAS-Nummer: 847163-28-4
• Molekulargewicht: 249.27
• MDL number: MFCD04183120
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥97% (HPLC)
• Form: powder
• Storage condition: OK to freeze, protect from light

Eigenschaften

• assay: ≥97% (HPLC)
• Quality Segment: 100
• form: powder
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: yellow
• solubility: DMSO: 100 mg/mL
• storage temp.: 2-8°C
• SMILES string: N(C)c1[o]c(nc1C#N)c2c3c(ccc2)cccc3
• InChI: 1S/C15H11N3O/c1-17-15-13(9-16)18-14(19-15)12-8-4-6-10-5-2-3-7-11(10)12/h2-8,17H,1H3
• InChI key: DYXYXTDIFMDJIR-UHFFFAOYSA-N

Beschreibung

General description

A cell-permeable, non-toxic naphthyl-oxazole compound that acts as a highly potent, selective, active site directed, mixed type inhibitor of lipoxygenase-12/15 (IC₅₀ = 200 nM for human). The inhibition appears to be non-reductive and reversible in nature. Displays excellent selectivity over 5-LOX (IC₅₀ >50 µM), 12-LOX (IC₅₀ >100 µM), and 15-LOX (IC₅₀ >100 µM) and does not affect the activity of COX-1 and -2 in any significant manner (<10% inhibition at 15 µM). Can cross the blood brain barrier (brain to plasma ratio = 2.8). Offers protection against glutamate-induced oxidative toxicity in mouse neuronal HT22 cells and reduces the size of infarcts in a murine model of ischemic stroke. Displays good aqueous stability over a wide range of pH. Exhibits attractive pharmacokinetic properties (t_1/2 ~ 1 h in both plasma and brain; C_max of 13.8 and 28.8 µM in plasma and brain, respectively; at 30 mg/kg, i.p).

Please note that the molecular weight for this compound is batch-specific due to variable water content.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
12/15-LOX

Reversible: yes

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Rai, G., et al. 2014. J. Med. Chem.57, 4035.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable