164640

Aminopurvalanol A

A cell-permeable 2,6,9-trisubstituted purine analog that displays anti-mitotic as well as anti-tumor properties.

• Synonym(s): Aminopurvalanol A, (2R)-2-((6-((3-Amino-5-chlorophenyl)amino)-9-(1-methylethyl)-9H-purin-2-yl)amino)-3-methyl-1-butanol, NG-97
• Empirical Formula (Hill Notation): C₁₉H₂₆ClN₇O
• CAS Number: 220792-57-4
• Molecular Weight: 403.91
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: pale yellow
• solubility: DMSO: 40 mg/mL
• shipped in: ambient
• storage temp.: 2-8°C
• InChI: 1S/C19H26ClN7O/c1-10(2)15(8-28)24-19-25-17(23-14-6-12(20)5-13(21)7-14)16-18(26-19)27(9-22-16)11(3)4/h5-7,9-11,15,28H,8,21H2,1-4H3,(H2,23,24,25,26)/t15-/m0/s1
• InChI key: RAMROQQYRRQPDL-HNNXBMFYSA-N

Description

General description

A cell-permeable 2,6,9-trisubstituted purine analog that displays anti-mitotic as well as anti-tumor properties (GI₅₀ = ~ 1.8 µM in the NCI 60-cell panel in vitro activity screen; potently inhibits the growth of KM12 colon cancer cells with a GI₅₀ of 30 nM). Acts as a reversible and ATP-competitive inhibitor of Cdks (IC₅₀ = 33 nM for Cdk1/cyclin B and Cdk2/cyclin A, 28 nM for Cdk2/cyclin E, and 20 nM for Cdk5/p35), and displays ~ 100-fold greater selectivity over a panel of kinases tested (IC₅₀ ≥ 2.4 µM). Shown to induce cell differentiation by preferentially targeting the G₂/M-phase and act intracellularly by inhibiting both Cdks and MAPKs.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
Cdk1/cyclin B, Cdk2/cyclin A, Cdk2/cyclin E, and Cdk5/p35

Product competes with ATP.

Reversible: yes

Target IC₅₀: 33 nM for Cdk1/cyclin B and Cdk2/cyclin A, 28 nM for Cdk2/cyclin E, and 20 nM for Cdk5/p35

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

Breton, M.L., et al. 2003. Biochem. Biophys. Res. Commun.306, 880.
Knockaert, M., et al. 2002.Oncogene21, 6413.
Adachi, S., et al. 2001. Mol. Cell. Biol.21, 4929.
Knockaert, M., et al. 2000. Chem. Biol.7, 411.
Rosiana, G.R., et al. 1999. Proc. Natl. Acad. Sci. USA96, 4797.
Chang, Y.T., et al. 1999. Chem. Biol.6, 361.

Legal Information

Sold under license of U.S. Patent 6,255,485 and 6,617,331.

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

Disclaimer

Toxicity: Irritant (B)

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1