324630

EHNA, Hydrochloride

The racemic mixture of a cell-permeable adenine derivative that acts as a PDE II-selective phosphodiesterase inhibitor and adenosine deaminase.

• Synonym(s): EHNA, Hydrochloride, erythro-9-(2-Hydroxy-3-nonyl)adenine, HCl
• Empirical Formula (Hill Notation): C₁₄H₂₃N₅O · xHCl
• CAS Number: 51350-19-7
• Molecular Weight: 277.37 (free base basis)
• MDL number: MFCD00151066
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥97% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; desiccated (hygroscopic)
• color: white
• solubility: water: 25 mg/mL
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: [n]1(c2ncnc(c2nc1)N)[C@H]([C@@H](O)C)CCCCCC
• InChI: 1S/C14H23N5O/c1-3-4-5-6-7-11(10(2)20)19-9-18-12-13(15)16-8-17-14(12)19/h8-11,20H,3-7H2,1-2H3,(H2,15,16,17)/t10-,11-/m0/s1
• InChI key: IOSAAWHGJUZBOG-QWRGUYRKSA-N

Description

General description

The racemic mixture of a cell-permeable adenine derivative that acts as a PDE II-selective phosphodiesterase inhibitor (IC50 = 0.8 and 2 µM against human and procine PDE II, respectively) and adenosine deaminase (K_i = 4 nM), while exhibiting little or much reduced potency toward PDE I/II/IV isozymes (IC50 >100 µM) of both human and porcine species. EHNA at 10 µM concentration is also reported to effectively and reversibly block the differentiation and maintain the pluripotency of hES (human embryonic stem) cell line SA121 in feeder-free cultures without exogenously added FGF for up to 30 passages in a manner independent of its known ADA and PDE inhibitory activities.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
PDE 2

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 0.8 and 2 µM against human and procine PDE II, respectively

Target K_i: 4 nM against adenosine deaminase

Warning

Toxicity: Standard Handling (A)

Other Notes

Burton, P., et al. 2010. Biochem. J.in press.
Lorbar, M., et al. 1999. J. Mol. Cell. Cardiol.31, 401.
Verde, I., et al. 1999. Br. J. Pharmacol.127, 65.
Reynolds, A.J., et al. 1996. Brain Res.798, 67.
Mery, P.F., et al. 1995. Mol. Pharmacol.48, 121.
Podzuweit, T., et al. 1995. Cell. Signal.7, 733.
Bessodes, M., et al. 1982. Biochem. Pharmacol.31, 879.
Bouchard, P., et al. 1981. Proc. Natl. Acad. Sci. USA78, 1033.

Legal Information

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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable