EHNA (hydrochloride)

Cayman Chemical Item Number 13352

NSC 263164; erythro-9-(2-Hydroxy-3-nonyl)adenine (CAS 58337-38-5)

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Description

EHNA is a reversible adenosine deaminase inhibitor (IC50 = 1.2 μM in human red blood cells) that also selectively inhibits the cGMP-specific phosphodiesterase (PDE2) (IC50s = 0.8 and 2 μM from human and porcine myocardium, respectively, 3.5 μM in rat hepatocyte, and 5.5 μM in human platelet).1,2 Comparatively, EHNA is much less potent at inhibiting PDE1, PDE3, or PDE4 (IC50s > 100 μM).1 EHNA has been used to evaluate cardioprotective and neuroprotective effects during ischemia, to study the role of cAMP/cGMP signaling, and to maintain pluripotency/prevent differentiation of human embryonic stem cells.3,4,5

1. Podzuweit, T., Nennstiel, P., and Müller, A. Isozyme selective inhibition of cGMP-stimulated cyclic nucleotide phosphodiesterases by erythro-9-(2-hydroxy-3-nonyl) adenine. Cell Signal 7(7) 733-738 (1995).

2. Michie, A.M., Lobban, M., Müller, T., et al. Rapid regulation of PDE-2 and PDE-4 cyclic AMP phosphodiesterase activity following ligation of the T cell antigen receptor on thymocytes: Analysis using the selective inhibitors erythro-9-(2-hydroxy-3-nonyl)-adenine (EHNA) and rolipram. Cell Signal 8(2) 97-110 (1996).

3. Barankiewicz, J., Danks, A.M., Abushanab, E., et al. Regulation of adenosine concentration and cytoprotective effects of novel reversible adenosine deaminase inhibitors. J Pharmacol Exp Ther 283(3) 1230-1238 (1997).

4. Dickinson, N.T., Jang, E.K., and Haslam, R.J. Activation of cGMP-stimulated phosphodiesterase by nitroprusside limits cAMP accumulation in human platelets: Effects on platelet aggregation. Biochem J 323 371-377 (1997).

5. Burton, P., Adams, D.R., Abraham, A., et al. Erythro-9-(2-hydroxy-3-nonyl)adenine (EHNA) blocks differentiation and maintains the expression of pluripotency markers in human embryonic stem cells. Biochem J 432(3) 1-22 (2010).

Synonyms
  • NSC 263164
  • erythro-9-(2-Hydroxy-3-nonyl)adenine
Formal Name (αR,​βS)-​rel-​6-​amino-​β-​hexyl-​α-​methyl-​9H-​purine-​9-​ethanol,​ monohydrochloride
CAS Number 58337-38-5
Molecular Formula C14H23N5O • HCl
Formula Weight 313.8
Formulation A crystalline solid
Purity ≥98%
λmax 210, 261 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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NC1=C2C(N([C@@H]​(CCCCCC)​[C@H]​(O)​C)​C=N2)​=NC=N1.Cl
InCHI Code
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​1S/C14H23N5O.ClH/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)​;1H/t10-,11+;/m1./s1
InCHI Key
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VVDXNJRUNJMYOZ-DHXVBOOMSA-N

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Size Price Quantity Subtotal
5 mg $25.00 $0.00
10 mg $48.00 $0.00
25 mg $113.00 $0.00
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