EHNA HYDROCHLORIDE Chemical Properties

Melting point:

183～184℃

storage temp. 

0-6°C

solubility 

DMSO: 12 mg/mL

form 

solid

color 

white

Water Solubility 

water: 25mg/mL

Stability:

Stable for 2 years as supplied. Solutions in distilled water may be stored at -20°C for up to 3 months.

CAS DataBase Reference

51350-19-7

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

EHNA HYDROCHLORIDE Usage And Synthesis

Description

EHNA (51350-19-7) inhibits phosphodiesterase 2 (PDE2) (IC50 = 0.8 – 5.5 μM in a variety of tissues and species) over PDE1, PDE3, or PDE4 (IC50 values > 100 μM).1,2 It also inhibits adenosine deaminase (ADA), IC50 = 1.2 and 1.5 μM in human RBCs and astrocytoma cells, respectively3, which may be responsible for its ability to induce apoptosis in malignant pleural mesothelioma cell lines4. Because it blocks breakdown of adenosine to inosine and hypoxanthine, EHNA prevents formation of free radical substrates, protecting against cardiac reperfusion-mediated injury.5 It inhibits differentiation and maintains expression of pluripotency markers in hESCs, but not through inhibition of PDEs or ADA.6

Chemical Properties

White Solid

Uses

A potent inhibitor of phosphodiesterase II (PDE II) (IC50=800nM). Does ot inhibit other PDE isozymes (IC50>100uM). Inhibits the retrograde transport motor, dynein. Also inhibits adenosine deaminase (Ki=4nM)

Uses

9-erythro-(2-Hydroxyl-3-nonyl)adenine is an intermediate in the synthesis of potent inhibitor of phosphodiesterase II.

Definition

ChEBI: (2R,3S)-EHNA is eHNA of absolute configuration 2R,3S. Selective inhibitor of cGMP-stimulated phosphodiesterase (PDE2) (IC50 = 0.8 - 4 mM). Also a potent inhibitor of adenosine deaminase. It has a role as an EC 3.5.4.4 (adenosine deaminase) inhibitor and an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor. It is a conjugate base of a (2R,3S)-EHNA(1+). It is an enantiomer of a (2S,3R)-EHNA.

Biological Activity

Selective inhibitor of cGMP-stimulated phosphodiesterase (PDE2) (IC 50 = 0.8 - 4 mM). Also a potent inhibitor of adenosine deaminase.

References

[1] THOMAS PODZUWEIT  Antje M  Peter Nennstiel. Isozyme selective inhibition of cGMP-stimulated cyclic nucleotide phosphodiesterases by erythro-9-(2-hydroxy-3-nonyl) adenine[J]. Cellular signalling, 1995, 7 7: Pages 733-738. DOI:10.1016/0898-6568(95)00042-n
[2] P F MÉRY. Erythro-9-(2-hydroxy-3-nonyl)adenine inhibits cyclic GMP-stimulated phosphodiesterase in isolated cardiac myocytes.[J]. Molecular Pharmacology, 1995, 48 1: 121-130.
[3] J BARANKIEWICZ. Regulation of adenosine concentration and cytoprotective effects of novel reversible adenosine deaminase inhibitors.[J]. Journal of Pharmacology and Experimental Therapeutics, 1997, 283 3: 1230-1238.
[4] YASUHIRO NAKAJIMA. Adenosine deaminase inhibitor EHNA exhibits a potent anticancer effect against malignant pleural mesothelioma.[J]. Cellular Physiology and Biochemistry, 2015: 51-60. DOI:10.1159/000369674
[5] ANWAR S. ABD-ELFATTAH PH.D.  Andrew S W M D. Separation Between Ischemic and Reperfusion Injury by Site Specific Entrapment of Endogenous Adenosine and Inosine Using NBMPR and EHNA[J]. Journal of Cardiac Surgery, 1994, 9 3S: 387-396. DOI:10.1111/jocs.1994.9.3s.387
[6] PETER BURTON. Erythro-9-(2-hydroxy-3-nonyl)adenine (EHNA) blocks differentiation and maintains the expression of pluripotency markers in human embryonic stem cells.[J]. Biochemical Journal, 2010, 432 3: 575-584. DOI:10.1042/bj20100726

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