Inhibitor of S-adenosylhomocysteine hydrolase
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3-Deazaadenosine

Item No. 9000785

Technical Information
Formal Name
1-β-D-ribofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine
CAS Number
6736-58-9
Synonyms
  • c3Ado
  • deaza-Ado
  • 3-DZA
Molecular Formula
C11H14N4O4
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 5 mg/mlDMSO: 20 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
267 nm
SMILES
NC1=C2C(N([C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)C=N2)=CC=N1
InChi Code
InChI=1S/C11H14N4O4/c12-10-7-5(1-2-13-10)15(4-14-7)11-9(18)8(17)6(3-16)19-11/h1-2,4,6,8-9,11,16-18H,3H2,(H2,12,13)/t6-,8-,9-,11-/m1/s1
InChi Key
DBZQFUNLCALWDY-PNHWDRBUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    3-Deazaadenosine (3-DZA) is an inhibitor of SAH hydrolase (Ki = 3.9 μM).1,2 It has anti-inflammatory properties, inhibiting leukocyte adhesion and chemotaxis, lymphocyte-mediated cytolysis, phagocytosis, degranulation, and NF-κB signaling.3,4 3-DZA also has antiviral and antibacterial activities.1,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chiang, P.K. Biological effects of inhibitors of S-adenosylhomocysteine hydrolase. Pharmacol. Ther. 77(2), 115-134 (1998).

    2. Gordon, R.K., Ginalski, K., Rudnicki, W.R., et alAnti-HIV-1 activity of 3-deaza-adenosine analogs: Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners. Eur. J. Biochem. 270(17), 3507-3517 (2003).

    3. Jurgensen, C.H., Huber, B.E., Zimmerman, T.P., et al3-Deazaadenosine inhibits leukocyte adhesion and ICAM1 biosynthesis in tumor necrosis factor-stimulated human endothelial cells. J. Immunol. 144(2), 653-661 (1990).

    4. Jeong, S.Y., Ahn, S.G., Lee, J.H., et al3-Deazaadenosine, a S-adenosylhomocysteine hydrolase inhibitor, has dual effects on NF-κB regulation. The Journal of Biological Chemisty 274(27), 18981-18988 (1999).

    5. Long, M.C., Allan, P.W., Luo, M.Z., et alEvaluation of 3-deaza-adenosine analogues as ligands for adenosine kinase and inhibitors of Mycobacterium tuberculosis growth. J. Antimicrob. Chemother. 59(1), 118-121 (2007).

    6. Huggins, J., Zhang, Z.X., and Bray, M. Antiretroviral drug therapy of filovirus infections: S-adenosylhomocysteine hydrolase inhibitors inhibit ebola virus in vitro and in a lethal mouse model. J. Infect. Dis. 179(Suppl. 1), S240-S247 (1999).