Synonym
3-Deazaadenosine (hydrochloride); c3Ado; deaza-Ado; 3-DZA
IUPAC/Chemical Name
(2R,3R,4S,5R)-2-(4-amino-1H-imidazo[4,5-c]pyridin-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol hydrochloride
InChi Key
WQRKYGAAEYXMKZ-RPWKAPHTSA-N
InChi Code
InChI=1S/C11H14N4O4.ClH/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);1H/t6-,8-,9-,11-;/m1./s1
SMILES Code
[H]Cl.NC1=NC=CC2=C1N=CN2[C@@]3([H])[C@@](O)([H])[C@@](O)([H])[C@](CO)([H])O3
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
302.72
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
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 al. Anti-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 al. 3-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 al. 3-Deazaadenosine, a S-adenosylhomocysteine hydrolase inhibitor, has dual effects on NF-κB regulation. J. Biol. Chem. 274(27), 18981-18988 (1999).
5: Long, M.C., Allan, P.W., Luo, M.Z., et al. Evaluation 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).
