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2′,5′-Dideoxyadenosine (CAS 6698-26-6) - chemical structure image
Molecular structure of 2′,5′-Dideoxyadenosine, CAS Number: 6698-26-6
2′,5′-Dideoxyadenosine (CAS 6698-26-6) - chemical structure image
Molecular structure of 2′,5′-Dideoxyadenosine, CAS Number: 6698-26-6
Molecular structure of 2′,5′-Dideoxyadenosine, CAS Number: 6698-26-6

2′,5′-Dideoxyadenosine (CAS 6698-26-6)

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Application:
2′,5′-Dideoxyadenosine is a cell-permeable adenylate cyclase inhibitor
CAS Number:
6698-26-6
Purity:
≥98%
Molecular Weight:
235.2
Molecular Formula:
C10H13N5O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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SDS & Certificate of Analysis

2′,5′-Dideoxyadenosine is a nucleoside analog that functions by inhibiting the activity of the enzyme reverse transcriptase, which is essential for the replication of retroviruses such as HIV. 2′,5′-Dideoxyadenosine interferes with the synthesis of viral DNA by acting as a chain terminator during the reverse transcription process. 2′,5′-dideoxyadenosine lacks the 3′ hydroxyl group necessary for the formation of the phosphodiester bond, preventing the addition of further nucleotides to the growing DNA chain. As a result, the viral genome cannot be fully synthesized, ultimately halting the replication of the virus. This mechanism of action makes 2′,5′-dideoxyadenosine a potent inhibitor of retroviral replication, used to study the molecular processes involved in viral infection. Its ability to disrupt the reverse transcription process highlights its significance in understanding the fundamental mechanisms of viral replication and in the development of antiviral strategies.


2′,5′-Dideoxyadenosine (CAS 6698-26-6) References

  1. Synthesis and use of 3'-(azidoiodosalicyl) derivatives of 2', 5'-dideoxyadenosine as photoaffinity ligands for adenylyl cyclase.  |  Shoshani, I., et al. 2000. Arch Biochem Biophys. 376: 221-8. PMID: 10729209
  2. Pyrimidinoceptor potentiation of macrophage PGE(2) release involved in the induction of nitric oxide synthase.  |  Chen, BC. and Lin, WW. 2000. Br J Pharmacol. 130: 777-86. PMID: 10864883
  3. Pro-nucleotide inhibitors of adenylyl cyclases in intact cells.  |  Laux, WH., et al. 2004. J Biol Chem. 279: 13317-32. PMID: 14699161
  4. Enhancement of cellular adenosine triphosphate levels in PC12 cells by 2,5-dideoxyadenosine, a P-site inhibitor of adenylate cyclase.  |  Fujimori, H. and Pan-Hou, H. 2005. Biol Pharm Bull. 28: 358-60. PMID: 15684499
  5. Inhibition of adenylate cyclase attenuates adenosine receptor-mediated relaxation in coronary artery.  |  Sabouni, MH., et al. 1991. J Pharmacol Exp Ther. 259: 508-12. PMID: 1658301
  6. Fast manipulation of cellular cAMP level by light in vivo.  |  Schröder-Lang, S., et al. 2007. Nat Methods. 4: 39-42. PMID: 17128267
  7. Extracellular 3',5'-cAMP-adenosine pathway inhibits glomerular mesangial cell growth.  |  Dubey, RK., et al. 2010. J Pharmacol Exp Ther. 333: 808-15. PMID: 20194527
  8. Evidence for cAMP-independent bTREK-1 inhibition by ACTH and NPS-ACTH in adrenocortical cells.  |  Enyeart, JJ., et al. 2012. Mol Cell Endocrinol. 348: 305-12. PMID: 21952081
  9. Pharmacological distinction between soluble and transmembrane adenylyl cyclases.  |  Bitterman, JL., et al. 2013. J Pharmacol Exp Ther. 347: 589-98. PMID: 24091307
  10. Extracellular NAD(+) inhibits human neutrophil apoptosis.  |  Pliyev, BK., et al. 2014. Apoptosis. 19: 581-93. PMID: 24292505
  11. Role of adenylate cyclase in immunologic release of mediators from rat mast cells: agonist and antagonist effects of purine- and ribose-modified adenosine analogs.  |  Holgate, ST., et al. 1980. Proc Natl Acad Sci U S A. 77: 6800-4. PMID: 6256761
  12. Regulation of the catalytic component of adenylate cyclase. Potentiative interaction of stimulatory ligands and 2',5'-dideoxyadenosine.  |  Florio, VA. and Ross, EM. 1983. Mol Pharmacol. 24: 195-202. PMID: 6310361
  13. Erythroid differentiation and growth inhibition of K562 cells by 2',5'-dideoxyadenosine: synergism with interferon-alpha.  |  Ogawa, K., et al. 1995. Leuk Res. 19: 749-55. PMID: 7500653
  14. Isoproterenol antagonistic effect of 2',5'-dideoxyadenosine in the isolated perfused guinea-pig heart.  |  Hartmann, M. and Schrader, J. 1993. J Mol Cell Cardiol. 25: 331-8. PMID: 8389889
  15. Conversion of 2',3'-dideoxyadenosine (ddA) and 2',3'-didehydro-2',3'-dideoxyadenosine (d4A) to their corresponding aryloxyphosphoramidate derivatives markedly potentiates their activity against human immunodeficiency virus and hepatitis B virus.  |  Balzarini, J., et al. 1997. FEBS Lett. 410: 324-8. PMID: 9237655

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2′,5′-Dideoxyadenosine, 5 mg

sc-201562
5 mg
$143.00

2′,5′-Dideoxyadenosine, 25 mg

sc-201562A
25 mg
$612.00

What is the shipping temperature of this product?

Asked by: hawkeye11
Thank you for your question. The compound, sc-201562, ships at ambient temperatures. If you have any further questions or concerns, please feel free to contact our Technical Service department by calling 800-457-3801 option 2, emailing scbt@scbt.com, or using the Live Chat function on our website.
Answered by: Tech Service 8
Date published: 2017-02-07
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Rated 5 out of 5 by from BurgoyneBurgoyne, et. al. (PubMed ID 19726669) found that 2',5'-Dideoxyadenosine did not inhibit CysNO vasorelaxation of the rat thoracic aorta. It was found, however, to inhibit SNAP vasorelaxation. -SCBT Publication Review
Date published: 2015-07-16
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2′,5′-Dideoxyadenosine is rated 5.0 out of 5 by 1.
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