2',5'-Dideoxyadenosine

Modify Date: 2024-01-03 17:12:36

2',5'-Dideoxyadenosine Structure
2',5'-Dideoxyadenosine structure
Common Name 2',5'-Dideoxyadenosine
CAS Number 6698-26-6 Molecular Weight 235.24300
Density 1.77 g/cm3 Boiling Point 547ºC at 760 mmHg
Molecular Formula C10H13N5O2 Melting Point N/A
MSDS USA Flash Point 284.6ºC

 Use of 2',5'-Dideoxyadenosine


2',5'-Dideoxyadenosine is a potent and non-competitive adenylyl cyclase inhibitor via binding the P-site with an IC50 of 3 µM . 2',5'-Dideoxyadenosine is a nucleoside analog and exerts a potent antiadrenergic action in heart[1][2].

 Names

Name 2′,5′-Dideoxyadenosine
Synonym More Synonyms

 2',5'-Dideoxyadenosine Biological Activity

Description 2',5'-Dideoxyadenosine is a potent and non-competitive adenylyl cyclase inhibitor via binding the P-site with an IC50 of 3 µM . 2',5'-Dideoxyadenosine is a nucleoside analog and exerts a potent antiadrenergic action in heart[1][2].
Related Catalog
Target

IC50: 3 µM (adenylyl cyclase)[1]

In Vitro 2',5'-Dideoxyadenosine (10 μM, 30 min) reduces cAMP production and blocks the phosphorylation of GluA1 at Ser845 induced by carbachol (CCh)[3]. 2',5'-Dideoxyadenosine (10 μM, 30 min) blocks CCh-induced increase of phosphorylation of Akt and attenuates CCh-induced phosphorylation of Ser2448[3]. 2',5'-Dideoxyadenosine (20-150 mM), like adenosine, dependently and reversibly inhibits the positive inotropic and chronotropic effect of beta-adrenergic stimulation with isoproterenol (8-54 pmol) up to 70% and 50%, respectively[2]. Western Blot Analysis[3] Cell Line: Primary hippocampal neurons Concentration: 10 μM Incubation Time: 30 min Result: Reduced cAMP production and blocked the phosphorylation of GluA1 at Ser845 induced by carbachol (CCh).
In Vivo 2',5'-Dideoxyadenosine (0.1 mg/kg; IP; 15 min pre-treated) fully inhibits the diuretic, natriuretic and K+ and Cl- sparing effect of Fr•EtOAc in rats[4]. Animal Model: Male Wistar rats (3-4 months old)[3] Dosage: 0.1 mg/kg Administration: IP; 15 min pre-treated Result: Fully inhibited the diuretic, natriuretic and K+ and Cl- sparing effect of Fr•EtOAc in rats.
References

[1]. Bushfield M, et al. Tissue levels, source, and regulation of 3'-AMP: an intracellular inhibitor of adenylyl cyclases. Mol Pharmacol. 1990 Dec;38(6):848-53.

[2]. Hartmann M, et al. Isoproterenol antagonistic effect of 2',5'-dideoxyadenosine in the isolated perfused guinea-pig heart. J Mol Cell Cardiol. 1993 Mar;25(3):331-8.

[3]. Zhao LX, et al. M1 muscarinic receptors regulate the phosphorylation of AMPA receptor subunit GluA1 via a signaling pathway linking cAMP-PKA and PI3K-Akt. FASEB J. 2019 May;33(5):6622-6631.

[4]. Leme Tdos S, et al. Role of prostaglandin/cAMP pathway in the diuretic and hypotensive effects of purified fraction of Maytenus ilicifolia Mart ex Reissek (Celastraceae). J Ethnopharmacol. 2013 Oct 28;150(1):154-61.

 Chemical & Physical Properties

Density 1.77 g/cm3
Boiling Point 547ºC at 760 mmHg
Molecular Formula C10H13N5O2
Molecular Weight 235.24300
Flash Point 284.6ºC
Exact Mass 235.10700
PSA 99.08000
LogP 0.65800
Index of Refraction 1.825
Storage condition -20°C

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
RIDADR NONH for all modes of transport
HS Code 2934999090

 Synthetic Route

~72%

2',5'-Dideoxyadenosine Structure

2',5'-Dideoxyad...

CAS#:6698-26-6

Literature: Desaubry; Shoshani; Johnson Nucleosides and Nucleotides, 1995 , vol. 14, # 6 p. 1453 - 1460

~%

2',5'-Dideoxyadenosine Structure

2',5'-Dideoxyad...

CAS#:6698-26-6

Literature: Nucleosides and Nucleotides, , vol. 14, # 6 p. 1453 - 1460

 Customs

HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

2',5'-dideoxyadenosine