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2',5'-Dideoxyadenosine

Names

[ CAS No. ]:
6698-26-6

[ Name ]:
2',5'-Dideoxyadenosine

[Synonym ]:
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]:

Signaling Pathways >> GPCR/G Protein >> Adenylate Cyclase
Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor
Research Areas >> Metabolic Disease

[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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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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Related Compounds