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Chemical Structure| 4097-22-7 Chemical Structure| 4097-22-7

Structure of 2',3'-Dideoxyadenosine
CAS No.: 4097-22-7

Chemical Structure| 4097-22-7

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2′,3′-Dideoxyadenosine is a nucleoside analog of deoxyadenosine. It inhibits adenylyl cyclase and may play a key role in the inhibition of tumor progression. It is a potent inhibitor of reverse transcriptase enzyme of HIV.

Synonyms: 2′,3′-Dideoxyadenosine; ddA; D2A

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Product Details of 2',3'-Dideoxyadenosine

CAS No. :4097-22-7
Formula : C10H13N5O2
M.W : 235.24
SMILES Code : OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C23)CC1
Synonyms :
2′,3′-Dideoxyadenosine; ddA; D2A
MDL No. :MFCD00010534
InChI Key :WVXRAFOPTSTNLL-NKWVEPMBSA-N
Pubchem ID :20039

Safety of 2',3'-Dideoxyadenosine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Related Pathways of 2',3'-Dideoxyadenosine

GPCR

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
HeLa cells 0.1-50 µM 4 days Inhibited T. cruzi growth, with effects similar to ddI Antimicrob Agents Chemother. 1996 Nov;40(11):2455-8
rat brain astrocytes 20 μM 15 min Investigate the mechanism of DHA and AA release under ATP stimulation, finding that DDA (2',3'-Dideoxyadenosine) almost completely blocks ATP-induced AA release. Br J Pharmacol. 2003 Jul;139(5):1014-22
Human bronchial epithelial cells (16HBE14o- cell line) 200 µM Inhibited adenylate cyclase activity, thereby completely abolishing the aldosterone-induced [Ca2+]i decrease J Physiol. 2001 Nov 15;537(Pt 1):267-75
Guinea-pig thalamic slice relay neurones of the dorsal lateral geniculate nucleus (LGND) 50-100 μM 2',3'-Dideoxyadenosine mimicked the decrease in Ih evoked by A1 receptor activation through inhibition of adenylyl cyclase activity. J Physiol. 1992 Feb;447:729-53
Rat ventral tegmental area neurons 100 μM 2',3'-Dideoxyadenosine, an adenylyl cyclase inhibitor, was used to study its effect on Ih current. Results showed that 2',3'-dideoxyadenosine did not affect Ih current nor alter dopamine's inhibition of Ih. J Physiol. 1993 Mar;462:753-64
TM3 cells 100 μM 20 days Protect cells from viral infection and maintain their immune reactivity. Proc Natl Acad Sci U S A. 1987 Apr;84(7):2033-7
ATH8 cells 50 μM 30 days Inhibit HTLV-III/LAV DNA synthesis and mRNA expression, protecting cells from viral infection. Proc Natl Acad Sci U S A. 1987 Apr;84(7):2033-7

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Swiss albino mice Systemic infection model Oral or subcutaneous 12 to 219 mg/kg Treatment immediately, 5, 24, 29, 48, and 72 hours post-infection, observed for 14 days Evaluate the antibacterial activity of DDA in a mouse systemic infection model, showing protective effects against multiple strains at doses well below toxic levels. Antimicrob Agents Chemother. 1981 Mar;19(3):424-8.

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