D1285
2′,3′-Dideoxyadenosine
≥97% (HPLC)
Synonym(s):
Dideoxyadenosine, ddA
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About This Item
Empirical Formula (Hill Notation):
C10H13N5O2
CAS Number:
Molecular Weight:
235.24
Beilstein:
619924
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51
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Quality Level
Assay
≥97% (HPLC)
form
powder
optical activity
[α]/D -28.0±1.0
mp
181-184 °C (lit.)
solubility
water: 100 mg/mL, clear, colorless
storage temp.
2-8°C
SMILES string
Nc1ncnc2n(cnc12)[C@H]3CC[C@@H](CO)O3
InChI
1S/C10H13N5O2/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(3-16)17-7/h4-7,16H,1-3H2,(H2,11,12,13)/t6-,7+/m0/s1
InChI key
WVXRAFOPTSTNLL-NKWVEPMBSA-N
Gene Information
human ... DCK(1633)
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General description
2′,3′-Dideoxyadenosine is a nucleoside analog of deoxyadenosine. On deamination, it is converted to dideoxyinosine. 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 human immunodeficiency virus.
Application
2′,3′-Dideoxyadenosine (ddA), a specific adenylyl cyclase inhibitor, is useful in biological process and pathway studies involving adenylyl cyclase activity and cAMP pool modulation.
Storage Class Code
11 - Combustible Solids
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Christopher Tubbs et al.
Endocrinology, 150(1), 473-484 (2008-09-20)
Progestin stimulation of sperm hypermotility remains poorly understood despite having been described in numerous vertebrate species. We show here that progestin stimulation of sperm hypermotility in a teleost, the Atlantic croaker (Micropogonias undulatus) is associated with activation of an olfactory
Elena Grossini et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 23(1-3), 87-96 (2009-03-04)
Urocortin II has previously been shown in anesthetized pigs to increase coronary blood flow through activation of the endothelial nitric oxide synthase (eNOS) pathway and involvement of the subtype 2 of corticotropin releasing factor receptors (CRFR2). However, little information has
Electrochemical oxidation of 2′, 3′-dideoxyadenosine at pyrolytic graphite electrode
Goyal RN, et al.
Electrochimica Acta, 53(16), 5354-5360 (2008)
Katharina Schönrath et al.
Molecular carcinogenesis, 50(5), 319-333 (2011-04-12)
VILIP-1 (visinin-like protein 1) is downregulated in various human squamous cell carcinoma (SCC). In a mouse skin SCC model VILIP-1 expression is reduced in aggressive tumor cells, accompanied by reduced cAMP levels. Overexpression of VILIP-1 in aggressive SCC cells led
Anabolism and mechanism of action of Ro24-5098, an isomer of 2',3'-dideoxyadenosine (ddA) with anti-HIV activity.
K B Frank et al.
Annals of the New York Academy of Sciences, 616, 408-414 (1990-01-01)
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