D7408
2′,5′-Dideoxyadenosine
≥95% (HPLC), Adenylyl cyclase inhibitor, solid
Synonym(s):
2ʹ,5ʹ-dd-Ado, NSC 95943
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About This Item
Empirical Formula (Hill Notation):
C10H13N5O2
CAS Number:
Molecular Weight:
235.24
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.77
Product Name
2′,5′-Dideoxyadenosine, ≥95% (HPLC), solid
SMILES string
C[C@H]1O[C@H](C[C@@H]1O)n2cnc3c(N)ncnc23
InChI key
FFHPXOJTVQDVMO-DSYKOEDSSA-N
InChI
1S/C10H13N5O2/c1-5-6(16)2-7(17-5)15-4-14-8-9(11)12-3-13-10(8)15/h3-7,16H,2H2,1H3,(H2,11,12,13)/t5-,6+,7-/m1/s1
assay
≥95% (HPLC)
form
solid
color
white
solubility
DMSO: soluble
storage temp.
−20°C
Quality Level
Gene Information
rat ... Adcy2(81636)
Related Categories
Application
2′,5′-Dideoxyadenosine has been used to elucidate the mechanism of diligustilide (DLG). It has also been used to inhibit adenylate cyclase (AC).
Biochem/physiol Actions
Cell-permeable adenylyl cyclase inhibitor. IC50 = 2.7 μM in detergent-dispersed rat brain preparations.
Features and Benefits
This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Adenylyl cyclases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
Preparation Note
Store at −20 °C after reconstitution.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Jorge A Rodriguez et al.
American journal of physiology. Heart and circulatory physiology, 290(1), H30-H36 (2005-09-07)
Vascular smooth muscle cell proliferation and migration play an important role in the pathophysiology of several vascular diseases, including atherosclerosis. Prostaglandins that have been implicated in this process are synthesized by two isoforms of cyclooxygenase (COX), with the expression of
Zhixiong Chen et al.
International journal for parasitology, 37(7), 743-761 (2007-02-20)
Trichinella spiralis infection causes hyperexcitability in enteric after-hyperpolarising (AH) sensory neurons that is mimicked by neural, immune or inflammatory mediators known to stimulate adenylyl cyclase (AC)/cyclic 3',5'-adenosine monophosphate (cAMP) signaling. The hypothesis was tested that ongoing modulation and sustained amplification
Hisatoshi Sugiura et al.
Journal of cellular physiology, 210(1), 99-110 (2006-09-26)
Prostaglandin E(2) (PGE(2)) has been shown to have a strong cytoprotective effect, inhibiting apoptosis. In the present study, we evaluated whether PGE(2) has a protective effect on cigarette smoke extract (CSE)-induced apoptosis in human lung fibroblasts. Apoptosis was assessed by
Rhona W Baxendale et al.
Molecular reproduction and development, 66(2), 181-189 (2003-09-02)
In addition to a bicarbonate-regulated soluble adenylyl cyclase (sAC), mammalian spermatozoa, like somatic cells, appear to contain receptor/G protein-regulated AC activity that contributes to the modulation of specialized cell processes. This study provides evidence that agents, known to influence somatic
Xiangdong Wu et al.
American journal of physiology. Endocrinology and metabolism, 293(6), E1836-E1844 (2007-10-18)
Adiponectin is a protein secreted from adipocytes that exhibits salutary effects in the vascular endothelium by signaling mechanisms that are not well understood. In obesity-related disease states and type 2 diabetes, circulating substances, including tumor necrosis factor-alpha (TNFalpha) and high
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Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.
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