C9137
Cordycepin 5′-triphosphate sodium salt
≥95%
Synonym(s):
3′-dATP, 3′-deoxy-ATP, 3′-Deoxyadenosine 5′-triphosphate
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About This Item
Empirical Formula (Hill Notation):
C10H16N5O12P3
CAS Number:
Molecular Weight:
491.18
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
MDL number:
Assay:
≥95%
Form:
powder
assay
≥95%
form
powder
mol wt
491.18 g/mol
storage temp.
−20°C
SMILES string
[Na].Nc1ncnc2n(cnc12)C3OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)CC3O
InChI
1S/C10H16N5O12P3.Na.H/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(16)1-5(25-10)2-24-29(20,21)27-30(22,23)26-28(17,18)19;;/h3-6,10,16H,1-2H2,(H,20,21)(H,22,23)(H2,11,12,13)(H2,17,18,19);;
InChI key
FRGBONDYLMUOMH-UHFFFAOYSA-N
General description
Cordycepin (3′-deoxyadenosine) is a cytotoxic adenosine analog and a bioactive agent extracted from Cordyceps militaris. Cordycepin 5′-triphosphate is a toxic derivative of cordycepin.
Application
Cordycepin 5′-triphosphate sodium salt has been used:
- as a transcriptional inhibitor in RNA decay assay
- to inhibit polyadenylation in HEK293T cells before harvesting for in- vitro interaction studies through co-immunoprecipitation (co-Ips)
- as a positive control in in vitro assays for polymerase inhibition
- as a precursor to produce cordycepin monophosphate
Biochem/physiol Actions
Cordycepin 5′-triphosphate is incorporated into nucleic acid by poly(A) polymerase. Because it lacks a 3′-hydroxyl group chain production it can be used for 3′-end labeling of RNA.
Cordycepin exhibits various metabolic effects by activating AMP-activated protein kinase (AMPK) in humans. Cordycepin triphosphate inhibits picornavirus polymerase-specific RNA synthesis by blocking in vitro [3H]GMP incorporation. It also retards cell growth by inhibiting RNA synthesis.
signalword
Warning
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
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3′-end labeling of RNA with recombinant yeast poly(A) polymerase.
Lingner J, Keller W.
Nucleic Acids Research, 25, 2917-2920 (1993)
Nicole Montreau et al.
Comptes rendus biologies, 326(12), 1135-1147 (2004-01-30)
Using an in vivo heterologous system to study the stability of Xenopus laevis RNA injected into axolotl (Ambystoma mexicanum) fertilized eggs, we have previously observed unexpected fluctuations in RNA level during early development [Andéol et al., Differentiation 63 (1998) 69-79].
D L Panicali et al.
Journal of virology, 25(1), 124-128 (1978-01-01)
Cordycepin triphosphate inhibited in vitro [3H]GMP incorporation by pricornavirus-specific polymerase complexes isolated from infected HeLa cells. The inhibition of [3H]GMP incorporation could be reversed with ATP added to the reaction mixture along with the inhibitor, but not with GTP so