C9137

Cordycepin 5′-triphosphate sodium salt

≥95%

• Synonym(s): 3′-dATP, 3′-deoxy-ATP, 3′-Deoxyadenosine 5′-triphosphate
• Empirical Formula (Hill Notation): C₁₀H₁₆N₅O₁₂P₃
• CAS Number: 71997-32-5
• Molecular Weight: 491.18
• NACRES: NA.51
• PubChem Substance ID: 24893135
• UNSPSC Code: 41106305
• MDL number: MFCD00057015
• Assay: ≥95%
• Form: powder

Properties

• Quality Segment: 200
• 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

Description

General description

Cordycepin (3′-deoxyadenosine) is a cytotoxic adenosine analog and a bioactive agent extracted from Cordyceps militaris.[1] Cordycepin 5′-triphosphate is a toxic derivative of cordycepin.[2]

Application

Cordycepin 5′-triphosphate sodium salt has been used:

• as a transcriptional inhibitor in RNA decay assay[3]
• to inhibit polyadenylation in HEK293T cells before harvesting for in- vitro interaction studies through co-immunoprecipitation (co-Ips)[4]
• as a positive control in in vitro assays for polymerase inhibition[5]
• as a precursor to produce cordycepin monophosphate[1]

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.[1] Cordycepin triphosphate inhibits picornavirus polymerase-specific RNA synthesis by blocking in vitro [3H]GMP incorporation.[2] It also retards cell growth by inhibiting RNA synthesis.[6]

Safety Information

• pictograms: GHS08,GHS07
• signalword: Warning
• hcodes: H302 + H332,H315,H319,H335,H351
• pcodes: P202 - P301 + P312 - P302 + P352 - P304 + P340 + P312 - P305 + P351 + P338 - P308 + P313
• 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