An active metabolite of nebularine
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Parent Compound(s)
31329Nebularine
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Purine riboside-5'-O-triphosphate (sodium salt)

Item No. 38491

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-[5-O-[hydroxy[[hydroxy(phosphonooxy)phosphinyl]oxy]phosphinyl]-β-D-ribofuranosyl]-9H-purine, tetrasodium salt
CAS Number
35892-95-6
Synonyms
  • PRTP
  • Purine Riboside Triphosphate
  • PTP
  • PuTP
Molecular Formula
C10H11N4O13P3 • 4Na
Formula Weight
580.1
Purity
≥95%
Formulation (Request formulation change)
A solution in water
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
[O-]P([O-])(OP([O-])(OP([O-])(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)N2C3=NC=NC=C3N=C2)=O)=O)=O.[Na+].[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C10H15N4O13P3.4Na/c15-7-6(2-24-29(20,21)27-30(22,23)26-28(17,18)19)25-10(8(7)16)14-4-13-5-1-11-3-12-9(5)14;;;;/h1,3-4,6-8,10,15-16H,2H2,(H,20,21)(H,22,23)(H2,17,18,19);;;;/q;4*+1/p-4/t6-,7-,8-,10-;;;;/m1..../s1
InChi Key
MVLIGYOSEAYNOT-KLZZHCBDSA-J
Origin
Synthetic
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    2.5 mg

    $280

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    Product Description

    Purine riboside-5'-O-triphosphate (PRTP) is an active metabolite of the antiviral, antibacterial, and anticancer agent nebularine (Item No. 31329).1 It is formed from nebularine by adenosine kinase, which results in depletion of intracellular ATP levels and induces cell death in isolated rat thymocytes, an effect that can be reduced by the adenosine kinase inhibitor 5-iodotubercidin (Item No. 10010375). PRTP is an inhibitor of DNA primase ATP and GTP polymerization activities (IC50s = 35 and 28 µM, respectively, for the human enzyme) and of calmodulin-dependent protein kinase II (CaMKII; Ki = 590 µM).2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kozlowska, M., Smolenski, R.T., Makarewicz, W., et al. ATP depletion, purine riboside triphosphate accumulation and rat thymocyte death induced by purine riboside. Toxicol. Lett. 104(3), 171-181 (1999).

    2. Moore, C.L., Zivkovic, A., Engels, J.W., et al. Human DNA primase uses Watson-Crick hydrogen bonds to distinguish between correct and incorrect nucleoside triphosphates. Biochemistry 43(38), 12367-12374 (2004).

    3. Kwiatkowski, A.P., and King, M.M. Mapping of the adenosine 5'-triphosphate binding site of type II calmodulin-dependent protein kinase. Biochemistry 26(24), 7636-7640 (1987).