An active metabolite of 8-chloro cAMP
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8-Chloroadenosine-5'-triphosphate (sodium salt)

Item No. 38448

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8-chloro-adenosine 5′-(tetrahydrogen triphosphate), tetrasodium salt
CAS Number
793671-47-3
Synonyms
  • 8-chloro ATP
Molecular Formula
C10H11ClN5O13P3 • 4Na
Formula Weight
629.6
Purity
≥95%
Formulation (Request formulation change)
A solution in water
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
O[C@@H]1[C@@H](COP(OP(OP([O-])([O-])=O)([O-])=O)([O-])=O)O[C@@H](N2C3=NC=NC(N)=C3N=C2Cl)[C@@H]1O.[Na+].[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C10H15ClN5O13P3.4Na/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(18)5(17)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21;;;;/h2-3,5-6,9,17-18H,1H2,(H,22,23)(H,24,25)(H2,12,13,14)(H2,19,20,21);;;;/q;4*+1/p-4/t3-,5-,6-,9-;;;;/m1..../s1
InChi Key
BIFUJGGPLKGBNZ-ZVQJTLEUSA-J
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    2.7 mg

    $280

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    Product Description

    8-Chloroadenosine-5’-triphosphate (8-chloro ATP) is an active metabolite of the anticancer agent 8-chloro cAMP and a derivative of the nucleotide adenosine 5’-triphosphate (ATP; Item No. 14498).1 It is formed from 8-chloro cAMP via 8-chloroadenosine (Item No. 35766) and mono- and diphosphate intermediates. 8-chloro ATP accumulates for up to 12 hours following application of 8-chloro cAMP or 8-chloroadenosine and is associated with inhibition of cell growth, decreases in endogenous ATP levels, and a reduction in RNA, but not DNA, synthesis in patient-derived multiple myeloma cells. It inhibits topoisomerase II-α-dependent relaxation of supercoiled pUC19 DNA when used at concentrations of 1.5 to 8 mM, as well as reduces topoisomerase II-α-catalyzed ATP hydrolysis by 50% at 1 mM, in K562 human myelocytic leukemia cells.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gandhi, V., Ayres, M., Halgren, R.G., et al. 8-chloro-cAMP and 8-chloro-adenosine act by the same mechanism in multiple myeloma cells. Cancer Res. 61(14), 5474-5479 (2001).

    2. Yang, S.-Y., Jia, X.-Z., Feng, L.-Y., et al. Inhibition of topoisomerase II by 8-chloro-adenosine triphosphate induces DNA double-stranded breaks in 8-chloro-adenosine-exposed human myelocytic leukemia K562 cells. Biochem. Pharmacol. 77(3), 433-443 (2009).