An ADP derivative and active metabolite of N6-benzyladenine
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Parent Compound(s)
21711N6-Benzyladenine
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N6-Benzyladenosine-5'-O-diphosphate (sodium salt)

Item No. 38370

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
((2R,3S,4R,5R)-5-(6-(benzylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl diphosphate, trisodium salt
Synonyms
  • N6-benzyl ADP
Molecular Formula
C17H18N5O10P2 • 3Na
Formula Weight
583.3
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([O-])([O-])=O)([O-])=O)O[C@@H](N2C3=NC=NC(NCC4=CC=CC=C4)=C3N=C2)[C@@H]1O.[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C17H21N5O10P2.3Na/c23-13-11(7-30-34(28,29)32-33(25,26)27)31-17(14(13)24)22-9-21-12-15(19-8-20-16(12)22)18-6-10-4-2-1-3-5-10;;;/h1-5,8-9,11,13-14,17,23-24H,6-7H2,(H,28,29)(H,18,19,20)(H2,25,26,27);;;/q;3*+1/p-3/t11-,13-,14-,17-;;;/m1.../s1
InChi Key
FBHDDKIBMKYJAQ-ZWHBHHBYSA-K
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    2.6 mg

    $366

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    Product Description

    N6-Benzyladenosine-5'-O-diphosphate is a derivative of ADP (Item Nos. 16778 | 21121) and an active metabolite of the cytokinin N6-benzyladenine (Item No. 21711).1,2,3 It inhibits the ATPase activities of mortalin, heat shock protein 70 (Hsp70), and heat shock cognate 71 kDa protein (Hsc70; apparent Kis = 86.51, 294.5, and 1,612 µM, respectively, for the human enzymes).2 N6-Benzyladenosine-5'-O-diphosphate inhibits the proliferation of CEM, HL-60, and K562 leukemia, RPMI-8226 multiple myeloma, and MCF-7 breast cancer cells (IC50s = 2, 1.3, 4, 4.5, and 8 µM, respectively).3 It has also been used in the synthesis of radiolabeled and unlabeled forms of N6-benzyladenosine 5'-(γ-thio)-triphosphate (N6-benzyl-ATPγS), which have been used to determine kinase activity.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Auer, C.A., Cohen, J.D., Laloue, M., et al. Comparison of benzyl adenine metabolism in two Petunia hybrida Lines differing in shoot organogenesis. Plant Physiol. 98(3), 1035-1041 (1992).

    2. Moseng, M.A., Nix, J.C., and Page, R.C. 2- and N6-functionalized adenosine-5'-diphosphate analogs for the inhibition of mortalin. FEBS Lett. 593(15), 2030-2039 (2019).

    3. Voller, J., Zatloukal, M., Lenobel, R., et al. Anticancer activity of natural cytokinins: A structure-activity relationship study. Phytochemistry 71(11-12), 1350-1359 (2010).

    4. Dephoure, N., Howson, R.W., Blethrow, J.D., et al. Combining chemical genetics and proteomics to identify protein kinase substrates. Proc. Natl. Acad. Sci. USA 102(50), 17940-17945 (2005).

    5. Allen, J.J., Li, M., Brinkworth, C.S., et al. A semisynthetic epitope for kinase substrates. Nat. Methods 4(6), 511-516 (2007).