An isomer of ATP-α-S and a P2Y1 receptor agonist
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Rp-Adenosine-5'-O-(1-thiotriphosphate) (sodium salt)

Item No. 38535

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
Adenosine, 5′→P′′-ester with [P′′(R)]-thiotriphosphoric acid ((HO)2P(O)OP(O)(OH)OP(O)(OH)(SH)), tetrasodium salt
Synonyms
  • Rp-ATP-α-S
Molecular Formula
C10H12N5O12P3S • 4Na
Formula Weight
611.2
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](CO[P@](OP(OP([O-])([O-])=O)([O-])=O)([S-])=O)O[C@@H](N2C3=NC=NC(N)=C3N=C2)[C@@H]1O.[Na+].[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C10H16N5O12P3S.4Na/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(25-10)1-24-30(23,31)27-29(21,22)26-28(18,19)20;;;;/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,31)(H2,11,12,13)(H2,18,19,20);;;;/q;4*+1/p-4/t4-,6-,7-,10-,30-;;;;/m1..../s1
InChi Key
YDIKIZFBYNZKKC-QSYGCOILSA-J
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    2.6 mg

    $264

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    Product Description

    Rp-Adenosine-5'-O-(1-thiotriphosphate) (Rp-ATP-α-S) is an isomer of the sulfur-containing nucleotide derivative ATP-α-S and an agonist of the purinergic P2Y1 receptor.1 It increases calcium mobilization in HEK293 cells expressing the human P2Y1 receptor (EC50 = 75 nM). Rp-ATP-α-S binds to washed isolated human platelets (Ki = 156 nM), inhibits ADP-induced aggregation of isolated human platelet-rich plasma (PRP; pA2 = 4.74), and inhibits cAMP production induced by prostaglandin E1 (PGE1; Item No. 13010) in isolated human PRP (pA2 = 5.26).2,3 It also induces relaxation of carbamoylcholine-preconstricted guinea pig taenia coli strips (EC50 = 56 nM).4 Rp-ATP-α-S has been used in the synthesis of cyclic dinucleotides that are recognized by bacterial riboswitches.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Major, D.T., Nahum, V., Wang, Y., et al. Molecular recognition in purinergic receptors. 2. Diastereoselectivity of the h-P2Y1-receptor. J. Med. Chem. 47(18), 4405-4416 (2004).

    2. Agarwal, A.K., Tandon, N.N., Greco, N.J., et al. Evaluation of the binding to fixed platelets of agonists and antagonists of ADP-induced aggregation. Thromb. Haemost. 62(4), 1103-1106 (1989).

    3. Cusack, N.J., and Hourani, S.M. Adenosine 5-diphosphate antagonists and human platelets: No evidence that aggregation and inhibition of stimulated adenylate cyclase are mediated by different receptors. Br. J. Pharmacol. 76(1), 221-227 (1982).

    4. Burnstock, G., Cusack, N.J., and Meldrum, L.A. Effects of phosphorothioate analogues of ATP, ADP and AMP on guinea-pig taenia coli and urinary bladder. Br. J. Pharmacol. 82(2), 369-374 (1984).

    5. Launer-Felty, K.D., and Strobel, S.A. Enzymatic synthesis of cyclic dinucleotide analogs by a promiscuous cyclic-AMP-GMP synthetase and analysis of cyclic dinucleotide responsive riboswitches. Nucleic Acids Res. 46(6), 2765-2776 (2018).