A second messenger and inducer of IFN-β production
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Labeled Version(s)
396082'3'-cGAMP-d8 (ammonium salt)
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2'3'-cGAMP (sodium salt)

Item No. 19887

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
adenylyl-(3'→5')-2'-guanylic acid, cyclic nucleotide, disodium salt
CAS Number
2734858-36-5
Synonyms
  • 2'3'-Cyclic GMP-AMP
  • Guanosine-Adenosine 2',3'-cyclic monophosphate
Molecular Formula
C20H22N10O13P2 • 2Na
Formula Weight
718.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
O=P1([O-])O[C@]([C@@H](O)[C@H](N2C=NC3=C2N=CN=C3N)O4)([H])[C@@]4([H])COP(O[C@@]5([H])[C@H](N6C=NC7=C6NC(N)=NC7=O)O[C@]([C@H]5O)([H])CO1)([O-])=O.[Na+].[Na+]
InChi Code
InChI=1S/C20H24N10O13P2.2Na/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33;;/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33);;/q;2*+1/p-2/t6-,7-,10-,11-,12-,13-,18-,19-;;/m1../s1
InChi Key
CNVCOPPPOWRJAV-DQNSRKNCSA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    2’3’-cGAMP is a second messenger produced from ATP and GTP by cGMP-AMP synthase (cGAS) in the cytoplasm of mammalian cells in response to the presence of DNA.1,2,3 It contains a non-canonical 2’5’-phosphodiester bond and binds tightly to the adapter protein STING (stimulator of interferon genes) with a Kd value of 3.79 nM, which is significantly lower than that observed for 2’2’-cGAMP, 3’3’-cGAMP (Item No. 17966), cyclic di-GMP (Item No. 17144), and 3’2’-cGAMP (Kds = 0.287, 1.04, 1.21, and 1.61 µM, respectively).3 It is a potent inducer of IFN-β mRNA expression with an EC50 value of 19.4 nM in L929 cells.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wu, J., Sun, L., Chen, X., et al. Cyclic GMP-AMP is an endogenous second messenger in innate immune signaling by cytosolic DNA. Science 339(6121), 826-830 (2013).

    2. Sun, L., Wu, J., Du, F., et al. Cyclic GMP-AMP synthase is a cytosolic DNA sensor that activates the type I interferon pathway. Science 339(6121), 786-791 (2013).

    3. Zhang, X., Shi, H., Wu, J., et al. Cyclic GMP-AMP containing mixed phosphodiester linkages is an endogenous high-affinity ligand for STING. Mol. Cell 51(2), 226-235 (2013).