A synthetic dinucleotide
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2’2’-cGAMP (sodium salt)

Item No. 22419

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
adenylyl-(2’ → 5’)-2’-guanylic acid, cyclic nucleotide, disodium salt
CAS Number
1465774-27-9
Synonyms
  • Adenosine-Guanosine 2’,2’-cyclic monophosphate
  • cGAMP(2’-5’)
  • 2’,2’-Cyclic GMP-AMP
Molecular Formula
C20H22N10O13P2 • 2Na
Formula Weight
718.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Water: soluble
λmax
256 nm
SMILES
O=P(OC[C@](O[C@H]1N2C=NC3=C2NC(N)=NC3=O)([H])C(O)[C@@]1([H])O4)([O-])O[C@]([C@H](N5C=NC6=C5N=CN=C6N)O7)([H])C(O)[C@@]7([H])COP4([O-])=O.[Na+].[Na+]
InChi Code
InChI=1S/C20H24N10O13P2.2Na/c21-14-8-15(24-3-23-14)29(4-25-8)18-12-10(31)6(40-18)1-38-45(36,37)43-13-11(32)7(2-39-44(34,35)42-12)41-19(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
SCPBVQDKYSCDAE-RENITANYSA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    2’2’-cGAMP is a synthetic dinucleotide (CDN) that contains non-canonical 2'5'-phosphodiester bonds.1 It binds to the adapter protein stimulator of interferon genes (STING; Item Nos. 22816 | 22815), which is a component of the innate immune response that activates the type I interferon pathway when bound to cyclic dinucleotides. 2’2-cGAMP shows weaker binding to STING than 2’3’-cGAMP (Item No. 19887; Kd = 287 and 3.79 nM, respectively) but binds more strongly than 3’3’-cGAMP (Item No. 17966), cyclic di-GMP (Item No. 17144), or 3’2’-cGAMP, which bind in the micromolar range (Kds = 1.04, 1.21, or 1.61 µM, respectively).1 Despite weaker binding, 2’2’-cGAMP induces IFN-β production in the same concentration range as 2’3’-cGAMP (EC50s = 15.8 and 19.4 nM, respectively, in L929 cells).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).