2'3'-cGAMP (sodium salt)
2’,3’-cGAMP (sodium salt) is a second messenger generated by the enzyme cGAMP synthase (cGAS) in the cytoplasm of mammalian cells, in response to the presence of double-stranded DNA. As a second messenger, 2’,3’-cGAMP sodium salt activates innate immune responses via binding of STING (stimulator of IFN genes) and initiates the TBK1-IRF3-dependent production of IFN-β.
It is used to identify small compounds that bind to STING. It is also applicable in the research of type I interferon response to cytosolic DNA. The binding affinity of 2’,3’-cGAMP to STING is 3.79 nM (Kd value), which is stronger than other cyclic di-nucleotides, e.g. cyclic di-GMP, 3’2’-cGAMP, 3’3’-cGAMP and 2’2’-cGAMP (Kds = 1.21 μM, 1.61 μM, 1.04 μM and 287 nM, respectively).
References:
Zhang X. et al., 2013. Cyclic GMP-AMP containing mixed phosphdiester linkages is an endogenous high-affinity ligand for STING. Mol Cell.51(2):226-35.
Samira Khiar et al., 2017. Identification of a small molecule that primes the type I interferon response to cytosolic DNA. Sci Rep, 7 (1), 2561
Zhong B. et al., 2008. The adaptor protein MITA links virus-sensing receptors to IRF3 transcription factor activation. Immunity. 29(4):538-50.
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Physical Appearance | A solid |
Storage | Store at -20°C |
M.Wt | 718.37 |
Cas No. | 1441190-66-4 |
Formula | C20H22N10Na2O13P2 |
Synonyms | Guanosine-Adenosine 2',3'-cyclic monophosphate,2'-3'-Cyclic GMP-AMP |
Solubility | insoluble in EtOH; insoluble in DMSO; ≥7.56 mg/mL in H2O |
Chemical Name | adenylyl-(3'→5')-2'-guanylic acid, cyclic nucleotide, disodium salt |
SDF | Download SDF |
Canonical 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+] |
Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
General tips | We do not recommend long-term storage for the solution, please use it up soon. |
Quality Control & MSDS
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Chemical structure

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