cGAMP diammonium

• CAT Number: I045632
• Molecular Formula: C20H30N12O13P2
• Molecular Weight: 708.47
• Purity: ≥95%
• Synonyms: 2-amino-9-[(1S,6R,8R,9R,10S,15R,17R,18R)-17-(6-aminopurin-9-yl)-3,9,12,18-tetrahydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3λ5,12λ5-diphosphatricyclo[13.3.0.06,10]octadecan-8-yl]-1H-purin-6-one;azane
• InChI: InChI=1S/C20H24N10O13P2.2H3N/c21-14-8-15(24-3-23-14)29(4-25-8)18-10(31)12-6(40-18)1-38-45(36,37)43-13-7(2-39-44(34,35)42-12)41-19(11(13)32)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);2*1H3/t6-,7-,10-,11-,12-,13-,18-,19-;;/m1../s1
• InChIKey: FBSYGJFUOMICSJ-DQNSRKNCSA-N
• SMILES: C1C2C(C(C(O2)N3C=NC4=C3N=C(NC4=O)N)O)OP(=O)(OCC5C(C(C(O5)N6C=NC7=C(N=CN=C76)N)O)OP(=O)(O1)O)O.N.N

cGAMP (Cyclic GMP-AMPP) diammonium functions as an endogenous second messenger in metazoans and triggers interferon production in response to cytosolic DNA. cGAMP diammonium activates stimulator of interferon genes (STING), which activates a signaling cascade leading to the production of type I interferons and other immune mediators[1][2][3][4].
cGAMP diammonium promotes the antigen-specific proliferation capacity of spleen cells in mice[2].
cGAMP diammonium directly activates murine and human dendritic cells in vitro[2].
On stimulation with cGAMP diammonium, fibroblasts from the patients showed increased transcription of IFNB1 but not of the genes encoding interleukin-1 (IL1), interleukin-6 (IL6), or tumor necrosis factor (TNF)[3].
cGAMP diammonium activates the endoplasmic reticulum (ER)-resident receptor STING, thereby inducing an antiviral state and the secretion of type I IFNs[4].
cGAMP (5 µg; nostril mucosal adjuvant) diammonium promotes the antigen-specific cytokine production by spleen cells of immunized mice[2].

Reference

[1]. Wu J, et al. Cyclic GMP-AMP is an endogenous second messenger in innate immune signaling by cytosolic DNA. Science. 2013 Feb 15;339(6121):826-30.
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[2]. Skrnjug I, et al. Cyclic GMP-AMP displays mucosal adjuvant activity in mice. PLoS One. 2014 Oct 8;9(10):e110150.
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[3]. Ablasser A, et al. Cell intrinsic immunity spreads to bystander cells via the intercellular transfer of cGAMP. Nature. 2013 Nov 28;503(7477):530-4.
 [Content Brief]