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cGAMP

Names

[ CAS No. ]:
849214-04-6

[ Name ]:
cGAMP

[Synonym ]:
Cyclic GMP-AMP
Cyclic AMP-GMP
cGAMP
c-GpAp
2-Amino-9-[(2R,3R,3aS,7aR,9R,10R,10aS,14aR)-9-(6-amino-9H-purin-9-yl)-3,5,10,12-tetrahydroxy-5,12-dioxidooctahydro-2H,7H-difuro[3,2-d:3',2'-j][1,3,7,9,2,8]tetraoxadiphosphacyclododecin-2-yl]-1,9-dihyd ro-6H-purin-6-one
c[G(3',5')pA(3',5')p]
6H-Purin-6-one, 2-amino-9-[(2R,3R,3aS,7aR,9R,10R,10aS,14aR)-9-(6-amino-9H-purin-9-yl)octahydro-3,5,10,12-tetrahydroxy-5,12-dioxido-2H,7H-difuro[3,2-d:3',2'-j][1,3,7,9,2,8]tetraoxadiphosphacyclododecin -2-yl]-1,9-dihydro-

Biological Activity

[Description]:

cGAMP(Cyclic GMP-AMP) is an endogenous second messenger in metazoans and triggers interferon production in response to cytosolic DNA; STING ligand.Target:in vitro: cGAMP induced IFNβ RNA robustly even at concentrations as low as 10 nM. cGAMP was much more potent than c-di-GMP in inducing IFNβ based on ELISA assays. cGAMP was also more potent than c-di-GMP and c-di-AMP in activating IRF3. cGAMP binds to and activates STING to trigger the downstream signaling cascades [1]. On stimulation with cGAMP, 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 activates the endoplasmic reticulum (ER)-resident receptor STING, thereby inducing an antiviral state and the secretion of type I IFNs [4].in vivo: cGAMP can enhance the adaptive immune response to the model antigen ovalbumin in mice. cGAMP promotes antigen specific IgG and a balanced Th1/Th2 lymphocyte response in immunized mice [2].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> STING
Research Areas >> Inflammation/Immunology

[References]

[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.

[2]. Skrnjug I, et al. Cyclic GMP-AMP displays mucosal adjuvant activity in mice. PLoS One. 2014 Oct 8;9(10):e110150.

[3]. Liu Y, et al. Activated STING in a vascular and pulmonary syndrome. N Engl J Med. 2014 Aug 7;371(6):507-18.

[4]. 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.


[Related Small Molecules]

CCCP | ADU-S100 ammonium salt | DMXAA (Vadimezan) | G10, STING signaling activator | C 176 | Cyclic-di-GMP | STING agonist-1(compound 3)trihydrochloride

Chemical & Physical Properties

[ Density]:
2.6±0.1 g/cm3

[ Molecular Formula ]:
C20H24N10O13P2

[ Molecular Weight ]:
674.41100

[ Exact Mass ]:
674.10000

[ PSA ]:
349.27000

[ Index of Refraction ]:
2.071

[ Storage condition ]:
2-8℃


Related Compounds