3'3'-cGAMP - CAS 849214-04-6
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
3'3'-cGAMP
Catalog Number:
849214-04-6
Synonyms:
Cyclic [G(3’,5’)pA(3’,5’)p], cyclic GMP-AMP; c-GpAp sodium salt
CAS Number:
849214-04-6
Description:
STING agonist
Molecular Weight:
718.38
Molecular Formula:
C20H22N10O13P2 .2Na
Quantity:
Milligrams-Grams
Quality Standard:
In-house
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
C1C2C(C(C(O2)N3C=NC4=C3NC(=NC4=O)N)O)OP(=O)(OCC5C(C(C(O5)N6C=NC7=C6N=CN=C7N)O)OP(=O)(O1)O)O
InChI:
1S/C20H24N10O13P2/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)/t6-,7-,10-,11
InChIKey:
RFCBNSCSPXMEBK-RPKOMYRRSA-N
Targets:
STING | Others
Chemical Structure
CAS 849214-04-6 3'3'-cGAMP

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Reference Reading


1.Antitumor Activity of cGAMP via Stimulation of cGAS-cGAMP-STING-IRF3 Mediated Innate Immune Response.
Li T1, Cheng H2, Yuan H2, Xu Q2, Shu C3, Zhang Y1, Xu P2, Tan J3, Rui Y1, Li P3, Tan X2. Sci Rep. 2016 Jan 12;6:19049. doi: 10.1038/srep19049.
Immunotherapy is one of the key strategies for cancer treatment. The cGAS-cGAMP-STING-IRF3 pathway of cytosolic DNA sensing plays a pivotal role in antiviral defense. We report that the STING activator cGAMP possesses significant antitumor activity in mice by triggering the STING-dependent pathway directly. cGAMP enhances innate immune responses by inducing production of cytokines such as interferon-β, interferon-γ, and stimulating dendritic cells activation, which induces the cross-priming of CD8(+) T cells. The antitumor mechanism of cGAMP was verified by STING and IRF3, which were up-regulated upon cGAMP treatment. STING-deficiency dramatically reduced the antitumor effect of cGAMP. Furthermore, cGAMP improved the antitumor activity of 5-FU, and clearly reduced the toxicity of 5-FU. These results demonstrated that cGAMP is a novel antitumor agent and has potential applications in cancer immunotherapy.
2.Hybrid promiscuous (Hypr) GGDEF enzymes produce cyclic AMP-GMP (3', 3'-cGAMP).
Hallberg ZF1, Wang XC2, Wright TA1, Nan B3, Ad O1, Yeo J1, Hammond MC4. Proc Natl Acad Sci U S A. 2016 Feb 16;113(7):1790-5. doi: 10.1073/pnas.1515287113. Epub 2016 Feb 2.
Over 30 years ago, GGDEF domain-containing enzymes were shown to be diguanylate cyclases that produce cyclic di-GMP (cdiG), a second messenger that modulates the key bacterial lifestyle transition from a motile to sessile biofilm-forming state. Since then, the ubiquity of genes encoding GGDEF proteins in bacterial genomes has established the dominance of cdiG signaling in bacteria. However, the observation that proteobacteria encode a large number of GGDEF proteins, nearing 1% of coding sequences in some cases, raises the question of why bacteria need so many GGDEF enzymes. In this study, we reveal that a subfamily of GGDEF enzymes synthesizes the asymmetric signaling molecule cyclic AMP-GMP (cAG or 3', 3'-cGAMP). This discovery is unexpected because GGDEF enzymes function as symmetric homodimers, with each monomer binding to one substrate NTP. Detailed analysis of the enzyme from Geobacter sulfurreducens showed it is a dinucleotide cyclase capable of switching the major cyclic dinucleotide (CDN) produced based on ATP-to-GTP ratios.