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SML1232

Sigma-Aldrich

cGAMP sodium salt

≥98% (HPLC)

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Synonym(s):
3′3′-cGAMP sodium salt, Cyclic AMP-GMP sodium salt, c-GMP-AMP sodium salt, cyclic GMP-AMP sodium salt
Empirical Formula (Hill Notation):
C20H24N10O13P2 · xNa+
CAS Number:
849214-04-6
Molecular Weight:
674.41 (free acid basis)
UNSPSC Code:
12352200
PubChem Substance ID:
329825735
NACRES:
NA.77

description

contains 0.5μmol of powder (approx. 0.335mg)

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

storage temp.

−20°C

SMILES string

O=C1N=C(N)NC2=C1N=CN2[C@H](O3)[C@H](O)[C@H](OP4(O)=O)[C@H]3COP(O)(O[C@H]5[C@@H](O)[C@H](N6C=NC7=C6N=CN=C7N)O[C@@H]5CO4)=O.C

Related Categories

Application

cGAMP sodium salt has been used in cGAS-cGAMP Activity Assay.

Biochem/physiol Actions

Cyclic AMP-GMP (cGAMP) is one of several naturally occurring cyclic dinucleotides that act as a bacterial second messengers to regulate important signaling mechanisms in prokaryotes that control bacterial survival, adhesion, colonization, biofilm formation, and virulence factors production. In cholera c-AMP-GMP promotes intestinal colonization by down-regulating chemotaxis. During infections bacterial cGAMP is bound by host STING (stimulator of interferon genes) activating innate immune responses leading to expression of interferon genes.
cGAMP induces the formation of cytokines (interferon-β, interferon-γ), activation of dendritic cells and CD8+ T cell cross priming. Through this action, it promotes innate immune response. cGAMP possesses antitumor activity and is prefered for immunotherapy in cancer treatment.

Preparation Note

Cyclic AMP-GMP is soluble in water and aqueous buffers (> 10 mM, limits have not been determined).

related product

Product No.
Description
Pricing

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Yong Shen et al.
Cell reports, 35(12), 109272-109272 (2021-06-24)
The type I interferon (IFN) pathway is a key component of innate immune response upon invasion of foreign pathogens. It is also under precise control to prevent excessive upregulation and undesired inflammation cascade. In the present study, we report that
Antitumor activity of cGAMP via stimulation of cGAS-cGAMP-STING-IRF3 mediated innate immune response.
Li T, et al.
Scientific Reports, 6, 19049-19049 (2016)
manganese Increases the Sensitivity of the cgas-sting Pathway for Double-stranded Dna and Is Required for the Host Defense against Dna Viruses.
Wang C, et al.
Immunity, 48(4), 675-687 (2018)
Andrea Annibal et al.
Analytical and bioanalytical chemistry, 413(26), 6457-6468 (2021-09-04)
Cyclic dinucleotides (CDNs) are key secondary messenger molecules produced by cyclic dinucleotide synthases that trigger various cellular signaling cascades from bacteria to vertebrates. In mammals, cyclic GMP-AMP synthase (cGAS) has been shown to bind to intracellular DNA and catalyze the
Chenguang Wang et al.
Immunity, 48(4), 675-687 (2018-04-15)
Manganese (Mn) is essential for many physiological processes, but its functions in innate immunity remain undefined. Here, we found that Mn2+ was required for the host defense against DNA viruses by increasing the sensitivity of the DNA sensor cGAS and

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