2'3'-cGAMP

Product Name: 2'3'-cGAMP
CAS No.: 1441190-66-4
Chemical Name: 2'3'-cGAMP
Synonyms: -cGAMP;5’)pA(3’;2'3'-cGAMP;cyclic [G(2’;Cgamp（C-20640）;cGAMP(2'3'-cGAMP);2'-3'-cyclic GMP-AMP;2',3'-cGAMP (free acid);2',3'-cGAMP sodium salt;STING Agonist, 2′3′-cGAMP
CBNumber: CB03175651
Molecular Formula: C20H24N10O13P2
Formula Weight: 674.41
MOL File: 1441190-66-4.mol

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2'3'-cGAMP Property

Boiling point:: 1159.9±75.0 °C(Predicted)
Density: 2.61±0.1 g/cm3(Predicted)
storage temp.: -20°C
solubility: Soluble in DMSO (up to at least 25 mg/ml) or in Water (up to 10 mg/ml)
form: powder
pka: 0.89±0.70(Predicted)
color: white to beige
Water Solubility: H2O: soluble
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months.
InChIKey: CNVCOPPPOWRJAV-WOWVFUNENA-L

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML1229
Product name: 2′,3′-cGAMP sodium salt
Purity: ≥98% (HPLC)
Packaging: 0.335 mg
Price: $296.4
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML1229
Product name: 2′,3′-cGAMP sodium salt
Purity: ≥98% (HPLC)
Packaging: .5UMO
Price: $282
Updated: 2023/06/20

Cayman Chemical

Product number: 19887
Product name: 2''3''-cGAMP (sodium salt)
Packaging: 500μg
Price: $276
Updated: 2024/03/01

Cayman Chemical

Product number: 19887
Product name: 2''3''-cGAMP (sodium salt)
Packaging: 1mg
Price: $522
Updated: 2024/03/01

Biosynth Carbosynth

Product number: NC159040
Product name: 2',3'-Cyclic guanosine monophosphate-adenosine monophosphate
Packaging: 1mg
Price: $590
Updated: 2021/12/16

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2'3'-cGAMP Chemical Properties,Usage,Production

Description

2′,3′-cGAMP (CAS 1441190-66-4) is an endogenous STING (stimulator of interferon genes) agonist.[1] Produced from ATP and GTP via the action of cGMP-AMP synthase (cGAS) which acts as a cytosolic DNA sensor.[2,3] Induces autophagy which is a mechanism for clearance of DNA and viruses in the cytosol.[4] DNA damage stimulates 2’,3’-cGAMP which stimulates an inflammatory response.[5]

Chemical Properties

White to colorless lyophilized solid.

Uses

2′,3′-cGAMP sodium salt has been used to identify small compounds capable of binding human stimulator of interferon genes (STING). It is also used to study type I interferon response to cytosolic DNA.

Definition

ChEBI: 2'-3'-cGAMP is a cyclic purine dinucleotide that consists of AMP and GMP units cyclised via 3',5'- and 2',5'-linkages respectively. It is a cyclic purine dinucleotide, a guanyl ribonucleotide and an adenyl ribonucleotide. It is functionally related to a Gp[2'-5']Ap[3']. It is a conjugate acid of a 2'-3'-cGAMP(2-).

Biochem/physiol Actions

2′,3′-cGAMP (cyclic [G(2′,5′)pA(3′,5′)p]) is the natural agonist for the STING (STimulator of INterferon Genes) pathway, discovered to be a pathway for antiviral innate immunity. 2′3′-cGAMP is a second messenger produced in mammalian cells by the cytosolic DNA sensor cGAS (cGAMP synthase) to activate innate immune responses by binding to STING and initiating an interferon response. The affinity of 2′3′-cGAMP for human STING is much higher than that of the bacterial 3′3′-cyclic dinucleotides (CDNs), with a Kd of 4.59 nM compared to >1 μM for bacterial 3′3′-CDNs.

Mode of action

2’3’-cGAMP (cyclic [G(2’,5’)pA(3’,5’)p]) is produced in mammalian cells by cGAS (cGAMP synthase) in response to double-stranded DNA in the cytoplasm. Similar to the canonical 3’3’-cGAMP, 2’3’-cGAMP serves as a second messenger to activate innate immune responses by binding to and activating STING. Upon activation, STING induces type I IFNs via the TANK-binding kinase 1 (TBK1)/interferon regulatory factor 3 (IRF3) pathway [1], and pro-inflammatory cytokines via the NF-κB pathway [1, 2]. Structural and functional studies have revealed that 2’3’-cGAMP is distinct from the canonical 3’3’-cGAMP produced by bacteria [3, 4]. 2'3'-cGAMP binds to STING with a much greater affinity than 3'3'-cGAMP does [1]. Interestingly, certain variants of STING are able to distinguish between noncanonical and canonical cGAMP [3].

References

[1] XU ZHANG. Cyclic GMP-AMP containing mixed phosphodiester linkages is an endogenous high-affinity ligand for STING.[J]. Molecular Cell, 2013, 51 2: 226-235. DOI:10.1016/j.molcel.2013.05.022
[2] JIAXI WU. Cyclic GMP-AMP is an endogenous second messenger in innate immune signaling by cytosolic DNA.[J]. Science, 2013, 339 6121: 826-830. DOI:10.1126/science.1229963
[3] LIJUN SUN. Cyclic GMP-AMP Synthase Is a Cytosolic DNA Sensor That Activates the Type I Interferon Pathway[J]. Science, 2012, 339 6121.
[4] XIANG GUI. Autophagy induction via STING trafficking is a primordial function of the cGAS pathway[J]. Nature, 2019, 567 7747: 262-266. DOI:10.1038/s41586-019-1006-9
[5] TUO LI Zhijian J C. The cGAS-cGAMP-STING pathway connects DNA damage to inflammation, senescence, and cancer.[J]. Journal of Experimental Medicine, 2018, 215 5: 1287-1299. DOI:10.1084/jem.20180139

2'3'-cGAMP Preparation Products And Raw materials

Raw materials

Preparation Products

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2'3'-cGAMP Suppliers

China 103 United States 6 Global 109

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1441190-66-4, 2'3'-cGAMPRelated Search:

Sivelestat sodium BAY 11-7082 EPA Zafirlukast

2'3'-cGAMP

2',3'-cGAMP sodium salt

c[G(2',5')pA(3',5')p] / 2'3'-cGAMP

5’)pA(3’

cyclic [G(2’

Mammalian (non-canonical) CDN

MAMMALIAN (NON-CANONICAL) CDN; CYCLIC [G(2';5')PA(3';5')P]

2′,3′-Cyclic guanosine adenosine monophosphate

2'-3'-cyclic GMP-AMP

2'-Guanylic acid, adenylyl-(3'→5')-, cyclic nucleotide

2',3'-cGAMP (free acid)

-cGAMP

Cgamp（C-20640）

2-Amino-9-((5R,7R,8R,12aR,14R,15R,15aS)-14-(6-amino-9H-purin-9-yl)-2,10,15,16-tetrahydroxy-2,10-dioxidooctahydro-12H-5,8-methanofuro[3,2-l][1,3,6,9,11]pentaoxa[2,10]diphosphacyclotetradecin-7-yl)-3,9-dihydro-6H-purin-6-one

2'-O,5'-O-[(Adenosine-3'-O,5'-O-diyl)bisphosphinico]guanosine

Cyclic guanosine monophosphate-adenosine monophosphate

(1R,6R,8R,9R,10S,15R,17R)-17-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-8-(6-amino-9H-purin-9-yl)-3,9,12,18-tetrahydroxy-2,4,7,11,13,16-hexaoxa-3λ?,12λ?-diphosphatricyclo[13.2.1.0?,1?]octadecane-3,12-dione

STING Agonist, 2′3′-cGAMP

cGAMP(2'3'-cGAMP)

2',3'-Cyclic guanosine monophosphate-adenosine monophosphate

1441190-66-4

C20H24N10O13P2

C20H22N10Na2O13P2

Nucleotide