2'3'-cGAMP

ChemicalBook > CAS DataBase List > 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;2'3'-cGAMP;cyclic [G(2’;Cgamp（C-20640）;2'-3'-cyclic GMP-AMP;2',3'-cGAMP (free acid);2',3'-cGAMP sodium salt;2',3'-cGAMP Sodium Salt
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
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.

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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: .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

Biorbyt Ltd

Product number: orb545945
Product name: 2',3'-cGAMP
Purity: >98%
Packaging: 1mg
Price: $720.8
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

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.

References

1) Zhang?et al.?(2015), Cyclic GMP-AMP containing mixed phosphodiester linkages is an endogenous high-affinity ligand for STING; Mol. Cell?51?226 2) Wu?et al.?(2013), Cyclic GMP-AMP is an endogenous second messenger in innate immune signaling by cytosolic DNA; Science?339?826 3) Sun?et al.?(2013), Cyclic GMP-AMP synthase is a cytosolic DNA sensor that activates the type I interferon pathway; Science?339?786 4) Gui?et al.?(2019),?Autophagy induction via STING trafficking is a primordial function of the cGAS pathway;??Nature,?567?262 5) Li and Chen (2018),?The cGAS-cGAMP-STING pathway connects DNA damage to inflammation, senescence and cancer;??J. Exp. Med.,?215?1287

2'3'-cGAMP Preparation Products And Raw materials

Raw materials

Preparation Products

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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

2',3'-cGAMP Sodium Salt

2'3'-cGAMP

(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

1441190-66-4

C20H24N10O13P2

Nucleotide