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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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2'3'-cGAMP Suppliers

BOC Sciences
Tel
16314854226
Email
info@bocsci.com
Country
United States
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9923
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TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
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United States
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32161
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58
BOC Sciences
Tel
+1-631-485-4226
Fax
1-631-614-7828
Email
inquiry@bocsci.com
Country
United States
ProdList
19553
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Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
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58
Focus Biomolecules
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sales@focusbiomolecules.com
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United States
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Cayman Chemical Company
Tel
--
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Email
cayman@caymanchem.com
Country
United States
ProdList
6213
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81

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


  • 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