This product is soluble in water, as well as aqueous buffers. Solutions are stable for up to three months in working aliquots at -20°C. Avoid repeated freeze/thaw cycles. A product datasheet is not available at this time.
SML1229
2′,3′-cGAMP sodium salt
≥98% (HPLC)
Synonym(s):
2′,5′-3′,5′-cGAMP, Cyclic [G(2′,5′)pA(3′,5′)p], cGAMP(2′-5′), c[G(2′,5′)pA(3′,5′)p] sodium salt
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About This Item
Empirical Formula (Hill Notation):
C20H24N10O13P2 · xNa+
CAS Number:
Molecular Weight:
674.41 (free acid basis)
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.
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description
contains 0.5μmol of powder (approx. 0.335mg)
Quality Level
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](OP(OC[C@@H]4[C@@H](O5)[C@@H](O)[C@H](N6C=NC7=C6N=CN=C7N)O4)(O)=O)[C@H](O)[C@H]3COP5(O)=O
InChI
1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)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-,12-,13-,18-,19-/m1/s1
InChI key
XRILCFTWUCUKJR-INFSMZHSSA-N
Application
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.[1]
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.
2′,3′-cGAMP is the natural agonist for the hSTING; second messenger cyclic dinucleotide.
Preparation Note
2′,3′-cGAMP is soluble in water and aqueous buffers (>> 5 mM, limits have not been determined).
related product
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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