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Merck

SML1229

2′,3′-cGAMP sodium salt

≥98% (HPLC), STimulator of INterferon Genes (STING) pathway agonist , powder

Sinónimos:

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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Fórmula empírica (notación de Hill):
C20H24N10O13P2 · xNa+
Número CAS:
Peso molecular:
674.41 (free acid basis)
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
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Nombre del producto

2′,3′-cGAMP sodium salt, ≥98% (HPLC)

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

description

contains 0.5μmol of powder (approx. 0.335mg)

assay

≥98% (HPLC)

form

powder

color

white to beige

storage temp.

−20°C

Quality Level

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.

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).

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Qingyuan Zhu et al.
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