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Merck

SML1229

2′,3′-cGAMP sodium salt

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

Synonyme(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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A propos de cet article

Formule empirique (notation de Hill) :
C20H24N10O13P2 · xNa+
Numéro CAS:
1441190-66-4
Poids moléculaire :
674.41 (free acid basis)
UNSPSC Code:
51111800
PubChem Substance ID:
329825733
NACRES:
NA.77

Principaux documents

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Nom du produit

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

100

Catégories apparentées

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).

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000197234
0000385454
0000383503
0000383503
0000197234

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Consulter la Bibliothèque de documents

Qingyuan Zhu et al.
Antiviral research, 187, 105015-105015 (2021-01-15)
The newly emerged severe acute respiratory syndrome-coronavirus-2 (SARS-CoV-2) coronavirus initiated a pneumonia outbreak (COVID-19) that rapidly spread worldwide and quickly became a public health emergency of international concern; However to date, except Remdesivir, there are no clinically approved specific or
Christos Dogrammatzis et al.
mBio, 15(4), e0037324-e0037324 (2024-03-12)
The STimulator of INterferon Genes (STING) constitutes a major DNA-sensing pathway that restricts HSV-1 infection in different models by activating type I interferon and pro-inflammatory responses. To counteract STING, HSV-1 has evolved numerous strategies including mechanisms to interfere with its
Hua-Fang Bao et al.
The FEBS journal, 291(15), 3432-3453 (2024-04-28)
Inflammatory signals from immunological cells may cause damage to intestinal epithelial cells (IECs), resulting in intestinal inflammation and tissue impairment. Interferon-γ-inducible protein 16 (IFI16) was reported to be involved in the pathogenesis of Behçet's syndrome (BS). This study aimed to
Alice E Denton et al.
The Journal of experimental medicine, 216(3), 621-637 (2019-02-07)
Ectopic lymphoid structures form in a wide range of inflammatory conditions, including infection, autoimmune disease, and cancer. In the context of infection, this response can be beneficial for the host: influenza A virus infection-induced pulmonary ectopic germinal centers give rise
Jacques Greenberg et al.
JCI insight, 7(23) (2022-10-28)
Pancreatic neuroendocrine tumors (PNETs) are malignancies arising from the islets of Langerhans. Therapeutic options are limited for the over 50% of patients who present with metastatic disease. We aimed to identify mechanisms to remodel the PNET tumor microenvironment (TME) to
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