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SML1229

Sigma-Aldrich

2′,3′-cGAMP sodium salt

≥98% (HPLC)

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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About This Item

Formule empirique (notation de Hill):
C20H24N10O13P2 · xNa+
Numéro CAS:
Poids moléculaire :
674.41 (free acid basis)
Code UNSPSC :
51111800
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Description

contains 0.5μmol of powder (approx. 0.335mg)

Niveau de qualité

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Notes préparatoires

2′,3′-cGAMP is soluble in water and aqueous buffers (>> 5 mM, limits have not been determined).

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Consulter la Bibliothèque de documents

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
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
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
Qingyuan Zhu et al.
Antiviral research, 183, 104933-104933 (2020-09-20)
Stimulator of interferon genes (STING), as a signaling hub in innate immunity, plays a central role for the effective initiation of host defense mechanisms against microbial infections. Upon binding of its ligand cyclic dinucleotides (CDNs) produced by the cyclic GMP-AMP
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

Articles

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

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