SML1229

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

Propriétés

• Description: contains 0.5μmol of powder (approx. 0.335mg)
• Niveau de qualité: 100
• 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

Description

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).

Informations sur la sécurité

• 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