C-di-AMP

C-di-AMP (Cyclic diadenylate) is a STING agonist, which binds to the transmembrane protein STING thereby activating the TBK3-IRF3 signaling pathway, subsequently triggering the production of type I IFN and TNF. c-di-AMP (Cyclic diadenylate) is also a bacterial second messenger, which regulates cell growth, survival, and virulence, primarily within Gram-positive bacteria, and also regulates host immune response. c-di-AMP (Cyclic diadenylate) acts as a potent mucosal adjuvant stimulating both humoral and cellular responses[1][2][3][4].

Product Specifications

CAS Number

[54447-84-6]

Product Name Alternative

Cyclic diadenylate; Cyclic-di-AMP

UNSPSC

12352005

Hazard Statement

H302-H315-H319

Target

Bacterial; Endogenous Metabolite; STING

Type

Reference compound

Related Pathways

Anti-infection; Immunology/Inflammation; Metabolic Enzyme/Protease

Applications

COVID-19-immunoregulation

Field of Research

Inflammation/Immunology

Assay Protocol

https://www.medchemexpress.com/c-di-AMP.html

Purity

99.29

Solubility

H2O : 3.33 mg/mL (ultrasonic)

Smiles

O[C@H]([C@@](OP(O)(OC[C@](O[C@@H](N1C2=NC=NC(N)=C2N=C1)[C@@H]3O)([H])[C@@]3([H])O4)=O)([H])[C@](COP4(O)=O)([H])O5)[C@@H]5N6C7=NC=NC(N)=C7N=C6

Molecular Formula

C20H24N10O12P2

Molecular Weight

658.41

Precautions

P264-P270-P280-P302+P352-P305+P351+P338-P330-P362+P364-P501

References & Citations

[1]Fahmi T, et al. c-di-AMP: An Essential Molecule in the Signaling Pathways that Regulate the Viability and Virulenceof Gram-Positive Bacteria. Genes (Basel) . 2017 Aug 7;8 (8) .|[2]Ning H, et al. Recombinant BCG With Bacterial Signaling Molecule Cyclic di-AMP as Endogenous AdjuvantInduces Elevated Immune Responses After Mycobacterium tuberculosis Infection. Front Immunol. 2019 Jul 3;10:1519.|[3]Ebensen T, et al. The Combination Vaccine Adjuvant System Alum/c-di-AMP Results in Quantitative and QualitativeEnhanced Immune Responses Post Immunization. Front Cell Infect Microbiol. 2019 Feb 19;9:31.|[4]Sanchez MV, et al. Intranasal delivery of influenza rNP adjuvanted with c-di-AMP induces strong humoral and cellularimmune responses and provides protection against virus challenge. PLoS One. 2014 Aug 20;9 (8) :e104824.