c-di-AMP sodium(x)

c-di-AMP (Cyclic diadenylate) sodium 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 sodium 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 sodium acts as a potent mucosal adjuvant stimulating both humoral and cellular responses.

Product information

Molecular Weight: 657.40

Formula: C20H23N10O12P2

Synonym:

Cyclic diadenylate sodium

Cyclic-di-AMP sodium

Chemical Name: (1S,6R,8R,9R,10S,15R,17R,18R)-8,17-bis(6-amino-9H-purin-9-yl)-3,9,12,18-tetrahydroxy-2,4,7,11,13,16-hexaoxa-3λ⁵,12λ⁵-diphosphatricyclo[13.3.0.0⁶,¹⁰]octadecane-3,12-dione sodium

Smiles: NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@@H]3[C@@H](COP(O)(=O)O[C@H]2[C@H]1O)O[C@H]([C@@H]3O)N1C=NC2=C([NH])N=CN=C12 |^1:39|

InChiKey: MVLHCKQLAICDLT-XPWFQUROSA-N

InChi: InChI=1S/C20H23N10O12P2/c21-15-9-17(25-3-23-15)29(5-27-9)19-11(31)13-7(39-19)1-37-43(33,34)42-14-8(2-38-44(35,36)41-13)40-20(12(14)32)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-21,31-32H,1-2H2,(H,33,34)(H,35,36)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: To be determined

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

c-di-AMP (Cyclic diadenylate) sodium signaling is a central factor in many Gram-positive bacteria regulating cell wall synthesis, potassium ion channels, DNA repair, and biofilm formation. c-di-AMP sodium is also essential for cell growth, survival, and virulence of several well-known human pathogenic bacteria including S. aureus, L. monocytogenes, S. pyogenes, and Mycobacterium spp. c-di-AMP sodium combines with model antigens, such as OVA or β-Gal, acts as a potent mucosal adjuvant stimulating both humoral and cellular responses.

References:

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.

Products are for research use only. Not for human use.