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c-di-AMP disodium

Cat No.:V51261 Purity: ≥98%
Sodium c-di-AMP (cyclic diadenylate) is a STING agonist that binds to STING, thereby activating the TBK3-IRF3 signaling pathway and triggering the production of type I IFN and TNF.
c-di-AMP disodium
c-di-AMP disodium Chemical Structure CAS No.: 2734909-87-4
Product category: STING
This product is for research use only, not for human use. We do not sell to patients.
Size Price
500mg
1g
Other Sizes

Other Forms of c-di-AMP disodium:

  • c-di-AMP
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Sodium c-di-AMP (cyclic diadenylate) is a STING agonist that binds to STING, thereby activating the TBK3-IRF3 signaling pathway and triggering the production of type I IFN and TNF. c-di-AMP sodium is a bacterial second-generation messenger primarily in Gram-positive (Gram+) cells that regulates cell growth and ultimately virulence. c-di-AMP (cyclic diadenylate) also regulates the next step in the immune response. c-di-AMP sodium works as a potent mucosal adjuvant, stimulating humoral and cellular responses
Biological Activity I Assay Protocols (From Reference)
ln Vitro
In many Gram-positive bacteria, the manufacture of cell walls, potassium channels, DNA repair, and the formation of biofilms are all regulated by c-di-AMP (cyclic diadenylate) sodium signaling. A number of well-known human pathogenic bacteria, such as Staphylococcus aureus, Listeria monocytogenes, Streptococcus pyogenes, and Mycobacterium spp., depend on sodium c-di-AMP for cell growth, survival, and virulence. It's quite significant [1]. When combined with model antigens like OVA or β-Gal, c-di-AMP sodium functions as a strong mucosal adjuvant that stimulates cellular and humoral responses [4].
References

[1]. 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]. 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]. 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]. 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.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H25N10NAO12P2
Molecular Weight
682.409595251083
Exact Mass
702.068
CAS #
2734909-87-4
Related CAS #
c-di-AMP diammonium;c-di-AMP;54447-84-6
PubChem CID
122714672
Appearance
White to off-white solid powder
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
20
Rotatable Bond Count
2
Heavy Atom Count
46
Complexity
1070
Defined Atom Stereocenter Count
8
SMILES
O[C@@H]1[C@]2([H])OP(OC[C@@]3([H])O[C@@H](N4C=NC5=C(N=CN=C45)N)[C@H](O)[C@]3([H])OP(O)(=O)OC[C@@]2([H])O[C@H]1N1C=NC2=C(N=CN=C12)N)(O)=O.[NaH]
InChi Key
IXWPEIRAKLMJQW-VEQUCWRQSA-L
InChi Code
InChI=1S/C20H24N10O12P2.2Na/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;;/h3-8,11-14,19-20,31-32H,1-2H2,(H,33,34)(H,35,36)(H2,21,23,25)(H2,22,24,26);;/q;2*+1/p-2/t7-,8-,11-,12-,13-,14-,19-,20-;;/m1../s1
Chemical Name
disodium;(1S,6R,8R,9R,10S,15R,17R,18R)-8,17-bis(6-aminopurin-9-yl)-3,12-dioxido-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3λ5,12λ5-diphosphatricyclo[13.3.0.06,10]octadecane-9,18-diol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.  (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~270 mg/mL (~384.41 mM)
H2O : ≥ 50 mg/mL (~71.19 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 6.75 mg/mL (9.61 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 67.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 6.75 mg/mL (9.61 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 67.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 6.75 mg/mL (9.61 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 67.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.4654 mL 7.3270 mL 14.6539 mL
5 mM 0.2931 mL 1.4654 mL 2.9308 mL
10 mM 0.1465 mL 0.7327 mL 1.4654 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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