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Cyclic-di-GMP disodium (c-di-GMP disodium; cyclic diguanylate disodium; 5GP-5GP disodium)

Cat No.:V74307 Purity: ≥98%
Cyclic-di-GMP disodium is a STING agonist and bacterial second messenger that coordinates different aspects of bacterial growth and behavior such as motility, virulence, biofilm formation, and cell cycle progression.
Cyclic-di-GMP disodium (c-di-GMP disodium; cyclic diguanylate disodium; 5GP-5GP disodium)
Cyclic-di-GMP disodium (c-di-GMP disodium; cyclic diguanylate disodium; 5GP-5GP disodium) Chemical Structure CAS No.: 2222132-40-1
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
Other Sizes

Other Forms of Cyclic-di-GMP disodium (c-di-GMP disodium; cyclic diguanylate disodium; 5GP-5GP disodium):

  • Cyclic-di-GMP diammonium (c-di-GMP diammonium; cyclic diguanylate diammonium; 5GP-5GP diammonium)
  • Cyclic-di-GMP sodium (c-di-GMP sodium; cyclic diguanylate sodium; 5GP-5GP sodium)
  • Cyclic-di-GMP
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Cyclic-di-GMP disodium is a STING agonist and bacterial second messenger that coordinates different aspects of bacterial growth and behavior such as motility, virulence, biofilm formation, and cell cycle progression. Cyclic-di-GMP disodium has anti-cancer cell proliferation/growth activity and can also induce increased CD4 receptor expression and cell cycle arrest. Cyclic-di-GMP disodium may be utilized in cancer research.
Biological Activity I Assay Protocols (From Reference)
Targets
STING[1][2][3][4].
ln Vitro
Human colon cancer cells cannot proliferate when exposed to cyclic-di-GMP disodium (0.5-50 μM; 5 days)[1]. ?In Jurkat cells, cyclic-di-GMP disodium (0.5-50 μM; 5 days) selectively increases CD4 expression[2]. ?In Jurkat cells, cyclic-di-GMP disodium (0.5-50 μM; 5 days) causes cell cycle arrest at the S-phase[2].
ln Vivo
The administration of two consecutive vaccinations, separated by nine days, with 100 μg/per of cyclic-di-GMP disodium (iv) improves the immune responses TriVax elicits in mice against melanoma and amplifies its anti-tumor effects[3].
Cell Assay
Cell Proliferation Assay[1]
Cell Types: H508 cells
Tested Concentrations: 0.5- 50 µM
Incubation Duration: 5 days
Experimental Results: diminished basal H508 cell proliferation by approx 15%, even inhibited acetylcholine- and EGF-induced cell proliferation.

Cell Viability Assay[2]
Cell Types: Jurkat cells
Tested Concentrations: 50 µM
Incubation Duration: 24 h
Experimental Results: Specifically induced of CD4 (no effect on the expression of CD8), with a 6.3-fold upregulation over control and in a dose-dependent manner.

Cell Cycle Analysis[2]
Cell Types: Jurkat cells
Tested Concentrations: 50 µM
Incubation Duration: 24 h
Experimental Results: Increased the percentage of cells in S-phase by 79%, with almost complete disappearance of G2/M-phase cells which diminished by 93%.
Animal Protocol
Animal/Disease Models: C57BL/ 6 (B6) mice (8- to 10weeks old)[3].
Doses: 100 µg/per
Route of Administration: intravenous (iv) injection; two sequential vaccinations 9 days apart; combine with TriVax.
Experimental Results: Dramatically higher numbers of antigen-specific CD8 T cells when combined with TriVax. (TriVax consisted of a mixture of 120 μg Pam-hgp100, 100 μg hgp100 or 100 μg Ova, 50 or 25 μg anti-CD40 antibody, and 25 μg Poly-IC). Enhanced the anti- tumor activity of TriVax.
References

[1]. 3',5'-Cyclic diguanylic acid (c-di-GMP) inhibits basal and growth factor-stimulated human colon cancer cell proliferation. Biochem Biophys Res Commun. 2005 Apr 1;329(1):40-5.

[2]. Elevated expression of the CD4 receptor and cell cycle arrest are induced in Jurkat cells by treatment with the novel cyclic dinucleotide 3',5'-cyclic diguanylic acid. FEBS Lett. 1999 Feb 5;444(1):125-9.

[3]. STING activator c-di-GMP enhances the anti-tumor effects of peptide vaccines in melanoma-bearing mice. Cancer Immunol Immunother. 2015 Aug;64(8):1057-66.

[4]. Cyclic di-GMP: second messenger extraordinaire. Nat Rev Microbiol. 2017 May;15(5):271-284.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H25N10NAO14P2
Molecular Weight
714.408395528793
Exact Mass
734.058
CAS #
2222132-40-1
Related CAS #
Cyclic-di-GMP diammonium;609343-82-0;Cyclic-di-GMP;61093-23-0;Cyclic-di-GMP sodium
PubChem CID
137120247
Appearance
Off-white to light yellow solid powder
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
18
Rotatable Bond Count
2
Heavy Atom Count
48
Complexity
1320
Defined Atom Stereocenter Count
8
SMILES
O=C1N=C(N)NC2N([C@@H]3O[C@]4([H])COP(O[C@@]5([H])[C@@H](O)[C@H](N6C=NC7C(N=C(N)NC6=7)=O)O[C@]5([H])COP(O)(=O)O[C@@]4([H])[C@H]3O)(O)=O)C=NC1=2.[NaH]
InChi Key
SVIXOIGPVFFABR-XDODWTFASA-L
InChi Code
InChI=1S/C20H24N10O14P2.2Na/c21-19-25-13-7(15(33)27-19)23-3-29(13)17-9(31)11-5(41-17)1-39-45(35,36)44-12-6(2-40-46(37,38)43-11)42-18(10(12)32)30-4-24-8-14(30)26-20(22)28-16(8)34;;/h3-6,9-12,17-18,31-32H,1-2H2,(H,35,36)(H,37,38)(H3,21,25,27,33)(H3,22,26,28,34);;/q;2*+1/p-2/t5-,6-,9-,10-,11-,12-,17-,18-;;/m1../s1
Chemical Name
disodium;2-amino-9-[(1S,6R,8R,9R,10S,15R,17R,18R)-17-(2-amino-6-oxo-1H-purin-9-yl)-9,18-dihydroxy-3,12-dioxido-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3λ5,12λ5-diphosphatricyclo[13.3.0.06,10]octadecan-8-yl]-1H-purin-6-one
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)
H2O: 160 mg/mL (217.87 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 50 mg/mL (68.09 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.3998 mL 6.9988 mL 13.9976 mL
5 mM 0.2800 mL 1.3998 mL 2.7995 mL
10 mM 0.1400 mL 0.6999 mL 1.3998 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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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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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