A bacterial second messenger and cyclic dinucleotide
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Cyclic di-GMP (sodium salt)

Item No. 17144

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
guanylyl-(3'→5')-3'-guanylic acid, cyclic nucleotide, disodium salt
CAS Number
2222132-40-1
Synonyms
  • c-di-GMP
  • Cyclic diguanylate
  • 3',5'-Cyclic diguanylic acid
Molecular Formula
C20H22N10O14P2 • 2Na
Formula Weight
734.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Water: 1 mg/ml
λmax
245 nm
SMILES
O=C1NC(N)=NC2=C1N=CN2[C@@H]([C@@H]3O)O[C@@]([H])([C@]3(OP([O-])(OC[C@]([H])([C@]4(O5)[H])O[C@H]([C@@H]4O)N6C(N=C(N7)N)=C(N=C6)C7=O)=O)[H])COP5([O-])=O.[Na+].[Na+]
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
InChi Key
SVIXOIGPVFFABR-XDODWTFASA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Cyclic di-GMP is a second messenger in bacteria involved in diverse prokaryotic processes, including biofilm formation, motility, virulence, and cell cycling.1,2 In eukaryotic cells, cyclic di-GMP is detected by and binds to the transmembrane protein stimulator of interferon genes (STING; Kd = 1.21 µM), leading to activation of the innate immune system.3,4 It has been used at a preset molar ratio with STING dimers in binding assays to determine the binding constants of particularly tight binding partners, such as 2’3’-cGAMP. Cyclic di-GMP induces IFN-β mRNA expression in vitro (EC50 = 537.8 nM) but less potently than 2’3’-cGAMP (Item No. 19887), 3’2’-cGAMP, 3’3’-cGAMP (Item No. 17966), and 2’2’-cGAMP (Item No. 22419).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Römling, U., Galperin, M.Y., and Gomelsky, M. Cyclic di-GMP: The first 25 years of a universal bacterial second messenger. Microbiol. Mol. Biol. Rev. 77(1), 1-52 (2013).

    2. Martínez, L.C., and Vadyvaloo, V. Mechanisms of post-transcriptional gene regulation in bacterial biofilms. Front. Cell. Neurosci. 4(38), 1-15 (2014).

    3. Schaap, P. Cyclic di-nucleotide signaling enters the eukaryote domain. IUBMB Life 65(11), 897-903 (2013).

    4. Zhang, X., Shi, H., Wu, J., et al. Cyclic GMP-AMP containing mixed phosphodiester linkages is an endogenous high-affinity ligand for STING. Mol. Cell 51(2), 226-235 (2013).