Cyclic-di-GMP disodium

• CAT Number: I025373
• CAS Number: 2222132-40-1
• Molecular Formula: C20H22N10Na2O14P2
• Molecular Weight: 734.37
• Purity: ≥95%
• Synonyms: 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
• InChI: 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
• InChIKey: SVIXOIGPVFFABR-XDODWTFASA-L
• SMILES: C1C2C(C(C(O2)N3C=NC4=C3N=C(NC4=O)N)O)OP(=O)(OCC5C(C(C(O5)N6C=NC7=C6N=C(NC7=O)N)O)OP(=O)(O1)[O-])[O-].[Na+].[Na+]

Cyclic-di-GMP disodium (Cat No.: I025373) is a soluble bacterial second messenger analog widely used in immunology and microbiology research. It activates the STING (stimulator of interferon genes) pathway, inducing type I interferon production and enhancing innate immune responses. This compound helps researchers explore host–pathogen interactions, immune signaling, and potential adjuvant applications in vaccine development. Its disodium salt form improves stability and solubility for experimental use. While not approved for therapeutic purposes, cyclic-di-GMP disodium remains a valuable tool in studying immune regulation and microbial signaling.

Reference

[1]. Karaolis DK, et al. 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.
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[2]. Steinberger O, et al. 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.
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[3]. Wang Z, et al. 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.
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[4]. Jenal U, et al. Cyclic di-GMP: second messenger extraordinaire. Nat Rev Microbiol. 2017 May;15(5):271-284.
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