| Identification | Back Directory | [Name]
bis(3',5')-cyclic diguanylic acid | [CAS]
61093-23-0 | [Synonyms]
5GP-5GP
c-di-GMP
Cyclic di-GMP
cyclic diguanylate
Cyclic-di-GMP(c-di-GMP)
Cyclic-di-GMP，cyclic diguanylate
bis(3',5')-cyclic diguanylic acid
3'-Guanylic acid, guanylyl-(3'→5')-, cyclic nucleotide
Cyclic diguanosine monophosphate ( c-diGMP/c-di-GMP ) / cyclic bis ( 3' > 5' ) diguanylic acid | [Molecular Formula]
C20H24N10O14P2 | [MDL Number]
MFCD31563661 | [MOL File]
61093-23-0.mol | [Molecular Weight]
690.41 |
| Chemical Properties | Back Directory | [Melting point ]
193-196 °C (decomp) | [density ]
2.70±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [form ]
powder | [pka]
0.66±0.70(Predicted) | [color ]
white to beige | [Water Solubility ]
Soluble in Water | [InChIKey]
PKFDLKSEZWEFGL-MHARETSRSA-N | [SMILES]
O[C@@H]1[C@H](OP(OC[C@H]2O[C@@H](N3C(N=C(N)NC4=O)=C4N=C3)[C@H](O)[C@@H]2O5)(O)=O)[C@@H](COP5(O)=O)O[C@H]1N6C(N=C(N)NC7=O)=C7N=C6.C |
| Hazard Information | Back Directory | [Uses]
Cyclic-di-GMP sodium salt has been used as a quorum sensing molecule. | [Definition]
ChEBI: A cyclic purine dinucleotide that is the 3',5'-cyclic dimer of MP. | [Biochem/physiol Actions]
Cyclic-di-GMP is a naturally occurring small molecule that acts as a bacterial second messenger to regulate important signaling mechanisms in prokaryotes that control bacterial survival, adhesion, colonization, biofilm formation, and virulence factors production. During infections Cyclic-di-GMP is bound by host STING (stimulator of interferon genes) leading to expression of interferon genes, activating innate immune responses. c-di-GMP has been found in eukarotic systems acting not only in immune response, but as an inhibitor of the pacemaker I(f) current in the heart. | [in vivo]
Cyclic-di-GMP (100 μg/per; i.v.; two sequential vaccinations 9 days apart) enhances TriVax-induced immune responses to melanoma in mice and further increased the anti-tumor effects of TriVax[3]. | Animal Model: | C57BL/6 (B6) mice (8- to 10-week-old)[3]. | | Dosage: | 100 μg/per | | Administration: | Intravenous injection; two sequential vaccinations 9 days apart; combine with TriVax. | | Result: | Significantly 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.
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Sigma-Aldrich
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https://www.sigmaaldrich.cn |
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