Merck
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SML1228

Sigma-Aldrich

Cyclic-di-GMP sodium salt

≥98% (HPLC)

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Synonym(s):
3′,5′-Cyclic diguanylic acid sodium salt, Bis(3′,5′)-cyclic diguanylic acid sodium salt, Cyclic Diguanosine-5′-monophosphate sodium salt, c-di-GMP sodium salt, c-diGMP sodium salt, cGpGp sodium salt
Empirical Formula (Hill Notation):
C20H24N10O14P2 · xNa+
CAS Number:
Molecular Weight:
690.41 (free acid basis)
PubChem Substance ID:
NACRES:
NA.77

description

contains 1μmol of powder (approx. 0.7mg)

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to beige

storage temp.

−20°C

SMILES string

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

InChI

1S/C20H24N10O14P2/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)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1

InChI key

PKFDLKSEZWEFGL-MHARETSRSA-N

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This Item
G6129A6885C9630
form

powder

form

powder

form

powder

form

powder

color

white to beige

color

white

color

white

color

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

description

contains 1μmol of powder (approx. 0.7mg)

description

-

description

-

description

-

Application

Cyclic-di-GMP sodium salt has been used as a quorum sensing molecule.

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.

Preparation Note

Cyclic-di-GMP is soluble in water and aqueous buffers.

related product

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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An Aphrodisiac Produced By Vibrio fischeri Stimulates Mating In The Closest Living Relatives Of Animals.
Woznica A, et al.
bioRxiv, 139022-139022 (2017)
Miguel Angel De la Cruz-Villegas et al.
Journal of microbiology and biotechnology, 30(6), 811-821 (2020-04-03)
Mycobacterium tuberculosis produces mycolic acids which are relevant for persistence, recalcitrance to antibiotics and defiance to host immunity. c-di-GMP is a second messenger involved in transition from planktonic cells to biofilms, whose levels are controlled by diguanylate cyclases (DGC) and
Emily N Chin et al.
Science (New York, N.Y.), 369(6506), 993-999 (2020-08-21)
Stimulator of interferon genes (STING) links innate immunity to biological processes ranging from antitumor immunity to microbiome homeostasis. Mechanistic understanding of the anticancer potential for STING receptor activation is currently limited by metabolic instability of the natural cyclic dinucleotide (CDN)
Andrea Annibal et al.
Analytical and bioanalytical chemistry, 413(26), 6457-6468 (2021-09-04)
Cyclic dinucleotides (CDNs) are key secondary messenger molecules produced by cyclic dinucleotide synthases that trigger various cellular signaling cascades from bacteria to vertebrates. In mammals, cyclic GMP-AMP synthase (cGAS) has been shown to bind to intracellular DNA and catalyze the
Lei Zhang et al.
Nature communications, 11(1), 5371-5371 (2020-10-25)
Autoinducer-2 (AI-2) is a quorum sensing signal that mediates communication within and between many bacterial species. However, its known receptors (LuxP and LsrB families) are not found in all the bacteria capable of responding to this signaling molecule. Here, we

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