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c-di-GMP Fluorinated

c-di-GMP Fluorinated Unit size Cat. code Docs Qty Price
STING ligand
100 µg
tlrl-nacdgf
+-
$245.00

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STING Ligand - Difluoro 3'3'-c-di-GMP, cyclic [FdG(3’,5’)pFdG(3’,5’)p]

c-di-GMP Fluorinated (c-di[2’FdGMP]) is a synthetic analog of cyclic diguanylate monophosphate (c-di-GMP) with a fluorine atom at 2’ position of the nucleoside. c-di-GMP is a bacterial second messenger that acts a potent immunostimulant in mammals. It induces production of type I interferons (IFNs) by directly binding to the endoplasmic reticulum-resident receptor STING (stimulator of interferon genes) [1].

The incorporation of fluorine into biologically active molecules is commonly used in medicinal chemistry to improve their metabolic stability or to modulate physicochemical properties such as lipophilicity [2, 3]. Moreover, the introduction of a fluorine atom can change the biological activities of a molecule. Interestingly, when used at low concentrations in various cellular assays, c-di-GMP Fluorinated induces higher levels of type I IFNs than does c-di-GMP.

 

References:

1. Burdette DL. et al., 2011. STING is a direct innate immune sensor of cyclic di-GMP. Nature. 478(7370):515-8.
2. Liu P. et al., 2008. Fluorinated Nucleosides: Synthesis and biological implication. J Fluor Chem. 129(9): 743–766.
3. Böhm HJ. et al., 2004.Fluorine in medicinal chemistry. Chembiochem. 5(5):637-43.

Figures

IRF INDUCTION (Lucia luciferase reporter)
IRF INDUCTION (Lucia luciferase reporter)

THP1-Dual™ cells were stimulated for 24 hours with the STING ligands as shown (all at 10 μg/ml). IRF induction was determined by measuring the relative light units (RLUs) in a luminometer using QUANTI‑Luc™, a Lucia luciferase detection reagent.


THP1-Dual™ cells were stimulated for 24 hours with the STING ligands as shown (all at 10 μg/ml). NF‑kB induction was determined using QUANTI‑Blue™, a SEAP detection reagent, and by reading the optical density (OD) at 655 nm. Non-induced cells (NI) have been included as a negative control.

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Specifications

Description: STING agonist

Synonym: 2’Fluoro-c-di-GMP sodium salt, 2',2''-di-F-c-didGMP, c-di(2’FdGMP)

CAS number: 1334145-18-4

Formula: C20H20F2N10O12P2 .2Na

Molecular weight: 738.36

Purity: ≥ 95% by LC/MS

Solubility: 50 mg/ml in water

Quality control:

  • The biological activity is assessed by measuring induction of the interferon pathway in THP1-Blue™ ISG cells.
  • The absence of endotoxins and other bacterial contaminants has been confirmed using HEK-Blue™ TLR4 and HEK-Blue™ TLR2 cells.
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Contents

  • 100 μg lyophilized c-di-GMP Fluorinated
  • 1.5 ml endotoxin-free water

room temperature Product is shipped at room temperature.

store Product should be stored at -20 °C.

Product is sterile filtered prior to lyophilization.

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Details

Structure of c-di-GMP Fluorinated

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