c-di-GMP Fluorinated

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

THP1-Dual™ cells were stimulated for 24 hours with the STING ligands as shown (all at 10 μg/ml). The interferon regulatory factor (IRF) response was assessed by measuring the activity of Lucia luciferase in the supernatant using QUANTI-Luc™ 4 Lucia/Gaussia. Data are shown in fold response over non-induced cells (mean ± SEM).

THP1-Dual™ cells were stimulated for 24 hours with the STING ligands as shown (all at 10 μg/ml). The NF-κB-induced SEAP activity was assessed using QUANTI‑Blue™ Solution, a SEAP detection reagent. Data are shown as optical density (OD) at 630 nm (mean ± SEM). Non‑induced cells (NI) have been included as a negative control.

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 has been assessed by measuring the induction of the interferon pathway using cellular assays.
• The absence of endotoxins and other bacterial contaminants has been confirmed using HEK-Blue™ TLR4 and HEK-Blue™ TLR2 cells.

Contents

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

Product is shipped at room temperature.

 Upon receipt, store at -20 °C.

Details