3'3'-cGAMP (sodium salt)

• Catalog Number: orb757686
• Category: Small Molecules
• Description: 3’3’-cGAMP Fluorinated (c-[2'FdGMP]-[2'FdAMP]) is a synthetic analog of cyclic guanosine monophosphate- adenosine monophosphate (cyclic GMP-AMP, cGAMP) with a fluorine atom at 2’ position of the nucleosides. 3’3’-cGAMP is a cyclic di-nucleotide produced by bacteria. It is also referred to as "canonical" cGAMP due the presence of the classical 3’-5’ phosphodiester linkages between the guanosine and the adenosine. It has been reported that cGAMP binds STING (stimulator of IFN genes) and subsequently induces TBK1-IRF3-dependent production of IFN-β [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, 3’3’-cGAMP Fluorinated induces higher levels of type I IFNs than does cGAMP. STING ligands such as cGAMP induce type I IFNs and activate interferon stimulated genes (ISG) through IRFs. To facilitate their study, InvivoGen has developed stable reporter cells in two well established immune cell models: THP-1 human monocytes and RAW 264.7 murine macrophages. These cells express a reporter gene (SEAP or Lucia luciferase), under control of an IRF-inducible promoter.
• CAS Number: [849214-04-6]
• MW: 674.417
• SMILES: O[C@@H]1[C@@H]2OP(OC[C@H]3O[C@@H](N4C=NC5C(=NC=NC4=5)N)[C@H](O)[C@@H]3OP(OC[C@H]2O[C@H]1N1C=NC2C(N=C(NC1=2)N)=O)(O)=O)(O)=O
• Formula: C₂₀H₂₄N₁₀O₁₃P₂
• Note: For research use only
• Expiration Date: 12 months from date of receipt.