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3'3'-cGAMP (sodium salt)

  Cat. No.:  DC50039   Featured
Chemical Structure
849214-04-6
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More than 5000 active chemicals with high quality for research!
Field of application
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.
Chemicals PropertiesBiological activity COA & MSDSRelated productsDatasheet
Cas No.: 849214-04-6
Chemical Name: c-GpAp
Synonyms: c-GpAp;Cyclic AMP-GMP;Cyclic GMP-AMP;3'3'-cGAMP;2-Amino-9-[(1S,6S,8R,9S,10S,15S,17R,18S)-17-(6-aminopurin-9-yl)-3,9,12,18-tetrahydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.3.0.06,10]octadecan-8-yl]-1H-purin-6-one;ro-6H-purin-6-on;ro-6H-purin-6-one;3',5'-cyclic GMP-AMP;-2-yl]-1,9-dihydro-;c-GMP-AMP;4BW;adenylyl-(3'?5')-3'-guanylic acid, cyclic nucleotide;cGAMP;Cyclic AMP-GMP;Cyclic GMP-AMP;cGAMP sodium salt;3'3'-cGAMP (sodium salt);2′,3′-CGAMP;3′,3′-Cyclic guanosine adenosine monophosphate;Cyclic [G(3′,5′)pA(3′,5′)p]
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
M.Wt: 674.411284446716
Purity: >98%
Sotrage: 2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO
MSDS
COA
LOT NO. DOWNLOAD
2018-0101
Cat. No. Product name Field of application
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DC39220 STING agonist compound 17 STING agonist compound 17 is a selective stimulator of interferon genes (STING) receptor agonist.
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DC39030 SR-717 SR-717 is a non-nucleotide, small-molecule STING agonist and functions as a direct cyclic guanosine monophosphate-adenosine monophosphate (cGAMP) mimetic that induces the same "closed" conformation of STING.SR-717 functions as a direct cyclic guanosine mo
DC72041 BSP16 BSP16 is a potent, orally active stimulator of interferon genes (STING) agonist. BSP16 can selectively stimulate the STING pathway. BSP16 can be used for the research of cancer.
DC50039 3'3'-cGAMP (sodium salt) 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.
DC48024 cGAMP diammonium cGAMP (Cyclic GMP-AMPP) diammonium functions as an endogenous second messenger in metazoans and triggers interferon production in response to cytosolic DNA. cGAMP diammonium activates stimulator of interferon genes (STING), which activates a signaling cascade leading to the production of type I interferons and other immune mediators.
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