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Referencia número: HY-137709

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2'2'-cGAMP

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2'2'-cGAMP, a synthetic CDN, binds STING in the immune response, inducing IFN-β. 2'2'-cGAMP binds weaker binding to STING than 2'3'-cGAMP (HY-100564) but stronger than other CDNs.

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No. CAS: 1465774-27-9
Fòrmula: C₂₀H₂₄N₁₀O₁₃P₂
Peso molecular:674.41

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2'2'-cGAMP Chemical Structure

No. CAS: 1465774-27-9

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Descripciòn

2'2'-cGAMP, a synthetic CDN, binds STING in the immune response, inducing IFN-β. 2'2'-cGAMP binds weaker binding to STING than 2'3'-cGAMP (HY-100564) but stronger than other CDNs^[1].

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Cellular Effect

Cell Line	Type	Value	Description	References
H69AR	EC₅₀	2.63 μM Compound: 2',2'-cGAMP	Activation of wild-type human STING expressed in human THP1-Dual cells co-expressing IRF3-activated ISRE assessed as IRF3 reporter activation measured after 7 hrs by luciferase reporter gene assay Activation of wild-type human STING expressed in human THP1-Dual cells co-expressing IRF3-activated ISRE assessed as IRF3 reporter activation measured after 7 hrs by luciferase reporter gene assay	[PMID: 34019405]
H69AR	EC₅₀	28.47 μM Compound: 2',2'-cGAMP	Activation of wild-type human STING expressed in digitonin treated human THP1-Dual cells co-expressing IRF3-activated ISRE assessed as IRF3 reporter activation measured after 30 mins by luciferase reporter gene assay Activation of wild-type human STING expressed in digitonin treated human THP1-Dual cells co-expressing IRF3-activated ISRE assessed as IRF3 reporter activation measured after 30 mins by luciferase reporter gene assay	[PMID: 34019405]
PBMC	EC₅₀	11.46 μM Compound: 2',2'-cGAMP	Induction of INF-gamma production in healthy human PBMC incubated for 16 hrs Induction of INF-gamma production in healthy human PBMC incubated for 16 hrs	[PMID: 34019405]
PBMC	EC₅₀	11.75 μM Compound: 2'2'-cGAMP	Induction of IFNgamma secretion in human PBMC incubated for 16 hrs Induction of IFNgamma secretion in human PBMC incubated for 16 hrs	[PMID: 36201304]
PBMC	EC₅₀	17.3 μM Compound: 2',2'-cGAMP	Induction of INF-alpha production in healthy human PBMC incubated for 16 hrs Induction of INF-alpha production in healthy human PBMC incubated for 16 hrs	[PMID: 34019405]
PBMC	EC₅₀	44.54 μM Compound: 2'2'-cGAMP	Induction of TNFalpha secretion in human PBMC incubated for 16 hrs Induction of TNFalpha secretion in human PBMC incubated for 16 hrs	[PMID: 36201304]
PBMC	EC₅₀	7.21 μM Compound: 2'2'-cGAMP	Induction of IFNalpha secretion in human PBMC incubated for 16 hrs Induction of IFNalpha secretion in human PBMC incubated for 16 hrs	[PMID: 36201304]
PBMC	EC₅₀	72.63 μM Compound: 2',2'-cGAMP	Induction of TNF-alpha production in healthy human PBMC incubated for 16 hrs Induction of TNF-alpha production in healthy human PBMC incubated for 16 hrs	[PMID: 34019405]

Chemical Information

No. CAS 1465774-27-9
Peso molecular 674.41
Fòrmula C₂₀H₂₄N₁₀O₁₃P₂
SMILES

O[C@H]1[C@](O[P](O)(OC[C@@]([C@H]2O)([H])O[C@](N3C4=NC=NC(N)=C4N=C3)([H])[C@]2([H])O5)=O)([H])[C@](O[C@]1([H])CO[P]5(O)=O)([H])N6C(NC(N)=NC7=O)=C7N=C6
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Room temperature in continental US; may vary elsewhere.
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Please store the product under the recommended conditions in the Certificate of Analysis.

Publications (1)

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J Biol Chem

Dynamic control of bacterial antiphage defense through the CdnG-Cap5 cyclic oligonucleotide-based antiphage pathway in Vibrio cholerae. [Abstract]

2025 Dec 6;302(1):111021. PMID: 41360261

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Ficha de datos (272 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Instrucciones de manejo (2659 KB)

Referencias

[1]. Zhang X, et al. Cyclic GMP-AMP containing mixed phosphodiester linkages is an endogenous high-affinity ligand for STING. Mol Cell. 2013;51(2):226-235. [Content Brief]

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2'2'-cGAMP

1 Cited Publications

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2'2'-cGAMP

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