5.31889

STING Agonist, 2′3′-cGAMP

≥98% (HPLC), solid, STING agonist, Calbiochem^®

• Synonym(s): STING Agonist, 2′3′-cGAMP, c[G(2ʹ,5ʹ)pA(3ʹ,5ʹ)p], 2ʹ,5ʹ-3ʹ,5ʹ-cGAMP
• CAS Number: 1441190-66-4
• MDL number: MFCD31563596
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥98% (HPLC)
• Form: solid
• Storage condition: OK to freeze, desiccated (hygroscopic), protect from light

Properties

• Product Name: STING Agonist, 2′3′-cGAMP,
• assay: ≥98% (HPLC)
• Quality Segment: 100
• form: solid
• potency: 4 nM K_i
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, desiccated (hygroscopic), protect from light
• color: white
• solubility: H₂O: soluble
• storage temp.: −20°C
• SMILES string: [P]1(=O)(O[C@@H]2[C@H](O[C@H]([C@@H]2O)[n]6c7ncnc(c7nc6)N)CO[P](=O)(O[C@H]3[C@@H](O[C@@H]([C@H]3O)CO1)[n]4c5[nH]c(n[c](c5nc4)=O)N)O)O
• InChI: 1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1
• InChI key: XRILCFTWUCUKJR-INFSMZHSSA-N

Description

General description

A cyclic-dinucleotide (cyclic-GMP-AMP) based compound that binds to the C-terminal domain of adaptor endoplasmic reticulum protein known as STING with high affinity (K_d = 4 nM) and induces the synthesis of interferon-b (IFN-b) in mammalian cells (EC₅₀ = 20 nM). Shown to increase IFN-b production in M2-polarized macrophages associated with non-small cell lung carcinoma and enhances the expression of M1 markers iNOS and IL-12p40, while simultaneously reducing the expression of the M2 markers, Arg-1 and Fizz1. Exhibits about 300 fold greater affinity for STING than c-DiGMP, 3′,2′-cGAMP, and 3′,3′-cGAMP and about 75 fold greater affinity over 2′,2′-cGAMP.

Biochem/physiol Actions

Primary Target
STING

Cell permeable: yes

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Wu, X., et al. 2014. Nuc. Aci. Res.42, 8243.
Zhang, X., et al. 2013. Mol. Cell.51, 226.
Wu, J., et al. 2013. Science.339, 26.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable