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5.31889

Sigma-Aldrich

STING Agonist, 2′3′-cGAMP

Synonym(s):

STING Agonist, 2′3′-cGAMP, c[G(2ʹ,5ʹ)pA(3ʹ,5ʹ)p], 2ʹ,5ʹ-3ʹ,5ʹ-cGAMP

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About This Item

CAS Number:
1441190-66-4
UNSPSC Code:
12352200

assay

≥98% (HPLC)

Quality Level

100

form

solid

potency

4 nM Ki

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated (hygroscopic)
protect from light

color

white

solubility

H2O: soluble

storage temp.

−20°C

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

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 (Kd = 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.
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 (Kd = 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.

Please note that the molecular weight for this compound is batch-specific due to variable water content.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
STING

Warning

Toxicity: Standard Handling (A)

Reconstitution

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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