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ADU-S100 ammonium salt

Names

[ CAS No. ]:
1638750-96-5

[ Name ]:
ADU-S100 ammonium salt

[Synonym ]:
5,8-Methano-12H-furo[3,2-l]-1,3,6,9,11,2,10-pentaoxadiphosphacyclotetradecin-15,16-diol, 7,14-bis(6-amino-9H-purin-9-yl)octahydro-2,10-dimercapto-, 2,10-dioxide, diammonium salt, (5S,7R,8R,12aR,14R,15R,15aS,16S)-
(1R,6R,8R,9R,10S,15S,17R,18S)-8,17-Bis(6-amino-9H-purin-9-yl)-3,12-disulfanyl-2,4,7,11,13,16-hexaoxa-3,12-diphosphatricyclo[13.2.1.06,10]octadecane-9,18-diol 3,12-dioxide diammoniate
ML RR-S2 CDA (ammonium salt)

Biological Activity

[Description]:

ADU-S100 ammonium salt is an activator of stimulator of interferon genes (STING).

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> STING
Research Areas >> Inflammation/Immunology

[Target]

STING[1]


[In Vitro]

ADU-S100 shows enhanced type I IFN production over CDA in THP-1 human monocytes. In contrast, the dithio, mixed-linkage cyclic dinucleotide (CDN) derivatives (ML RR-CDA, ML RR-S2 CDG, and ML RR-S2 cGAMP) potently activate all five hSTING alleles, including the refractory hSTINGREF and hSTINGQ alleles. ADU-S100 induces the highest expression of IFN-β and the pro-inflammatory cytokines TNF-α, IL-6, and MCP-1 on a molar equivalent basis, as compared to endogenous ML cGAMP and the TLR3 agonist poly I:C. ADU-S100 is also found to induce aggregation of STING and induce phosphorylation of TBK1 and IRF3 in mouse bone marrow macrophage (BMM). ADU-S100 induces significantly higher levels of IFN-α when compared to ML cGAMP[1].

[In Vivo]

ADU-S100 shows higher anti-tumor control than the endogenous ML cGAMP. A dose response of the ADU-S100 compound is performed in B16 tumor-bearing mice, which identifies an optimal antitumor dose level that also elicites maximum tumor antigen-specific CD8+ T cell responses, and improves long-term survival to 50%[1].

[Cell Assay]

Cryopreserved hPBMCs are thawed and 1×106 cells per well are plated in a 96 well plate in RPMI media supplemented with 10% FBS, 1% non-essential amino acids, 1% penicillin/streptomycin, L-glutamine, 10 mM HEPES buffer, 1 mM Sodium Pyruvate, 0.055 mM β-ME at 37°C with 5% CO2. Cells are stimulated with 10 μM ADU-S100 or ML cGAMP for 6 hours and supernatants are harvested. Supernatants are diluted 1:2 and assayed for IFN-α protein using Cytometric Bead Array (CBA) Human Flex Set. Data is collected using a FACSVerse cytometer and analyzed by FCAP Array Software[1].

[Animal admin]

Mice[1] WT C57BL/6 mice are inoculated with 5×104 B16.F10 cells in the left flank (n=8). When tumor volumes are 100 mm3 mice receive three IT doses of either ML RR-S2 CDG (25 μg), ADU-S100 (50 μg), or HBSS as control. WT C57BL/6 mice are inoculated with 5×104 B16.F10 cells in the left flank (n=5). When tumor volumes are 100 mm3 they received three IT doses of ADU-S100 at 5, 25, 50 or 100 μg or HBSS as control. WT C57BL/6 mice are inoculated with 5×104 B16.F10 cells in the left flank (n=8). When tumor volumes are 100 mm3 they receive three IT doses of 100 μg ADU-S100 or HBSS as control. Treatments are administered on days 13, 17 and 20 and tumor measurements are taken twice weekly. Results are shown as percent survival by Log-rank (Mantel-Cox) test (A and C).

[References]

[1]. Corrales L, et al. Direct Activation of STING in the Tumor Microenvironment Leads to Potent and Systemic Tumor Regression and Immunity. Cell Rep. 2015 May 19;11(7):1018-30.


[Related Small Molecules]

CCCP | DMXAA (Vadimezan) | G10, STING signaling activator | ML RR-S2 CDA | C 176 | Cyclic-di-GMP | cGAMP | STING agonist-1(compound 3)trihydrochloride

Chemical & Physical Properties

[ Molecular Formula ]:
C20H30N12O10P2S2

[ Molecular Weight ]:
724.604

[ Exact Mass ]:
724.112427


Related Compounds