ADU-S100 disodium salt

ADU-S100 disodium salt (MIW815 disodium salt) is an activator of stimulator of interferon genes (STING).

Product information

CAS Number: 1638750-95-4

Molecular Weight: 734.51

Formula: C20H22N10Na2O10P2S2

Synonym:

MIW815 disodium salt

ML RR-S2 CDA disodium salt

Chemical Name: disodium (1R,3R,6R,8R,9R,10S,12R,15R,17R)-8,17-bis(6-amino-9H-purin-9-yl)-1,6,10,15,18-pentahydrogenio-3,12-dioxo-3,12-disulfanyl-2,4,7,11,13,16-hexaoxa-3λ⁵,12λ⁵-diphosphatricyclo[13.2.1.0⁶,¹⁰]octadecane-9,18-bis(olate)

Smiles: [Na+].[Na+].NC1N=CN=C2C=1N=CN2[C@@H]1O[C@@H]2CO[P@@](=O)(S)O[C@H]3[C@@H](O[C@H](CO[P@@](=O)(S)O[C@H]2[C@H]1[O-])C3[O-])N1C=NC2C1=NC=NC=2N

InChiKey: QSNYMJBPLDPGOV-WUQMEGSCSA-N

InChi: InChI=1S/C20H22N10O10P2S2.2Na/c21-15-9-17(25-3-23-15)29(5-27-9)19-12(32)13-8(38-19)2-36-42(34,44)40-14-11(31)7(1-35-41(33,43)39-13)37-20(14)30-6-28-10-16(22)24-4-26-18(10)30;;/h3-8,11-14,19-20H,1-2H2,(H,33,43)(H,34,44)(H2,21,23,25)(H2,22,24,26);;/q-2;2*+1/t7-,8-,11?,12-,13-,14-,19-,20-,41-,42-;;/m1../s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: H2O : 100 mg/mL (136.15 mM; ultrasonic and adjust pH to 7 with NaOH).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

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.

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%.

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.

Products are for research use only. Not for human use.