SML1957

ML RR-S2 CDA sodium salt

≥95% (HPLC)

• Synonym(s): Dithio-(Rp, Rp)-2′,3′-CDA sodium salt, Dithio-(Rp, Rp)-2′,3′-c-diAMP sodium salt, Dithio-(Rp, Rp)-2′,5′-3′,5′-c-diAMP sodium salt, Dithio-(Rp, Rp)-[cyclic[A(2′,5′)pA(3′,5′)p]] sodium salt
• Empirical Formula (Hill Notation): C₂₀H₂₄N₁₀O₁₀P₂S₂ · xNa⁺
• CAS Number: 1638241-89-0
• Molecular Weight: 690.54 (free acid basis)
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥95% (HPLC)
• form: powder
• color: white to beige
• shipped in: wet ice
• storage temp.: −20°C
• SMILES string: NC1=NC=NC2=C1N=CN2[C@H]3[C@H](O)[C@H](OP4([S-])=O)[C@@H](COP(O[C@H]5[C@@H](O)[C@H](N(C=N6)C7=C6C(N)=NC=N7)O[C@@H]5CO4)([S-])=O)O3.[R].[R].[Na+]

Description

Biochem/physiol Actions

A mixed linkage (ML) cyclic di-adenosine bisthiophosphate with potent STING-activating activity and in vivo anti-tumor efficacy.

ML-RR-S2 CDA is a potent STING-activating cyclic di-adenosine (CDA or c-diAMP) nucleotide ligand with the 2′-5′, 3′-5′ mixed phosphodiester linkage (ML) in the [Rp,Rp] configuration and doubly substituted thiophosphate (S2) for optimal phosphodiesterase-resistance and thereby enhanced cellular potency. ML-RR-S2 CDA effectively induces IRF3, NF-kB, and STAT6 transcription activities in a STING-dependent manner in both murine (DC2.4 & BMMs) and human (THP1 & PBMCs) cultures (5-100 μM) as well as displays profound anti-tumor efficacy in vivo (100% growth inhibition of established B16.F10, 4T-1 or CT26 tumor with 3X 50 μg/mouse/96 hr intratumoral injections) with lasting immune-mediated tumor rejection.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable