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SML1957

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C20H24N10O10P2S2 · xNa+
CAS Number:
1638241-89-0
Molecular Weight:
690.54 (free acid basis)
UNSPSC Code:
12352200

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+]

Biochem/physiol Actions

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Emily Curran et al.
Cell reports, 15(11), 2357-2366 (2016-06-07)
Type I interferon (IFN), essential for spontaneous T cell priming against solid tumors, is generated through recognition of tumor DNA by STING. Interestingly, we observe that type I IFN is not elicited in animals with disseminated acute myeloid leukemia (AML). Further
Leticia Corrales et al.
Cell reports, 11(7), 1018-1030 (2015-05-12)
Spontaneous tumor-initiated T cell priming is dependent on IFN-β production by tumor-resident dendritic cells. On the basis of recent observations indicating that IFN-β expression was dependent upon activation of the host STING pathway, we hypothesized that direct engagement of STING
Juan Fu et al.
Science translational medicine, 7(283), 283ra52-283ra52 (2015-04-17)
Stimulator of interferon genes (STING) is a cytosolic receptor that senses both exogenous and endogenous cytosolic cyclic dinucleotides (CDNs), activating TBK1/IRF3 (interferon regulatory factor 3), NF-κB (nuclear factor κB), and STAT6 (signal transducer and activator of transcription 6) signaling pathways

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