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2'3'-c-di-AM(PS)2 (Rp,Rp) VacciGrade™

2’3’-c-di-AM(PS)2 (Rp,Rp) VacciGrade™ Unit size Cat. code Docs Qty Price
Analog of c-di-AMP
500 µg
vac-nacda2r
+-
$749.00

2’3’-c-diAM(PS)2(Rp,Rp) endotoxin-free, sterile STING ligand

2’3’-c-di-AM(PS)2 (Rp,Rp) is the Rp, Rp-isomer of the 2’3’ bisphosphorothioate analog of 3’3’-cyclic adenosine monophosphate (c-di-AMP), a  cyclic dinucleotide (CDN). c-di-AMP is a second messenger molecule produced by bacteria and has potent immunostimulant activity in mammals [1]. It activates innate immunity by directly binding the endoplasmic reticulum-resident receptor STING (stimulator of interferon genes), leading to the expression of interferon-β (IFN-β) and nuclear factor-κB (NF-κB) dependent inflammatory cytokines [2].
 

Key Features

  • 2’3’-c-di-AM(PS)2 (Rp,Rp) has a higher affinity for STING than c-di-AMP due to the presence of a 2’-5’, 3’-5’ mixed linkage, as found in endogenous human CDNs produced by cGAS (cyclic GMP-AMP (cGAMP) synthase) [3]. It activates all known human STING alleles, as well as mouse STING.
     
  • In addition, this c-di-AMP analog contains two phosphorothioate diester linkages, which prevent its degradation by the phosphodiesterases that are present in host cells or in the systemic circulation [4].
     
  • Finally, this Rp, Rp dithio diastereoisomer was found to induce higher type I IFN production when compared to the Rp/Sp dithio diastereoisomers or c-di-AMP [3].

 

2’3’-c-di-AM(PS)2 (Rp,Rp) VacciGrade™ is a high-quality pre-clinical grade.
2’3’-c-di-AM(PS)2 (Rp,Rp)​ VacciGrade™​ is for research use only, and not for human or veterinary use.

 

Read our review Read our review on STING: Deciphering the STING Paradox

 

References:

1. Woodward JJ. et al., 2010. c-di-AMP secreted by intracellular Listeria monocytogenes activates a host type I interferon response. Science.328(5986):1703-5.
2. Jin L. et al., 2011. MPYS is required for IFN response factor 3 activation and type I IFN production in the response of cultured phagocytes to bacterial second messengers cyclic-di-AMP and cyclic-di- GMP. J Immunol. 187(5):2595-601.
3. Corrales L et al., 2015. Direct activation of STING in the tumor microenvironment leads to potent and systemic tumor regression and immunity. Cell Rep. 11(7):1018-30.
4. Yan H. et al., 2008. Synthesis and immunostimulatory properties of the phosphorothioate analogs of cdiGMP. Bioorg. Med. Chem. Lett. 18, 5631–5634.

Figures

IRF INDUCTION (Lucia luciferase reporter)
IRF INDUCTION (Lucia luciferase reporter)

THP1-Dual™ cells were stimulated for 24 hours with the STING ligands as shown (all at 10 μg/ml). IRF induction was determined by measuring the relative light units (RLUs) in a luminometer using QUANTI‑Luc™, a Lucia luciferase detection reagent.

NF-kB INDUCTION (SEAP reporter)
NF-kB INDUCTION (SEAP reporter)

THP1-Dual™ cells were stimulated for 24 hours with the STING ligands as shown (all at 10 μg/ml). NF‑kB induction was determined using QUANTI‑Blue™, a SEAP detection reagent, and by reading the optical density (OD) at 655 nm. Non-induced cells (NI) have been included as a negative control.

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Specifications

Description: STING agonist VacciGrade™

Synonyms: (R,R)-(2',3')c-diAM(PS)2, (2',3')-Rp,Rp-c-diAMPSS

CAS number: 1638750-95-4

Formula: C20H22N10O10P2S2•2Na

Molecular weight: 734.50 g/mol

Purity: ≥ 95% by LC/MS and NMR

Solubility: 50 mg/ml in water

Quality control:

 

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Contents

  • 500 μg of lyophilized 2’3’-c-di-AM(PS)2 (Rp,Rp) VacciGrade™
  • 10 ml sterile endotoxin-free physiological water (NaCl 0.9%)

2'3'-c-di-AM(PS)2 (Rp,Rp) VacciGrade™ is shipped at room temperature and

2'3'-c-di-AM(PS)2 (Rp,Rp) VacciGrade™ should be stored at -20°C.

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VacciGrade™

VacciGrade™ is a high-quality pre-clinical grade. VacciGrade™ products are filter-sterilized (0.2 µm) and filled under strict aseptic conditions in a clean room*. The absence of bacterial contamination is assessed by a sterility test using a pharmacopeia-derived assay. The level of bacterial contaminants (endotoxins and lipoproteins) in each lot is verified using a LAL assay and/or a TLR2 and TLR4 reporter assay.
*Except for LPS VacciGrade™, which is prepared in a laminar flow hood dedicated to LPS.

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Details

Structure of 23-cdiAMPS2

 

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Citations

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