A synthetic second messenger
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Cyclic di-IMP (sodium salt)

Item No. 22485

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
inosinylyl-(3’ → 5’)-3’-inosinic acid, cyclic nucleotide, disodium salt
Synonyms
  • c-di-IMP
  • Cyclic di-inosine monophosphate
Molecular Formula
C20H20N8O14P2 • 2Na
Formula Weight
704.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: 50 mg/ml
λmax
249 nm
SMILES
[H][C@@]([C@@]1([H])CO2)([C@@H](O)[C@H](N3C=NC4=C3N=CNC4=O)O1)OP(OC[C@]5([H])[C@@]([C@@H](O)[C@H](N6C(N=CNC7=O)=C7N=C6)O5)([H])OP2([O-])=O)([O-])=O.[Na+].[Na+]
InChi Code
InChI=1S/C20H22N8O14P2.2Na/c29-11-13-7(39-19(11)27-5-25-9-15(27)21-3-23-17(9)31)1-37-43(33,34)42-14-8(2-38-44(35,36)41-13)40-20(12(14)30)28-6-26-10-16(28)22-4-24-18(10)32;;/h3-8,11-14,19-20,29-30H,1-2H2,(H,33,34)(H,35,36)(H,21,23,31)(H,22,24,32);;/q;2*+1/p-2/t7-,8-,11-,12-,13-,14-,19-,20-;;/m1../s1
InChi Key
JBHJGFWGJASJST-VEQUCWRQSA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Cyclic di-IMP (sodium salt) (c-di-IMP) is a synthetic second messenger structurally related to the bacterial second messengers cyclic di-GMP (Item No. 17144) and cyclic di-AMP (Item No. 17753).1 C-di-IMP has adjuvant properties when co-administered with antigens in vitro and by mucosal routes in vivo. C-di-IMP enriches the population of MHC class I and II, CD80, CD86, CD40, and CD54 positive dendritic cells derived from murine bone marrow. It also stimulates macrophages at 500 ng/ml. Mice immunized with β-galactosidase (β-gal) plus c-di-IMP through the intranasal route show a humoral immune response, evidenced by an increase in IgG titers up to 2-fold compared to mice immunized with β-gal alone. Mice immunized with β-gal plus c-di-IMP also exhibit a Th1/Th2 response, indicating that the adjuvant activity of c-di-IMP leads to a cellular immune response as well.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Libanova, R., Ebensen, T., Schulze, K., et al. The member of the cyclic di-nucleotide family bis-(3', 5')-cyclic dimeric inosine monophosphate exerts potent activity as mucosal adjuvant. Vaccine 28(10), 2249-2258 (2010).