Cyclic adenosine-inosine monophosphate

Cyclic adenosine-inosine monophosphate
Identifiers
	IUPAC name 9-[(1S,6R,8R,9R,10S,15R,17R,18R)-17-(6-aminopurin-9-yl)-3,9,12,18-tetrahydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3λ5,12λ5-diphosphatricyclo[13.3.0.06,10]octadecan-8-yl]-1H-purin-6-one;
CAS Number	1507367-51-2;
PubChem CID	136247207;
ChEMBL	ChEMBL4776666;
Chemical and physical data
Formula	C20H23N9O13P2
Molar mass	659.402 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C3N=CNC4=O)O)OP(=O)(OC[C@@H]5[C@H]([C@H]([C@@H](O5)N6C=NC7=C(N=CN=C76)N)O)OP(=O)(O1)O)O;
	InChI InChI=1S/C20H23N9O13P2/c21-15-9-16(23-3-22-15)28(5-26-9)19-11(30)13-7(39-19)1-37-44(35,36)42-14-8(2-38-43(33,34)41-13)40-20(12(14)31)29-6-27-10-17(29)24-4-25-18(10)32/h3-8,11-14,19-20,30-31H,1-2H2,(H,33,34)(H,35,36)(H2,21,22,23)(H,24,25,32)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1; Key:SBNULQXUGGEMOY-XPWFQUROSA-N;

Cyclic adenosine-inosine monophosphate (cAIMP, CL-592) is an experimental antiviral drug. It is the best studied of a range of related analogues which act as agonists of the Stimulator of interferon genes (STING) receptor which mediates interferon production by the immune system. It shows broad spectrum antiviral activity against a range of viruses including SARS-CoV-2 and enterovirus 68, and in studies on mice prevented the development of arthritis following infection with Chikungunya virus.^[1]^[2]^[3]^[4]

References

^ Lioux T, Mauny MA, Lamoureux A, Bascoul N, Hays M, Vernejoul F, et al. (November 2016). "Design, Synthesis, and Biological Evaluation of Novel Cyclic Adenosine-Inosine Monophosphate (cAIMP) Analogs That Activate Stimulator of Interferon Genes (STING)". Journal of Medicinal Chemistry. 59 (22): 10253–10267. doi:10.1021/acs.jmedchem.6b01300. PMID 27783523.
^ Ding C, Song Z, Shen A, Chen T, Zhang A (December 2020). "Small molecules targeting the innate immune cGAS‒STING‒TBK1 signaling pathway". Acta Pharmaceutica Sinica. B. 10 (12): 2272–2298. doi:10.1016/j.apsb.2020.03.001. PMC 7745059. PMID 33354501.
^ Garcia G, Irudayam JI, Jeyachandran AV, Dubey S, Chang C, Castillo Cario S, et al. (May 2023). "Innate immune pathway modulator screen identifies STING pathway activation as a strategy to inhibit multiple families of arbo and respiratory viruses". Cell Reports. Medicine. 4 (5): 101024. doi:10.1016/j.xcrm.2023.101024. PMC 10213809. PMID 37119814.
^ Wang M, Fan B, Lu W, Ryde U, Chang Y, Han D, et al. (June 2024). "Unraveling the Binding Mode of Cyclic Adenosine-Inosine Monophosphate (cAIMP) to STING through Molecular Dynamics Simulations". Molecules. 29 (11). doi:10.3390/molecules29112650. PMC 11173896. PMID 38893524.

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[1] Lioux T, Mauny MA, Lamoureux A, Bascoul N, Hays M, Vernejoul F, et al. (November 2016). "Design, Synthesis, and Biological Evaluation of Novel Cyclic Adenosine-Inosine Monophosphate (cAIMP) Analogs That Activate Stimulator of Interferon Genes (STING)". Journal of Medicinal Chemistry. 59 (22): 10253–10267. doi:10.1021/acs.jmedchem.6b01300. PMID 27783523.

[2] Ding C, Song Z, Shen A, Chen T, Zhang A (December 2020). "Small molecules targeting the innate immune cGAS‒STING‒TBK1 signaling pathway". Acta Pharmaceutica Sinica. B. 10 (12): 2272–2298. doi:10.1016/j.apsb.2020.03.001. PMC 7745059. PMID 33354501.

[3] Garcia G, Irudayam JI, Jeyachandran AV, Dubey S, Chang C, Castillo Cario S, et al. (May 2023). "Innate immune pathway modulator screen identifies STING pathway activation as a strategy to inhibit multiple families of arbo and respiratory viruses". Cell Reports. Medicine. 4 (5): 101024. doi:10.1016/j.xcrm.2023.101024. PMC 10213809. PMID 37119814.

[4] Wang M, Fan B, Lu W, Ryde U, Chang Y, Han D, et al. (June 2024). "Unraveling the Binding Mode of Cyclic Adenosine-Inosine Monophosphate (cAIMP) to STING through Molecular Dynamics Simulations". Molecules. 29 (11). doi:10.3390/molecules29112650. PMC 11173896. PMID 38893524.

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See also

References