Synonym
cAIMP; CL592; CL 592; CL-592; CHEMBL4776666;
IUPAC/Chemical 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
InChi Key
SBNULQXUGGEMOY-XPWFQUROSA-N
InChi Code
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
SMILES Code
NC1=NC=NC2=C1N=CN2[C@@H]([C@@H]3O)O[C@@H]([C@H]3OP4(O)=O)COP(O)(O[C@@H]([C@@H](O)[C@H](N5C=NC6=C5N=CN=C6O)O7)[C@H]7CO4)=O
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
659.40
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Wang M, Fan B, Lu W, Ryde U, Chang Y, Han D, Lu J, Liu T, Gao Q, Chen C, Xu Y. Unraveling the Binding Mode of Cyclic Adenosine-Inosine Monophosphate (cAIMP) to STING through Molecular Dynamics Simulations. Molecules. 2024 Jun 4;29(11):2650. doi: 10.3390/molecules29112650. PMID: 38893524; PMCID: PMC11173896.
2: Garcia G Jr, Irudayam JI, Jeyachandran AV, Dubey S, Chang C, Castillo Cario S, Price N, Arumugam S, Marquez AL, Shah A, Fanaei A, Chakravarty N, Joshi S, Sinha S, French SW, Parcells MS, Ramaiah A, Arumugaswami V. Innate immune pathway modulator screen identifies STING pathway activation as a strategy to inhibit multiple families of arbo and respiratory viruses. Cell Rep Med. 2023 May 16;4(5):101024. doi: 10.1016/j.xcrm.2023.101024. Epub 2023 Apr 28. PMID: 37119814; PMCID: PMC10213809.
3: Andersen AHF, Olesen R, Jønsson KL, Højen JF, Krapp C, Mack K, Thomsen MK, Østergaard L, Tolstrup M, Dagnaes-Hansen F, Jakobsen MR, Denton PW. cAIMP administration in humanized mice induces a chimerization-level-dependent STING response. Immunology. 2019 Jun;157(2):163-172. doi: 10.1111/imm.13061. Epub 2019 May 6. PMID: 30919991; PMCID: PMC6526644.
