| AICA ribonucleotide | |
|---|---|
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| Identifiers | |
| CAS number | 3031-94-5 |
| PubChem | 65110 |
| MeSH | AICA+ribonucleotide |
| SMILES |
O=P(O)(O)OC[C@H]2O[C@@H](n1cnc(C(=O)N)c1N)[C@H](O)[C@@H]2O
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| InChI |
1/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
|
| InChI key | NOTGFIUVDGNKRI-UUOKFMHZBG |
| ChemSpider ID | 58620 |
| Properties | |
| Molecular formula | C9H15N4O8P |
| Molar mass | 338.211 g/mol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
AICA ribonucleotide or AICAR (aminoimidazole carboxamide ribonucleotide) is an intermediate in the generation of inosine monophosphate, which acts as an AMP-activated protein kinase agonist.[1] It stimulates glucose uptake and increases the activity of p38 mitogen-activated protein kinases α and β in skeletal muscle tissue,[2] as well as suppressing apoptosis by reducing production of reactive oxygen compounds inside the cell.[3]
In 2008, researchers at the Salk Institute discovered that AICAR given to experimental mice significantly improves their performance in endurance-type exercise, apparently by converting fast-twitch muscle fibers to the more energy-efficient, fat-burning, slow-twitch type. They also looked at the administration of GW 501516 (also called GW1516) in combination with AICAR. Given to mice that did not exercise, this combination activated 40% of the genes that were turned on when mice were given GW1516 and made to exercise. This suggests it may be possible to obtain some of the benefits of exercising without actually exercising.[4] Because of the enhanced endurance effects, this could potentially be used by athletes to enhance their performance. One of the lead researchers from this study has developed a urine test to detect it and has made the test available to the International Olympic Committee, and the World Anti-Doping Agency has added AICAR to the prohibited list from 2009 onwards.[5]
See also
References
- ^ Corton JM, Gillespie JG, Hawley SA, Hardie DG (April 1995). "5-aminoimidazole-4-carboxamide ribonucleoside. A specific method for activating AMP-activated protein kinase in intact cells?". Eur. J. Biochem. 229 (2): 558–65. doi:. PMID 7744080.
- ^ Lemieux K, Konrad D, Klip A, Marette A (September 2003). "The AMP-activated protein kinase activator AICAR does not induce GLUT4 translocation to transverse tubules but stimulates glucose uptake and p38 mitogen-activated protein kinases alpha and beta in skeletal muscle". Faseb J. 17 (12): 1658–65. doi:. PMID 12958172.
- ^ Kim JE, Kim YW, Lee IK, Kim JY, Kang YJ, Park SY (March 2008). "AMP-activated protein kinase activation by 5-aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside (AICAR) inhibits palmitate-induced endothelial cell apoptosis through reactive oxygen species suppression". J. Pharmacol. Sci. 106 (3): 394–403. doi:. PMID 18360094.
- ^ Narkar VA, Downes M, Yu RT, Embler E, Wang YX, Banayo E, Mihaylova MM, Nelson MC, Zou Y, Juguilon H, Kang H, Shaw RJ, Evans RM (August 2008). "AMPK and PPARdelta agonists are exercise mimetics". Cell 134 (3): 405–15. doi:. PMID 18674809.
- ^ WADA 2009 Prohibited List
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