New synthetic AICAR derivatives with enhanced AMPK and ACC activation

References

• Nigro E, Scudiero O, Monaco ML, et al. New insight into adiponectin role in obesity and obesity-related diseases. Biomed Res Int 2014;2014:658913
   PubMed Web of Science ®Google Scholar
• Wong AK, Howie J, Petrie JR, Lang CC. AMP-activated protein kinase pathway: a potential therapeutic target in cardiometabolic disease. Clin Sci (Lond) 2009;116:607–20
   PubMed Web of Science ®Google Scholar
• Daignan-Fornier B, Pinson B. 5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphate (AICAR), a highly conserved purine intermediate with multiple effects. Metabolites 2012;2:292–302
   PubMedGoogle Scholar
• Van den Neste E, Van den Berghe G, Bontemps F. AICA-riboside (acadesine), an activator of AMP-activated protein kinase with potential for application in hematologic malignancies. Expert Opin Investig Drugs 2010;19:571–8
   PubMed Web of Science ®Google Scholar
• Rattan R, Giri S, Singh AK, Singh I. 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranoside inhibits cancer cell proliferation in vitro and in vivo via AMP-activated protein kinase. J Biol Chem 2005;280:39582–93
   PubMed Web of Science ®Google Scholar
• Xiang X, Saha AK, Wen R, et al. AMP-activated protein kinase activators can inhibit the growth of prostate cancer cells by multiple mechanisms. Biochem Biophys Res Commun 2004;321:161–7
   PubMed Web of Science ®Google Scholar
• Montraveta A, de Frias M, Campas C, et al. The nucleoside analogue acadesine exerts antitumoral activity and cooperates with anti-CD20 monoclonal antibodies in vitro and in vivo models of mantle cell lymphoma. Mol Cancer Ther 2011;10 Supplement 1: A209
   Google Scholar
• Bracci A, Colombo G, Ronchetti F, Compostella F. 2-O-Alkyl derivatives and 5′-analogues of 5-aminoimidazole-4-carboxamide-1-β-D-ribofuranoside (AICAR) as potential Hsp90 inhibitors. Eur J Org Chem 2009;2009:5913–19
   Web of Science ®Google Scholar
• Joshi S, Platanias LC. Mnk kinase pathway: cellular functions and biological outcomes. World J Biol Chem 2014;5:321–33
   PubMedGoogle Scholar
• Ewart MA, Kennedy S. Diabetic cardiovascular disease AMP-activated protein kinase (AMPK) as a therapeutic target. Cardiovasc Hematol Agents Med Chem 2012;10:190–211
   PubMedGoogle Scholar
• D'Errico S, Oliviero G, Borbone N, et al. Synthesis of new acadesine (AICA-riboside) analogues having acyclic D-ribityl or 4-hydroxybutyl chains in place of the ribose. Molecules 2013;18:9420–31
   PubMed Web of Science ®Google Scholar
• Oliviero G, Amato J, Borbone N, et al. Synthesis of 4-N-alkyl and ribose-modified AICAR analogues on solid support. Tetrahedron 2008;64:6475–81
   Web of Science ®Google Scholar
• Oliviero G, Errico S, Borbone N, et al. A solid-phase approach to the synthesis of N-1-alkyl analogues of cyclic inosine-diphosphate-ribose (cIDPR). Tetrahedron 2010;66:1931–6
   Web of Science ®Google Scholar
• Nigro E, Scudiero O, Sarnataro D, et al. Adiponectin affects lung epithelial A549 cell viability counteracting TNFα and I1β toxicity through AdipoR1. Int J Biochem Cell Biol 2013;45:1145–53
   PubMed Web of Science ®Google Scholar
• Scudiero O, Galdiero S, Nigro E, et al. Chimeric beta-defensin analogs, including the novel 3NI analog, display salt-resistant antimicrobial activity and lack toxicity in human epithelial cell lines. Antimicrob Agents Chemother 2013;57:1701–8
   PubMed Web of Science ®Google Scholar
• D'Errico S, Oliviero G, Borbone N, et al. Solid-phase synthesis of a new diphosphate 5-aminoimidazole-4-carboxamide riboside (AICAR) derivative and studies toward cyclic AICAR diphosphate ribose. Molecules 2011;16:8110–18
   PubMed Web of Science ®Google Scholar
• Oliviero G, Amato J, Borbone N, et al. Synthesis of N-1 and ribose modified inosine analogues on solid support. Tetrahedron Lett 2007;48:397–400
   Web of Science ®Google Scholar
• De Napoli L, Messere A, Montesarchio D, et al. 1-Substituted 2′-deoxyinosine analogues. J Chem Soc Perkin Trans 1997;14:2079–82
   Google Scholar
• Petti C, Vegetti C, Molla A, et al. AMPK activators inhibit the proliferation of human melanomas bearing the activated MAPK pathway. Melanoma Res 2012;22:341–50
   PubMed Web of Science ®Google Scholar
• Rana S, Blowers EC, Natarajan A. Small molecule adenosine 5′-monophosphate activated protein kinase (AMPK) modulators and human diseases. J Med Chem 2015;58:2–29
   PubMed Web of Science ®Google Scholar
• Riley CM, Mummert MA, Zhou J, et al. Hydrolysis of the prodrug, 2′,3′,5′-triacetyl-6-azauridine. Pharm Res 1995;12:1361–70
   PubMed Web of Science ®Google Scholar
• Rattan R, Giri S, Singh AK, Singh I. 5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside inhibits cancer cell proliferation in vitro and in vivo via AMP-activated protein kinase. J Biol Chem 2005;280:39582–93
   PubMed Web of Science ®Google Scholar
• Kim JH, Park JM, Yea K, et al. Phospholipase D1 mediates AMP-activated protein kinase signaling for glucose uptake. PLoS One 2010;5:e9600
   Google Scholar
• Peyton KJ, Liu XM, Yu Y, et al. Activation of AMP-activated protein kinase inhibits the proliferation of human endothelial cells. J Pharmacol Exp Ther 2012;342:827–34
   PubMed Web of Science ®Google Scholar
• Guan TJ, Qin FJ, Du JH, et al. AICAR inhibits proliferation and induced S-phase arrest, and promotes apoptosis in CaSki cells. Acta Pharmacol Sin 2007;28:1984–90
   PubMed Web of Science ®Google Scholar
• Baumann P, Mandl-Weber S, Emmerich B, et al. Activation of adenosine monophosphate activated protein kinase inhibits growth of multiple myeloma cells. Exp Cell Res 2007;313:3592–603
   PubMed Web of Science ®Google Scholar
• Kim JE, Ahn MW, Baek SH, et al. AMPK activator, AICAR, inhibits palmitate-induced apoptosis in osteoblast. Bone 2008;43:394–404
   PubMed Web of Science ®Google Scholar