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      A Facile Synthesis of 5′-Fluoro-5′-deoxyacadesine (5′-F-AICAR): A Novel Non-phosphorylable AICAR Analogue

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          Abstract

          The substitution of a hydroxyl group by a fluorine atom in a potential drug is an efficient reaction that can, in principle, improve its pharmacological properties. Herein, the synthesis of the novel compound 5′-fluoro-5′-deoxyacadesine (5′-F-AICAR), a strict analogue of AICAR that cannot be 5′-phosphorylated to ZMP by cellular kinases, is reported.

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          AICA riboside increases AMP-activated protein kinase, fatty acid oxidation, and glucose uptake in rat muscle.

          G Merrill, E J Kurth, D Hardie … (1997)
          5-Aminoimidazole-4-carboxamide ribonucleoside (AICAR) has previously been reported to be taken up into cells and phosphorylated to form ZMP, an analog of 5'-AMP. This study was designed to determine whether AICAR can activate AMP-activated protein kinase (AMPK) in skeletal muscle with consequent phosphorylation of acetyl-CoA carboxylase (ACC), decrease in malonyl-CoA, and increase in fatty acid oxidation. Rat hindlimbs were perfused with Krebs-Henseleit bicarbonate containing 4% bovine serum albumin, washed bovine red blood cells, 200 microU/ml insulin, and 10 mM glucose with or without AICAR (0.5-2.0 mM). Perfusion with medium containing AICAR was found to activate AMPK in skeletal muscle, inactivate ACC, and decrease malonyl-CoA. Hindlimbs perfused with 2 mM AICAR for 45 min exhibited a 2.8-fold increase in fatty acid oxidation and a significant increase in glucose uptake. No difference was observed in oxygen uptake in AICAR vs. control hindlimb. These results provide evidence that decreases in muscle content of malonyl-CoA can increase the rate of fatty acid oxidation.
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            Fluorine in medicinal chemistry: A review of anti-cancer agents

            Chukwuemeka Isanbor, David O'Hagan (2006)
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              Fluorine in medicinal chemistry: Recent therapeutic applications of fluorinated small molecules

              Kenneth L Kirk (2006)
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                Author and article information

                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 02 November 2012
                Publication date Collection: November 2012
                Volume: 17
                Issue: 11
                Pages: 13036-13044
                Affiliations
                [1 ] Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131, Napoli, Italy
                [2 ] Dipartimento di Scienze Chimiche, Università degli Studi di Napoli Federico II, Via Cintia 21, 80126, Napoli, Italy
                Author notes
                [* ] Author to whom correspondence should be addressed; Email: golivier@ 123456unina.it ; Tel.: +39-081-679-986.
                Article
                Publisher ID: molecules-17-13036
                DOI: 10.3390/molecules171113036
                PMC ID: 6268913
                PubMed ID: 23124472
                SO-VID: 5e9f5330-5529-4c27-8400-bf4cad73e21d
                Copyright © © 2012 by the authors; licensee MDPI, Basel, Switzerland.
                License:

                This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

                History
                Date received : 29 September 2012
                Date revision received : 31 October 2012
                Date accepted : 31 October 2012
                Categories
                Subject: Communication

                Keywords: aicar,zmp,ampk,ampk activation,fluorinated nucleosides,fluorination,imidazole nucleosides,nucleoside analogues,modified nucleosides
                Data availability:
                Keywords: aicar, zmp, ampk, ampk activation, fluorinated nucleosides, fluorination, imidazole nucleosides, nucleoside analogues, modified nucleosides

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