期刊论文详细信息
Parasite
The antimalarial ferroquine: from bench to clinic
and D. Dive5  J. Khalife5  D. Ter-Minassian4  L. Fraisse2  F. Nosten3  C. Biot1 
[1] Unité de Catalyse et Chimie du Solide, CNRS UMR 8181, Université Lille Nord de France, Université Lille 1,BP 90108,59652 Villeneuve d’Ascq Cedex,France Present address: Unité de Glycobiologie Structurale et Fonctionnelle, CNRS UMR 8576, IFR 147, Université Lille Nord de France, Université de Lille 1,59650 Villeneuve d’Ascq Cedex,France;Sanofi-Aventis, Centre de Toulouse, 195, route d’Espagne,BP 13669,31036 Toulouse,France;Shoklo Malaria Research Unit, PO Box 46 Mae Sot Tak 63110, Thailand. Faculty of Tropical Medicine, Mahidol University, Bangkok 10400, Thailand. Centre for Clinical Vaccinology and Tropical Medicine, Nuffield Department of Clinical Medicine, University of Oxford, Oxford,United Kingdom;Sanofi-Aventis Research and Development, 1, avenue Pierre Brossolette,91385 Chilly Mazarin Cedex,France;CIIL, Inserm U1019, CNRS UMR 8024, Université Lille Nord de France, Institut Pasteur de Lille, 1, rue du Pr Calmette,59019 Lille Cedex,France
关键词: resistance;    mechanism of action;    ferroquine;    drug candidate;    bioorganometallics;    malaria;   
Others  :  808852
DOI  :  doi:10.1051/parasite/2011183207
 received in 2011-01-10, accepted in 2011-03-28,  发布年份 2011
PDF
【 摘 要 】

Ferroquine (FQ, SSR97193) is currently the most advanced organometallic drug candidate and about to complete phase II clinical trials as a treatment for uncomplicated malaria. This ferrocenecontaining compound is active against both chloroquine-susceptible and chloroquine-resistant Plasmodium falciparum and P. vivax strains and/or isolates. This article focuses on the discovery of FQ, its antimalarial activity, the hypothesis of its mode of action, the current absence of resistance in vitro and recent clinical trials.

【 授权许可】

   
© PRINCEPS Editions, Paris, 2011

【 预 览 】
附件列表
Files Size Format View
20140708175435450.pdf 473KB PDF download
Fig 2. 46KB Image download
Fig 1. 75KB Image download
【 图 表 】

Fig 1.

Fig 2.

【 参考文献 】
  • [1]Anstey N.M., Russell B., Yeo T.W. & Price R.N. The pathophysiology of vivax malaria. Trends Parasitol, 2009, 25, 220–227. [PubMed]
  • [2]Atteke C., Ndong J.M., Aubouy A., Maciejewski L., Brocard J., Lebibi J. & Deloron P. In vitro susceptibility to a new antimalarial organometallic analogue, ferroquine, of Plasmodium falciparum isolates from the Haut-Ogooue region of Gabon. J Antimicrob Chemother, 2003, 51, 1021–1024. [PubMed]
  • [3]Baird J.K. Effectiveness of antimalarial drugs. N Engl J Med, 2005, 352, 1565–1577. [PubMed]
  • [4]Baird J.K. Resistance to therapies for infection by Plasmodium vivax. Clin Microbiol Rev, 2009, 22, 508–534. [PubMed]
  • [5]Barends M., Jaidee A., Khaohirun N., Singhasivanon P. & Nosten F. In vitro activity of ferroquine (SSR97193) against Plasmodium falciparum isolates from the Thai-Burmese border. Malaria J, 2007, 6, 81.
  • [6]Beagley P., Blackie M.A.L., Chibale K., Clarkson C., Moss J.R. & Smith P.J. Synthesis and antimalarial activity in vitro of new ruthenocene-chloroquine analogues. Dalton Trans, 2002, 2002, 4426–4433.
  • [7]Beagley P., Blackie M.A.L., Chibale K., Clarkson C., Meijboom R., Moss J.R., Smith P.J. & Su H. Synthesis and antiplasmodial activity in vitro of new ferrocene-chloroquine analogues. Dalton Trans, 2003, 2003, 3046–3051.
  • [8]Biot C., Glorian G., Maciejewski L.A., Brocard J.S., Millet P., Georges A.J., Abessolo H., Dive D. & Lebibi J. Synthesis and antimalarial activity in vitro and in vivo of a new ferrocene-chloroquine analogue. J Med Chem, 1997, 40, 3715–3718. [PubMed]
  • [9]Biot C., Delhaës L., N’DIAYE C.M., Maciejewski L.A., Camus D., Dive D. & Brocard J.S. Synthesis and antimalarial activity in vitro of potential metabolites of ferrochloroquine and related compounds. Bioorg Med Chem, 1999, 7, 2843–2847. [PubMed]
  • [10]Biot C., Taramelli D., Forfar-Bares I., Maciejewski L.A., Boyce M., Nowogrocki G., Brocard J.S., Basilico N., Olliaro P., Egan T.J. Insights into the mechanism of action of ferroquine. Relationship between physicochemical properties and antiplasmodial activity. Mol Pharm, 2005, 2, 185–193. [PubMed]
  • [11]Biot C., Daher W., Jarry C., Ndiaye C.H., Pelinski L., Khalife J., Fraisse L., Brocard J., Melnyk P., Forfar-Bares I. & Dive D. Probing the role of the covalent linkage of ferrocene into a chloroquine template. J Med Chem, 2006a, 49, 4707–4714.
  • [12]Biot C., Daher W., Chavain N., Fandeur T., Khalife J., Dive D. & de Clercq E. Design and synthesis of hydroxyferroquine derivatives with antimalarial and antiviral activities. J Med Chem, 2006b, 49, 2845–2849.
  • [13]Biot C, Pradines B., Sergeant M.H., Gut J., Rosenthal P.J. & Chibale K. Design, synthesis, and antimalarial activity of structural chimeras of thiosemicarbazone and ferroquine analogues. Bioorg Med Chem Lett, 2007, 17, 6434–6438. [PubMed]
  • [14]Biot C, Chavain N., Dubar F., Pradines B., Brocard J., Forfar I. & Dive D Structure-activity relationships of 4-N-substituted ferroquine analogues. Time to re-evaluate the mechanism of action of ferroquine. J Organomet Chem, 2009, 694, 845–854.
  • [15]Biot C. & Dive D. Bioorganometallic chemistry and malaria. Top Organomet Chem, 2010, 32, 155–193.
  • [16]Blackie M.A., Beagley P., Croft S.L., Kendrick H., Moss J.R. & Chibale K. Metallocene-based antimalarials: an exploration into the influence of the ferrocenyl moiety on in vitro antimalarial activity in chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum. Bioorg Med Chem, 2007, 15, 6510–6516. [PubMed]
  • [17]Blackie M.A. & Chibale K. Metallocene antimalarials: the continuing quest. Met Based Drugs, 2008, 2008, 495123. [PubMed]
  • [18]Chavain N., Vezin H., Dive D., Touati N., Paul J.F., Buisine E. & Biot C. Investigation of the redox behavior of ferroquine, a new antimalarial. Mol Pharm, 2008, 5, 710–716. [PubMed]
  • [19]Chavain N., Davioud-Charvet E., Trivelli X., Mbeki L., Rottmann M., Brun R. & Biot C. Antimalarial activities of ferroquine conjugates with either glutathione reductase inhibitors or glutathione depletors via a hydrolyzable amide linker. Bioorg Med Chem, 2009, 17, 8048–8059. [PubMed]
  • [20]Chavain N. & Biot C. Organometallic complexes: new tools for chemotherapy. Curr Med Chem, 2010, 17, 2729–2745. [PubMed]
  • [21]Chim P., Lim P., Sem R., Nhem S., Maciejewski L. & Fandeur T. The in-vitro antimalarial activity of ferrochloroquine, measured against Cambodian isolates of Plasmodium falciparum. Ann Trop Med Parasitol, 2004, 98, 419–424. [PubMed]
  • [22]Daher W.E., Pelinski L., Klieber S., Sadoun F., Meunier V., Bourrie M., Biot C., Guillou F., Fabre G., Brocard J., Fraisse L., Maffrand J.P., Khalife J. & Dive D. In vitro metabolism of ferroquine (SSR97193) in animal and human hepatic models and antimalarial activity of major metabolites on Plasmodium falciparum. Drug Metab Dispos, 2006a, 34, 667–682.
  • [23]Daher W., Biot C., Fandeur T., Jouin H., Pelinski L., Viscogliosi E., Fraisse L., Pradines B., Brocard J., Khalife J. & Dive D. Assessment of P. falciparum resistance to ferroquine in field isolates and in W2 strain under pressure. Malaria J, 2006b, 5, 11.
  • [24]Delhaës L., Biot C., Berry L., Maciejewski L.A., Camus D., Brocard J.S. & Dive D. Novel ferrocenic artemisinin derivatives: synthesis, in vitro antimalarial activity and affinity of binding with ferroprotoporphyrin IX. Bioorg Med Chem, 2000, 8, 2739–2745. [PubMed]
  • [25]Delhaës L., Abessolo H., Biot C., Deloron P., Karbwang J., Mortuaire M., Maciejewski L.A., Camus D., Brocard J. & Dive D. Ferrochloroquine, a ferrocenyl analogue of chloroquine, retains a potent activity against resistant Plasmodium falciparum in vitro and P. vinckei in vivo. Parasitol Res, 2001, 87, 239–244. [PubMed]
  • [26]Delhaës L., Biot C., Berry L., Delcourt P., Maciejewski L.A., Camus D., Brocard J.S. & Dive D. Synthesis of ferroquine enantiomers. First investigation of metallocenic, chirality upon antimalarial activity and cytotoxicity. ChemBioChem, 2002, 3, 101–106. [PubMed]
  • [27]Desjardin R.E., Canfield C., Haynes J. & Chulay J. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrob Agents Chemother, 1979, 16, 710–718. [PubMed]
  • [28]Dhanawat M., Das N., Nagarwal R.C. & Shrivastava S.K. Antimalarial drug development: past to present scenario. Mini Rev Med Chem, 2009, 9, 1447–1469. [PubMed]
  • [29]Dive D. & Biot C. Ferrocene conjugates of chloroquine and other antimalarials: the development of ferroquine, a new antimalarial. ChemMedChem, 2008, 3, 383–391. [PubMed]
  • [30]Dondorp A.M., Yeung S., White L., Nguon C., Day N.P., Socheat D. & von Seidlein L. Artemisinin resistance: current status and scenarios for containment. Nat Rev Microbiol, 2010, 8, 272–280. [PubMed]
  • [31]Dubar F., Egan T.J., Pradines B., Kuter D., Ncokazi K.K., Forge D., Paul J.P., Pierrot C., Kalamou H., Khalife J., Buisine E., Rogier C., Vezin H., Forfar I., Slomianny C., Trivelli X., Kapishnikov S., Leiserowitz L., Dive D. & Biot C. The antimalarial ferroquine: role of the metal and intramolecular hydrogen bond in activity and resistance. ACS Chem Biol, 2011, 6 (3), 275–287. [PubMed]
  • [32]Dunitz J., Orgel L. & Rich A. The crystal structure of ferrocene. Acta Cryst, 1956, 9, 373–375.
  • [33]Henry M., Briolant S., Fontaine A., Mosnier J., Baret E., Amalvict R., Fusaï T., Fraisse L., Rogier C. & Pradines B. In vitro activity of ferroquine is independent of polymorphisms in transport protein genes implicated in quinoline resistance in Plasmodium falciparum. Antimicrob Agents Chemother, 2008, 52, 2755–2759. [PubMed]
  • [34]Kreidenweiss A., Kremsner PG., Dietz K. & Mordmueller B. In vitro activity of ferroquine (SSR97193) is independent of chloroquine resistance in Plasmodium falciparum. Amer J Trop Med Hyg, 2006, 75, 1178–1181.
  • [35]Leimanis M.L., Jaidee A., Sriprawat K., Kaewpongsri S., Suwanarusk R., Barends M., Phyo A.P., Russell B., Renia L. & Nosten F. Plasmodium vivax susceptibility to ferroquine. Antimicrob Agents Chemother, 2010, 54, 2228–2230. [PubMed]
  • [36]Nosten F. & White NJ. Artemisinin-based combination treatment of falciparum malaria. Am J Trop Med Hyg, 2007, 77, 181–192. [PubMed]
  • [37]Olliaro P. & Wells TN. The global portfolio of new antimalarial medicines under development. Clin Pharmacol Ther, 2009, 85, 584–595. [PubMed]
  • [38]Peters W. , in: Chemotherapy, and drug resistance in malaria. Peters W. (ed.). Liverpool: LiverpoolSchool of Tropical Medicine, 1987, Vol. 1, 145–273.
  • [39]Pradines B., Fusaï T., Daries W., Laloge V., Rogier C., Millet P., Panconi E., Kombila M. & Parzy D. Ferrocene-chloroquine analogues as antimalarial agents: in vitro activity of ferrochloroquine against 103 Gabonese isolates of Plasmodium falciparum. J Antimicrob Chemother, 2001, 48, 179–184. [PubMed]
  • [40]Pradines B., Tall A., Rogier C., Spiegel A., Mosnier J., Marrama L., Fusï T., Millet P., Panconi E., Trape J.F. & Parzy D. In vitro activities of ferrochloroquine against 55 Senegalese isolates of Plasmodium falciparum in comparison with those of standard antimalarial drugs. Trop Med Int Health, 2002, 7, 265–270. [PubMed]
  • [41]Stratton L., O’Neill MS., Kruk M.E. & Bell M.L. The persistent problem of malaria: addressing the fundamental causes of a global killer. Social Sci Med, 2008, 67, 854–862. [PubMed]
  • [42]Vessieres A., Jaouen G., Gruselle M., Rossignol JL., Savignac M., Top S. & Greenfield S. Synthesis and receptor binding of polynuclear organometallic estradiol derivatives. J Steroid Biochem, 1988, 30, 301–316. [PubMed]
  • [43]White NJ. Antimalarial drug resistance and combination therapy. Philos Trans R Soc London B Biol Sci, 1999, 354, 739–749.
  文献评价指标  
  下载次数:15次 浏览次数:12次