Biological evaluation of hydroxynaphthoquinones as anti-malarials

Malaria Journal

Volumn 12, Issue 1, 2013, Pages

  Schuck, Desiree C ^a   Ferreira, Sabrina B ^b,c   Cruz, Laura N ^a   Da Rocha, David R ^b   Moraes, Miriam S ^a   Nakabashi, Myna ^a   Rosenthal, Philip J ^d   Ferreira, Vitor F ^b   Garcia, Celia R S ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

^c FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

2 hydroxy 1; 4 naphthoquinone; Hydroxynaphthoquinone; Malaria; Mitochondria; Plasmodium berghei; Plasmodium falciparum

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; ANTIMALARIAL AGENT; FLUORESCENT DYE; HYDROXYNAPHTHOQUINONE DERIVATIVE; UNCLASSIFIED DRUG; NAPHTHOQUINONE; ORGANIC COMPOUND; RED DYE CMXROS;

ANTIMALARIAL ACTIVITY; ARTICLE; CELL DEATH; CONCENTRATION (PARAMETERS); DRUG CYTOTOXICITY; ELECTRON TRANSPORT; EMBRYO; HUMAN; HUMAN CELL; HUMAN TISSUE; IC 50; IN VITRO STUDY; INCUBATION TIME; MITOCHONDRIAL MEMBRANE POTENTIAL; NONHUMAN; PLASMODIUM FALCIPARUM; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; HEK293 CELL LINE; IC50;

ANTIMALARIALS; CELL SURVIVAL; FLUORESCENT DYES; HEK293 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; MEMBRANE POTENTIAL, MITOCHONDRIAL; NAPHTHOQUINONES; ORGANIC CHEMICALS; PLASMODIUM FALCIPARUM;

EID: 84880017110     PISSN: None     EISSN: 14752875     Source Type: Journal    
DOI: 10.1186/1475-2875-12-234     Document Type: Article

References (26)

1. Antimalarial drugs disrupt ion homeostasis in malarial parasites. Gazarini ML, Sigolo CA, Markus RP, Thomas AP, Garcia CR, Mem Inst Oswaldo Cruz 2007 102 329 334 10.1590/S0074-02762007000300012 17568938 (Pubitemid 46869330)
2. Plasmodium in the postgenomic era: new insights into the molecular cell biology of malaria parasites. Garcia CR, de Azevedo MF, Wunderlich G, Budu A, Young JA, Bannister L, Int Rev Cell Mol Biol 2008 266 85 156 18544493
3. Malaria chemotherapeutics part I: History of antimalarial drug development, currently used therapeutics, and drugs in clinical development. Schlitzer M, Chem Med Chem 2007 2 944 986 17530725
4. WHO, World Malaria Report Geneva: World Health Organization 2010
5. Atovaquone, a broad spectrum antiparasitic drug, collapses mitochondrial membrane potential in a malarial parasite. Srivastava IK, Rottenberg H, Vaidya AB, J Biol Chem 1997 272 3961 3966 10.1074/jbc.272.7.3961 9020100 (Pubitemid 27078454)
6. Lomatiol. II. Its occurrence, constitution, relation to and conversion into lapachol. Also a synthesis of lapachol. Hooker SC, J Am Chem Soc 1936 58 1181 1190 10.1021/ja01298a032
7. Naphthoquinone antimalarials.4.5.6.7.8.9.10.11. synthesis. Fieser LF, Berliner E, Bondhus FJ, Chang FC, Dauben WG, Ettlinger MG, Fields GFM, Fieser M, Heidelberger C, Heymann H, Seligman AM, Vaughan WR, Wilson AG, Wilson E, Wu M, Leffler MT, Hamlin KE, Hathaway RJ, Matson EJ, Moore EE, Moore MB, Rapala RT, Zaugg HE, J Am Chem Soc 1948 70 3174 3215 10.1021/ja01190a004 18891815
8. Inhibiting Plasmodium cytochrome bc1: a complex issue. Barton V, Fisher N, Biagini GA, Ward SA, O'Neill PM, Curr Opin Chem Biol 2010 14 440 446 10.1016/j.cbpa.2010.05.005 20570550
9. Antiparasitic agent atovaquone. Baggish AL, Hill DR, Antimicrob Agents Chemother 2002 46 1163 1173 10.1128/AAC.46.5.1163-1173.2002 11959541 (Pubitemid 34415287)
10. In vitro-in vivo correlations for lipophilic, poorly water-soluble drugs. Dressman JB, Reppas C, Eur J Pharm Sci 2000 11 Suppl 2 73 S80 11033429
11. Synthesis and protozoocidal activity of new 1,4-naphthoquinones. Danoun S, Baziard-Mouysset G, Stigliani J, Ane-Margail M, Payard M, Leger J, Canron X, Vial H, Loiseau P, Bories C, Recoche C, Heterocycl Comm 1999 5 343 348
12. Synthesis and antimalarial activity of new atovaquone derivatives. El Hage S, Ane M, Stigliani J, Marjorie M, Vial H, Baziard-Mouysset G, Payard M, Eur J Med Chem 2009 44 4778 4782 10.1016/j.ejmech.2009.07.021 19747753
13. Design of anti-parasitic and anti-fungal hydroxy-naphthoquinones that are less susceptible to drug resistance. Hughes L, Lanteri C, O'Neil M, Johnson J, Gribble G, Trumpower B, Mol Biochem Parasitol 2011 177 12 19 10.1016/j.molbiopara.2011.01.002 21251932
14. Probing binding determinants in center P of the cytochrome bc(1) complex using novel hydroxy-naphthoquinones. Hughes L, Covian R, Gribble G, Trumpower B, Biochim Biophys Acta 2010 1797 38 43 19660431
15. A new method to prepare 3-Alkyl-2-hydroxy-1,4-naphthoquinones: synthesis of lapachol and phthiocol. Ferreira S, da Rocha D, Carneiro J, Santos W, Ferreira V, Synlett 2011 2011 1551 1554 10.1055/s-0030-1260771
16. Human malaria parasites in continuous culture. Trager W, Jensen J, Science 1976 193 673 675 10.1126/science.781840 781840
17. Synchronization of Plasmodium falciparum erythrocytic stages in culture. Lambros C, Vanderberg J, J Parasitol 1979 65 418 420 10.2307/3280287 383936 (Pubitemid 10222999)
18. Flow cytometric readout based on Mitotracker Red CMXRos staining of live asexual blood stage malarial parasites reliably assesses antibody dependent cellular inhibition. Jogdand PS, Singh SK, Christiansen M, Dziegiel MH, Singh S, Theisen M, Malar J 2012 11 235 10.1186/1475-2875-11-235 22818754
19. Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing. Carmichael J, DeGraff WG, Gazdar AF, Minna JD, Mitchell JB, Cancer Res 1987 47 936 942 3802100 (Pubitemid 17027905)
20. Modeling the molecular basis of atovaquone resistance in parasites and pathogenic fungi. Kessl JJ, Meshnick SR, Trumpower BL, Trends Parasitol 2007 23 494 501 10.1016/j.pt.2007.08.004 17826334 (Pubitemid 47465093)
21. Transforming rhinacanthin analogues from potent anticancer agents into potent antimalarial agents. Kongkathip N, Pradidphol N, Hasitapan K, Grigg R, Kao WC, Hunte C, Fisher N, Warman AJ, Biagini GA, Kongsaeree P, Chuawong P, Kongkathip B, J Med Chem 2010 53 1211 1221 10.1021/jm901545z 20067272
22. Addition of thiols to o-quinone methide: New 2-hydroxy-3- phenylsulfanylmethyl [1,4]naphthoquinones and their activity against the human malaria parasite Plasmodium falciparum (3D7). Sharma A, Santos I, Gaur P, Ferreira V, Garcia C, Rochab D, Eur J Med Chem 2013 59 48 53 23202850
23. Novel anti-malarial hydroxynaphthoquinones with potent broad spectrum anti-protozoal activity. Hudson A, Randall A, Fry M, Ginger C, Hill B, Latter V, McHardy N, Williams R, Parasitology 1985 90 45 55 10.1017/S0031182000049003 3920634 (Pubitemid 15151736)
24. Inhibition of pyrimidine biosynthesis de novo in Plasmodium falciparum by 2-(4-t-butylcyclohexyl)-3-hydroxy-1,4-naphthoquinone in vitro. Hammond D, Burchell J, Pudney M, Mol Biochem Parasitol 1985 14 97 109 10.1016/0166-6851(85) 90109-4 3885032 (Pubitemid 15171433)
25. Cytochrome P450 2C9 is responsible for hydroxylation of the naphthoquinone antimalarial drug 58C80 in human liver. Weaver R, Dickins M, Burke M, Biochem Pharmacol 1993 46 1183 1197 10.1016/0006-2952(93)90467-B 8216369 (Pubitemid 23306739)
26. Parameters determining the relative efficacy of hydroxy-naphthoquinone inhibitors of the cytochrome bc1 complex. Kessl JJ, Moskalev NV, Gribble GW, Nasr M, Meshnick SR, Trumpower BL, Biochim Biophys Acta 2007 1767 319 326 10.1016/j.bbabio.2007.02.014 17383607 (Pubitemid 46550341)