Design of anti-parasitic and anti-fungal hydroxy-naphthoquinones that are less susceptible to drug resistance

Molecular and Biochemical Parasitology

Volumn 177, Issue 1, 2011, Pages 12-19

  Hughes, Louise M ^a   Lanteri, Charlotte A ^b   Oneil, Michael T ^b   Johnson, Jacob D ^b   Gribble, Gordon W ^c   Trumpower, Bernard L ^a  

^a DARTMOUTH MEDICAL SCHOOL   (United States)

^b WALTER REED ARMY INSTITUTE OF RESEARCH   (United States)

^c Lamont Doherty Earth Observatory   (United States)

Author keywords

Atovaquone; Cytochrome bc1 complex; Hydroxy naphthoquinones; Malaria; Plasmodium; Pneumocystis; Toxoplasma

Indexed keywords

2 HYDROXY 3 (2 METHYL OCTYL) 8 METHYL NAPHTHOQUINONE; 2 HYDROXY 3 (2 METHYL TRIFLUOROOCTYL) 8 METHYL NAPHTHOQUINONE; 2 HYDROXY 3 (2 METHYL TRIFLUOROOCTYL)NAPHTHOQUINONE; ANTIFUNGAL AGENT; ANTIPARASITIC AGENT; ATOVAQUONE; NAPHTHOQUINONE; S 10576; UBIQUINOL CYTOCHROME C REDUCTASE; UNCLASSIFIED DRUG;

ANTIFUNGAL RESISTANCE; ARTICLE; COMPETITIVE INHIBITION; CONTROLLED STUDY; DRUG BINDING SITE; DRUG DESIGN; DRUG EFFICACY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVITY; FUNGAL STRAIN; GROWTH INHIBITION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LIVER CELL CULTURE; LIVER TOXICITY; MICROBIAL RESPIRATION; MITOCHONDRIAL MEMBRANE; MUTATION; NUCLEOTIDE SEQUENCE; PLASMODIUM (LIFE CYCLE STAGE); PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; PNEUMOCYSTIS; PRIORITY JOURNAL; TOXOPLASMA GONDII;

ANTIFUNGAL AGENTS; ANTIPROTOZOAL AGENTS; CELL LINE; DRUG DESIGN; DRUG RESISTANCE; HUMANS; MALARIA; MOLECULAR STRUCTURE; NAPHTHOQUINONES; PLASMODIUM; STRUCTURE-ACTIVITY RELATIONSHIP; YEASTS;

FUNGI; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; PNEUMOCYSTIS; TOXOPLASMA; TOXOPLASMA GONDII;

EID: 79952443716     PISSN: 01666851     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molbiopara.2011.01.002     Document Type: Article

References (36)

1. H.J. Painter, J.M. Morrisey, M.W. Mather, and A.B. Vaidya Specific role of mitochondrial electron transport in blood-stage Plasmodium falciparum Nature 446 2007 88 91 (Pubitemid 46348043)
2. C.L. Yeates, J.F. Batchelor, E.C. Capon, N.J. Cheeseman, J.M. Bueno, J. Chicharro, E. Fernandez, J.M. Fiandor, D. Gargallo-Viola, F.G. de las Heras, E. Herreros, and M.L. Leon Synthesis and structure-activity relationships of 4-pyridones as potential antimalarials J Med Chem 51 2008 2845 2852 (Pubitemid 351620805)
3. G.A. Biagini, N. Fisher, N. Berry, P.A. Stocks, B. Meunieer, D.P. Williams, R. Bonar-Law, P.G. Bray, A. Owen, P.M. ONeill, and S.A. Ward Acridinediones: selective and potent inhibitors of the malaria parasite mitochondrial bc1 complex Mol Pharmacol 73 2008 1347 1355 (Pubitemid 351574824)
4. H. Xiang, J. McSurdy-Freed, G.S. Moorthy, E. Hugger, R. Bambal, C. Hau, S. Ferrer, D. Gargallo, and C.B. Davis Preclinical drug metabolism and pharmacokinetic evaluation of GW844520, a novel anti-malarial mitochondrial electron transport inhibitor J Pharm Sci 95 2006 2657 2672 (Pubitemid 46093173)
5. N. Kongkathip, N. Pradidphol, K. Hasitapan, R. Grigg, W.-C. Kao, C. Hunte, N. Fisher, A.J. Warman, G.A. Biagini, P. Kongsaeree, P. Chuawong, and B. Kongkathip Transforming rhinacanthin analogues from potent anticancer agents into potent antimalarial agents J Med Chem 53 2010 1211 11221
6. I.K. Srivastava, J.M. Morrisey, E. Darrouzet, F. Daldal, and A.B. Vaidya Resistance mutations reveal the atovaquone-binding domain of cytochrome b in malaria parasites Mol Microbiol 33 1999 704 711 (Pubitemid 29392651)
7. C.J. Sutherland, M. Laundy, N. Price, M. Burke, Q.L. Fivelman, G. Pasvol, J.L. Klein, and P.L. Chiodini Mutations in the Plasmodium falciparum cytochrome b gene are associated with delayed parasite recrudescence in malaria patients treated with atovaquone-proguanil Malar J 7 2008 240 261
8. 1 complex and confer anti-malarial drug resistance in Saccharomyces cerevisiae J Biol Chem 280 2005 17142 17148 (Pubitemid 41389179)
9. J.J. Kessl, S. Meshnick, and B.L. Trumpower Modeling the molecular basis of atovaquone resistance in parasites and pathogenic fungi Trends Parasitol 23 2007 494 501 (Pubitemid 47465093)
10. P. Hill, J.J. Kessl, N. Fisher, S. Meshnick, B.L. Trumpower, and B. Meunier Recapitulation in Saccharomyces cerevisiae of cytochrome b mutations conferring resistance to atovaquone in Pneumocystis jiroveci Antimicrob Agents Chemother 47 2003 2725 2731 (Pubitemid 37040240)
11. 1 complex of Saccharomyces cerevisiae J Biol Chem 279 2004 2817 2824 (Pubitemid 38114272)
12. o domain mutants as a mechanism of atovaquone-resistance Mol Biochem Parasitol 108 2000 1 12 (Pubitemid 30236311)
13. 1 complex using novel hydroxynaphthoquinones Biochim Biophys Acta 1797 2010 38 43
14. L.F. Fieser, E. Berliner, F.J. Bondhus, F.C. Chang, W.G. Dauben, M.G. Ettlinger, G. Fawaz, M. Fields, M. Fieser, C. Heidelberger, H. Heyman, A.M. Seligman, W.R. Vaughan, A.G. Wilson, E. Wilson, M.I. Wu, M.J.T. Leffler, K.E. Hamlin, R.J. Hathaway, E.J. Matson, E.E. Moore, M.B. Moore, R.T. Rapala, and H.E. Zaugg Naphthoquinone antimalarials: general survey J Amer Chem Soc 70 1948 3151 3155
15. L.F. Fieser, F.C. Chang, W.G. Dauben, C. Heidelberger, H. Heymann, and A.M. Seligman Naphthoquinone anti-malarials XVIII. Metabolic oxidation products J Pharmacol Exptl Therapeut 94 1948 85 96
16. 1 complex Biochim Biophys Acta 1767 2007 319 326 (Pubitemid 46550341)
17. J.J. Kessl, K.H. Ha, A.K. Merritt, S.R. Meshnick, and B.L. Trumpower Molecular basis of Toxoplasma gondii atovaquone resistance modeled in Saccharomyces cerevisiae Mol Biochem Parasitol 146 2006 255 258 (Pubitemid 43356366)
18. 1 complex and can be suppressed by over-expression of subunit 9 J Biol Chem 266 1991 14958 14963 (Pubitemid 21907603)
19. 1 complexes containing site-directed mutants of the Rieske iron-sulfur protein Biochim Biophys Acta 1365 1998 125 134 (Pubitemid 29359249)
20. 1 J Biol Chem 247 1972 1012 1019
21. J.A. Berden, and E.C. Slater The reaction of antimycin with a cytochrome b preparation active in reconstitution of the respiratory chain Biochim Biophys Acta 216 1970 237 249
22. R.E. Desjardins, C.J. Canfield, J.D. Haynes, and J.D. Chulay Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique Antimicrob Agents Chemother 16 1979 710 718 (Pubitemid 10082023)
23. W.K. Milhous, N.F. Weatherly, J.H. Bowdre, and R.E. Desjardins In vitro activities of and mechanisms of resistance to antifol antimalarial drugs Antimicrob Agents Chemother 27 1985 525 530 (Pubitemid 15097653)
24. J.B. Sacci Jr. Inhibition of liver-stage development assay Methods Mol. Med 72 2002 517 520
25. L.S. Ozaki, R.W. Gwadz, and G.N.G. Stable Simple centrifugation method for rapid separation of sporozoites from mosquitoes J Parasit 70 1984 831 833 (Pubitemid 15194313)
26. C.J. Janse, B. Franke-Fayard, G.R. Mair, J. Ramesar, C. Thiel, S. Engelmann, K. Matuschewski, G.J. van Gemert, R.W. Sauerwein, and A.P. Waters High efficiency transfection of Plasmodium berghei facilitates novel selection procedures Mol Biochem Parasitol 145 1 2006 60 70 (Pubitemid 41691855)
27. D. Caridha, D. Yourick, M. Cabezas, L. Wolf, T.H. Hudson, and G.S. Dow Mefloquine-induced disruption of calcium homeostasis in mammalian cells is similar to that induced by ionomycin Antimicrob Agents Chemother 52 2 2008 684 693 (Pubitemid 351170845)
28. S.R.N. Solmaz, and C. Hunte Structure of Complex III with bound cytochrome c in reduced state and definition of a minimal core interface for electron transfer J Biol Chem 283 2008 17542 17549
29. R.A. Laskowski, M.W. MacArthur, D.S. Moss, and J.M. Thornton PROCHECK: A program to check the stereochemical quality of protein structures J Appl Cryst 26 1993 283 291
30. M.J. Smilkstein, I. Forquer, A. Kanazawa, J.X. Kelly, R.W. Winter, D.J. Hinrichs, D.M. Kramer, and M.K. Riscoe A drug-selected Plasmodium falciparum lacking the need for conventional electron transport Mol Biochem Parasitol 159 2008 64 68
31. 1 complex Biochemistry 42 2003 13636 13645
32. 1 segment of the mitochondrial respiratory chain J. Biol Chem 257 1982 8321 8330
33. o site inhibitor bound J Biol Chem 278 2003 31303 31311 (Pubitemid 36994649)
34. 1 complex: evidence for anti-cooperative ubiquinol oxidation and communication between center P ubiquinol oxidation sites. J Biol Chem 282 2007 22289 22297 (Pubitemid 47267334)
35. M.G. Ding, C.A. Butler, S.A. Saracco, T.D. Fox, F. Godard, J.P. di Rago, and B.L. Trumpower Introduction of cytochrome b mutations in Saccharomcyes cerevisiae by a method that allows selection for both functional and non-functional cytochrome b Proteins Biochim Biophys Acta 1777 2008 1147 1156
36. H. Nakato, R. Vivancos, and P.R. Hunter A systematic review and meta-analysis of the effectiveness and safety of atovaquone-proguanil (Malarone) for chemoprophylaxis against malaria J Antimicrob Chemo 60 2007 929 936 (Pubitemid 47617737)