Sequence variation in CYP51A from the y strain of Trypanosoma cruzi alters its sensitivity to inhibition

FEBS Letters

Volumn 588, Issue 21, 2014, Pages 3878-3885

  Cherkesova, Tatiana S ^b   Hargrove, Tatiana Y ^a   Vanrell, M Cristina ^c   Ges, Igor ^d   Usanov, Sergey A ^b   Romano, Patricia S ^c   Lepesheva, Galina I ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

^c FACULTAD DE CIENCIAS MÉDICAS   (Argentina)

^d VANDERBILT UNIVERSITY   (United States)

Author keywords

CYP51 sequence variation; Drug resistance; Sterol 14a demethylase; Structure based drug design; Trypanosoma cruzi

Indexed keywords

ANTITRYPANOSOMAL AGENT; BENZAMIDE DERIVATIVE; CYTOCHROME P450; CYTOCHROME P450 51A; N [1 (2,4 DICHLOROPHENYL) 2 (1H 1,2,4 TRIAZOL 1 YL)ETHYL] 4 (5 PHENYL 1,3,4 OXADIAZOL 2 YL)BENZAMIDE; N [1 (2,4 DICHLOROPHENYL) 2 (1H IMIDAZOL 1 YL)ETHYL] 4 (5 PHENYL 1,3,4 OXADIAZOL 2 YL)BENZAMIDE; N [1 (3,4' DIFLUOROBIPHENYL 4 YL) 2 (1H IMIDAZOL 1 YL)ETHYL] 4 (5 PHENYL 1,3,4 OXADIAZOL 2 YL)BENZAMIDE; PROLINE; SERINE; UNCLASSIFIED DRUG; STEROL 14ALPHA DEMETHYLASE INHIBITOR;

AMASTIGOTE; AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ANTHELMINTIC ACTIVITY; ARTICLE; CATALYSIS; CONTROLLED STUDY; DRUG SENSITIVITY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME INHIBITOR COMPLEX; ENZYME STRUCTURE; EPITHELIUM CELL; INSECT; MAMMAL CELL; NONHUMAN; NUCLEOTIDE SEQUENCE; TRYPANOSOMA CRUZI; TRYPOMASTIGOTE; ANIMAL; BIOCATALYSIS; CHAGAS DISEASE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ENZYMOLOGY; GENETICS; HUMAN; METABOLISM; MOLECULAR GENETICS; PROTEIN CONFORMATION;

14-ALPHA DEMETHYLASE INHIBITORS; AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ANIMALS; BIOCATALYSIS; CHAGAS DISEASE; CONSERVED SEQUENCE; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PROTEIN CONFORMATION; TRYPANOSOMA CRUZI;

EID: 84908239030     PISSN: 00145793     EISSN: 18733468     Source Type: Journal    
DOI: 10.1016/j.febslet.2014.08.030     Document Type: Article

References (30)

1. G.I. Lepesheva Design or screening of drugs for the treatment of Chagas disease: what shows the most promise? Expert Opin. Drug Discovery 8 2013 1479 1489
2. C. Chagas Nova trypanozomiaze humana: estudos sobre a morfolojia e o ciclo evolutivo do Schizotrypanum cruzi n. gen., n. sp., ajente etiolojico de nova entidade morbida do homem Mem. Inst. Oswaldo Cruz 1 1909 159 218
3. WHO. < http://www.who.int/mediacentre/factsheets/fs340/en/ > Chagas disease (American trypanosomiasis); Fact sheet 340: Updated May 2014.
4. P.J. Hotez Neglected infections of poverty in the United States of America PLoS Negl. Trop. Dis. 2 2008 e256
5. E.J. Hanford, F.B. Zhan, Y. Lu, and A. Giordano Chagas disease in Texas: recognizing the significance and implications of evidence in the literature Soc. Sci. Med. 65 2007 60 79
6. J.A. Urbina, G. Payares, C. Sanoja, R. Lira, and A.J. Romanha In vitro and in vivo activities of ravuconazole on Trypanosoma cruzi, the causative agent of Chagas disease Int. J. Antimicrob. Agents 21 2003 27 38
7. J.A. Urbina Ergosterol biosynthesis and drug development for Chagas disease Mem. Inst. Oswaldo Cruz 104 Suppl 1 2009 311 318
8. J.A. Urbina, G. Payares, L.M. Contreras, A. Liendo, C. Sanoja, J. Molina, M. Piras, R. Piras, N. Perez, P. Wincker, and D. Loebenberg Antiproliferative effects and mechanism of action of SCH 56592 against Trypanosoma (Schizotrypanum) cruzi: in vitro and in vivo studies Antimicrob. Agents Chemother. 42 1998 1771 1777
9. J. Clayton Chagas disease: pushing through the pipeline Nature 465 2010 S12 S15
10. I. Molina, J. Gómez i Prat, F. Salvador, B. Treviño, E. Sulleiro, N. Serre, D. Pou, S. Roure, J. Cabezos, L. Valerio, A. Blanco-Grau, A. Sánchez-Montalvá, X. Vidal, and A. Pahissa Randomized trial of posaconazole and benznidazole for chronic Chagas' disease N. Engl. J. Med. 370 2014 1899 1908
11. F. Villalta, M.C. Dobish, P.N. Nde, Y.Y. Kleshchenko, T.Y. Hargrove, C.A. Johnson, M.R. Waterman, J.N. Johnston, and G.I. Lepesheva VNI cures acute and chronic experimental Chagas disease J. Infect. Dis. 208 2013 504 511
12. L.S. Filardi, and Z. Brener Susceptibility and natural resistance of Trypanosoma cruzi strains to drugs used clinically in Chagas disease Trans. R. Soc. Trop. Med. Hyg. 81 1987 755 759
13. S.M.F. Murta, R.T. Gazzinelli, Z. Brener, and A.J. Romanha Molecular characterization of susceptible and naturally resistant strains of Trypanosoma cruzi to benznidazole and nifurtimox Mol. Biochem. Parasitol. 93 1998 203 214
14. M.d.N.C. Soeiro, E.M. De Souza, C.F. Da Silva, D.d.G.J. Batista, M.M. Batista, B.P. Pavão, J.S. Araújo, J. Lionel, C. Britto, K. Kim, G. Sulikowski, T.Y. Hargrove, M.R. Waterman, and G.I. Lepesheva In vitro and in vivo studies of the antiparasitic activity of sterol 14α-demethylase (CYP51) inhibitor VNI against drug-resistant strains of Trypanosoma cruzi Antimicrob. Agents Chemother. 57 2013 4151 4163
15. J.J. Barclay, L.G. Morosi, M.C. Vanrell, E.C. Trejo, P.S. Romano, and C. Carrillo Trypanosoma cruzi coexpressing ornithine decarboxylase and green fluorescence proteins as a tool to study the role of polyamines in Chagas disease pathology Enzyme Res. 2011 2011 10
16. E. Medina-Acosta, and G.A. Cross Rapid isolation of DNA from trypanosomatid protozoa using a simple 'mini-prep' procedure Mol. Biochem. Parasitol. 59 1993 327 330
17. G.I. Lepesheva, N.G. Zaitseva, W.D. Nes, W. Zhou, M. Arase, J. Liu, G.C. Hill, and M.R. Waterman CYP51 from Trypanosoma cruzi: a phyla-specific residue in the B' helix defines substrate preferences of sterol 14alpha-demethylase J. Biol. Chem. 281 2006 3577 3585
18. T.Y. Hargrove, Z. Wawrzak, P.W. Alexander, J.H. Chaplin, M. Keenan, S.A. Charman, M.R. Waterman, E. Chatelain, and G.I. Lepesheva Complexes of Trypanosoma cruzi sterol 14α-demethylase (CYP51) with two pyridine-based drug candidates for Chagas disease: structural basis for pathogen selectivity J. Biol. Chem. 288 2013 31602 31615
19. G.I. Lepesheva, R.D. Ott, T.Y. Hargrove, Y.Y. Kleshchenko, I. Schuster, W.D. Nes, G.C. Hill, F. Villalta, and M.R. Waterman Sterol 14 alpha-demethylase as a potential target for antitrypanosomal therapy: enzyme inhibition and parasite cell growth Chem. Biol. 14 2007 1283 1293
20. G.I. Lepesheva, T.Y. Hargrove, S. Anderson, Y. Kleshchenko, V. Furtak, Z. Wawrzak, F. Villalta, and M.R. Waterman Structural insights into inhibition of sterol 14 alpha-demethylase in the human pathogen Trypanosoma cruzi J. Biol. Chem. 285 2010 25582 25590
21. G.I. Lepesheva, H.W. Park, T.Y. Hargrove, B. Vanhollebeke, Z. Wawrzak, J.M. Harp, M. Sundaramoorthy, W.D. Nes, E. Pays, M. Chaudhuri, F. Villalta, and M.R. Waterman Crystal structures of Trypanosoma brucei sterol 14 alpha-demethylase and implications for selective treatment of human infections J. Biol. Chem. 285 2010 1773 1780
22. O. Gotoh Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences J. Biol. Chem. 267 1992 83 90
23. G.I. Lepesheva, and M.R. Waterman Sterol 14alpha-demethylase (CYP51) as a therapeutic target for human trypanosomiasis and leishmaniasis Curr. Top. Med. Chem. 11 2011 2060 2071
24. G.I. Lepesheva, F. Villalta, and M.R. Waterman Targeting Trypanosoma cruzi sterol 14α-demethylase (CYP51) Adv. Parasitol. 75 2011 65 87
25. T.Y. Hargrove, K. Kim, M. De Nazaré Correia Soeiro, C.F. Da Silva, D. Da Gama Jaen Batista, M.M. Batista, E.M. Yazlovitskaya, M.R. Waterman, G.A. Sulikowski, and G.I. Lepesheva CYP51 structures and structure-based development of novel, pathogen-specific inhibitory scaffolds Int. J. Parasitol. Drugs Drug Resist. 2 2012 178 186
26. G.I. Lepesheva, and M.R. Waterman Structural basis for conservation in the CYP51 family Biochim. Biophys. Acta 1814 2011 88 93
27. J. Fan, M. Urban, J.E. Parker, H.C. Brewer, S.L. Kelly, K.E. Hammond-Kosack, B.A. Fraaije, X. Liu, and H.J. Cools Characterization of the sterol 14α-demethylases of Fusarium graminearum identifies a novel genus-specific CYP51 function New Phytol. 198 2013 821 835
28. N.J. Hawkins, H.J. Cools, H. Sierotzki, M.W. Shaw, W. Knogge, S.L. Kelly, D.E. Kelly, and B.A. Fraaije Paralog re-emergence: a novel, historically contingent mechanism in the evolution of antimicrobial resistance Mol. Biol. Evol. 31 2014 1793 1802
29. T.Y. Hargrove, Z. Wawrzak, J. Liu, W.D. Nes, M.R. Waterman, and G.I. Lepesheva Substrate preferences and catalytic parameters determined by structural characteristics of sterol 14α-demethylase (CYP51) from Leishmania infantum J. Biol. Chem. 286 2011 26838 26848
30. C.B. Moraes, M.A. Giardini, H. Kim, C.H. Franco, A.M. Araujo-Junior, S. Schenkman, E. Chatelain, and L.H. Freitas-Junior Nitroheterocyclic compounds are more efficacious than CYP51 inhibitors against Trypanosoma cruzi: implications for Chagas disease drug discovery and development Sci. Rep. 4 2014 10.1038/srep04703