A possible model of benzimidazole binding to β-tubulin disclosed by invoking an inter-domain movement

Journal of Molecular Graphics and Modelling

Volumn 23, Issue 3, 2004, Pages 275-284

  Robinson, Mark W ^a   McFerran, Neil ^b   Trudgett, Alan ^b   Hoey, Liz ^b   Fairweather, Ian ^b  

^a UNIVERSITY OF ABERDEEN   (United Kingdom)

^b QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

Benzimidazole; Benzimidazole resistance; Domain movement; Fasciola hepatica; Haemonchus contortus; Tubulin

Indexed keywords

BENZIMIDAZOLES (BZM); NEMATODES; PARASITES; THERAPEUTIC EFFECTS;

MATHEMATICAL MODELS; MOLECULES; MUTAGENESIS; PROTEINS;

INORGANIC COMPOUNDS;

ALBENDAZOLE SULFOXIDE; BENZIMIDAZOLE; BETA TUBULIN; ISOPROTEIN; PHENYLALANINE; TYROSINE;

AMINO ACID SUBSTITUTION; ARTICLE; DRUG BINDING SITE; DRUG PROTEIN BINDING; HAEMONCHUS CONTORTUS; MOLECULAR MECHANICS; MOLECULAR MODEL; PRIORITY JOURNAL; SITE DIRECTED MUTAGENESIS;

ALBENDAZOLE; AMINO ACID SEQUENCE; ANIMALS; ANTHELMINTICS; BENZIMIDAZOLES; BINDING SITES; DRUG RESISTANCE; FASCIOLA HEPATICA; HAEMONCHUS; HELMINTH PROTEINS; MODELS, CHEMICAL; MOLECULAR SEQUENCE DATA; MUTATION; PROTEIN STRUCTURE, TERTIARY; TUBULIN;

FASCIOLA; FASCIOLA HEPATICA; FUNGI; HAEMONCHUS CONTORTUS; HEPATICA; NEMATODA; VERMES;

EID: 7744237554     PISSN: 10933263     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jmgm.2004.08.001     Document Type: Article

References (29)

1. E. Lacey The role of the cytoskeletal protein, tubulin, in the mode of action and mechanism of drug resistance to benzimidazoles Int. J. Parasitol. 18 1988 885 936
2. G.W. Lubega, and R.K. Prichard Specific interaction of benzimadazole anthelmintics with tubulin: high-affinity binding and benzimidazole resistance in Haemonchus contortus Mol. Biochem. Parasitol. 38 1990 221 232
3. R.K. Prichard Genetic variability following selection of Haemonchus contortus with anthelmintics Trends Parasitol. 17 2001 445 453
4. M.W. Robinson, A. Trudgett, I. Fairweather, and N. McFerran Benzimidazole binding to Haemonchus contortus tubulin: a question of structure Trends Parasitol. 18 2002 153 154
5. M.S.G. Kwa, J.G. Veenstra, and M.H. Roos Benzimadazole resistance in Haemonchus contortus is correlated with a conserved mutation at amino acid 200 in β-tubulin isotype 1 Mol. Biochem. Parasitol. 63 1994 299 303
6. A. Silvestre, and J. Cabaret Mutation in position 167 of isotype-I β-tubulin gene of Trichostrongylid nematodes: roles in benzimidazole resistance? Mol. Biochem. Parasitol. 120 2002 297 300
7. B. Nare, G. Lubega, R.K. Prichard, and E. Georges p-Azidosalicyl-5-amino- 6-phenoxybenzimidazole photolabels the N-terminal 63-103 amino acids of Haemonchus contortus β-tubulin 1 J. Biol. Chem. 271 1996 8575 8581
8. K.H. Downing Structural basis for the action of drugs that affect microtubule dynamics Emerg. Ther. Targets 4 2000 219 237
9. E. Nogales, S.G. Wolf, and K.H. Downing Structure of the αβ-tubulin dimer by electron crystallography Nature 391 1998 199 203
10. M.K. Jung, and B.R. Oakley Identification of an amino acid substitution in the benA β-tubulin gene of Aspergillus nidulans that confers thiabendazole resistance and benomyl supersensitivity Cell Motil. Cytoskeleton 17 1990 87 94
11. M.K. Jung, I. Wilder, and B.R. Oakley Amino acid alterations in the benA (β-tubulin) gene of Aspergillus nidulans that confer benomyl resistance Cell. Motil. Cytoskeleton 22 1992 170 174
12. J. Li, S.K. Katiyar, and T.D. Edlind Site-directed mutagenesis of Saccharomyces cerevisiae β-tubulin: interaction between residue 167 and benzimidazole compounds FEBS Lett. 385 1996 7 10
13. E. Nogales, K.H. Downing, L.A. Amos, and J. Lowe Tubulin and FtsZ form a distinct family of GTPases Nat. Struct. Biol. 5 1998 451 458
14. ® stabilises microtubule structure Chem. Biol. 6 1999 R65 R69
15. M.W. Robinson, E.M. Hoey, I. Fairweather, J.P. Dalton, S. McGonigle, and A. Trudgett Characterisation of a β-tubulin gene from the liver fluke Fasciola hepatica Int. J. Parasitol. 31 2001 1264 1268
16. T.G. Geary, S.C. Nulf, M.A. Favreau, L. Tang, R.K. Prichard, N.T. Hatzenbuhler, M.H. Shea, S.J. Alexander, and R.D. Klein Three β-tubulin cDNAs from the parasitic nematode Haemonchus contortus Mol. Biochem. Parasitol. 50 1992 295 306
17. J. Lowe, H. Li, K.H. Downing, and E. Nogales Refined structure of αβ-tubulin at 3.50 Å J. Mol. Biol. 2001 313
18. J.P. Snyder, J.H. Nettles, B. Cornett, K.H. Downing, and E. Nogales The binding conformation of taxol in β-tubulin: a model based on electron crystallographic density Proc. Nat. Acad. Sci. U.S.A. 98 2001 5312 5316
19. R. Bai, D.G. Covell, X. Pei, J.B. Ewell, N.Y. Nguyen, A. Brossi, and H. Hamel Mapping the binding site of colchicinoids on β-tubulin. 2-Chloroacetyl-2-demethyliocolchicine covalently reacts predominantly with cysteine 239 and secondarily with cysteine 354 J. Biol. Chem. 275 2000 40443 40452
20. J. Lowe, and L.A. Amos Crystal structure of the bacterial cell division protein FtsZ Nature 391 1998 203 206
21. O. Millet, R.P. Hudson, and L.E. Kay The energetic cost of domain reorientation in maltose-binding protein as studied by NMR and fluorescence spectrometry Proc. Nat. Acad. Sci. U.S.A. 100 2003 12700 12705
22. Y.H. Song, A. Marx, J. Muller, G. Woehlke, M. Schliwa, A. Krebs, A. Hoenger, and E. Mandelkow Structure of a fast kinesin: implications for ATPase mechanism and interactions with microtubules EMBO J. 20 2001 6213 6225
23. J.F. Buchanan, I. Fairweather, G.P. Brennan, A. Trudgett, and E.M. Hoey Fasciola hepatica: surface and internal tegumental changes induced by treatment in vitro with the sulphoxide metabolite of albendazole ('Valbazen') Parasitology 126 2003 141 153
24. S. Nagano, H. Li, H. Shimizu, C. Nishida, H. Ogura, P.R. Ortiz de Montellano, and T.L. Poulos Crystal structures of epithilone D-bound, epithilone B-bound, and substrate-free forms of cytochrome P450epoK J. Biol. Chem. 278 2003 44886 44893
25. G.W. Lubega, and R.K. Prichard Interaction of benzimidazole anthelmintics with Haemonchus contortus tubulin: binding affinity and anthelmintic efficacy Exp. Parasitol. 73 1991 203 213
26. E. Lacey, K.L. Snowdon, G.K. Eagleston, and E.F. Smith Further investigations of the primary mechanism of benzimidazole resistance in Haemonchus contortus Int. J. Parasitol. 17 1987 1421 1429
27. H.W. Detrich III, S.K. Parker, R.C. Williams, E. Nogales, and K.H. Downing Cold adaptation of microtubule assembly and dynamics, Structural interpretation of primary sequence changes present in the α- and β-tubulins of Antarctic fishes J. Biol. Chem. 275 2000 37038 37047
28. S. William, A. Sabra, F. Ramzy, M. Mousa, Z. Demerdash, J.L. Bennett, T.A. Day, and S. Botros Stability and reproductive fitness of Schistosoma mansoni isolates with decreased sensitivity to praziquantel Int. J. Parasitol. 31 2001 1093 1100
29. R.B.G. Ravelli, B. Gigant, P.A. Curmi, I. Jourdain, S. Lachkar, A. Sobel, and M. Knossow Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain Nature 428 2004 198 202