Binding and interaction of dinitroanilines with apicomplexan and kinetoplastid α-tubulin

Journal of Medicinal Chemistry

Volumn 49, Issue 17, 2006, Pages 5226-5231

  Mitra, Arpita ^a,b   Sept, David ^a,b  

^a WASHINGTON UNIVERSITY IN ST LOUIS   (United States)

^b WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA TUBULIN; ORYZALIN; TRIFLURALIN; UNCLASSIFIED DRUG;

APICOPLAST; ARTICLE; LEISHMANIA; MICROTUBULE; MICROTUBULE ASSEMBLY; NONHUMAN; NUCLEOTIDE SEQUENCE; PROTEIN STRUCTURE;

ANILINE COMPOUNDS; ANIMALS; APICOMPLEXA; BINDING SITES; BINDING, COMPETITIVE; DINITROBENZENES; KINETOPLASTIDA; MOLECULAR STRUCTURE; PROTEIN CONFORMATION; PROTEIN STRUCTURE, TERTIARY; STRUCTURE-ACTIVITY RELATIONSHIP; SULFANILAMIDES; TRIFLURALIN; TUBULIN;

EID: 33747451719     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060472+     Document Type: Article

References (28)

1. Hugdahl, J. D.; Morejohn, L. C. Rapid and reversible high-affinity binding of the dinitroaniline herbicide oryzalin to tubulin from Zea mays L. Plant Physiol. 1993, 102, 725-740.
2. Morejohn, L. C.; Bureau, T. E.; Mole-Bajer, J.; Bajer, A. S.; Fosket, D. E. Oryzalin, a dinitroaniline herbicide, binds to plant tubulin and inhibits microtubule polymerization in vitro. Planta 1987, 172, 252-264.
3. Murthy, J. V.; Kim, H. H.; Hanesworth, V. R.; Hugdahl, J. D.; Morejohn, L. C. Competitive-inhibition of high-affinity oryzalin binding to plant tubulin by the phosphoric amide herbicide amiprophos-methyl. Plant Physiol. 1994, 105, 309-320.
4. Bogitsh, B. J.; Middleton, O. L.; Ribeiro-Rodrigues, R. Effects of the antitubulin drug trifluralin on the proliferation and metacyclogenesis of Trypanosoma cruzi epimastigotes. Parasitol. Res. 1999, 85, 475-480.
5. Traub-Cseko, Y. M.; Ramalho-Ortigao, J. M.; Dantas, A. P.; de Castro, S. L.; Barbosa, H. S.; Downing, K. H. Dinitroaniline herbicides against protozoan parasites: the case of Trypanosoma cruzi. Trends Parasitol. 2001, 17, 136-141.
6. Bhattacharya, G.; Salem, M. M.; Werbovetz, K. A. Antileishmanial dinitroaniline sulfonamides with activity against parasite tubulin. Bioorg Med. Chem. Lett. 2002, 12, 2395-2398.
7. Chan, M. M.; Fong, D. Inhibition of leishmanias but not host macrophages by the antitubulin herbicide trifluralin. Science 1990, 249, 924-926.
8. Chan, M. M.; Tzeng, J.; Emge, T. J.; Ho, C. T.; Fong, D. Structure-function analysis of antimicrotubule dinitroanilines against promastigotes of the parasitic protozoan Leishmania mexicana. Antimicrob. Agents Chemother. 1993, 37, 1909-1913.
9. Nath, J.; Schneider, I. Antimalarial effects of the antitubulin herbicide trifluralin: studies in Plasmodium-falciparum. Clin. Res. 1992, 40, A331-A331.
10. Stokkermans, T. J.; Schwartzman, J. D.; Keenan, K.; Morrissette, N. S.; Tilney, L. G.; Roos, D. S. Inhibition of Toxoplasma gondii replication by dinitroaniline herbicides. Exp. Parasitol. 1996, 84, 355-370.
11. Chan, M. M.; Triemer, R. E.; Fong, D. Effect of the anti-microtubule drug oryzalin on growth and differentiation of the parasitic protozoan Leishmania mexicana. Differentiation 1991, 46, 15-21.
12. Bhattacharya, G.; Herman, J.; Delfin, D.; Salem, M. M.; Barszcz, T.; Mollet, M.; Riccio, G.; Brun, R.; Werbovetz, K. A. Synthesis and antitubulin activity of N1- and N4-substituted 3,5-dinitro sulfanilamides against African trypanosomes and Leishmania. J. Med. Chem. 2004, 47, 1823-1832.
13. Werbovetz, K. A.; Sackett, D. L.; Delfin, D.; Bhattacharya, G.; Salem, M.; Obrzut, T.; Rattendi, D.; Bacchi, C. Selective antimicrotubule activity of N1-phenyl-3,5-dinitro-N4,N4-di-n-propylsulfanilamide (GB-II-5) against kinetoplastid parasites. Mol. Pharmacol. 2003, 64, 1325-1333.
14. Fowler, R. E.; Fookes, R. E.; Lavin, F.; Bannister, L. H.; Mitchell, G. H. Microtubules in Plasmodium falciparum merozoites and their importance for invasion of erythrocytes. Parasitology 1998, 117, 425-433.
15. Kaidoh, T.; Nath, J.; Fujioka, H.; Okoye, V.; Aikawa, M. Effect and localization of trifluralin in Plasmodium falciparum gametocytes: an electron microscopic study. J. Eukaryot. Microbiol. 1995, 42, 61-64.
16. Morrissette, N. S.; Mitra, A.; Sept, D.; Sibley, L. D. Dinitroanilines bind alpha-tubulin to disrupt microtubules. Mol. Biol. Cell 2004, 15, 1960-1968.
17. Vriend, G. WHAT IF: a molecular modeling and drug design program. J. Mol. Graph. 1990, 8, 52-56.
18. Kale, L.; Skeel, R.; Bhandarkar, M.; Brunner, R.; Gursoy, A.; Krawetz, N.; Phillips, J.; Shinozaki, A.; Varadarajan, K.; Schulten, K. NAMD2: Greater scalability for parallel molecular dynamics. J. Comput. Phys. 1999, 151, 283-312.
19. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using a Lamarckian genetic algorithm and empirical binding free energy function. J. Comput. Chem. 1998, 19, 1639-1662.
20. Mitra, A.; Sept, D. Localization of the antimitotic peptide and depsipeptide binding site on beta-tubulin. Biochemistry 2004, 43, 13955-13962.
21. Allinger, N. L.; Yuh, Y. H.; Lu, J. H. Molecular mechanics: the Mm3 force-field for hydrocarbons 0.1. J. Am. Chem. Sac. 1989, 111, 8551-8566.
22. MacKerell, A. D.; Bashford, D.; Bellott, M.; Dunbrack, R. L. Evanseck, J. D.; Field, M. J.; Fischer, S.; Gao, J.; Guo, H.; Ha, S. Joseph-McCarthy, D.; Kuchnir, L.; Kuczera, K.; Lau, F. T. K. Mattos, C.; Michnick, S.; Ngo, T.; Nguyen, D. T.; Prodhom, B. Reiher, W. E.; Roux, B.; Schlenkrich, M.; Smith, J. C.; Stote, R. Straub, J.; Watanabe, M.; Wiorkiewicz-Kuczera, J.; Yin, D.; Karplus, M. All-atom empirical potential for molecular modeling and dynamics studies of proteins. J. Phys. Chem. B 1998, 102, 3586-3616.
23. Feller, S. E.; MacKerell, A. D. An improved empirical potential energy function for molecular simulations of phospholipids. J. Phys. Chem. B 2000, 104, 7510-7515.
24. Pearson, W. R. Rapid and sensitive sequence comparison with Fastp and Fasta. Methods Emymol. 1990, 183, 63-98.
25. Berman, J. D. Human leishmaniasis: clinical, diagnostic, and chemotherapeutic developments in the last 10 years. Clin. Infect. Dis. 1997, 24, 684-703.
26. Amos, L. A. Microtubule structure and its stabilisation. Org. Biomol. Chem. 2004, 2, 2153-2160.
27. Blume, Y. B.; Nyporko, A. Y.; Yemets, A. I.; Baird, W. V. Structural modeling of the interaction of plant alpha-tubulin with dinitroaniline and phosphoroamidate herbicides. Cell. Biol. Int. 2003, 27, 171-174.
28. Humphrey, W.; Dalke, A.; Schulten, K. VMD: Visual molecular dynamics. J. Mol. Graphics 1996, 14, 33-38.