Pharmacophore identification of ascofuranone, potent inhibitor of cyanide-insensitive alternative oxidase of Trypanosoma brucei

Journal of Biochemistry

Volumn 153, Issue 3, 2013, Pages 267-273

  Saimoto, Hiroyuki ^a   Kido, Yasutoshi ^b   Haga, Yasushi ^a   Sakamoto, Kimitoshi ^b   Kita, Kiyoshi ^b  

^a TOTTORI UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

alternative oxidase; ascofuranone; neglected tropical disease; structure activity relationship; trypanosome

Indexed keywords

ASCOFURANONE; OXIDOREDUCTASE; PROTEIN INHIBITOR; TRYPANOSOME ALTERNATIVE OXIDASE; UNCLASSIFIED DRUG;

AFRICAN TRYPANOSOMIASIS; ARTICLE; BIOCHEMISTRY; DRUG STRUCTURE; ENZYME INHIBITION; HYDROGEN BOND; NONHUMAN; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA BRUCEI;

ALKENES; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; HUMANS; MOLECULAR STRUCTURE; OXIDOREDUCTASES; PHENOLS; PROTOZOAN PROTEINS; RECOMBINANT PROTEINS; SESQUITERPENES; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOSOMA BRUCEI BRUCEI; TRYPANOSOMIASIS, AFRICAN;

EID: 84874298806     PISSN: 0021924X     EISSN: 17562651     Source Type: Journal    
DOI: 10.1093/jb/mvs135     Document Type: Article

References (20)

1. Chaudhuri, M., Ott, R.D., and Hill, G.C. (2006) Trypanosome alternative oxidase: From molecule to function. Trends Parasit. 22, 484-491
2. Moore, A.L. and Siedow, J.N. (1991) The regulation and nature of the cyanide-resistant alternative oxidase of plant mitochondria. Biochim. Biophys. Acta 1059, 121-140
3. Rhoads, D.M. and McIntosh, L. (1991) Isolation and characterization of a cDNA clone encoding an alternative oxidase protein of Sauromatum guttatum. Proc. Natl Acad. Sci. USA 88, 2122-2126
4. McDonald, A.E. and Vanlerberghe, G.C. (2006) Origins, evolutionary history, and taxonomic distribution of alternative oxidase and plastoquinol terminal oxidase. Comp. Biochem. Physiol. Part D Genomics Proteomics 357-364
5. McDonald, A.E., Vanlerberghe, G.C., and Staples, J.F. (2009) Alternative oxidase in animals: Unique characteristics and taxonomic distribution. J. Exp. Biol. 212, 2627-2634
6. Lambowitz, A.M. and Slayman, C.W. (1971) Cyanide-resistant respiration in Neurospora crassa. J. Bacteriol. 108, 1087-1096
7. Clarkson, A.B. Jr and Brohn, F.H. (1976) Trypanosomiasis: An approach to chemotherapy by the inhibition of carbohydrate catabolism. Science 194, 204-206
8. Minagawa, N., Yabu, Y., Kita, K., Nagai, K., Ohta, N., Meguro, K., Sakajo, S., and Yoshimoto, A. (1997) An antibiotic, ascofuranone, specifically inhibits respiration and in vitro growth of long slender bloodstream forms of Trypanosoma brucei. Mol. Biochem. Parasitol. 84, 271-280
9. Nihei, C., Fukai, Y., and Kita, K. (2002) Trypanosome alternative oxidase as a target of chemotherapy. Biochim. Biophys. Acta 1587, 234-239
10. Nakamura, K., Fujioka, S., Fukumoto, S., Inoue, N., Sakamoto, K., Hirata, H., Kido, Y., Yabu, Y., Suzuki, T., Watanabe, Y., Saimoto, H., Akiyama, H., and Kita, K. (2010) Trypanosome alternative oxidase, a potential therapeutic target for sleeping sickness, is conserved among Trypanosoma brucei subspecies. Parasitol. Int. 59, 560-564
11. Yabu, Y., Yoshida, A., Suzuki, T., Nihei, C., Kawai, K., Minagawa, N., Hosokawa, T., Nagai, K., Kita, K., and Ohta, N. (2003) The efficacy of ascofuranone in a consecutive treatment on Trypanosoma brucei brucei in mice. Parasitol. Int. 52, 155-164
12. Yabu, Y., Suzuki, T., Nihei, C., Minagawa, N., Hosokawa, T., Nagai, K., Kita, K., and Ohta, N. (2006) Chemotherapeutic efficacy of ascofuranone in Trypanosoma vivax-infected mice without glycerol. Parasitol. Int. 55, 39-43
13. Kido, Y., Sakamoto, K., Nakamura, K., Harada, M., Suzuki, T., Yabu, Y., Saimoto, H., Yamakura, F., Ohmori, D., Moore, A.L., Harada, S., and Kita, K. (2010) Purification and kinetic characterization of recombinant alternative oxidase from Trypanosoma brucei brucei. Biochim. Biophys. Acta 1797, 443-450
14. Ito, K., Ogata, T., Kakizaki, Y., Elliott, C., Albury, M.S., and Moore, A.L. (2011) Identification of a gene for pyruvate-insensitive mitochondrial alternative oxidase expressed in the thermogenic appendices in Arum maculatum. Plant Physiol. 157, 1721-1732
15. Williams, B.A., Elliot, C., Burri, L., Kido, Y., Kita, K., Moore, A.L., and Keeling, P.J. (2010) A broad distribution of the alternative oxidase in microsporidian parasites. PLoS Pathog. 6, e1000761
16. Yoshida, T., Murai, M., Abe, M., Ichimaru, N., Harada, T., Nishioka, T., and Miyoshi, H. (2007) Crucial structural factors and mode of action of polyene amides as inhibitors for mitochondrial NADH-ubiquinone oxidoreductase (complex I). Biochemistry 46, 10365-10372
17. Kido, Y., Shiba, T., Inaoka, D.K., Sakamoto, K., Nara, T., Aoki, T., Honma, T., Tanaka, A., Inoue, M., Matsuoka, S., Moore, A.L., Harada, S., and Kita, K. (2010) Crystallization and preliminary crystallographic analysis of cyanide-insensitive alternative oxidase from Trypanosoma brucei. Acta Crystallogr. Sect. F Struct. Biol. Cryst. Commun. 66, 275-278
18. Moore, A.L. and Albury, M.A. (2008) Further insights into the structure of the alternative oxidase: From plants to parasites. Biochem. Soc. Trans. 36, 1022-1026
19. Siedow, J.N. and Girvin, M.E. (1980) Alternative respiratory pathway: Its role in seed respiration and its inhibition by propyl gallate. Plant Physiol. 65, 669-674
20. Hoefnagel, M.H., Wiskich, J.T., Madgwick, S.A., Patterson, Z., Oettmeier, W., and Rich, P.R. (1995) New inhibitors of the ubiquinol oxidase of higher plant mitochondria. Eur. J. Biochem. 233, 531-537