Screening for Microtubule-Disrupting Antifungal Agents by Using a Mitotic-Arrest Mutant of Aspergillus nidulans and Novel Action of Phenylalanine Derivatives Accompanying Tubulin Loss

Antimicrobial Agents and Chemotherapy

Volumn 48, Issue 5, 2004, Pages 1739-1748

  Kiso, Tetsuo ^a   Fujita, Ken Ichi ^a   Ping, Xu ^a   Tanaka, Toshio ^a   Taniguchi, Makoto ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 (1 ANILINOETHYLIDENE) 5 BENZYL 2,4 PYRROLIDINEDIONE; ALDEHYDE; ALPHA TUBULIN; AMINO ACID; ANSAMITOCIN P 3; ANTIFUNGAL AGENT; ARPHAMENINE A; BENOMYL; BENZIMIDAZOLE DERIVATIVE; BETA TUBULIN; CARBENDAZIM; CITRININ; COLCHICINE; DEMECOLCINE; GRISEOFULVIN; MYCOTOXIN; NOCODAZOLE; PACLITAXEL; PATULIN; PHENYLALANINE DERIVATIVE; PODOPHYLLOTOXIN; POLYGODIAL; RHIZOXIN; SESQUITERPENE DERIVATIVE; TIABENDAZOLE; TUBULIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINBLASTINE; VINCRISTINE; WARBURGANAL;

AGAR GEL DIFFUSION; ARTICLE; ASPERGILLUS NIDULANS; CONTROLLED STUDY; CYTOSKELETON; DRUG SCREENING; DRUG TARGETING; FLUORESCENCE MICROSCOPY; FUNGUS GROWTH; FUNGUS HYPHAE; FUNGUS MUTANT; GROWTH INHIBITION; HEAT SENSITIVITY; MICROTUBULE; MICROTUBULE ASSEMBLY; MITOSIS INHIBITION; NONHUMAN; PRIORITY JOURNAL; WESTERN BLOTTING;

ADENINE; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; ASPERGILLUS NIDULANS; BLOTTING, WESTERN; CELL NUCLEUS; CHROMOSOMES, FUNGAL; COLORING AGENTS; DRUG EVALUATION, PRECLINICAL; ELECTROPHORESIS, POLYACRYLAMIDE GEL; FUNGAL PROTEINS; FUNGI; MICROBIAL SENSITIVITY TESTS; MICROSCOPY, FLUORESCENCE; MICROTUBULES; MITOSIS; MITOTIC INDEX; NOCODAZOLE; OXAZINES; PHENYLALANINE; TUBULIN; XANTHENES;

EID: 2142760084     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.48.5.1739-1748.2004     Document Type: Article

References (44)

1. Bennett, J. W., and M. Klich. 2003. Mycotoxins. Clin. Microbiol. Rev. 16:497-516.
2. Bergen, L. G., and N. R. Morris. 1983. Kinetics of the nuclear division cycle of Aspergillus nidulans. J. Bacteriol. 156:155-160.
3. Bradford, M. M. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:248-254.
4. Espinel-Ingroff, A., M. Bartlett, R. Bowden, N. X. Chin, Jr., C. Cooper, A. Fothergill, M. R. McGinnis, P. Menezes, S. A. Messer, P. W. Nelson, F. C. Odds, L. Pasarell, J. Peter, M. A. Pfaller, J. H. Rex, M. G. Rinaldi, G. S. Shankland, T. J. Walsh, and I. Weitzman. 1997. Multicenter evaluation of proposed standardized procedure for antifungal susceptibility testing of filamentous fungi. J. Clin. Microbiol. 35:139-143.
5. Friedman, P. A., and E. G. Platzer. 1978. Interaction of anthelmintic benzimidazoles and benzimidazole derivatives with bovine brain tubulin. Biochim. Biophys. Acta 544:605-614.
6. Gambino, J., L. G. Bergen, and N. R. Morris. 1984. Effects of mitotic and tubulin mutations on microtubule architecture in actively growing protoplasts of Aspergillus nidulans. J. Cell Biol. 99:830-838.
7. Genghof, D. S. 1970. 2,5-Dihydrophenylalanine as an inhibitor of microbial growth. Can. J. Microbiol. 16:545-547.
8. Grishchuk, E. L., J. L. Howe, and J. R. McIntosh. 1998. A screen for genes involved in the anaphase proteolytic pathway identifies tsml(+), a novel Schizosaccharomyces pombe gene important for microtubule integrity. Genetics 149:1251-1264.
9. Grover, J. K., V. Vats, G. Uppal, and S. Yadav. 2001. Anthelmintics: a review. Trop. Gastroenterol. 22:180-189.
10. Haraguchi, H., K. Hashimoto, K. Shibata, M. Taniguchi, T. Tanaka, and S. Oi. 1987. Mechanism of antifungal action of citrinin. Agric. Biol. Chem. 51:1373-1378.
11. Haraguchi, H., M. Taniguchi, T. Tanaka, S. Oi, and K. Hashimoto. 1989. Citrinin, an electron-acceptor having antifungal activity. Agric. Biol. Chem. 53:1741-1742.
12. Hollomon, D. W., J. A. Butters, and H. Barker. 1997. Tubulins: a target for anti-fungal agents, p. 152-156. In P. H. Bentley and P. J. O'Hanlon (ed.), Anti-infectives: recent advances in chemistry and structure activity relationships. Royal Society of Chemistry, London, United Kingdom.
13. Hyams, J. S., and C. W. Lloyd (ed.). 1993. Microtubules. Wiley-Liss, New York, N.Y.
14. Iwasaki, S. 1998. Natural organic compounds that affect to microtubule functions. Yakugaku Zasshi 118:112-126.
15. Johnson, L. A., K. E. Moon, and M. Eisenberg. 1988. Inactivation of chymotrypsin and human skin chymase: kinetics of time-dependent inhibition in the presence of substrate. Biochim. Biophys. Acta 953:269-279.
16. Jung, M. K., G. S. May, and B. R. Oakley. 1998. Mitosis in wild-type and β-tubulin mutant strains of Aspergillus nidulans. Fungal Genet. Biol. 24:146-160.
17. Jung, M. K., N. Prigozhina, C. E. Oakley, E. Nogales, and B. R. Oakley. 2001. Alanine-scanning mutagenesis of Aspergillus γ-tubulin yields diverse and novel phenotypes. Mol. Biol. Cell 12:2119-2136.
18. Katiyar, S. K., V. R. Gordon, G. L. McLaughlin, and T. D. Edlind. 1994. Antiprotozoal activities of benzimidazoles and correlations with β-tubulin sequence. Antimicrob. Agents Chemother. 38:2086-2090.
19. Kiso, T., Y. Usuki, X. Ping, K. Fujita, and M. Taniguchi. 2001. L-2,5-Dihydrophenylalanine, an inducer of cathepsin-dependent apoptosis in human promyelocytic leukemia cells (HL-60). J. Antibiot. (Tokyo) 54:810-817.
20. Kubo, I., and M. Taniguchi. 1988. Polygodial, an antifungal potentiator. J. Nat. Prod. 51:22-29.
21. Kubo, I., and M. Himejima. 1992. Potentiation of antifungal activity of sesquiterpene dialdehydes against Candida albicans and 2 other fungi. Experientia 48:1162-1164.
22. Llop, C., I. Pujol, C. Aguilar, J. Sala, D. Riba, and J. Guarro. 2000. Comparison of three methods of determining MICs for filamentous fungi using different end point criteria and incubation periods. Antimicrob. Agents Chemother. 44:239-242.
23. Machida, K., T. Tanaka, and M. Taniguchi. 1999. Depletion of glutathione as a cause of the promotive effects of polygodial, a sesquiterpene on the production of reactive oxygen species in Saccharomyces cerevisiae. J. Biosci. Bioeng. 88:526-530.
24. MacRae, T. H. 1992. Towards an understanding of microtubule function and cell organization: an overview. Biochem. Cell Biol. 70:835-841.
25. Maxwell, W. A., and G. Brody. 1971. Antifungal activity of selected benzimidazole compounds. Appl. Microbiol. 21:944-945.
26. Mikhailov, A., and G. G. Gundersen. 1998. Relationship between microtubule dynamics and lamellipodium formation revealed by direct imaging of microtubules in cells treated with nocodazole or taxol. Cell Motil. Cytoskelet. 41:325-340.
27. Mirabito, P. M., and N. R. Morris. 1993. BIMA, a TPR-containing protein required for mitosis, localizes to the spindle pole body in Aspergillus nidulans. J. Cell Biol. 120:959-968.
28. Morris, N. R., and C. E. Oakley. 1979. Evidence that p-fluorophenylalanine has a direct effect on tubulin in Aspergillus nidulans. J. Gen. Microbiol. 114:449-454.
29. National Committee for Clinical Laboratory Standards. 1995. Reference method for broth dilution antifungal susceptibility testing of yeasts. Tentative standard M27-T. National Committee for Clinical Laboratory Standards, Wayne, Pa.
30. Oakley, B. R., and N. R. Morris. 1981. A β-tubulin mutation in Aspergillus nidulans that blocks microtubule function without blocking assembly. Cell 24:837-845.
31. Ovechkina, Y. Y., R. K. Pettit, Z. A. Cichacz, G. R. Pettit, and B. R. Oakley. 1999. Unusual antimicrotubule activity of the antifungal agent spongistatin 1. Antimicrob. Agents Chemother. 43:1993-1999.
32. Owellen, R. J., Jr., A. H. Owens, and D. W. Donigian. 1972. The binding of vincristine, vinblastine and colchicine to tubulin. Biochem. Biophys. Res. Commun. 47:685-691.
33. Parekh, H., and H. Simpkins. 1997. The transport and binding of taxol. Gen. Pharmacol. 29:167-172.
34. Parry, J. M. 1993. An evaluation of the use of in vitro tubulin polymerisation, fungal and wheat assays to detect the activity of potential chemical aneugens. Mutat. Res. 287:23-28.
35. Pfeiffer, E., K. Gross, and M. Metzler. 1998. Aneuploidogenic and clastogenic potential of the mycotoxins citrinin and patulin. Carcinogenesis 19:1313-1318.
36. Pine, M. J. 1975. Incorporation of L-2,5-dihydrophenylalanine into cell proteins of Escherichia coli and sarcoma 180. Antimicrob. Agents Chemother. 7:601-605.
37. Schoellmann, G., and E. Shaw. 1963. Direct evidence for the presence of histidine in the active center of chymotrypsin. Biochemistry 2:252-255.
38. Taniguchi, M., T. Adachi, H. Haraguchi, S. Oi, and I. Kubo. 1983. Physiological activity of warburganal and its reactivity with sulfhydryl-groups. J. Biochem. 94:149-154.
39. Umezawa, H., T. Aoyagi, S. Ohuchi, A. Okuyama, H. Suda, T. Takita, M. Hamada, and T. Takeuchi. 1983. Arphamenines A and B, new inhibitors of aminopeptidase B, produced by bacteria. J. Antibiot. (Tokyo) 36:1572-1575.
40. Van Tuyl, J. M. 1977. Genetics of fungal resistance to systemic fungicides. Meded. Landbouwhogesch. Wagening. 2:1-137.
41. Vasquez, R. J., B. Howell, A.-M. C. Yvon, P. Wadsworth, and L. Cassimeris. 1997. Nanomolar concentrations of nocodazole alter microtubule dynamic instability in vivo and in vitro. Mol. Biol. Cell 8:973-985.
42. Vogel, J., and M. Snyder. 2000. The carboxy terminus of Tub4p is required for γ-tubulin function in budding yeast. J. Cell Sci. 113:3871-3882.
43. Yamaji, K., Y. Fukushi, Y. Hashidoko, T. Yoshida, and S. Tahara. 1999. Characterization of antifungal metabolites produced by Penicillium species isolated from seeds of Picea glehnii. J. Chem. Ecol. 25:1643-1653.
44. Yoon, Y., and B. R. Oakley. 1995. Purification and characterization of assembly-competent tubulin from Aspergillus nidulans. Biochemistry 34:6373-6381.