Bis(glutathionyl)spermine and other novel trypanothione analogues in Trypanosoma cruzi

Journal of Biological Chemistry

Volumn 278, Issue 30, 2003, Pages 27612-27619

  Ariyanayagam, Mark R ^a   Oza, Sandra L ^a   Mehlert, Angela ^a   Fairlamb, Alan H ^a  

^a UNIVERSITY OF DUNDEE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; BIOSYNTHESIS; CATALYSIS; CELLS; ENZYMES; IONIZATION;

ENZYMATIC SYNTHESIS;

KETONES;

ANTIOXIDANT; BIS(GLUTATHIONYL)SPERMINE DERIVATIVE; CADAVERINE; CYSTEINE; GAMMA GLUTAMYLCYSTEINE; GLUTATHIONE; GLUTATHIONE DERIVATIVE; GLUTATHIONYLSPERMIDINE; HYDROGEN SULFIDE; N (3 AMINOPROPYL) 1,5 DIAMINOPENTANE; N ACETYLSPERMINE; N1 GLUTATHIONYL N12 ACETYLSPERMINE; N1 GLUTATHIONYL N8 ACETYLSPERMIDINE; N1,N12 BIS(GLUTATHIONYL)SPERMINE; N8 ACETYLSPERMIDINE; OVOTHIOL A; POLYAMINE; PUTRESCINE; RECOMBINANT ENZYME; RECOMBINANT TRYPANOTHIONE SYNTHETASE; SPERMIDINE; SPERMIDINE DERIVATIVE; SPERMINE; SPERMINE DERIVATIVE; SYNTHETASE; TRYPANOTHIONE; TRYPANOTHIONE AMIDASE; TRYPANOTHIONE DERIVATIVE; TRYPANOTHIONE SYNTHETASE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AMASTIGOTE; ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; BINDING AFFINITY; CHEMICAL COMPOSITION; CONJUGATION; CONTROLLED STUDY; ENZYME SPECIFICITY; ENZYME STRUCTURE; ENZYME SUBSTRATE; EPIMASTIGOTE; FLAGELLATE; GLUTATHIONE METABOLISM; LIFE CYCLE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; METABOLIC REGULATION; METABOLITE; NONHUMAN; POLYAMINE SYNTHESIS; PRIORITY JOURNAL; PROTEIN PURIFICATION; STRUCTURE ANALYSIS; SYNTHESIS; TRYPANOSOMA CRUZI; TRYPOMASTIGOTE;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUTATHIONE; KINETICS; MASS SPECTROMETRY; MODELS, CHEMICAL; POLYAMINES; RECOMBINANT PROTEINS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SPERMIDINE; SPERMINE; SUBSTRATE SPECIFICITY; SULFHYDRYL COMPOUNDS; TIME FACTORS; TRYPANOSOMA CRUZI;

ANIMALIA; MASTIGOPHORA (FLAGELLATES); PROTOZOA; TRYPANOSOMA; TRYPANOSOMA CRUZI;

EID: 0041461862     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M302750200     Document Type: Article

References (53)

1. Schafer, F. Q., and Buettner, G. R. (2001) Free Radic. Biol. Med. 30, 1191-1212
2. Meister, A. (1989) in Glutathione: Chemical, Biochemical, and Medical Aspects (Dolphin, D., Poulson, R., and Avramovic, O., eds) Part A, pp. 367-474, John Wiley & Sons, Inc., New York
3. Carmel-Harel, O., and Storz, G. (2000) Annu. Rev. Microbiol. 54, 439-461
4. Hofmann, B., Hecht, H. J., and Flohe, L. (2002) Biol. Chem. Hoppe-Seyler 383, 347-364
5. Holmgren, A. (1985) Annu. Rev. Biochem. 54, 237-271
6. Fairlamb, A. H., and Cerami, A. (1992) Annu. Rev. Microbiol. 46, 695-729
7. Reckenfelderbaumer, N., Ludemann, H., Schmidt, H., Steverding, D., and Krauth-Siegel, R. L. (2000) J. Biol. Chem. 275, 7547-7552
8. Fairlamb, A. H., Blackburn, P., Ulrich, P., Chait, B. T., and Cerami, A. (1985) Science 227, 1485-1487
9. Nogoceke, E., Gommel, D. U., Kiess, M., Kalisz, H. M., and Flohé, L. (1997) Biol. Chem. Hoppe-Seyler 378, 827-836
10. Tetaud, E., and Fairlamb, A. H. (1998) Mol. Biochem. Parasitol. 96, 111-123
11. Wilkinson, S. R., Meyer, D. J., Taylor, M. C., Bromley, E. V., Miles, M. A., and Kelly, J. M. (2002) J. Biol. Chem. 277, 17062-17071
12. Wilkinson, S. R., Taylor, M. C., Touitha, S., Mauricio, I. L., Meyer, D. J., and Kelly, J. M. (2002) Biochem. J. 364, 787-794
13. Wilkinson, S. R., Obado, S. O., Mauricio, I. L., and Kelly, J. M. (2002) Proc. Natl. Acad. Sci. U. S. A. 99, 13453-13458
14. Dormeyer, M., Reckenfelderbaumer, N., Ludemann, H., and Krauth-Siegel, R. L. (2001) J. Biol. Chem. 276, 10602-10606
15. Dumas, C., Ouellette, M., Tovar, J., Cunningham, M. L., Fairlamb, A. H., Tamar, S., Olivier, M., and Papadopoulou, B. (1997) EMBO J. 16, 2590-2598
16. Tovar, J., Cunningham, M. L., Smith, A. C., Croft, S. L., and Fairlamb, A. H. (1998) Proc. Natl. Acad. Sci. U. S. A. 95, 5311-5316
17. Krieger, S., Schwarz, W., Ariyanayagam, M. R., Fairlamb, A. H., Krauth-Siegel, R. L., and Clayton, C. (2000) Mol. Microbiol. 35, 542-552
18. Shames, S. L., Fairlamb, A. H., Cerami, A., and Walsh, C. T. (1986) Biochemistry 25, 3519-3526
19. Fairlamb, A. H. (1999) Medicina (Buenos Aires) 59, 179-187
20. Flohé, L., Hecht, H. J., and Steinert, P. (1999) Free Radic. Biol. Med. 27, 966-984
21. Smith, K., Nadeau, K., Walsh, C., and Fairlamb, A. H. (1992) Protein Sci. 1, 874-883
22. Augustyns, K., Amssoms, K., Yamani, A., Rajan, P. K., and Haemers, A. (2001) Curr. Pharm. Des. 7, 1117-1141
23. Fairlamb, A. H., Henderson, G. B., and Cerami, A. (1986) Mol. Biochem. Parasitol. 21, 247-257
24. Hunter, K. J., Le Quesne, S. A., and Fairlamb, A. H. (1994) Eur. J. Biochem. 226, 1019-1027
25. Lueder, D. V., and Phillips, M. A. (1996) J. Biol. Chem. 271, 17485-17490
26. Fairlamb, A. H., and Le Quesne, S. A. (1997) in Trypanosomiasis and Leishmaniasis: Biology and Control (Hide, G., Mottram, J. C., Coombs, G. H., and Holmes, P. H., eds) pp. 149-161, CAB International, Wallingford, UK
27. Le Quesne, S. A., and Fairlamb, A. H. (1996) Biochem. J. 316, 481-486
28. Tetaud, E., Manai, F., Barrett, M. P., Nadeau, K., Walsh, C. T., and Fairlamb, A. H. (1998) J. Biol. Chem. 273, 19383-19390
29. Oza, S. L., Tetaud, E., Ariyanayagam, M. R., Warnon, S. S., and Fairlamb, A. H. (2002) J. Biol. Chem. 277, 35853-35861
30. Bollinger, J. M., Jr., Kwon, D. S., Huisman, G. W., Kolter, R., and Walsh, C. T. (1995) J. Biol. Chem. 270, 14031-14041
31. Oza, S. L., Ariyanayagam, M. R., and Fairlamb, A. H. (2002) Biochem. J. 364, 679-686
32. Ariyanayagam, M. R., and Fairlamb, A. H. (1997) Mol. Biochem. Parasitol. 84, 111-121
33. Ebong, S., and Farkas, W. R. (1993) Comp. Biochem. Physiol. C Comp. Pharmacol. Toxicol. 106, 483-487
34. Shim, H., and Fairlamb, A. H. (1988) J. Gen. Microbiol. 134, 807-817
35. Fairlamb, A. H., Henderson, G. B., Bacchi, C. J., and Cerami, A. (1987) Mol. Biochem. Parasitol. 24, 185-191
36. Ariyanayagam, M. R., and Fairlamb, A. H. (1999) Mol. Biochem. Parasitol. 103, 61-69
37. Hunter, K. J. (1998) in Polyamine Protocols (Morgan, D., ed) pp. 119-123, Humana Press Inc., Totowa, NJ
38. Ariyanayagam, M. R., and Fairlamb, A. H. (2001) Mol. Biochem. Parasitol. 115, 189-198
39. Newton, G. L., and Fahey, R. C. (1995) Methods Enzymol. 251, 148-166
40. Borges, A., Cunningham, M. L., Tovar, J., and Fairlamb, A. H. (1995) Eur. J. Biochem. 228, 745-752
41. Vasquez, B., Ishibashi, F., and Howard, B. V. (1982) In Vitro (Rockville) 18, 643-649
42. Machado, C. A., and Ayala, F. J. (2001) Proc. Natl. Acad. Sci. U. S. A. 98, 7396-7401
43. Watanabe, S. I., Kusama-Eguchi, K., Kobayashi, H., and Igarashi, K. (1991) J. Biol. Chem. 266, 20803-20809
44. Seiler, N. (1987) in Inhibition of Polyamine Metabolism: Biological Significance and Basis for New Therapies (McCann, P. P., Pegg, A. E., and Sjoerdsma, A., eds) pp. 49-77, Academic Press, Inc., Orlando, FL
45. Casero, R. A., and Pegg, A. E. (1993) FASEB J. 7, 653-661
46. Mudumba, S., Menezes, A., Fries, D., and Blankenship, J. (2002) Biochem. Pharmacol. 63, 2011-2018
47. Wang, Z. J., Fries, D., and Blankenship, J. (1999) Biochem. Pharmacol. 57, 1095-1103
48. Freire-de-Lima, C. G., Nascimento, D. O., Soares, M. B., Bozza, P. T., Castro-Faria-Neto, H. C., De Mello, F. G., Dosreis, G. A., and Lopes, M. F. (2000) Nature 403, 199-203
49. Jiang, Y. Q., Roberts, S. C., Jardim, A., Carter, N. S., Shih, S., Ariyanayagam, M., Fairlamb, A. H., and Ullman, B. (1999) J. Biol. Chem. 274, 3781-3788
50. Roberts, S. C., Jiang, Y. Q., Jardim, A., Carter, N. S., Heby, O., and Ullman, B. (2001) Mol. Biochem. Parasitol. 115, 217-226
51. Ponasik, J. A., Strickland, C., Faerman, C., Savvides, S., Karplus, P. A., and Ganem, B. (1995) Biochem. J. 311, 371-375
52. Bond, C. S., Zhang, Y. H., Berriman, M., Cunningham, M. L., Fairlamb, A. H., and Hunter, W. N. (1999) Structure 7, 81-89
53. Hamilton, C. J., Fairlamb, A. H., and Eggleston, I. M. (2002) J. Chem. Soc. Perkin Trans. I 1, 1115-1123