Structure-activity study on the in vitro, antiprotozoal activity of glutathione derivatives

Journal of Medicinal Chemistry

Volumn 43, Issue 10, 2000, Pages 2072-2078

  D'Silva, Claudius ^a   Daunes, Sylvie ^a   Rock, Peter ^b   Yardley, Vanessa ^b   Croft, Simon L ^b  

^a MANCHESTER METROPOLITAN UNIVERSITY   (United Kingdom)

^b LONDON SCHOOL OF HYGIENE AND TROPICAL MEDICINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; ESTER DERIVATIVE; GLUTATHIONE DERIVATIVE;

ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SELECTIVITY; LEISHMANIA DONOVANI; LEISHMANIASIS; NONHUMAN; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA BRUCEI; TRYPANOSOMA CRUZI; TRYPANOSOMIASIS;

ANIMALS; ANTIPROTOZOAL AGENTS; CELL SURVIVAL; ESTERIFICATION; FEMALE; GLUTATHIONE; HUMANS; LEISHMANIA DONOVANI; LEUKEMIA, MYELOID, CHRONIC; MACROPHAGES, PERITONEAL; MICE; SPERMIDINE; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOSOMA BRUCEI BRUCEI; TRYPANOSOMA CRUZI; TUMOR CELLS, CULTURED;

EID: 0034117242     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990259w     Document Type: Article

References (39)

1. Barrett, M. P.; Fairlamb, A. H. The Biochemical Basis of Arsenical-Diamidine Crossresistance in African Trypanosomes. Parasitol. Today 1999, 15 (4), 136-140.
2. Krauth-Siegel, R. L.; Coombs, G. H. Enzymes of Parasite Thiol Metabolism as Drug Targets. Parasitol. Today 1999, 15 (10), 404-409.
3. Hajduk, S. L.; Englund, P. T.; Smith, D. H. In Tropical and Geographic Medicine; Warren, K. S., Mahmoud, A. A. F., Eds.; McGraw-Hill: New York, NY, 1989; pp 268-281; Tropical Disease Science at Work (World Health Organisation, Geneva, Switzerland, 1986).
4. Hajduk, S. L.; Englund, P. T.; Smith, D. H. In Tropical and Geographic Medicine; Warren, K. S., Mahmoud, A. A. F., Eds.; McGraw-Hill: New York, NY, 1989; pp 268-281; Tropical Disease Science at Work (World Health Organisation, Geneva, Switzerland, 1986).
5. Fairlamb, A. H.; Cerami, A. Metabolism and functions of trypanothione in the kinetoplastid. Annu. Rev. Microb. 1992, 46, 695-729.
6. Kosower, E. M.; Radkowsky, A. E.; Fairlamb, A. H.; Croft, S. L.; Neal, R. A. Bimane cyclic esters, possible stereologues of trypanothione as antitrypanosomal agents. Bimanes 29. Eur. J. Med. Chem. 1995, 30, 659-671.
7. DeCraecker, S.; Verbruggen, C.; Rajan, P. K.; Smith, K.; Haemers, A.; Fairlamb, A. H. Characterization of the peptide substrate specificity of glutathionylspermidine synthetase from Crithidia fasciculata. Mol. Biochem. Parasitol. 1997, 84, 25-32.
8. D'Silva, C.; Daunes, S. Glutathione peptides as anti-parasitic drugs. Symposium abstracts, 1st COST-B9 Congress on Anti-protozoal Chemotherapy, Sierra Nevada, Granada, Spain, May 31-June 3, 1998.
9. Sokolovsky, M.; Wilchek, M.; Patchornik, A. On the synthesis of cysteine peptides. J. Am. Chem. Soc. 1964, 86, 1202-1206.
10. D'Silva C.; Timari A. A.; Douglas K. T. Synthesis of N-acyl glutathione derivatives by (dimethylamino)pyridine catalysis. Biochem. J. 1982, 207, 329-332.
11. Douglas K. T.; Timari A. A.; D'Silva, C.; Gohel D. I. Role of the N-terminus of glutathione in the action of yeast glyoxalase I. Biochem. J. 1982, 207, 323-329.
12. D'Silva, C. Synthesis of carboxy-residue-modified coenzyme derivatives as probes to the mechanism of glutathione enzymes. Biochem, J. 1990, 271, 167-169. D'Silva. C. Correction. Biochem. J. 1990, 3, 483.
13. D'Silva, C. Synthesis of carboxy-residue-modified coenzyme derivatives as probes to the mechanism of glutathione enzymes. Biochem, J. 1990, 271, 167-169. D'Silva. C. Correction. Biochem. J. 1990, 3, 483.
14. D'Silva C. Reinvestigation of the roles of the carboxyl groups of glutathione with yeast glyoxalase I: Implications to the mechanism and coenzymic role of glutathione. FEBS Lett. 1986, 202, 240-244.
15. D'Silva C. Inhibition and Recognition Studies on the glutathione binding site of Equine liver glutathione-S-transferase. Biochem. J. 1990, 271, 161-165.
16. Norton, S. J.; Elia, A. C.; Chyan, M. K.; Gillis, G.; Frenzel, C.; Princpato, G. B. Inhibitors and inhibition studies of mammalian glyoxalase II. Biochem. Trans. 1993, 21, 545-549.
17. Al-Timari, A.; Douglas, K. T. Inhibition by glutathione derivatives of bovine liver glyoxalase II (hydroxyacylglutathione hydrolase) as a probe of the N-and S-sites for substrate binding. Biochim. Biophys. Acta 1986, 870, 219-225.
18. El-Waer, A. F.; Smith, K.; McKie, J. H.; Benson, T.; Fairlamb, A. H.; Douglas, K. T. The glutamyl binding site of trypanothione reductase from Crithidia fasciculata: enzyme kinetic properties of γ-glutamyl modified substrate analogues. Biochim. Biophys. Acta 1993, 1203, 93-98.
19. Thornalley, P. J.; Edwards, L. G.; Kang, Y.; Wyatt, C.; Davies, N.; Ladan, M. J.; Double, J. Antitumour activity of S-p-bromobenzylglutathione cyclopentyl diester in vitro and in vivo. Biochem. Pharmacol. 1996, 51, 1365-1372.
20. Thornalley, P. J.; Ladan, M. J.; Ridgway, J. S.; Kang, Y. Antitumour Activity of S-(p-Bromobenzyl)glutathione diesters in Vitro: A Structure-Activity Study. J. Med. Chem. 1996, 39, 3409-3411.
21. Levy, E. J.; Anderson, M. E.; Meister, A. Transport of glutathione diethyl esters in human cells. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 9171-9175.
22. 1 cells by reduced glutathione and its mono and di-ethyl ester derivatives. Biochem. Pharmacol. 1995, 49, 1475-1482.
23. Vince, R.; Daluge; S.; Wadd, W. B. Studies on the inhibition of glyoxalase I by S-substituted glutathiones. J. Med. Chem. 1971, 14, 402-405.
24. Blizer, M.; Krauth-Siegel, R. L.; Schirmer, R. H.; Akerboom, T. P. M.; Sies, H and Schulz, G. E. Eur. J. Biochem. 1984, 138, 373-378.
25. Bansal, A. K.; Dubey, R.; Khar, R. K. Quantitation of Activity of Alkyl ester Prodrugs of Ibuprofen. Drug Dev. Ind. Pharm. 1994, 20 (12), 2025-2034.
26. Smith, K.; Nadeau, K.; Bradley, M.; Walsh, C.; Fairlamb, A. H. Purification of glutathionylspermidine and trypanothione synthetases from Crithidia fasciculata. Protein Sci. 1992, 1, 874-883.
27. Davioud-Charvet, E.; Becker, K.; Landry, V.; Gromer, S.; Loge′, C.; Sergheraert, C.; Synthesis of 5,5′-Dithiobis(2-nitrobenz-amides) as Alternative Substrates for Trypanothione Reductase and Thioredoxin Reductase: A Microtitre Colorimetric Assay for Inhibitor Screening. Anal. Biochem. 1999, 268, 1-8.
28. S-Blocked Glutathiones. U.K. Patent filed Sept 1, 1997, Pub. no. GB2332676A.
29. D'Silva, C. Receptor based Biosensors. In Biosensors (Current Topics in Biophysics); Frangopol, P. T., Sanduloviciu, M., Eds.; Iasy University Press: Iasy, Romania, 1995; Vol. 5, pp 1-19.
30. Barnes, C.; D'Silva, C.; Jones, J. P.; Lewis, T. J. The Theory of operation of Piezoelectric Crystal Sensors for Biochemical Applications. Sensors Actuators A. 1992, 31, 159-163.
31. Montemartin, M.; Nogoceke, E.; Singh, M.; Steinert, P.; Flohe, L.; Kalisz, H. M. Sequence analysis of the Tryparedoxin Peroxidase Gene from Crithidia fasciculata and its Functional Expression inEscherichia coli. J. Biol. Chem. 1998, 273, 4864-4871.
32. Gommel, D. U.; Nogoceke, E.; Morr, M.; Kiess, M.; Kalisz, H. M.; Flohe, L. Catalytic characteristics of tryparedoxin. Eur J. Biochem. 1997, 248, 913-918.
33. Ludemann, H.; Dormeyer, M.; Sticherling, C.; Stallmann, D.; Follmann, H.; Krauth-Siegel, R. L. Trypanosoma brucei tryparedoxin, a thioredoxin-like protein in African trypanosomes. FEBS Lett. 1998, 431, 381-385.
34. Shames, S. L.; Fairlamb, A. H.; Cerami, A.; Walsh, C. T. Purification and Characterisation of Trypanothione Reductase from Crithidia fasciculata a Newly Discovered Member of the family of Disulphide-Containing Flavoprotein Reductases. Biochemistry 1986, 25, 3519-3526.
35. Hoog, J.-O.; Holmgren, A.; D'Silva, C.; Douglas, K. T.; Seddon, A. P. Glutathione Derivatives as inhibitors of Glutaredoxin and ribonucleotide Reductase from Escherichia coli. FEBS Lett. 1982, 138, 59-61.
36. Hirumi-H.; Hirumi-K. Continuous cultivation of Trypanosoma brucei blood stream forms in a medium containing a low concentration of serum proteins without feeder cell layers. J. Parasitol. 1989, 75, 985-989.
37. Ellis, J. A.; Fish, W. R.; Sileghem, M.; McOdimba, F. A colorimetric assay for trypanosome viability and metabolic function. Vet. Parasitol. 1993, 50, 143-149.
38. Neal, R. A.; Croft, S. L. An in vitro system for determining the activity of compounds against the intracellular amastigote form of Leishmania donovani. J. Antimicrob. Chemother. 1984, 14, 463-475.
39. Mossmann, T. Rapid Colorimetric assay for cellular growth and Survival. Application to Proliferation and Cytotoxicity Assay. J. Immunol. Methods 1983, 63, 55-66.