Glutathione-like tripeptides as inhibitors of glutathionylspermidine synthetase. Part 1: Substitution of the glycine carboxylic acid group

Bioorganic and Medicinal Chemistry Letters

Volumn 12, Issue 18, 2002, Pages 2553-2556

  Amssoms, Katie ^a   Oza, Sandra L ^b   Ravaschino, Esteban ^c   Yamani, Abdellah ^a   Lambeir, Anne Marie ^a   Rajan, Padinchare ^a   Bal, Gunther ^a   Rodriguez, Juan Bautista ^c   Fairlamb, Alan H ^b   Augustyns, Koen ^a   Haemers, Achiel ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

^b UNIVERSITY OF DUNDEE   (United Kingdom)

^c UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLSULFONAMIDE; AMIDE; BORONIC ACID DERIVATIVE; CARBOXYLIC ACID; ENZYME INHIBITOR; GLUTATHIONE; GLUTATHIONE DERIVATIVE; GLUTATHIONYLSPERMIDINE SYNTHETHASE; GLYCINE; HYDROXAMIC ACID; SYNTHETASE; TETRAZOLE DERIVATIVE; TRIPEPTIDE; UNCLASSIFIED DRUG;

ACIDITY; AMINO ACID SUBSTITUTION; AMINO ACID SYNTHESIS; ARTICLE; IC 50; PROTEIN ANALYSIS;

AMIDE SYNTHASES; CARBOXYLIC ACIDS; ENZYME INHIBITORS; GLUTATHIONE; GLYCINE; OLIGOPEPTIDES;

EID: 18644372980     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00489-4     Document Type: Article

References (15)

1. Fairlamb A.H., Blackburn P., Ulrich P., Chait B.T., Cerami A. Science. 227:1985;1485.
2. Fairlamb A.H., Cerami A. Ann. Rev. Microbiol. 46:1992;695.
3. Augystyns K., Amssoms K., Yamani A., Rajan P.K., Haemers A. Curr. Pharm. Des. 7:2001;1117.
4. Smith K., Nadeau K., Bradley M., Walsh C., Fairlamb A.H. Protein Sci. 1:1992;874.
5. Tetaud E., Manai F., Barrett M.P., Nadeau K., Walsh C.T., Fairlamb A.H. J. Biol. Chem. 273:1998;19383.
6. Verbruggen C., De Craecker S., Rajan P.K., Jiao X.-Y., Borloo M., Smith K., Fairlamb A.H., Haemers A. Bioorg. Med. Chem. Lett. 6:1996;253.
7. Chen S., Lin C.H., Kwon D.S., Walsh C.T., Coward J.K. J. Med. Chem. 40:1997;3842.
8. Chen S., Lin C.H., Walsh C.T., Coward J.K. Bioorg. Med. Chem. Lett. 7:1997;505.
9. De Craecker S., Verbruggen C., Rajan P.K., Smith K., Haemers A., Fairlamb A.H. Mol. Biochem. Parasitol. 84:1997;25.
10. Tilley J.W., Danko W., Loveu K., Wagner R., Swistok J., Makofske R., Michalewski J., Triscari J., Neslon D., Weatherford S. J. Med. Chem. 34:1991;1125.
11. Martichonok V., Jones B. J. Biorg. Med. Chem. 5:1997;679.
12. Odake S., Okayama T., Obata M., Morikawa T., Hattori S., Hori H., Nagai Y. Chem. Pharm. Bull. 38:1990;1007.
13. t: 17.1 min; purity: >99%.
14. s. In this equation, s is a slope factor. The equation assumes that y falls with increasing x. Initial velocity measurements were determined at three inhibitor concentrations and a serial dilution of glutathione, ranging from 0.03 to 1 mM. From these data, Michaelis-Menten and Lineweaver-Burk plots were constructed, and kinetic inhibitory values were determined by non-linear least squares regression analysis using the Grafit® programme. Inhibitors gave the best fit with mixed or competitive type inhibition. The indicated errors are the standard errors on the fit.
15. Oza, S. L.; Ariyanayagam, M. R.; Fairlamb, A. H. Biochem. J. 2002, 364, 679.