Selective inhibitors of human lactate dehydrogenases and lactate dehydrogenase from the malarial parasite Plasmodium falciparum

Journal of Medicinal Chemistry

Volumn 41, Issue 20, 1998, Pages 3879-3887

  Deck, Lorraine M ^a   Royer, Robert E ^a   Chamblee, Brian B ^a   Hernandez, Valerie M ^a   Malone, Richard R ^a   Torres, Jose E ^a   Hunsaker, Lucy A ^a   Piper, Robert C ^b   Makler, Michael T ^c   Vander Jagt, David L ^a  

^a UNIVERSITY OF NEW MEXICO SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF OREGON   (United States)

^c OREGON HEALTH AND SCIENCE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 DEOXYHEMIGOSSYLIC ACID (2,3 DIHYDROXY 6 METHYL 4 (1 METHYLETHYL) 1 NAPHTHOIC ACID DERIVATIVE; ENZYME INHIBITOR; LACTATE DEHYDROGENASE; LACTATE DEHYDROGENASE INHIBITOR; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPETITIVE INHIBITION; DISSOCIATION CONSTANT; DRUG SYNTHESIS; ENZYME INHIBITION; PLASMODIUM FALCIPARUM;

ANIMALS; ENZYME INHIBITORS; HUMANS; KINETICS; L-LACTATE DEHYDROGENASE; LACTIC ACID; NAD; OXIDATION-REDUCTION; PLASMODIUM FALCIPARUM; PYRUVIC ACID; SESQUITERPENES;

EID: 14444286004     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980334n     Document Type: Article

References (21)

1. Wu, D. An Overview of the Clinical Pharmacology and Therapeutic Potential of Gossypol as a Male Contraceptive Agent and in Gynaecological Disease. Drugs, 1989, 38, 333-341.
2. Benz, C. C.; Keniry, M. A.; Ford, J. M.; Townsend, A. J.; Cox, F. W.; Palayoor, S.; Matlin, S. A.; Hait, W. N.; Cowan, K. H. Biochemical Correlates of the Antitumor and Antimitochondrial Properties of Gossypol Enantiomers. Mol. Pharmacol. 1990, 37, 840-847.
3. Gonzalez-Garza, M. T.; Said-Fernandez, S. Entamoeba histolytica: Potent in Vitro Antiamoebic Effect of Gossypol. Exp. Parasitol. 1988, 66, 253-255.
4. Montamat, E. E.; Burgos, C.; Gerez de Burgos, N. M.; Rovai, L. E.; Blanco, A.; Segura, E. L. Inhibitory Activity of Gossypol on Enzymes and Growth of Trypanosoma cruzi. Science 1982, 218, 288-289.
5. Eid, J. E.; Veno, H.; Wang, C. C.; Donelson, J. E. Gossypol-induced Death of African Trypanosomes. Exp. Parasitol. 1989, 66, 140-142.
6. Rikihisa, Y.; Lin, Y. C. Taenia taeniaeformis: Inhibition of Metacestode Development in the Rat by Gossypol. Exp. Parasitol. 1989, 61, 127-133.
7. Wichmann, K.; Vaheri, A.; Luukkainen, T. Inhibiting Herpes Simplex Virus Type 2 Infection in Human Epithelial Cells by Gossypol, a Potent Spermicidal and Contraceptive Agent. Am. J. Obstet. Gynecol. 1982, 142, 593-594.
8. Lin, T.-S.; Schinazi, R.; Griffith, B. P.; August, E. M.; Eriksson, B. F. H.; Zheng, D.-K.; Huang, L.; Prusoff, W. H. Selective Inhibition of Human Immunodeficiency Virus Type 1 Replication by the (-) but Not the (+) Enantiomer of Gossypol. Antimicrob. Agents Chemother. 1989, 33, 2149-2151.
9. Deck, L. M.; Vander Jagt, D. L.; Royer, R. E. Gossypol and Derivatives: A New Class of Aldose Reductase Inhibitors. J. Med. Chem. 1991, 34, 3301-3305.
10. Heidrich, J. E.; Hunsaker, L. A.; Vander Jagt, D. L. Gossypol, an Antifertility Agent, Exhibits Antimalarial Activity in vitro. IRCS Med. Sci. 1983, 11, 304.
11. Vander Jagt, D. L.; Baack, B. R.; Campos, N. M.; Hunsaker, L. A.; Royer, R. E. A Derivative of Gossypol Retains Antimalarial Activity. IRCS Med. Sci. 1984, 12, 845-846.
12. Royer, R. E.; Deck, L. M.; Campos, N. M.; Hunsaker, L. A.; Vander Jagt, D. L. Biologically Active Derivatives of Gossypol: Synthesis and Antimalarial Activities of Peri-Acylated Gossylic Nitriles. J. Med. Chem. 1986, 29, 1799-1801.
13. Royer, R. E.; Mills, R. G.; Young, S. A.; Vander Jagt, D. L. Comparison of the Antiviral Activities of 3′-Azido-3′-Deoxythymidine (AZT) and Gossylic Iminolactone (GIL) Against Clinical Isolates of HIV-1. Pharmacol. Res. 1995, 31, 49-52.
14. Royer, R. E.; Deck, L. M.; Vander Jagt, T. J.; Martinez, F. J.; Mills, R. G.; Young, S. A.; Vander Jagt, D. L. Synthesis and Anti-HIV Activity of 1,1′-Dideoxygossypol and Related Compounds. J. Med. Chem. 1995, 38, 2427-2432.
15. Verlinde, C. L. M. J.; Callens, M.; Van Calenbergh, S.; Van Aerschot, A.; Herdewijn, P.; Hannaert, V.; Michels, P. A. M.; Opperdoes, F. R.; Hol, W. G. J. Selective Inhibition of Trypanosomal Glyceraldehyde-3-phosphate Dehydrogenase by Protein Structure-Based Design: Toward New Drugs for the Treatment of Sleeping Sickness. J. Med. Chem. 1994, 37, 3605-3613.
16. Bzik, D. J.; Fox, B. A.; Gonyer, K. Expression of Plasmodium falciparum Lactate Dehydrogenase in Escherichia coli. Mol. Biochem. Parasitol. 1993, 59, 155-166.
17. Gomez, M. S.; Piper, R. C.; Hunsaker, L. A.; Royer, R. E.; Deck, L. M.; Makler, M. T.; Vander Jagt, D. L. Substrate and Cofactor Specificity and Selective Inhibition of Lactate Dehydrogenase from the Malarial Parasite P. falciparum. Mol. Biochem. Parasitol. 1997, 90, 235-246.
18. Westheimer, F. H. In Pyridine Nucleotide Coenzymes. Chemical, Biochemical, and Medical Aspects Part A; Coenzyes and Cofactors II; Dolphin, D., Poulson, R., Avramovic, O., Eds.; J. Wiley and Sons: New York, 1987; pp 253-322.
19. Dunn, C. R.; Wilks, H. M.; Halsall, D. J.; Atkinson, T.; Clarke, A. R.; Muirhead, H.; Holbrook, J. J. Design and Synthesis of New Enzymes Based on the Lactate Dehydrogenase Framework. Philos. Trans. R. Soc. London B 1991, 332, 177-184.
20. Dunn, C. R.; Banfield, M. J.; Barker, J. J.; Higham, C. W.; Moreton, K. M.; Turgut-Balik, D.; Brady, R. L.; Holbrook, J. J. The Structure of Lactate Dehydrogenase from Plasmodium falciparum Reveals a New Target for Anti-malarial Design. Nature Struct. Biol. 1996, 3, 912-915.
21. Sheikh, S.; Weiner, H. Allosteric Inhibition of Human Liver Aldehyde Dehydrogenase by the Isoflavone Prunetin. Biochem. Pharmacol. 1997, 53, 471-478.