Indomethacin amides as a novel molecular scaffold for targeting trypanosoma cruzi sterol 14α-demethylase

Journal of Medicinal Chemistry

Volumn 52, Issue 9, 2009, Pages 2846-2853

  Konkle, Mary E ^a   Hargrove, Tatiana Y ^a   Kleshchenko, Yuliya Y ^b   Von Kries, Jens P ^c   Ridenour, Whitney ^a,d   Uddin, Md Jashim ^a   Caprioli, Richard M ^a,d   Marnett, Lawrence J ^a,d   Nes, W David ^e   Villalta, Fernando ^b   Waterman, Michael R ^a,d   Lepesheva, Galina I ^a  

^a VANDERBILT UNIVERSITY   (United States)

^b MEHARRY MEDICAL COLLEGE   (United States)

^c LEIBNIZ INSTITUT FÜR MOLEKULARE PHARMAKOLOGIE   (Germany)

^d VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^e TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ANTIPARASITIC AGENT; CYP51 INHIBITOR; ENZYME INHIBITOR; IMIDAZOLE DERIVATIVE; INDOMETACIN; INDOMETACIN DERIVATIVE; MOLECULAR SCAFFOLD; STEROL 14ALPHA DEMETHYLASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CELL CULTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DATA BASE; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG TARGETING; ENZYME INHIBITION; HIGH THROUGHPUT SCREENING; IN VITRO STUDY; LIGAND BINDING; NONHUMAN; STEROL SYNTHESIS; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA CRUZI;

AMIDES; ANIMALS; ANTIPARASITIC AGENTS; CYTOCHROME P-450 ENZYME SYSTEM; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; EXTRACELLULAR SPACE; INDOMETHACIN; INTRACELLULAR SPACE; LIGANDS; STEROLS; TRYPANOSOMA CRUZI;

EID: 65649090152     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801643b     Document Type: Article

References (27)

1. Centers for Disease Control and Prevention (CDC). Blood donor screening for Chagas diseases - United States, 2006-2007 Morb. Mortal. Wkly Rep. 2007, 56, 7, 141-143.
2. Ferreira, M. S.; Borges, A. S. Some aspects of protozoan infections in immunocompromised patientss - a review. Mem. Inst. Oswaldo Cruz 2002, 97, 443-457. (Pubitemid 135746784)
3. Wilkinson, S. R.; Taylor, M. C.; Horn, D.; Kelly, J. M.; Cheeseman, I. A mechanism for cross-resistance to nifurtimox and benznidazole in trypanosomes. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 5022-5027.
4. Croft, S. L.; Barrett, M. P.; Urbina, J. A. Chemotherapy of trypanosomiases and leishmaniasis. Trends Parasitol. 2005, 21, 508-512. (Pubitemid 41447021)
5. El-Sayed, N. M.; Myler, P. J.; Blandin, G.; Berriman, M.; Crabtree, J.; Aggarwal, G.; Caler, E.; Renauld, H.; Worthey, E. A.; Hertz-Fowler, C. Comparative genomics of trypanosomatid parasitic protozoa. Science 2005, 309, 404-409.
6. Cammerer, S. B.; Jimenez, C.; Jones, S.; Gros, L.; Lorente, S. O.; Rodrigues, C.; Rodrigues, J. C.; Caldera, A.; Ruiz Perez, L. M.; da Souza, W.; Kaiser, M.; Brun, R.; Urbina, J. A.; Gonzalez Pacanowska, D.; Gilbert, I. H. Quinuclidine derivatives as potential antiparasitics. Antimicrob. Agents Chemother. 2007, 51, 4049-4061.
7. Haughan, P. A.; Goad, L. J. Lipid Biochemistry of Trypanosomatids. In Biochemical Protozoology Coombs, G., North, M., Eds.; Taylor & Francis: London, 1991, pp 312-328.
8. Lepesheva, G. I.; Zaitseva, N. G.; Nes, W. D.; Zhou, W.; Arase, M.; Liu, J.; Hill, G. C.; Waterman, M. R. CYP51 from Trypanosoma cruzi: a phyla-specific residue in the B′ helix defines substrate preferences of sterol 14alpha-demethylase. J. Biol. Chem. 2006, 281, 3577-3585. (Pubitemid 43845975)
9. Lepesheva, G. I.; Ott, R. D.; Hargrove, T.; Kleshchenko, Y.; Schuster, I.; Nes, W. D.; Hill, G.; Villalta, F.; Waterman, M. W. Sterol 14α-Demethylase as a Potential Target for Antitrypanosomal Therapy: Enzyme Inhibition and Parasite Cell Growth. Chem. Biol. 2007, 14, 1283-1293. (Pubitemid 350102245)
10. Espinel-Ingroff, A. Mechanisms of resistance to antifungal agents: Yeasts and filamentous fungi. Rev. Iberoam Micol. 2008, 2, 101-106.
11. Kalgutkar, A. S.; Marnett, A. B.; Crews, B. C.; Remmel, R. P.; Marnett, L. J. Ester and amide derivatives of the nonsteroidal antiinflammatory drug, indomethacin, as selective cyclooxygenase-2 inhibitors. J. Med. Chem. 2000, 43, 2860-2870. (Pubitemid 30599644)
12. Kalgutkar, A. S.; Crews, B. C.; Rowlinson, S. W.; Marnett, A. B.; Kozak, K. R.; Remmel, R. P.; Marnett, L. J. Biochemically based design of cyclooxygenase-2 (COX-2) inhibitors: facile conversion of nonsteroidal antiinflammatory drugs to potent and highly selective COX-2 inhibitors. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 925-930. (Pubitemid 30070411)
13. Prusakiewicz, J. J.; Felts, A. S.; Mackenzie, B. S.; Marnett, L. J. Molecular basis of the time-dependent inhibition of cyclooxygenases by indomethacin. Biochemistry. 2004, 43, 15439-15445. (Pubitemid 39647468)
14. Ortiz de MontellanoP. R. CorreiaM. A. Inhibition of cytochrome P450 enxzymes. In Cytochrome P450: Structure, Mechanism, and Biochemistry; Ortiz de Montellano, P. R., Ed.; Plenum Publishing: New York, 1995; pp 305-364.
15. Lepesheva, G. I.; Waterman, M. R. Sterol 14alpha-demethylase cytochrome P450 (CYP51), a P450 in all biological kingdoms. Biochim. Biophys. Acta 2007, 1770, 467-477. (Pubitemid 46136743)
16. Poulos, T. L. Cytochrome P450 flexibility. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 13121-13122. (Pubitemid 37444704)
17. Lepesheva, G. I.; Seliskar, M.; Knutson, C. G.; Stourman, N. V.; Rozman, D.; Waterman, M. R. Conformational dynamics in the F/G segment of CYP51 from Mycobacterium tuberculosis monitored by FRET. Arch. Biochem. Biophys. 2007, 464, 221-227. (Pubitemid 47210936)
18. Atkins, W. M. Non-Michaelis-Menten kinetics in cytochrome P450-catalyzed reactions. Annu. Rev. Pharmacol. Toxicol. 2005, 45, 291-310. (Pubitemid 40261807)
19. Remmel, R. P.; Crews, B. C.; Kozak, K. R.; Kalgutkar, A. S.; Marnett, L. J. Studies on the metabolism of the novel, selective cyclooxygenase-2 inhibitor indomethacin phenethylamide in rat, mouse, and human liver microsomes: identification of active metabolites. Drug Metab. Dispos. 2004, 32, 113-122. (Pubitemid 38112543)
20. Faundez, M.; Pino, L.; Letelier, P.; Ortiz, C.; López, R.; Seguel, C.; Ferreira, J.; Pavani, M.; Morello, A.; Maya, J. D. Buthionine sulfoximine increases the toxicity of nifurtimox and benznidazole to Trypanosoma cruzi. Antimicrob. Agents Chemother. 2005, 49, 126-130. (Pubitemid 40065782)
21. de Castro, S. L.; de Meirelles, M. N. Effect of drugs on Trypanosoma cruzi and on its interaction with heart muscle cell in vitro. Mem. Inst. Oswaldo Cruz 1987, 82, 209-218.
22. Saraiva, J.; Vega, C.; Rolon, M.; da Silva, R. E.; Silva, M. L.; Donate, P. M.; Bastos, J. K.; Gomez-Barrio, A.; de Albuquerque, S. In vitro and in vivo activity of lignan lactones derivatives against Trypanosoma cruzi. Parasitol. Res. 2007, 100, 791-795.
23. Buckner, F. S.; Wilson, A. J.; White, T. C.; Van Voorhis, W. C. Induction of resistance to azole drugs in Trypanosoma cruzi. Antimicrob. Agents Chemother. 1998, 42, 3245-3250. (Pubitemid 28553748)
24. Omura, T.; Sato, R. The carbon monoxide-binding pigment of liver microsomes. II. Solubilization, purification, and properties. J. Biol. Chem. 1964, 239, 2379-2385.
25. Lepesheva, G. I.; Virus, C.; Waterman, M. R. Conservation in the CYP51 family. Role of the B′ helix/BC loop and helices F and G in enzymatic function. Biochemistry. 2003, 42, 9091-9101. (Pubitemid 36935417)
26. Lepesheva, G. I.; Nes, W. D.; Zhou, W.; Hill, G. C.; Waterman, M. R. CYP51 from Trypanosoma brucei is obtusifoliol-specific. Biochemistry 2004, 43, 10789-10799. (Pubitemid 39096721)
27. Nde, P. N.; Simmons, K. J.; Kleshchenko, Y.; Pratap, S.; Lima, M. F.; Villalta, F. Silencing of the laminin γ-1 gene blocks Trypanosoma cruzi infection. Infect. Immun. 2006, 74, 1643-1648. (Pubitemid 43346797)