Development of a new generation of 4-aminoquinoline antimalarial compounds using predictive pharmacokinetic and toxicology models

Journal of Medicinal Chemistry

Volumn 53, Issue 9, 2010, Pages 3685-3695

  Ray, Sunetra ^a   Madrid, Peter B ^a   Catz, Paul ^a   Levalley, Susanna E ^a   Furniss, Michael J ^a   Rausch, Linda L ^a   Guy, R Kiplin ^b   Derisi, Joseph L ^c   Iyer, Lalitha V ^a   Green, Carol E ^a   Mirsalis, Jon C ^a  

^a SRI INTERNATIONAL   (United States)

^b ST JUDE CHILDREN S RESEARCH HOSPITAL   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [[ 3 ( 7 CHLOROQUIN 4 YLAMINO)PROPYLAMINO]METHYL] 4 METHOXYPHENOL; 2 [[ 3 ( 7 CHLOROQUIN 4 YLAMINO)PROPYLAMINO]METHYL] 6 METHOXYPHENOL; 4 AMINOQUINOLINE; AMFEBUTAMONE; ANTIMALARIAL AGENT; ANTIRETROVIRUS AGENT; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; BUFURALOL; CHLOROQUINE; DICLOFENAC; INDINAVIR; MEPHENYTOIN; METOPROLOL; MIDAZOLAM; N BENZO[ 1,3]DIOXOL 4 YL METHYL N'' ( 7 CHLOROQUIN 4 YL)PROPANE 1,3 DIAMINE; QUINIDINE; QUININE; TESTOSTERONE; THIORIDAZINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANTIMALARIAL ACTIVITY; ANTIMALARIAL DRUG RESISTANCE; AREA UNDER THE CURVE; ARTICLE; CYTOTOXICITY; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG EFFICACY; DRUG EXCRETION; DRUG HALF LIFE; DRUG METABOLISM; DRUG POTENCY; FEMALE; HUMAN; IC 50; IN VITRO STUDY; IN VIVO STUDY; LIVER TOXICITY; MALE; MAXIMUM PLASMA CONCENTRATION; MOUSE; NONHUMAN; PHARMACOLOGICAL PARAMETERS; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION;

AMINOQUINOLINES; ANIMALS; ANTIMALARIALS; DRUG EVALUATION, PRECLINICAL; HALF-LIFE; MICE; PHARMACOKINETICS; PLASMODIUM FALCIPARUM; SMALL MOLECULE LIBRARIES; TOXICOLOGY;

EID: 77952067548     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100057h     Document Type: Article

References (25)

1. Kassel, D. B. Applications of high-throughput ADME in drug discovery Curr. Opin. Chem. Biol. 2004, 8, 339-345
2. Shearer, T. W.; Smith, K. S.; Diaz, D.; Asher, C.; Ramirez, J. The role of in vitro ADME assays in antimalarial drug discovery and development Comb. Chem. High Throughput Screening 2005, 8, 89-98
3. World Malaria Report; World Health Organization: Geneva, 2008.
4. Madrid, P. B.; Liou, A. P.; DeRisi, J. L.; Guy, R. K. Incorporation of an intramolecular hydrogen-bonding motif in the side chain of 4-aminoquinolines enhances activity against drug-resistant P. falciparum J. Med. Chem. 2006, 49, 4535-4543
5. Madrid, P. B.; Sherrill, J.; Liou, A. P.; Weisman, J. L.; Derisi, J. L.; Guy, R. K. Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities Bioorg. Med. Chem. Lett. 2005, 15, 1015-1018
6. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery Rev. 2001, 46, 3-26 (Pubitemid 33653411)
7. Schupbach, M. E. Mutagenicity evaluation of the two antimalarial agents chloroquine and mefloquine, using a bacterial fluctuation test Mutat. Res. 1979, 68, 41-49
8. Obaseiki-Ebor, E. E.; Obasi, E. E. Aspects of chloroquine mutagenicity Mutat. Res. 1986, 175, 51-59
9. Fluckiger-Isler, S.; Baumeister, M.; Braun, K.; Gervais, V.; Hasler-Nguyen, N.; Reimann, R.; Van Gompel, J.; Wunderlich, H. G.; Engelhardt, G. Assessment of the performance of the Ames II assay: a collaborative study with 19 coded compounds Mutat. Res. 2004, 558, 181-197
10. McCann, J.; Choi, E.; Yamasaki, E.; Ames, B. N. Detection of carcinogens as mutagens in the Salmonella/microsome test: assay of 300 chemicals Proc. Natl. Acad. Sci. U.S.A. 1975, 72, 5135-5139
11. Ansari, A. M.; Craig, J. C. Metabolites of chloroquine: some observations on desethylchloroquine and N -acetyldesethylchloroquine J. Pharm. Sci. 1994, 83, 1040-1042
12. Zhou, S. F. Drugs behave as substrates, inhibitors and inducers of human cytochrome P450 3A4 Curr. Drug Metab. 2008, 9, 310-322
13. Hutzler, J. M.; Walker, G. S.; Wienkers, L. C. Inhibition of cytochrome P450 2D6: Structure-activity studies using a series of quinidine and quinine analogues Chem. Res. Toxicol. 2003, 16, 450-459
14. AdedoyA.; Frye, R. F.; Mauro, K.; Branch, R. A. Chloroquine modulation of specific metabolizing enzymes activities: investigation with selective five drug cocktail Br. J. Clin. Pharmacol. 1998, 46, 215-219
15. Beverage, J. N.; Sissung, T. M.; Sion, A. M.; Danesi, R.; Figg, W. D. CYP2D6 polymorphisms and the impact on tamoxifen therapy J. Pharm. Sci. 2007, 96, 2224-2231
16. Lancaster, D. L.; Adio, R. A.; Tai, K. K.; Simooya, O. O.; Broadhead, G. D.; Tucker, G. T.; Lennard, M. S. Inhibition of metoprolol metabolism by chloroquine and other antimalarial drugs J. Pharm. Pharmacol. 1990, 42, 267-271
17. Savarino, A.; Lucia, M. B.; Rastrelli, E.; Rutella, S.; Golotta, C.; Morra, E.; Tamburrini, E.; Perno, C. F.; Boelaert, J. R.; Sperber, K.; Cauda, R. Anti-HIV effects of chloroquine: inhibition of viral particle glycosylation and synergism with protease inhibitors J. Acquired Immune Defic. Syndr. 2004, 35, 223-232
18. Traficante, L. J.; Hine, B.; Gershon, S.; Sakalis, G. Chloroquine potentiation of thioridazine effects in rats and drug-resistant schizophrenic patients: a preliminary report Commun. Psychopharmacol. 1977, 1, 407-419
19. Jamshidzadeh, A.; Niknahad, H.; Kashafi, H. Cytotoxicity of chloroquine in isolated rat hepatocytes J. Appl. Toxicol. 2007, 27, 322-326
20. Rossmann-Ringdahl, I.; Olsson, R. Porphyria cutanea tarda: effects and risk factors for hepatotoxicity from high-dose chloroquine treatment Acta Derm.-Venereol. 2007, 87, 401-405
21. Du, X. M.; Irino, N.; Furusho, N.; Hayashi, J.; Shoyama, Y. Pharmacologically active compounds in the Anoectochilus and Goodyera species Nat. Med. (Tokyo) 2008, 62, 132-148
22. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 1983, 65, 55-63
23. Medicines for Malaria Venture (MMV) Product Profiles for Antimalarial Drugs. http://www.mmv.org/IMG/pdf/PRODUCT-PROFILE-with-logo.pdf.
24. Madrid, P. B.; Wilson, N. T.; DeRisi, J. L.; Guy, R. K. Parallel synthesis and antimalarial screening of a 4-aminoquinoline library J. Comb. Chem. 2004, 6, 437-442
25. Green, C. E.; LeValley, S. E.; Tyson, C. A. Comparison of amphetamine metabolism using isolated hepatocytes from five species including human J. Pharmacol. Exp. Ther. 1986, 237, 931-936