Effect of human flavin-containing monooxygenase 3 polymorphism on the metabolism of aurora kinase inhibitors

International Journal of Molecular Sciences

Volumn 14, Issue 2, 2013, Pages 2707-2716

  Catucci, Gianluca ^a   Occhipinti, Andrea ^a   Maffei, Massimo ^a   Gilardi, Gianfranco ^a   Sadeghi, Sheila J ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

Drug metabolism; Enzyme kinetics; FMO3; LC MS; PHA 739358; Phase I; Polymorphism; VX 680

Indexed keywords

AURORA KINASE INHIBITOR; DANUSERTIB; DIMETHYLANILINE MONOOXYGENASE; DRUG METABOLITE; HUMAN FLAVIN CONTAINING MONOOXYGENASE 3; METHIONINE; TOZASERTIB; UNCLASSIFIED DRUG; VALINE; VERAPAMIL;

ARTICLE; CATALYSIS; CODON; CONTROLLED STUDY; DRUG EFFECT; DRUG OXIDATION; DRUG PURIFICATION; DRUG STRUCTURE; GENE; GENE ACTIVITY; GENETIC VARIABILITY; HUMAN FLAVIN CONTAINING MONOOXYGENASE 3 GENE; IN VITRO STUDY; NONHUMAN; PROTEIN EXPRESSION; SINGLE NUCLEOTIDE POLYMORPHISM;

EID: 84875093862     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms14022707     Document Type: Article

References (24)

1. Krueger, S.K.; Williams, D.E. Mammalian FMO: Structure/function, genetic polymorphism and role in drug metabolism. Pharmacol. Ther. 2005, 106, 357-387.
2. Overby, L.H.; Carver, G.C.; Philpot, R.M. Quantitation and kinetic properties of hepatic microsomal and recombinant flavin-containing monooxygenase 3 and 5 from humans. Chem. Biol. Interact. 1997, 106, 29-45.
3. Yeung, C.K.; Lang, D.H.; Thummel, K.E.; Rettie, A.E. Immunoquantitation of FMO1 in human liver, kidney and intestine. Drug Metab. Dispos. 2000, 28, 1107-1111.
4. Koukouritaki, S.B.; Poch, M.T.; Henderson, M.C.; Siddens, L.K.; Krueger, S.K.; VanDyke, J.E.; Williams, D.E.; Pajewski, N.M.; Wang, T.; Hines, R.N. Identification and functional analysis of common human flavin-containing monooxygenase 3 genetic variants. J. Pharm. Exp. Therap. 2007, 320, 266-273.
5. Koukouritaki, S.B.; Hines, R.N. Flavin-containing monooxygenase genetic polymorphism: Impact on chemical metabolism and drug development. Pharmacogenomics 2005, 6, 807-822.
6. Cashman, J.R.; Zhang, J.; Leushner, J.; Braun, A. Population distribution of human flavin-containing monooxygenase form 3: Gene polymorphisms. Drug Metab. Dispos. 2001, 29, 1629-1637.
7. Cashman, J.R.; Akerman, B.R.; Forrest, S.M.; Treacy, E.P. Population-specific polymorphisms of the human FMO3 gene: Significance for detoxication. Drug Metab. Dispos. 2000, 2, 169-173.
8. Li, Y.; Zhang, Z.F.; Chen, J.; Huang, D.; Ding, Y.; Tan, M.H.; Qian, C.N.; Resau, J.H.; Kim, H.; Teh, B.T. VX-680/MK-0457, a potent and selective Aurora kinase inhibitor, targets both tumor and endothelial cells in clear cell renal cell carcinoma. Am. J. Transl. Res. 2000, 3, 296-308.
9. Gautschi, O.; Heighway, J.; Mack, P.C.; Purnell, P.R.; Lara, P.N., Jr.; Gandara, D.R. Aurora kinases as anticancer drug targets. Clin. Cancer Res. 2008, 14, 1639-1648.
10. Vader, G.; Lens, S.M. The Aurora kinase family in cell division and cancer. Biochim. Biophys. Acta 2008, 1786, 60-72.
11. + leukaemia therapy. Best Pract. Res. Clin. Haematol. 2009, 3, 445-454.
12. Harrington, E.A.; Bebbington, D.; Moore, J.; Rasmussen, R.K.; Ajose-Adeogun, A.O.; Nakayama, T.; Graham, J.A.; Demur, C.; Hercend, T.; Diu-Hercend, A.; et al. VX-680 A potent and selective small-molecule inhibitor of aurora kinases suppresses tumor growth in vivo. Nat. Med. 2004, 10, 262-267.
13. Kitzen, J.J.; de Jonge, M.J.; Verweij, J. Aurora kinase inhibitors. Crit. Rev. Oncol. Hemat. 2010, 2, 99-110.
14. Fancelli, D.; Moll, J.; Varasi, M.; Bravo, R.; Artico, R.; Berta, D.; Bindi, S.; Cameron, A.; Candiani, I.; Cappella, P.; et al. 1,4,5,6-Tetrahydropyrrolo[3,4-c]pyrazoles: Identification of a potent Aurora kinase inhibitor with a favorable antitumor kinase inhibition profile. J. Med. Chem. 2006, 49, 7247-7251.
15. Carpinelli, P.; Ceruti, R.; Giorgini, M.L.; Cappella, P.; Gianellini, L.; Croci, V.; Degrassi, A.; Texido, G.; Rocchetti, M.; Vianello, P.; et al. PHA-739358, a potent inhibitor of Aurora kinases with a selective target inhibition profile relevant to cancer. Mol. Cancer Ther. 2007, 12, 3158-3168.
16. Ballard, J.E.; Prueksaritanont, T.; Tang, C. Hepatic metabolism of MK-0457, a potent aurora kinase inhibitor: Interspecies comparison and role of human cytochrome P450 and flavin-containing monooxygenase. Drug Metab. Dispos. 2007, 9, 1447-1451.
17. Roses, A.D. Pharmacogenetics and drug development: The path to safer and more effective drugs. Nat. Rev. Genet. 2004, 5, 645-656.
18. Panicco, P.; Dodhia, V.R.; Fantuzzi, A.; Gilardi, G. First enzyme-based amperometric platform to determine the polymorphic response in drug metabolism by cytochromes P450. Anal. Chem. 2011, 83, 2179-2186.
19. Sadeghi, S.J.; Meirinhos, R.; Catucci, G.; Dodhia, V.R.; di Nardo, G.; Gilardi, G. Direct electrochemistry of drug metabolizing hFMO3: Electrochemical turnover of benzydamine and tamoxifen. J. Am. Chem. Soc. 2010, 132, 458-459.
20. Castrignanò, S.; Sadeghi, S.J.; Gilardi, G. Electro-catalysis by immobilised human flavin-containing monooxygenase isoform 3 (hFMO3). Anal. Bioanal. Chem. 2010, 398, 1403-1409.
21. Catucci, G.; Gilardi, G.; Jeuken, L.; Sadeghi, S.J. In vitro drug metabolism by C-terminally truncated human flavin-containing monooxygenase 3. Biochem. Pharmacol. 2012, 83, 551-558.
22. Castrignanò, S.; Sadeghi, S.J.; Gilardi, G. Entrapment of human flavin-containing monooxygenase 3 in the presence of gold nanoparticles: TEM, FTIR and electrocatalysis. Biochim. Biophys. Acta 2012, 1820, 2072-2078.
23. Yeung, C.K.; Adman, E.T.; Rettie, A.E. Functional characterization of genetic variants of human FMO3 associated with TMAU. Arch. Biochem. Biophys. 2007, 464, 251-259.
24. Steeghs, N.; Mathijssen, R.H.; Wessels, J.A.; de Graan, A.J.; van der Straaten, T.; Mariani, M.; Laffranchi, B.; Comis, S.; de Jonge, M.J.A.; Gelderblom, H.; et al. Influence of pharmacogenetic variability on the pharmacokinetics and toxicity of the aurora kinase inhibitor danusertib. Invest. New Drugs 2010, 5, 953-962.