Pyrethroid activity-based probes for profiling cytochrome P450 activities associated with insecticide interactions

Proceedings of the National Academy of Sciences of the United States of America

Volumn 110, Issue 49, 2013, Pages 19766-19771

  Ismail, Hanafy M ^a,b   O'Neill, Paul M ^c   Hong, David W ^c   Finn, Robert D ^d,e   Henderson, Colin J ^d   Wright, Aaron T ^f   Cravatt, Benjamin F ^g   Hemingway, Janet ^a   Paine, Mark J I ^a  

^a LIVERPOOL SCHOOL OF TROPICAL MEDICINE   (United Kingdom)

^b ALEXANDRIA UNIVERSITY   (Egypt)

^c UNIVERSITY OF LIVERPOOL   (United Kingdom)

^d UNIVERSITY OF DUNDEE   (United Kingdom)

^e NORTHUMBRIA UNIVERSITY   (United Kingdom)

^f PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

^g SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Drug metabolism; Insecticide resistance; Interactome; Malaria

Indexed keywords

CYTOCHROME P450; CYTOCHROME P450 REDUCTASE; PYRETHROID;

ARTICLE; CHEMICAL INTERACTION; CONTROLLED STUDY; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME ANALYSIS; LIVER MICROSOME; MOLECULAR PROBE; MOUSE; NONHUMAN; PRIORITY JOURNAL; RAT;

ARTHROPODA; RATTUS; RODENTIA;

EID: 84889640693     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1320185110     Document Type: Article

References (35)

1. Khambay BPS, Jewess PJ (2004) Pyrethroids. Comprehensive Molecular Insect Science, eds Gilbert LI, Iatrou K, Gill SS (Pergamon Press, Oxford), Vol 6, pp 1-29.
2. WHO (2010) World Malaria Report (World Health Organization, Geneva, Switzerland).
3. Ranson H, et al. (2011) Pyrethroid resistance in African anopheline mosquitoes: What are the implications for malaria control? Trends Parasitol 27(2):91-98.
4. Casida JE, Gammon DW, Glickman AH, Lawrence LJ (1983) Mechanisms of selective action of pyrethroid insecticides. Annu Rev Pharmacol Toxicol 23:413- 438.
5. David JP, Ismail HM, Chandor-Proust A, Paine MJ (2013) Role of cytochrome P450s in insecticide resistance: Impact on the control of mosquito-borne diseases and use of insecticides on Earth. Philos Trans R Soc Lond B Biol Sci 368(1612):20120429.
6. Li X, Schuler MA, Berenbaum MR (2007) Molecular mechanisms of metabolic resistance to synthetic and natural xenobiotics. Annu Rev Entomol 52:231-253.
7. Godin SJ, et al. (2007) Identification of rat and human cytochrome p450 isoforms and a rat serum esterase that metabolize the pyrethroid insecticides deltamethrin and esfenvalerate. Drug Metab Dispos 35(9):1664-1671.
8. Nelson DR (2009) The cytochrome p450 homepage. Hum Genomics 4(1):59- 65.
9. Wright AT, Cravatt BF (2007) Chemical proteomic probes for profiling cytochrome p450 activities and drug interactions in vivo. Chem Biol 14(9):1043- 1051.
10. Wright AT, Song JD, Cravatt BF (2009) A suite of activity-based probes for human cytochrome P450 enzymes. J Am Chem Soc 131(30):10692-10700.
11. Stevenson BJ, et al. (2011) Cytochrome P450 6M2 from the malaria vector Anopheles gambiae metabolizes pyrethroids: Sequential metabolism of deltamethrin revealed. Insect Biochem Mol Biol 41(7):492-502.
12. Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF (2009) In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos 37(1):221-228.
13. Djouaka RF, et al. (2008) Expression of the cytochrome P450s, CYP6P3 and CYP6M2 are significantly elevated in multiple pyrethroid resistant populations of Anopheles gambiae s.s. from Southern Benin and Nigeria. BMC Genomics 9:538.
14. Müller P, et al. (2008) Pyrethroid tolerance is associated with elevated expression of antioxidants and agricultural practice in Anopheles arabiensis sampled from an area of cotton fields in Northern Cameroon. Mol Ecol 17(4):1145-1155.
15. McLaughlin LA, et al. (2008) Characterization of inhibitors and substrates of Anopheles gambiae CYP6Z2. Insect Mol Biol 17(2):125-135.
16. Chiu TL, Wen Z, Rupasinghe SG, Schuler MA (2008) Comparative molecular modeling of Anopheles gambiae CYP6Z1, a mosquito P450 capable of metabolizing DDT. Proc Natl Acad Sci USA 105(26):8855-8860.
17. Chandor-Proust A, et al. (2013) The central role of mosquito cytochrome P450 CYP6Zs in insecticide detoxification revealed by functional expression and structural modelling. Biochem J 455(1):75-85.
18. Henderson CJ, et al. (2003) Inactivation of the hepatic cytochrome P450 system by conditional deletion of hepatic cytochrome P450 reductase. J Biol Chem 278(15): 13480-13486.
19. McLaughlin LA, Ronseaux S, Finn RD, Henderson CJ, Roland Wolf C (2010) Deletion of microsomal cytochrome b5 profoundly affects hepatic and extrahepatic drug metabolism. Mol Pharmacol 78(2):269-278.
20. 5. J Biol Chem 283(46):31385-31393.
21. Paine MJI, Scrutton NS, Munro AW, Roberts GCK, Wolf CR (2004) Electron Transfer Partners of Cytochrome P450. Cytochromes P450: Structure, Mechanism and Biochemistry, ed Ortiz de Montellano PR (Kluwer Academic/Plenum Publishers, New York), 3rd Ed, pp 115-148.
22. Schenkman JB, Jansson I (1999) Interactions between cytochrome P450 and cytochrome b5. Drug Metab Rev 31(2):351-364.
23. Kotrbová V, et al. (2011) Cytochrome b(5) shifts oxidation of the anticancer drug ellipticine by cytochromes P450 1A1 and 1A2 from its detoxication to activation, thereby modulating its pharmacological efficacy. Biochem Pharmacol 82(6):669-680.
24. Ishihama Y, et al. (2005) Exponentially modified protein abundance index (emPAI) for estimation of absolute protein amount in proteomics by the number of sequenced peptides per protein. Mol Cell Proteomics 4(9):1265-1272.
25. Stresser DM, Turner SD, Blanchard AP, Miller VP, Crespi CL (2002) Cytochrome P450 fluorometric substrates: Identification of isoform-selective probes for rat CYP2D2 and human CYP3A4. Drug Metab Dispos 30(7):845-852.
26. Wiedner SD, et al. (2012) Multiplexed activity-based protein profiling of the human pathogen Aspergillus fumigatus reveals large functional changes upon exposure to human serum. J Biol Chem 287(40):33447-33459.
27. Cravatt BF, Wright AT, Kozarich JW (2008) Activity-based protein profiling: From enzyme chemistry to proteomic chemistry. Annu Rev Biochem 77:383-414.
28. Ishii Y, Takeda S, Yamada H (2010) Modulation of UDP- glucuronosyltransferase activity by protein-protein association. Drug Metab Rev 42(1):145-158.
29. Jensen NB, et al. (2011) Convergent evolution in biosynthesis of cyanogenic defence compounds in plants and insects. Nat Commun 2:273, 10.1038/ncomms1271.
30. Radominska-Pandya A, Bratton SM, Redinbo MR, Miley MJ (2010) The crystal structure of human UDP-glucuronosyltransferase 2B7 C-terminal end is the first mammalian UGT target to be revealed: The significance for human UGTs from both the 1A and 2B families. Drug Metab Rev 42(1):133-144.
31. Noort D, van Zuylen A, Fidder A, van Ommen B, Hulst AG (2008) Protein adduct formation by glucuronide metabolites of permethrin. Chem Res Toxicol 21(7): 1396- 1406.
32. WHO (2012) Global Plan for Insecticide Resistance Management (GPIRM) (World Health Organization, Geneva, Switzerland).
33. Finn RD, et al. (2011) Cytochrome b5 null mouse: A new model for studying inherited skin disorders and the role of unsaturated fatty acids in normal homeostasis. Transgenic Res 20(3):491-502.
34. Speers AE, Cravatt BF (2004) Profiling enzyme activities in vivo using click chemistry methods. Chem Biol 11(4):535-546.
35. Speers AE, Cravatt BF (2009) Activity-Based Protein Profiling (ABPP) and Click Chemistry (CC)-ABPP by MudPIT Mass Spectrometry. Curr Protoc Chem Biol 1:29-41.