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In vitro metabolism of 2,2',4,4'-tetrabromodiphenyl ether Moffatt, Sarah 2011

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  IN VITRO METABOLISM OF 2,2',4,4'-TETRABOMODIPHENYL ETHER  by   Sarah Moffatt  B.Sc., Memorial University of Newfoundland, 2008 B.Sc., Dalhousie University of Newfoundland, 2006   A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF   MASTER OF SCIENCE  in  THE FACULTY OF GRADUATE STUDIES   (Pharmaceutical Science)  THE UNIVERSITY OF BRITISH COLUMBIA  (Vancouver)  December 2011  © Sarah Moffatt, 2011  ii Abstract  Polybrominated diphenyl ethers (PBDEs) are halogenated aromatic hydrocarbons that have been used as additive flame-retardants in a variety of consumer products since 1965. The widespread use of PBDEs coupled with their high lipophilicity and chemical stability resulted in the ubiquitous distribution of PBDEs in the environment. 2,2',4,4-Tetrabromodiphenyl ether (BDE-47) is among the most prevalent PBDE detected in human, wildlife, and abiotic samples. BDE-47 has been detected in air, sediment, fish, marine mammals, and in human blood, adipose tissue, and breast milk. Laboratory studies have shown that PBDEs can be metabolized by hepatic cytochrome P450 (CYP) enzymes to hydroxylated PBDEs (OH-PBDEs). OH-PBDEs are of toxicological interest as OH-PBDEs show greater affinity for the thyroid hormone receptor than the natural ligand or PBDEs. OH-PBDEs have been detected in blood and feces of rodents treated with BDE-47 and various OH-PBDEs have been found in human plasma. The most common method for the detection and quantification of PBDEs and OH-PBDEs in environmental samples has been gas chromatography-mass spectrometry (GC/MS). GC-based methods are sensitive, but require derivatization of OH-PBDEs. Ultra performance liquid chromatography coupled with mass spectrometry (UPLC/MS) provides an alternative analytical technique that does not require derivatization. Although several UPLC/MS methods have been used to detect and quantify OH-PBDEs, a fully validated UPLC/MS method does not exist. The UPLC/MS method used in the present study was validated to detect and quantify two OH-tri- BDEs and five OH-tetra-BDEs in rat hepatic microsomes. This method was then applied to investigate the biotransformation of BDE-47 using hepatic microsomes prepared from rats that had been pretreated with known CYP enzyme inducers and using a panel of rat recombinant CYP enzymes. Five OH-tetra-BDE metabolites were identified (4-OH-BDE-42, 3-OH-BDE-47, 5-OH-BDE-47, 6-OH-BDE-47, and 4'-OH- BDE-49). The formation of OH-tri-BDEs was not detected. The kinetic parameters of all identified metabolites, with the exception of 6-OH-BDE-47, were determined. Using the rat recombinant enzyme panel, CYP1A1, CYP2A2, CYP2B1, CYP2C6, and CYP3A1 were identified as being involved in the biotransformation of BDE-47.   iii Preface  The Animal Care Committee at the University of British Columbia examined and approved the use of animals for the experimental project described in this thesis. The project, titled “Biotransformation of Organochlorine Compounds in Biota.” was completed under the Animal Care Certificate A06-0146 issued on May 1, 2006 and renewed on May 1, 2010 as Certificate A10-0225.       iv Table of Contents  Abstract .......................................................................................................................................... ii! Preface ........................................................................................................................................... iii! Table of Contents ......................................................................................................................... iv! List of Tables ............................................................................................................................... vii! List of Figures ............................................................................................................................... ix! List of Abbreviations .................................................................................................................... x! Acknowledgements ..................................................................................................................... xii! Dedication ................................................................................................................................... xiii! 1 : Introduction ............................................................................................................................. 1! 1.1! Polybrominated Diphenyl Ethers .................................................................................................... 6! 1.1.1! Commercial Mixtures .............................................................................................................. 7! 1.1.2! Commercial Use ....................................................................................................................... 9! 1.2! Behaviour in the Environment ...................................................................................................... 11! 1.2.1! Physicochemical Properties of PBDE .................................................................................... 11! 1.2.2! Global Distribution ................................................................................................................ 13! 1.2.3! Exposure Sources ................................................................................................................... 14! 1.2.4! Biomagnification within a Food Web .................................................................................... 15! 1.2.5! PBDE Concentration Trends .................................................................................................. 16! 1.2.6! PBDE Concentrations in Humans and Wildlife ..................................................................... 17! 1.3! Metabolism .................................................................................................................................... 19! 1.3.1! Cytochrome P450 Enzymes ................................................................................................... 19! 1.3.2! Major Xenobiotic Metabolizing Cytochrome P450 Enzymes ............................................... 24! 1.3.2.1! CYP1 Family .................................................................................................................. 24! 1.3.2.2! CYP2 Family .................................................................................................................. 25! 1.3.2.3! CYP3 Family .................................................................................................................. 28! 1.3.3! PBDE Hydroxylation ............................................................................................................. 29! 1.3.4! PBDE Debromination ............................................................................................................ 31! 1.4! Hydroxylated PBDEs .................................................................................................................... 33!  v 1.4.1! Origin and Detection of OH-PBDEs ...................................................................................... 33! 1.4.2! Toxicity of OH-PBDEs .......................................................................................................... 34! 1.5! Rationale ........................................................................................................................................ 37! 1.5.1! BDE-47 .................................................................................................................................. 37! 1.5.2! Detection and Quantification of OH-PBDEs ......................................................................... 39! 1.5.3! Hypotheses ............................................................................................................................. 41! 1.5.4! Specific Aims ......................................................................................................................... 41! 2 : Materials and Methods ......................................................................................................... 42! 2.1! Chemicals and Reagents ................................................................................................................ 42! 2.2! Authentic Standards and Stock Solutions ..................................................................................... 44! 2.3! Animal Treatment and Hepatic Microsome Preparation ............................................................... 44! 2.4! Calibration Standards and Quality Control Samples ..................................................................... 46! 2.5! Experimental Samples ................................................................................................................... 46! 2.6! Extraction Procedure ..................................................................................................................... 47! 2.7! Ultra Performance Liquid Chromatography-Mass Spectrometry Conditions ............................... 47! 2.8! Method Validation ......................................................................................................................... 48! 2.9! Assay Application ......................................................................................................................... 50! 2.9.1! Microsomal Preparation Comparison .................................................................................... 50! 2.9.2! Recombinant Enzymes ........................................................................................................... 51! 2.9.3! Data Analysis ......................................................................................................................... 51! 3 : Results ..................................................................................................................................... 53! 3.1! Rat Hepatic Microsome Preparations ............................................................................................ 53! 3.2! Optimization of UPLC/MS Parameters ......................................................................................... 53! 3.3! Calibration Standards and Stock Solutions ................................................................................... 54! 3.4! Extraction and Recovery of OH-PBDEs ....................................................................................... 55! 3.5! Method Validation ......................................................................................................................... 56! 3.6! Hepatic Microsomal Assay for the Biotransformation of BDE-47 ............................................... 62! 3.6.1! Optimization of Biotransformation Assay Parameters .......................................................... 63! 3.6.2! Kinetic Analysis of BDE-47 and Metabolite Formation ....................................................... 68! 3.6.3! Effects of CYP Inducers on BDE-47 Biotransformation ....................................................... 70! 3.6.4! Biotransformation Activities of Rat Recombinant Enzymes ................................................. 72! 4 : Discussion ............................................................................................................................... 76! 4.1! Optimization and Validation of the Analytical Method ................................................................ 76!  vi 4.1.1! Authentic Standards and Stock Solutions .............................................................................. 76! 4.1.2! Validation of UPLC/MS Method ........................................................................................... 77! 4.2! Hepatic Microsomal Metabolite Formation .................................................................................. 79! 4.2.1! Oxidative Metabolites of BDE-47 ......................................................................................... 79! 4.2.2! Toxicity of Oxidative BDE-47 Metabolites ........................................................................... 81! 4.2.3! PBDE Hydroxylation ............................................................................................................. 83! 4.2.4! Debromination ....................................................................................................................... 84! 4.3! Identification of CYP Enzymes Involved in the Biotransformation of BDE-47 .......................... 87! 4.4! Rates of Formation and Kinetic Parameters .................................................................................. 90! 4.5! Origin of OH-PBDEs .................................................................................................................... 92! 5 : Conclusions ............................................................................................................................ 94! 5.1! Future Experiments ....................................................................................................................... 95! 5.1.1! Human Hepatic Microsomes .................................................................................................. 95! 5.1.2! Biomagnification .................................................................................................................... 95! 5.1.3! MeO-PBDE Metabolism ........................................................................................................ 95! References .................................................................................................................................... 96! Appendices ................................................................................................................................. 111! Appendix A PBDE Background Information ....................................................................................... 111! Appendix A-1! Historical Timeline ............................................................................................... 111! Appendix A-2! Substitution Pattern of Individual PBDE Congeners ............................................ 113! Appendix A-3! PBDE Congeners Found in Commercial Mixtures and Chemical Abstracts Service (CAS) Numbers for PBDEs ............................................................................................................. 114! Appendix A-4! CYP Enzyme Content of Pretreated Hepatic Microsomes Prepared from Rats Pretreated with Corn Oil, DEX, MC, and PB. ................................................................................. 116! Appendix B Raw Data .......................................................................................................................... 117! Appendix B-1! Validation .............................................................................................................. 117! Appendix B-2! Kinetic Data Analysis ........................................................................................... 118! Appendix B-3! CYP Inducers ........................................................................................................ 119! Appendix B-4! Rat Recombinant Enzyme Data ............................................................................ 120! References .................................................................................................................................. 121!   vii List of Tables  Table 1-1: Substitution pattern and structure of select PBDE congeners. ...................................... 7! Table 1-2: Congener profile of the three commercial PBDE mixtures .......................................... 8! Table 1-3: Trade names of commercial PBDE mixtures ................................................................ 8! Table 1-4: Application of penta-, octa- and deca-PBDE mixtures ................................................. 9! Table 1-5: Physicochemical properties of selected PBDE congeners .......................................... 11! Table 1-6: Total CYP content of select human and rat organs ..................................................... 19! Table 1-7: Major drug metabolizing CYP families in humans and rats ....................................... 24! Table 1-8: Specific content and percentage of total CYP subfamilies in human and rat hepatic microsomes ................................................................................................................................... 24! Table 1-9:  In vivo and in vitro identification of BDE-47 metabolites ......................................... 38! Table 1-10: UPLC/MS techniques used to quantify OH-PBDE(s) .............................................. 40! Table 2-1: 1.25 µM OH-PBDE stock solution ............................................................................. 44! Table 2-2: Mobile phase gradient ................................................................................................. 48! Table 2-3: Optimization of reaction conditions ............................................................................ 50! Table 3-1: Protein concentration, CYP concentration, and specific content ................................ 53! Table 3-2: Limit of quantification and linearity of individual OH-PBDE standards ................... 58! Table 3-3: Inter-day accuracy and precision ................................................................................. 59! Table 3-4: Intra-day accuracy and precision ................................................................................. 60! Table 3-5: Recovery values of individual OH-PBDE standards .................................................. 61! Table 3-6: Apparent K', Vmax, and n values using the Hill equation ............................................ 68! Table 4-1: Previous publications that have identified 4-OH-BDE-42, 3-OH-BDE-47, 5-OH- BDE-47, 6-OH-BDE-47, or 4'-OH-BDE-49 in abiotic, animal, or human matrices. ................... 79! Table 4-2: Toxic effect(s) of OH-PBDE metabolites identified in this study. ............................. 82! Table A-1: Historical timeline for flame-retardant use. .............................................................. 111! Table A-2: Systematic numbering of PBDE congeners ............................................................. 113! Table A-3: Congeners detected in the commercial penta-PBDE mixture, Bromkal 70-5 DE ... 114! Table A-4: Congeners detected in the commercial penta-PBDE mixture, DE-71 ..................... 114! Table A-5: Congeners detected in the commercial octa-PBDE mixture, Bromkal 79-8 ............ 114! Table A-6: Congeners detected in the commercial octa-PBDE mixture, DE-79 ....................... 114!  viii Table A-7: Chemical abstracts service numbers for PBDEs ...................................................... 115! Table A-8: CYP content of pretreated hepatic microsomes prepared from rats pretreated with corn oil, DEX, MC, and PB.. ...................................................................................................... 116!   ix List of Figures  Figure 1-1: Loss of life due to fire in Canada and the United States .............................................. 1! Figure 1-2: The combustion triangle ............................................................................................... 2! Figure 1-3: Structures of brominated flame-retardants ................................................................... 5! Figure 1-4: General structure of PBDEs and PCBs ........................................................................ 6! Figure 1-5: Possible rotation of diphenyls and biphenyls. ............................................................ 12! Figure 1-6: Protoporphyrin IX prosthetic group of a CYP enzyme .............................................. 20! Figure 1-7: The CYP enzyme catalytic cycle ............................................................................... 22! Figure 1-8: Hydroxylation of BDE-47 via a NIH shift mechanism.. ............................................ 30! Figure 1-9: Thyroxine conversion to triiodothyronine by deiodinase enzymes and debromination of BDE-99 to BDE-47 .................................................................................................................. 32! Figure 3-1: Representative chromatograms .................................................................................. 57! Figure 3-2: Metabolite peaks obtained in preliminary experiments ............................................. 63! Figure 3-3: Effect of hepatic microsomal protein concentration on the formation of OH-PBDEs. ....................................................................................................................................................... 65! Figure 3-4: The effect of time on the formation of OH-PBDEs. .................................................. 66! Figure 3-5: The effect of substrate concentration on product formation. ..................................... 67! Figure 3-6: Rates of formation ...................................................................................................... 69! Figure 3-7: Comparison of rates of product formation using hepatic microsomes from rats pretreated with corn oil, DEX, MC or PB. ................................................................................... 71! Figure 3-8: Rat recombinant CYP enzymes responsible for the formation of OH-PBDE metabolites of BDE-47. ................................................................................................................ 73! Figure 3-9: Formation of OH-PBDE metabolites of BDE-47 by rat recombinant CYP enzymes 75! Figure 4-1: Possible OH-tetra-BDE metabolites of BDE-47. ....................................................... 83! Figure 4-2: Possible tri-BDE and OH-tri-BDE metabolites of BDE-47. ...................................... 85! Figure 5-1: Summary of BDE-47 metabolites formed by rat hepatic microsomes and the recombinant CYP enzymes identified as being involved in their formation. ............................... 94! Figure B-1: Calibration curves for each OH-PBDE standard. .................................................... 117!    x List of Abbreviations  AICc    Akaike information criterion APCI    Atmospheric pressure chemical ionization APPI   Atmospheric pressure photoionization CS   Calibration standards CYP    Cytrochrome P450 Deca-PBDE   Commercial deca-PBDE mixture DEX   Dexamethasone ESI    Electrospray ionization mode ISP    Ion spray ionization Koa   Octanol-air partition coefficient Kow    Octanol–water partition coefficient LOQ   Limit of quantification MC   3-methylcholanthrene MeO-PBDE   Methoxylated polybrominated diphenyl ether MS    Mass spectrometry NADPH  nicotinamide adenine dinucleotide phosphate NIH Shift  U.S. National Institute of Health shift Octa-PBDE  Commercial octa-PBDE mixture OH-PBDE   Hydroxylated polybrominated diphenyl ether PB   Sodium phenobarbital PCB   Polychlorinated biphenyl PBDE   Polybrominated diphenyl ether Penta-BDE  Commercial penta-BDE mixture QC   Quality control SIR    Selected ion recording Sw    Water solubility at 25°C Sy.x   Standard deviation of the residuals UPLC   Ultra performance liquid chromatography     xi Hydroxylated Polybrominated Diphenyl Ethers (OH-PBDE)  4'-OH-BDE-17 4'-Hydroxy-2,2',4-tribromodiphenyl ether 6'-OH-BDE-17  6'-Hydroxy-2,2',4-tribromodiphenyl ether 4'-OH-BDE-25  4'-Hydroxy-2,3',4-tribromodiphenyl ether 2'-OH-BDE-28 2'-Hydroxy-2,4,4'-tribromodiphenyl ether 3-OH-BDE-47 3-Hydroxy-2,2',4,4'-tetrabromodiphenyl ether 4-OH-BDE-42 4-Hydroxy-2,2',3,4'-tetrabromodiphenyl ether 3-OH-BDE-47 3-Hydroxy-2,2',4,4'-tetrabromodiphenyl ether 5-OH-BDE-47 5-Hydroxy-2,2',4,4'-tetrabromodiphenyl ether 6-OH-BDE-47 6-Hydroxy-2,2',4,4'-tetrabromodiphenyl ether 4'-OH-BDE-49 4'-Hydroxy-2,2',4,5'-tetrabromodiphenyl ether 6'-OH-BDE-49   6'-Hydroxy-2,2',4,5'-tetrabromodiphenyl ether 2'-OH-BDE-66 2'-Hydroxy-2,3',4,4'-tetrabromodiphenyl ether 2'-OH-BDE-68  2'-Hydroxy-2,3',4,5'-tetrabromodiphenyl ether 6-OH-BDE-85  6-Hydroxy-2,2',3,4,4'-pentabromodiphenyl ether 6-OH-BDE-90  6-Hydroxy-2,2',3,4',5-pentabromodiphenyl ether 6-OH-BDE-99 6'-Hydroxy-2,2',4,4',5-pentabromodiphenyl ether 6-OH-BDE-123 6'-Hydroxy-2,3',4,4',5-pentabromodiphenyl ether 6-OH-BDE-137 6'-Hydroxy-2,2',3,4,4',5-hexabromodiphenyl ether  Hydroxylated Polychlorinated Biphenyls (OH-PCB)  4'-OH-CB-50  4'-Hydroxy-2,2',4,6'-tetrachlorobiphenyl  Polybrominated Diphenyl Ethers (PBDE)  BDE-17  2, 2!,4-Tribromodiphenyl ether BDE-28  2,4,4!-Tribromodiphenyl ether BDE-47  2,2',4,4'-Tetrabromodiphenyl ether BDE-99  2,2!,4,4!,5-Pentabromodiphenyl ether BDE-100  2,2!,4,4!,6-Pentabromodiphenyl ether BDE-153  2,2!,4,4!,5,5!-Hexabromodiphenyl ether BDE-154  2,2!,4,4!,5,6!-Hexabromodiphenyl ether BDE-209  2,2!,3,3!,4,4!,5,5!,6,6!-Decabromodiphenyl ether  Polychlorinated Biphenyl (PCB) CB-28   2,4,4!-Trichlorobiphenyl CB-153  2,2!,4,4!,5,5!-hexachlorobiphenyl  Methoxylated Polybrominated Diphenyl Ethers (MeO-PBDE) 6-MeO-BDE-47 6-Methoxy-2,2',4,4'-tetrabromodiphenyl ether 4'-MeO-BDE-49 4'-Methoxy-2,2',4,5'-tetrabromodiphenyl ether 2′-MeO-BDE-68 2'-Methoxy-2,3',4,5'-tetrabromodiphenyl ether  xii Acknowledgements  I would like to thank my supervisor Dr. Stelvio Bandiera for his support and guidance. I would also like to thank my committee Dr. Thomas Chang, Dr. Ron Reid, and Dr. Judy Wong for taking the time to read and critique my work. Thank-you to Dr. Adam Frankel for chairing my defense.  A special thank you to András Szeitz for his help with the UPLC/MS. His operational knowledge of the UPLC/MS was invaluable during this project. I would also like to acknowledge Dr. Eugene Hrycay for his suggestions and help.  Also thank you to past and present graduate students: Anad Deo, Claudio Erratico, Ravindranath Gilibili, Si Zhang, and Subrata Deb. Thank you for your words of encouragement and help troubleshooting.  I would also like to extend a thank-you to my friends and family who have been there to encourage me every step of the way. A special thank-you to Hannah and Emily.   xiii Dedication        This thesis is dedicated to my Mum.   Each and every time I called discouraged or frustrated, my mother would remind me of a determined little girl who refused to be outrun by a boy at gymnastics practice. She would tell me that anyone who was determined enough to run until the boy chasing her threw up certainly had the determination to finish her thesis.  Thank you Mum, once again, you were right. !! R N!O!!"C:;ALH=:EAC! ! J60&!XX/a==!*2&07!90&0!&0T)&+0;!25!M%5%;%!;:&25U!<==R-!B'070!*2&07!.%:70;!aa\!;0%+'7/! </X==!25b:&207/!%5;!R-X!"2332)5!;)33%&7!25!T&)T0&+#!;%1%U0!OC%33/!<==XP-!E5!,&2+27'!M)3:1"2%/! 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' $()) $()( $(*$ $(*& $(*# $(*) $(*( $(($ $((& $((# $(() $((( %!!$ /"#) +,-,., /-012.341,125  2 Herodotus, a Greek historian (484-431 BC), who described Egyptians soaking wood in alum (potassium aluminum sulfate) to reduce flammability (Hindersinn, 1989). A history of flame- retardant use is found in Appendix A. In order to understand the use of flame-retardants, a general understanding of the combustion process is required. Combustion requires fuel, oxygen, and heat. If one of these components is removed, combustion will not occur (Figure 1-2).   Figure 1-2: The combustion triangle  Four distinct steps are required for the combustion of a solid material: 1) heat, 2) thermal decomposition or pyrolysis, 3) ignition, and 4) propagation (Alaee et al., 2003). During the heating phase, a material is heated until it reaches its decomposition temperature. At the decomposition temperature, covalent bonds within the material break down forming high-energy free radicals. Thermal decomposition is also known as pyrolysis, derived from the Greek words pyro meaning fire and lysis meaning breakdown. Once the covalent bonds within the material (RH) lyse (Equation 1-1), the newly formed free radicals combine with oxygen, a process known as the free radical chain-branching reaction (Equation 1-2). The propagation reaction (Equation 1-3) is highly exothermic and is responsible for ignition and flame propagation.  !"! → !∗ + !∗ Equation 1-1 !∗ + !! !→ !"∗ + !∗ Equation 1-2 !"∗ + !"! → !"! + !∗ Equation 1-3  There are more than 175 different types of flame-retardants produced commercially (Birnbaum and Staskal, 2004). Approximately 1.5 million tons of flame-retardants are added to Heat Oxygen  Fuel !! a 25+)!*):&!1%b)&!U&):T7!;072U5%+0;!%7!25)&U%52./!T')7T')&:7V.)5+%2525U/!52+&)U05V.)5+%2525U/!%5;! '%3)U05%+0;!*3%10V&0+%&;%5+7!O$0U06!0+!%3-/!<==WP-!E5)&U%52.!*3%10V&0+%&;%5+7!25.3:;0!10+%3! 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Q27:%3!.)1T%&27)5!)*!.'&)1%+)U&%17!)"+%250;!*&)1!"3%5]!7%1T307!92+'!.'&)1%+)U&%17! )"+%250;!*&)1!M$!7T2]0;!7%1T307!7')90;!5)!25+0&*0&25U!T0%]7!%+!+'0!7%10!1`^!%5;!&0+05+2)5! +2107!%7!+'0!JCVF,?D!7+%5;%&;7-!B'0!"3%5]!7%1T307!OI2U:&0!aVR/!T%503!A/!M/!%5;!DP!.)5+%250;! 7060&%3!T0%]7!":+!+'070!;2;!5)+!.)&&07T)5;!92+'!+')70!)*!+'0!%:+'05+2.!7+%5;%&;7!OI2U:&0!aVR/! T%503!,/!?/!%5;!IP-!B'0!.'012.%37!%5;!":**0&7!:70;!25!+'0!T&).0;:&0!90&0!+07+0;!+)!;0+0&1250!2*! +'0#!90&0!+'0!7):&.0!)*!.)5+%125%+2)5-!E+!9%7!;0+0&1250;!+'%+!+'0!T0%]7!7005!25!+'0! .'&)1%+)U&%T'7!.%10!*&)1!+'0!'0T%+2.!12.&)7)107!+'01703607-!E5!%5!%++01T+!+)!032125%+0!+'0! :5]5)95!T0%]7/!7060&%3!7+0T7!25!+'0!T&).0;:&0!90&0!%3+0&0;!%7!;07.&2"0;!25!$0.+2)5!a-[-! !  57  Figure 3-6: Representative chromatograms A) 1 mg/mL hepatic microsome protein at 421.3 m/z B) 1 mg/mL hepatic microsome protein and OH-tri-BDEs (concentration of 175 nM) at 421.3 m/z. C) 1 mg/mL hepatic microsome protein at 500.6 m/z  D) 1 mg/mL hepatic microsome protein, and OH-tetra-BDEs (concentration of 175 nM) at 500.6 m/z. E) 1 mg/mL hepatic microsome protein at 306.7 m/z m/z F) 1 mg/mL hepatic microsome protein and 4'-OH-CB-50 (concentration of 5 nM)  at 306.7 m/z.  Time (Minutes) Time (Minutes) Time (Minutes) R el at iv e Pe ak  In te ns ity  (% ) R el at iv e Pe ak  In te ns ity (% ) R el at iv e Pe ak  In te ns ity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',-.(%*'+,!+4!:;<8NQ!!2'*5!50?%*'-!F'-)+1+F01!4)+F!)%*1!?)0*)0%*03!2'*5!9:B!C5)00!F0*%(+&'*0! ?0%b1!20)0!'30,*'4'03!4+&&+2',H!',-.(%*'+,!2'*5!50?%*'-!F'-)+1+F01!4)+F!)%*1!?)0*)0%*03!2'*5! ;<UB!>!1',H&0!F0*%(+&'*0!?0%b!2%1!'30,*'4'03!4+&&+2',H!',-.(%*'+,!2'*5!50?%*'-!F'-)+1+F01! 4)+F!)%*1!?)0*)0%*03!2'*5!L$B!L0*%(+&'*0!?0%b1!20)0!,+*!+(10)/03!4+&&+2',H!',-.(%*'+,!2'*5! 50?%*'-!F'-)+1+F01!4)+F!)%*1!?)0*)0%*03!2'*5!-+),!+'&!=c'H.)0!M8JAB!c+)F%*'+,!+4!NO8678:;<8PQ! +)!JO8678:;<8J#!2%1!,+*!+(10)/03!2'*5!%,G!+4!*50!50?%*'-!F'-)+1+F0!?)0?%)%*'+,1!*01*03B! L0*%(+&'*0!?0%b1!20)0!,+*!+(10)/03!250,!50?%*'-!F'-)+1+F01!20)0!(+'&03!(04+)0!.10!,+)! 20)0!F0*%(+&'*0!?0%b1!+(10)/03!250,!50?%*'-!F'-)+1+F01!20)0!?)0*)0%*03!2'*5!-%)(+,! F+,+@'30B!C50!%33'*'+,!+4!PK!µD!+4!PKK!FL!W>;97!%*!MK!F',.*01!3'3!,+*!',-)0%10!+)!%440-*! F0*%(+&'*0!4+)F%*'+,!%*!ZK!F',.*01!4+)!%,G!F0*%(+&'*0B!! ! ! !! ZM !!! 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',-.(%*'+,!*'F0!+,!*50!4+)F%*'+,!+4!6789:;<1!2%1!',/01*'H%*03!.1',H!%!?)+*0',!-+,-0,*)%*'+,! +4!P!FHTFD!%,3!%!1.(1*)%*0!-+,-0,*)%*'+,!+4!"K!dLB!9)+3.-*!4+)F%*'+,!3'3!,+*!%??0%)!*+!(0! &',0%)!%4*0)!"!F',.*01!4+)!NO8678:;<8NX!%,3!M8678:;<8NQ!=c'H.)0!M8NAB!C5.1!%!"8F',.*0! ',-.(%*'+,!*'F0!2%1!.103!4+)!1.(10_.0,*!0@?0)'F0,*1B! C50!0440-*!+4!1.(1*)%*0!-+,-0,*)%*'+,!="8PKK!dL!:;<8NQA!+,!*50!4+)F%*'+,!+4!678 9:;<1!2%1!0@%F',03!.1',H!%!?)+*0',!-+,-0,*)%*'+,!+4!P!FHTFD!%,3!%!"8F',.*0!',-.(%*'+,!*'F0! =c'H.)0!M8"AB!C50!)%*01!+4!4+)F%*'+,!6789:;<!F0*%(+&'*01!20)0!.,-5%,H03!(0*200,!"K!%,3!PKK! dLB!C5.1!%!"K!dL!-+,-0,*)%*'+,!+4!:;<8NQ!2%1!10&0-*03!4+)!1.(10_.0,*!0@?0)'F0,*B !! Z" ! & & K,L26%&'('*&>00%4.&/0&I%A".,4&-,46/?/-"$&A6/.%,3&4/34%3.6".,/3&/3&.I%&0/6-".,/3&/0&9:(;<=>?E&&H&CS&UG&?2#?.6".%& 4/34%3.6".,/3&"35&C&-,32.%&,342#".,/3&O"?&2?%5E&="."&A/,3.?&"6%&-%"3&X&?."35"65&5%8,".,/3&/0&.I6%%&,35%A%35"3.& %NA%6,-%3.?E& K "K PKK P"K JKK J"K MKK K KB" P PB" J 9 ) + 3 . - * ! c + ) F % * ' + , ! = ? F + & T F ' , A 9)+*0',!$+,-0,*)%*'+,!=FHTFDA N8678:;<8NJ M8678:;<8NQ "8678:;<8NQ NO8678:;<8NX !! ZZ ! & K,L26%&'(B*&!I%&%00%4.&/0&.,-%&/3&.I%&0/6-".,/3&/0&9:(;<=>?E&H&CS&UG&?2#?.6".%&4/34%3.6".,/3&"35&V&-LT-+&/0&I%A".,4& -,46/?/-"$&A6/.%,3&O"?&2?%5E&="."&A/,3.?&"6%&-%"3&X&?."35"65&5%8,".,/3&/0&.I6%%&,35%A%35"3.&%NA%6,-%3.?E& K JK NK ZK #K PKK PJK K " PK P" JK J" MK 9 ) + 3 . - * ! c + ) F % * ' + , ! = ? F + & T F H ! ? ) + * 0 ' , A ],-.(%*'+,!C'F0!=F',A!%*!PFHTFD!9)+*0', N8678:;<8NJ M8678:;<8NQ "8678:;<8NQ NO8678:;<8NX  67    Figure 3-5: The effect of substrate concentration on product formation. A 5 minute incubation and 1 mg/mL of hepatic microsomal protein was used. Data points are mean ± standard deviation of  three independant experiments 0 20 40 60 80 100 10 20 40 50 100 Pr od uc t F ro m at io n (p m ol /m in /m g pr ot ei n)  BDE-47 Concentration ( µM) 4-OH-BDE-42 3-OH-BDE-47 5-OH-BDE-47 4'-OH-BDE-49  68 3.6.2 Kinetic Analysis of BDE-47 and Metabolite Formation  The rates of formation of the OH-PBDE metabolites of BDE-47 were evaluated over a range of substrate concentrations (10 to 100 µM) using hepatic microsomes from rats pretreated with PB to determine the kinetic parameters. All metabolites, with the exception of 6-OH-BDE- 47, which was formed at concentrations below the LOQ, were analyzed. Formation of 4-OH- BDE-42, 3-OH-BDE-47, 5-OH-BDE-47, and 4'-OH-BDE-49 exhibited sigmoidal product formation kinetics (Figure 3-6). The Hill equation (equation 2-1) rather than the Michaelis-Menten equation (equation 2- 2) provided the best fit. The coefficient of determination (R2), Akaike information criterion (AICc) and standard deviation of the residuals (Sy.x) values are presented in Appendix B. The apparent K' and Vmax for each individual OH-PBDE is presented in Table 3-6.  Table 3-6: Apparent K', Vmax, and n values using the Hill equation Metabolite Apparent Vmax (pmol/min/mg protein) Apparent K' (µM) N 4-OH-BDE-42  2.3±0.2 25.9±4.0 3.8±1.6 3-OH-BDE-47  6.5±0.7 24.5±4.1 5.1±3.1 5-OH-BDE-47  0.9±0.3   25.2±11.8 5.4±8.8 4'-OH-BDE-49 16.2±1.2 27.8±2.9 4.2±1.1 Mean ± SD. Three independent experiments were performed  69  Figure 3-6: Rates of formation A) 4-OH-BDE-42 B) 3-OH-BDE-47 C) 5-OH-BDE-47 D) 4'-OH-BDE-49. Five minute incubations with hepatic microsomes from PB-pretreated rats were carried out at a protein concentration of 1 mg/mL. Substrate concentration (BDE-47) ranged between 10 and 100 µM. Data points are mean±standard deviation of three independant experiments. 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Using human hepatic microsomes will provide insight into how BDE-47 is metabolized when it enters the body.  5.1.2 Biomagnification  One area that requires further investigation is the biomagnification of OH-PBDEs. The low rates of OH-PBDEs formation seen in vitro studies do not match the observed ratios of PBDEs and OH-PBDEs in biological samples. Further investigation is required to understand the origin of OH-PBDEs found in biotic samples.   5.1.3 MeO-PBDE Metabolism  It has been suggested that interconversion MeO-PBDEs to OH-PBDEs may be responsible for the discrepancy between the observed rates of in vivo and in vitro PBDE hydroxylation and the ratio of PBDEs to OH-PBDEs in biotic samples. Using a MeO-PBDE, such as 4'-MeO-BDE-49, as a substrate will help gain insight into the origin of the OH-PBDEs found in biotic samples.      !! Qb ! H.@.-.)&./' ! J8(**!=4!J&0(B!K4!$hu.0-!J!(-.!M*&H2(-!v!6:;;R<9!J-!1>*&>0*+!1'!)122*&)0(88N!%B*.! 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