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AR QR G-- 138K Protein Binding of Perfluorohexane Sulfonate, (Human, RatP,erafnlduoMroonokcteayn)e,SaunldfoVnaartieoaunsdHPuemrafnl-uDoerroiovcetdanPolaattsoemaPPlraostmeain Fractions STUDY ID: 9921.7 Southern Research Institute 2000 Ninth Avenue South P.O. Box 55537 Birmingham, AL 35255.5537 000090 StPuadgye92902f177 SUMMARY opTnlhaiesbpmoeaurtpcredonsttewpiirnosftrmeaiecnatsbiouinnrsdeiwdnaigsnofrdaeftt,oeumrrmiponeerdfn.lauonAkrddodhinetauitmoenyadancllopym,lpaposrumonatdisnibisndeivnegfodirftfhereenstahmuemapno-uderived `oZehe ipreottesipwbaosuinndcutbesatteardtifcolre 1wSamsisneuptaersataetd3f7roCm itnheeancohnp-lbaosuamntadfiptvreeottdeaiirftnficeflrreaecnbtycioounncloesrntpprllaatmsinomnaasss.aumsEpialncegh. sChteanentedrlaiurfedr.neteffrioltmratthieonudlervaiiciersatwiiotnh awansomainnaallyzmeodlfeoecuslatr `awretiigchlet c(oNncMeWnt)ractioun troelfoa3t0ifv,e0ft00sdacltaonss, 000081 RCeosrceanrncahKAesrssitstnaenrt-WIlolod, BS Bioanalytical Chemistry Group Lori Coward, BS Sr. Research Associate Bioanalytical Chemistry Group Greg Gorman, PD. Manager Bioanalytical Chemistry Group KEY PERSONNEL Sudy99217 Page3 of7 000082 StPuadgye9d9o2f1?7 1. OBJECTIVE hTuhmeaonb,jercatt,ivaendofmtohniskesytupdlyawsamas to as determine the well as various pheurmcaennt-doefriprvoetdeipnlabsimnadipnrgotfeoirn each test fractions article in 2. SAFETY ttAhhlielsMnsaettcuedeyrs.isaalrPySrapofrceoetcdyeudrauenrsdeosDuttaoltiaenneSsdhuerieenttSshOe(PMsaS2fDe-St2)y9,-o3ftphfrooerviahdnaaenlddylsbitynsgtwhheeuremspabonanssaeondrdofpnorriintmfhaeotretmeasttiaornticcolenstauisneedd ia the human-derived plasma protein fractions were also followed. plasma a6 well so 3. COMPLIANCE `T3ph5ei4rs8f,owr3om6re0dk6,iwn3at6sh0e7p)se.pirrfWiothorifmlteehdetuhrisseignwugolarvtkairowinoasusussniponrtgevaciuaodluiisbtlreaydteivdanlacindodamtpveladliiaadnnacatleeydtwiiicntashltrGmuLemtePnhtoradetgsiuoln(a,tions, it was 4. EXPERIMENTAL 4.1 Analytical Procedures aItndtiwvoidcuoanlceanqtureaotuisonssolasutiinodniscoafteedaicnhthheutmaablne derived below: plasma protein fraction were prepared =Plasma ProteinFraction GAaliphmaa--GGlloobbuluilnin FAilbphrai-n2o-gMeancroglobulin BTertaan-sLfieprorpinroteins El Physiological `Plasma Protein 956057--21501357mmgg//110000mmLL. 210500--640200 mmgg//110000mmLL 228000--434200 mmgg//110000mmLL Prepared Plasma Protein Prepared Plasma Protein {10Co%ncePnhtysriaotlioognical) (100Co%nPcheynstiroaltioognical) 113966mmgg//110000mmLL 3687 mmgg//110000mmLL 2402mmgg//110000mmLL 11276182mmgg//1010m0mL0L 240008 mmgg//110000mmLL 229070mmg/g1/010m0m0lL moSritxo2tcukcrosenotwlruaotsliovpnolsratosefmxaeeadmcafhotrrtei|sxtmtiaorntuiptcrleoedawunecdreienasceufpbianaratlaetdceolanytc3se7pnitrkCaetdfiioonrnt1oo5ftmh1ien0putlpeagssh.mmal.proTtehien factions resulting ouflttrhaefilitnzcautbioantidoenv,iecaec(h NsaMmpWlceutwoafsfa=gai3n0,v0o0r0tedxaeldtofnosr)1amnidnucetnetarinfdupgeldacaetdU2ip0not0on0acxoCemgnptlfreoirtfii3oe0ne minutes. The ultrafiltrate was analyzed to determine the amountofunbound test article 000033 SuPdayge99S2o1f7? 42 Results `The the resuolftalslofthe endofthe report. analysesarepresaseperncetntbeoudndtestartiincTalblee II at 5.0 Conclusion Tdehreivperdotpeliansbmiandpirnogtoeifn fforuarctpieornfslautotrownoatdiefdfceroemnpt opurontdesinwfarsacetviaolnucaotnecdenitnrsaetvieonnsse(pTaarbatlee1haunmdanI-. `mAoddnikteioynpallalys,mparoatte5indbififnedrienngtcfoonrctehnetrsaatmieonfso(uTracbolmepIoLuI.ndTshweads eavianltuTaatbealdeinI raant,dIhTusmhaonw,satnhdat baceoltnbacu-elmniitpnroiapstriobotyenisfn.asr.TthhTeehlfeaorupgrretoshttesciionnmgbplioenupdnridong,teePixFnpOebSri,inmdweeanrftssofrfotouhrnrtdeheetoorfabtte,hhheiufgmohaulnry,cbooamnudpndomuobnnydkbseoytthpelaalssbaumttmabieosnthdahonwd veryhigh levelsofbinding at all concentrations tested and no evidenceofsaturation. 000034 SuPadgyeomo1f77 Table I Percent Binding to Human Plasma Protein Fractions (~10% Physiological Conc.) Albumin| Gamma-| Alpha- | Fibrinogen| Alpha2- | Transferin| Beta: Fess Globulin| Globulin 50 Te Macroglobulin or-- [BEES[75005 | 150 | 336 | 156 | 50 | Lipoproteins. 7] - [PROS1990 1765 [PROC | 964 | 35 | 499| 01 | 285| 54 | | 125 75 75] | To | 25 90.1 Tos Table I Percent Binding to Human Plasma Protein Fractions (100% Physiological Conc) Albumin| GGlaombmulai-n|| GAllopbhual-in Fibrinogen Ma`cArlopghlao-b2u-lin Transferrin LipBoeptroat-eins el [BEES 1 5%5 TT [7261 | 157| <o1 | 1 <0 | 6a | @i [EROS1998 [PROC 957 T7241 1750 | 504 | 711.0 | <o1| <01 <o0 <1 | =of| 21 55% 396 Table I % Protein Binding to Rat, Human and Monkey Plasma 1 Ol dl cl dl [NominalTT peruorabeuanesuifonsie| fPecliuorooctanecarboxalate FT joo{=o 100 | =io6 | ou |=o =o|=os~] F Le e 2s TTTosoero| 5w0s0[|919090[][999575[15799999 995 | "swe | 994 | 995] 7909 | 576 | 995 | 06| % Bi n di n g Vales re ported 1 as 10" r ona 05 eflec nonquaniale 99a [900 1565 {995 amount ofst etl nh pla | 375 waterBQ L < s95[30 6.25 gf. 4] 000095 StaPayge99T2a1l.?7 60 References M(1o).sbKoyplPaurb,liLs.h,iPnegscCeo,. A., "Clinical Chemistry (Theory, Analysis andCorrelation) 1984, pg. 1416,C.V. 7.0 Review and Approvals fin Li Sond, renna Kerstner-Wood, BS Research Assistant ITI Bioanalytical Chemistry Group. Ze Gort Lori Coward, BS, Sr. Research Associate Bioanalytical Chemistry Group orman, Ph.D. Manager Bioanalytical Chemistry Group 06-03-03 Date 6363 Date &-oj-03 Date 000096 Method No.: BACG-3548 ANALYTICAL METHOD Page lof 13 Title: PDrepearattioen aornfdnPAeruifluyosariosoacbtaytneHciParLbCooalMnaatessin SMpoenckteryomSeetrryu/mMaasnsd USrpienec:trSoammeptrlye (HPLC/MS/MS) --_------e 10 PRINCIPLE SP(eePrrRfuOlmCuoo)rroisocuftoraritnniefeciaesrdabwmoiprtalhleiastnaeri(nePtFeorObnCta)al.isnteaTndhdfearrsdoe(mr1ucSm)y,noproemruforlilungoeuros(hcme.xgo.an,nke0s.eu5ylfsmotLnr)aetaceto(entdPaFwiHniiStnhg Tbhyeesxatmrpaclteisoanrweitthheentmhyilxaecdetwaitte.haTnhieone-tphayilriancegtraetaegelnaty,erbuifs freermaonvedd,wateevra,pfoorlatleodwe1)d0 HdarPmymLneoCsnsMi,aursmecsaoScnpesettcaittteur,toemfdieilttrneyre/9dM5,aa%snmsdSepttehrcaatnnrsooflemrecrtoerndyta(tiHonaPiuLntgCo/s1Ma.mS5p/lM%ef Sr)v.iaTolhse,ararcanidda,mn5al%i yzSedc mbMy rensgu/ltmsLeinxuritnfe.reoSmaanmbpoludets20csotnota1i0n0i,n0g0P0nFgO/CmLatocfoPncFeOntCriantisoenrsugmraeantdefrnrgtohemaon1f01re0tl0oi,z50b00l00e nwgil/lmbLemwiatyhibnetdhielurtaendgweiotfhrceolnitarbloelbrelsaunlktsmpartiroirxtso oantahlaystitsh,econcentroaftPiFoOnC TTrhheedeufmcoaetnshssseppfreacytosrooumrrectermovyfooolafttPhaetRgreOpiCoistseanenottdiaaPltnFlyH-iS2n0ite0sr0afvceocrloitmnsgpilWoihnsihscehedxiitsnrltaochtewendeegafaotuigvehitoongmreoadtel.y `Ionftohredenretgoatmiavexifmriazgmeesnetnsiiotinvi(tMy,-tChOiOsHm)e'thfoordiPsRbOaCs.edonmixedreactior ntmhoenomiattormriixn.g iCItAhUnTuIniOcvNbelr:solaoSlidn,pu cprelepcard asiummtaaitiaoennssd.mnsaeyRreg ucfmaer,rraytroeaSntuoOmbPbeencruomnosbfzieodroenrSoeRsdIaes2s,-b5a-li5 ufonorrheasaerazvnedadhartinsddslueessd, safety procedures to be used when handling unpreserved primate tissued.escription of 20 REAGENTS AND SOLUTIONS `The listed reagents or their equivalents may be used. 21 Neat Reagents 000097 ANALYTICAL METHOD Page20f 13 Method No.: BACG-3548 Title: PDreetpearrmaitniaotnionaonfdPeArnfalluyosriosoctbayneHcaPrLboCralMaatsesin MonkeySerum and Spectrometry/Mass Urine: Sample Spectrometry (HPLC/MS/MS) -_--m 211 ar, deionized and organic free (from in-house purification system; e.g, Ingalls 212 Methanol, HPLC grade 2.13 Perfluorooctanccarboxalate (analyte), as provided by the client 214 Perfluorohexanesulfonate (internal standard), 97% 2.15 Ammonium acetate, HPLC grade 21.6 Blank control monkey serum . 2.17 Sodium Carbonate, Certified ACS Grade or equivalent 2.18 Sodium Bicarbonate, Certified ACSGradeor equivalent 2.19 Ethyl Acetate, HPLC grade 2.110 Tetrabutylammonium Hydrogen Sulfate 2.111 Sodium Hydroxide 50% solution, Certified grade or equivalent 2.12 Blank control monkey urine 2113 Formic Acid 22 Prepared Solutions Appropriate changes in the solutions may be made at the discretionofthe analyst 221 5mMAmmaceo tatein norgi anicfu reewam ter 000038 Method No.: BACG-3548 ANALYTICAL METHOD Page3of 13 Title: DPerteepramriantaiotnionaonfdPAenalrysfislbuy oHPrLCooMacsistnMSapoeunckteeryomSceetraruyrm/MaabasdsoUrSripneaect:lrSoamameptelrye (HPLC/MS/MS) --_--mmm------ 22.1.1 2F4odrienxoamrplge,a0npriweaptcaer-e(4felgir.tere4s,Lem)e.aMsuirxe woeultlaamndmointieumtharcoeutgatheH(Pe.L5C.,mo1b.5i4l2egp)haasned filtration apparatus. 222 TBA lon-Pairing Solution (0.5 M tetrabutylammonium hydroxide) 222.1 Fsuolrfateexaimnpdleei,ontiozepdrewpaatreer 2a5ndmLad,judsittsshoelpvHe 4.24g to 10 woifthte5t0r%abuNtayOlaHmmsoonluituimonh.ydrogen Naodtjeu:stamemnotrs.e dilute solution of NaOiHn water may be used toeffect smaller pH 223 Carbonate/Bicarbonate Buffer Solution 223.1 wFaeonlrdleatpxopaermonpxsliuemr,taetocepolrmyep2pl.ae1rt0eegd1oi0sf0ssomoluLdt,iioudnmi.sbsioclavrebaopnparteoxiinma1t0e0lmyL2.6o5f gdoeifosnoizdeiduwmatcearr,bonMaixt.e 3.0 INSTRUMENTS, MATERIALS, AND APPARATUS The following or their equivalents may be used. 31 HPLC pump(s), autosampler, and triple quadrupole mass spectrometer 32 Auosampler vials with inserts 33 Vortex mixers (e.g. touch mixer and IKA-Vibirax platform mixer) 34 Solveaconceatration apparatus (.g., Zymark Turbo-Vap with source of nitrogen) 3.5 HPLC mobile phase filtration apparatus 36 Filters for HPLC mobile phase filtration apparatus (.g.. Nylon-66, 0.20 uz) 000099 MethodNo.: BACG-3548 ANALYTICAL METHOD Page dof 13 Title: (DPreHetPpeLarrCmai/tnMiaoStni/oMnaSno)df PAeurafluyosriosoctbaynscHaPrbLoCxalMaatseisnMSpoenckteroymSeetrryu/mMaasnsd USrpineec:trSoammeptlrey _ 37 Analy-- tical balance _--me 38 Volumetricflasks (e.g., 10an25mdL) 39 Disposable Pasteur pipets 310 Micropipettor(s) with tips 3.41 Culture tubes with teflon-lined caps 312 Centrifuge 313 Assorted glassware and syringes 3.14 Culture tubes (vials) for use with solvent-concentration apparatus 3.15 1m Plastic syringes with 0.2 um PVDF syringefilters 3.16 Variable speed horizontal platform shaker 317 pHmeter 40 PREPARATION OF STOCKS AND WORKING STOCKS Adipspcrroeptriioantoef sheets. changes in the analyst. theActcuonaclendtilruattiioonnss of will the be solutions may documented on be made at the the preparation 41 Main Stock Solution of PFOC ~1000 g/mL, 411 acoPcrrugerapanatirecelfyraenwee~wia1gth0ea0rb0ooduuigts/s1mo0llmv.eg.solDPuFtiiOoeCntoionftthoPeRamOaC1r0k-i.mnLdvAeloitloeurnmnieaztteirdvieoclryfg,laanswikc)-.ferAteedhidewcadtoeemiropno(ic.a5e.d, guhnd 000100 ANALYTICAL METHOD Page Sof 13 Method No.: BACG-3548 Title: `PDreetpearrmaitniaotnioanondfPeArufalluyosriosocbtayneHcaPrLboCralMaatsesin Monkey Serum and Spectrometry/Mass Urine: Sample Spectrometry (HPLC/MS/MS) _----mm---- intoan water. aMpixpwrelolp. vrTeirsasanestlfeer (te.hg.e, csuolltuutrieotnubtoe)aacnldeaanddves1s0eml iLf doefsdierieodn.izedorganic-free 42 Stock Solution of Internal Standard (PFE), ~200 g/mL 421 afPcrrceeuepraawtraeetleayrwneti~og2hd0i0assbooplugvt/em1la0.nmdsgoidlinulttuiotoenatSoof0t-PhmeFLHvmoSalruikmnedwtiertiihocnifdlzeaeisdokn)o.irzAgeaddndiocdr-egfiarnoeineci-zwfeardteoeerrgwa(aact.gs,. 2Aldtder5n0atmivLeolyf,dweeiiognihztehdeocrogmpaonuincdi-nwftaortearae.Mapipxrowperlila.teTvessrel a(teh.ge.ns,ocluuslttiuorfnettoubeae)ctalrenerad,n. vesselif desired. 43 Spiking solutionofInternal Standard (PFHS), ~ S0ug/mL 43.1 Pr2empLaorefatnhe~25000 gg//mmL.ssoloutlionuiotnftioPoaFcEnulitunrdeetiuobneiazneddoargdadni6cm-fLreoefwadetieornbiyzepidpweattteirn.g Mix well 44 Working Stock Solutions of PROC 44.1 ITffoodlelspoirwreiepndagrateambowldeoi.rfkiPierndedgpialsrutetoicioknns1sco0hl-uemtmiLoencvsoa,lnumbmaeetkuresiectdhfaleanspdkrdsooopcreourtmhedenilrtuaetpdipoirnnsotpharesisatstuehdogywlranescsiwnarteh.e ords. `Working Stock Level (WSL) Approximate Concentration (ng/mL) Sloe |] Volume of PFOC solution | Final Volume in deionized organic free water (mL) smiofswugml| 10 | 000101 ANALYTICAL METHOD Page 6 of 13 Method No.: BACG-3548 _ Title: Determination of Preparation and PAenrafllyusoriosocbtyaneHcaPrLboCxalMaatsesin Monkey Serum and Spectrometry/Mass Urine:Sample Spectrometry (HPLC/MS/MS) * om Tommi hoem [ow Tmoarammmoam|ereeo]] orosoma0ws]] oioom owwo oes vorn i omo e sowo s 0 o e0ep ] ] a]|| 4.42 Summary of concentrationsofserum standards: `Standard Level -- Volume and Spike Conc. _ `Approximate Concentration of PFOC in serum (ng/mL) [To [s,pm m | mo oo] [T=o1ow[wutsmmomoomnn]|usyoao mr]| 000102 Method No.: BACG-3548 ANALYTICAL METHOD Page 7 of 13 Title: _-- DP(reHetPpeLarrmCai/tnMiaoStni/oMnaSno)dfPeArnfalluyosriosoctbayneHcaPrLboCxalMaatseisn MSpoenckteroymSeetrryu/mMaasnsd SUpriencet:rSoammeptlrey TEER [oe [owosooosmmom]| [+ [asiomn|10| [o[wmosa| ssmw a| [x [oaosoomwer |aw| [+[omoso|omwwe| Lv[odozs |o0me| [~[omor|m2 mn| [0[wmosmw|om0wm| Lr [Tomoasomm |5] 5.0 PREPARATION OF SPIKED STANDARDS AND BLANKS dAipspcrroeptriionatoef cthheanagnaelsysti.n the concentrations of the solutions may be made at the 5.1 Multiple (e.g.,aboutthree) setsofmatrix standards and amatrixblank (blank +15) are analyzedwitheachsetofunknown samples. Amatrix double `blank (blank-1S)`may also be analyzed if desired. 000103 52 Ianptprooipnrdiiavtiedvuoallu~m2e0a-smdLecsuclrtiubreedtiunbtehse,ptiabpleetabbloavnekfmoarteraicxh(set.agn.da,r0d..5mFLo)r.tPihpeetblianntkhs,e pipet 10 uL of organic-free water insteadof theworkingstocksolution. Add the 10 ul ANALYTICAL METHOD Page8of 13 Method No.: BACG-3548 Title: PDreetpearrmaitniaotnionanodf PAenrafllyusoirsoocbtyaneHcaPrLboCxalMaatsesinSMpoenckteroymSeterryu/mMaasnsd USrpience:trSoammeptrlye (HPLC/MS/MS) _--_---- ooffionrtgearnniacl-fsrteaendwaartdesrtoicnkst(ea~d)50anpdg/vmorLt)extofcorac~h5tusbeeecxoncdesp.tthe blank-IS (pipet 10 pL 53 cTaorbocnaacthe/btiwcbareboanadtde b5uf0fe0r,uaLndo1fmtLhoefdTeiBonAizieodno-rpgaainriicnfgrseoelwuattieorn.,Vo1rmteLx eoacfh tube for about 5 seconds. 54 Add 2.5 setting. ml.ofethylacetateandextracton horizontal mixerfor 1 hourat a lowspeed 55 R5emmoinvuetetsh.etubefromtheshakerandplacein acentrifuge(e.g.,2500rpm)forabout 56 d`Traykneeosfsf(te.hge.t, o~p 5e0tmhiynluatceestiantethleaTyeurrabnod-pVaupti)twiinttho aagcelnetalnestturbeeaamnodfenviatproorgaentaentdo `moderate heat (e.g., 50C). 57 cRoenctoanisntiintgut1e.t5h%eforersmiidcuaeciind5a0n0duvoLrtofex5b%rie5flmytMomaimxm.oFinliteurmthaecestaatmep:le9s5t%hrmoeutghhan0o.2l 4am PVDF or Nylon syringe filters into autosampler vials. 60 PREPARATION OF SAMPLES 61 bAultloviwgeoraocuhslsye.rumPispaetmpalneatloiqtuhoatwotfoearcohomsatmemppleera(tc.ugr.e,.0.5VomrLte)xienatochinsdaimvpidlueablri~e2fl0y-, mL that culture tubes. the expected If necessary, concentration dilute of the an aliquotofany test article being samplewithblank analyzed will fall matrix so within the 5co0ngce/nmtrLa)tiotno eraancghetuobfethaendstvaonrdtaerxdfcourrvae.couApdledof10suecLoonfdisn.ternal standard stock (~ 62 To cach tube add carbonate/bicarbonate 500 buffer, uL and 1ofmLtohfe deTioBnAizeidono-rpgeainriicngfreesowlautteiro.n, 1 mL of Vortex each tube for about 5 seconds. 000104 ANALYTICAL METHOD Page9of 13 Method No.: BACG-3548 Title: PDreetpearrmaitniaotnioannodf PAenrafllyuscirsoocbtyanHecParLbCoraMlaasesin SMpoenckteryomSeetrryu/mMaasnds USrpience:trSoammeptlrey (HPLC/MS/MS) --_-- 63 Add2.5 setting. mLofethyl acetateandextractonhorizontal mixerfor 1hourat a low speed. 64 R5emmionvuteets.hetubefromtheshakerandplacein acentrifuge (e.g,,2500rpm)forabout 65 dTraykneesosff(et.gh.e,t~op50etmhiynlutaecestianttehleaTyeurrbaon-dVapupt%)itwiinttho aagcelaetalnestturbeeamaonfdnietvrapoogreantaentdo `moderate heat (e.g. 50 C). 66 Rcoenctoanisntiinugt1e.t5h%efrormeicaiscind5i0an0dduvoLruotefx5ebr%ief5lmytMomaimxm.oFniiltuemrtahceetsaatmep:le9s5t%hrmoeutghhan0o.l2 4am PVDF or Nylon syringe filers into autosampler vials. Cap vials for analysis, 7.0 AMNAASLSYSSPIESCTBYROHMIEGTHRYP/EMRAFSOSRSMPAENCCTEROMLEITQURIYD(CHPHLRCO/MMSA/TMOS)GRAPHY 71 Conditions are to be optimizedifnecessary. 7.1.1 HPLCConditions Analytical Column: Keystone Scientific equivalent Aquasil C18, 150 mm x 2 mm ID, or Guard Column: Elution Flow rate: Injection volume Mobile phase: Keystone Aquasil C18 400 uL/min. 10 mm x 2 mm 3uL A: B: SmM 1.5% ammonium formic acid acetate buffer in methanol GradientProfile: 00.-50-.75.m5imni.n. 510%0A:%:5900A%%BBlineargradient 7.58min. 10%A : 90% Bstepgradient 000105 ANALYTICAL METHOD Page 100f 13 Method No.: BACG-3548 Tide: DPreetpearrmaitniaotnionanodf PAenraflluyosriosocbtyancHcaPrLboCxalMaatsesinSMpoenckteroymSeterryu/mMaasnsd USrpineec:trSoammeptlrey (HPLC/MS/MS) --_--m ee `Temperature: 81lmin. Ambient S0%A:S0%B 7.12 PSoEftSwcairee:x APPIE 3S0c0ie0xTTruiprlbeoQQuuaadnrupole Mass Spectrometer Conditions TuNrotbeo:ioVnaSlpuersayliSsoteudrucneder "MS/MS Acquisition Conditions" override parameters in this table. . Auxiliary Gas Air (e.g,Grade0.1) at 85popuersnquadreis nch `Parameter Value s a0 xe o = "w on x mo 2 s El ` st 0 so ` 0 0 sn " so 2 oe 0 ca 1 000106 ANALYTICAL METHOD Page 11of 13 Method No.: BACG-3548 Title: DPreetpearrmaitniaotnionanodf PAenrafllyusoirsoocbtyancHcaPrLboCxalMaatsesinSMpoenckteroymSeterryu/mMaasnsd USrpineec:trSoammeptlrey (HPLC/MS/MS) _--_--mmm-- `Patameter a an oo a wo vou ve ---- Sean type: Polarity Acquisition mode: Pause time: Value i ` s o ' o o i MRM Negative Profile 5 milliseconds Masses requested: Qsaiosca: n) QEnuien Qruea ssaslim) Q0u5is iom ksy o@a 2 D=aiTie DEeS Tine 000107 ANALYTICAL METHOD Page 120f 13 Method No.: BACG-3548 Title: DPreetpearrmaitniaotnionanodf PAenrafllyusoirsoocbtyaneHcParLboCxalMaatseisnMSpoenckteryomSeterryu/mMaasnsd USrpineec:trSoammeptrlye (HPLC/MS/MS) ---- e m ee 80 CALCULATIONS 81 ttAihtmeeIt,Shpaeereaenkadcschoeafpptteah,belaaenn.daTlphyeteiacdkaalhtearimugnah,ytrabenevdispemweoaoektaahcrheedcaahdsreaotpmeparrtmoiporngiaratatimeo.ntooFfeotnrhsqeutureeasnttthaeirttriaecttleieaauotnsinode,n the ion profilesatthe following mass-to-charge ratios: AnPaFlOyCte PFHS I4o1n2Pr9o1f0i3l6e89 3989103989 82 P(lPoFtHSt)hefpreoamkalalrsetaanrdeasrpdosnsveerosfusPtFheOcCondcievnitdreadtiobnyoftthehepetaekstaarretiaclreesinptohnessetaonfdtahredsI,S Alfitteomfatthievdealtya,t(hce.pg.e,aqkuhaedirgahtticsmfiat ywbeieguhsteeddiwnistthea1d/ocfonpceeanktarraetiaosn.ofOthbe ttetshtebaaretsictilceuornrvae cquuradvreataincdiitt).maNoyteb:e Tnheecbeessstarcyutrvoehfaitvmeamyobreedtehpaennodennetsotnatnhdearradncguerovfetfhoerstvaanrdiaoruds concentration ranges using the following: y=ad+bx+c whete y= PethaekIhSe(iPghFtHrSe)spionnssteanodfarPdFs.OCdividedbypeakheightresponseof x= a,b,c Concentration of the = Constants derived PFOCin from the standards. regression analysis. 8:3 CUosrirnegctthtehesrteasnudltasrdofcusravmep,lecsalfcourlaatney the level dilutions. of PFHC in each unknown sample. 000108 Page 13 of 13 ANALYTICAL METHOD Method No.: BACG-3548 Title: -_ Determination of Perfluorooctanecarboxalate in Monkey Serum and Urine: Sample Preparation and Analysis by HPLC Mass Spectrometry/Mass Spectrometry (HPLC/MS/MS) NOTE: Due to unresolvable interferences with the test article and/orinternal stdaisncdraertidofnrooftmthheesmuapterrivxi,seixntgemrnaaslsstspaencdtarrodmqeutarnitsitt.ation may be usedatthe 9.0 9.1 10.0 10.1 ACCEPTANCE AND REJECTIONCRITERIA Refer to SOP SRI 91-3 for acceptance/rejection criteria except acceptable accuracy for standards is 80-120% of theoretical. REPORTING Results of reports are all to analyses are tabulated, and the be filed in the appropriate study raw file. data, original chromatograms, and Greg6ryS. Gorman, Ph.D.,StaffChemist Bioanalytical Chemistry Group Approved by: sD. Jol lytical IS, MBA, Manager `mistry Group Date A daopee Date 000109 Method No: BACG-3606 ANALYTICAL METHOD Page lof14 Tite: DPreetpearrmaitniaotnionaondfPeArnfalluyosrioshebxyaneHsPulLfConaMtaesisn MSoprekcetyroSmeertruymMaansds UrSipneec:trSoammeptlrey (HPLC/MS/MS) -------- 10 PRINCIPLE SPeerrfulmuroohrexuarnienseulfsoanmaptlee(sPFarEe).obTthaeinsedefrroofmuurcimynneo(mcogl,g0u.s5mmLon)kceoysnttraeaite(ndPiFwniStg)h sisamfporlteisfiaedrewitthhenamniixnetderwnailthsatanndaiornd-p(IaSi)r,inPgerrefalgueonrto,ocbiuafnfcecraarbnodxwaaltaeter,(fPoFOlCl).owTbehdye acreeetcxaontsett,iftirultwteiaedrtehicdne,ta9htny5dl%iatcrmeoaetnatsthnfeae.nrTorelhdetceootnhatayuiltnaoicsneagtmap1t.le5elra%yveirfaolirsm,riaecnmaodcvaiednd,a,l5eyvz%aepdoSrbamytMeHdPatmoLdmCroynnMeiasussm,s f`rSopmecatbrooumettr5yt/0Ma2s0s,0S0p0ecntgr/ommeLtorfy (PHFPHLSCi/nMsS/MeS).ranTdhuferrmoamng1e0otfroe5li0a0blnegre/sumlitLsnexurtienned.s `SwaitmhpclesoconnbtltaainnrkinmgoaPtrFliHxSsoattchoanctehnetcroantcieonntsragrteiaotnerotfhPaFnH2S0,w0i0l0l nbegw/imtLhimnatyhebeadnigleuotefd reliable results prior to analysis. TThheemiaosnsspsrpaeycstoruormceetvroylotfagPeFiHssSeatnadt -P2F0O0Civoslatcscwohmipclhiisshleodwienntoheugnhetgaotgirveeatiloynrmeodduec.e the formation ofother potentially interfering ionsextractedfromthematrix. inCcAluUdTiIngObNl:oodS,ipncleapsrmiamaantedsmsearuymc,ararryetoa nbuecmobnesriodferzeodoansobsieosh,aazlalrudnsparnedshearnveddletdiswsiuets, uprnoicveedrusraelsptroecbaeuutsieodnsw.heRnefhearndtloiSngOuPnpnruemsbeerrveSdRpIri2m-a5t-e5tifsosruea. description ofsafety 20 REAGENTS AND SOLUTIONS Thelistedreagentsortheir equivalents maybeused. 21 Neat Reagents 211 Water, deioannidozrgeandi fre (fromin-house purificasytsiteonns;e.g, Ingalls 210N) 212 Methanol, HPLC grade 000110 ANALYTICAL METHOD Page2of14 Method No.: BACG-3606 Title: PDreetpearrmaitniaotnioanondfPeArnfalluyosrioshebxyaneHsPulLfConaMtaesisn MSopnekcetryoSmeerturymMaansds UrSipneec:trSoammeptlrey (HPLC/MS/MS) _--m--m------------------------------ 213 Perfluorohexanesulfonate (analyte), as providedbythe client 214 Perfluorooctanccarboxalate (intemal standard), 97% 215 Ammonium acetate, HPLC grade 216 Blankcontrolmonkeyserum 217 Sodium Carbonate, Certified ACS Grade or equivalent 218 Sodium Bicarbonate,Certified ACSGradeorequivalent 219 Ethyl Acetate, HPLC grade 2110 Tetrabutylammonium Hydrogen Sulfate, Aldrich 97% 2111 Sodium Hydroxide 50% solution, Certified grade or equivalent 2112 Blankcontrolmonkeyurine 2113 Formic Acid, 88% 22 Prepared Solutions Appropriste changes in the solutions may be made at th discretionofthe analyst 221 5mMAmmaceto atein norgai nicfu reewm ater 2211 Fionroerxgaamnipcl-ef,rteeopwraetpearre(e4.lgi,te4rs1,)m.easMuirxeowuetllamamnodnfiiulemratchertoautgeh(eH.Pg,LC1.5m4o2bgi)laenpdhaadsde filtration apparatus. 222 TBA lon-Pairing Solution (0.5 M tetrabutylammonium hydro.xide) 000111 Page3of 14 ANALYTICAL METHOD Method No.: BACG-3606 Title: PDreetpearrmaitniaotnioanondfPeArnfalluyosrioshebxyaneHsPulLfConaMtaesisn MSopnekcetryoSmeerturymMaansds UrSipneec:trSoammeptlrey (HPLC/MS/MS) _--mmm-- 222.1 hFoyrdreoxgaemnplsuel,fattoepirnepdaerieon2i5zemdLw,adtiesrsaolnvdeaadpjpursotxtihmeapteHlyto4.1204wgiotfht5e0t%raNbuatOyHlasmomloutniiounm. Note: a more adjustments. dilate solution of NaOH in water may be used toeffect smaller pH 223 Carbonate/Bicarbonate Buffer Solution for Serum (0.25M/0.25M) 223.1 aForpexapmplre, t2oo.p1rx0egpaoirfes1om0d0imuamL,btidciasersbolovnleataeypiprnox1i0m0amteLloyf2d.6e5 igoofsnoidwziauteemdrc.aMriboxnwateellantdo ensure complete dissolution. 224 Carbonate/Bicarbonate Buffer Solution for Urine (1.0M/1.0M) 2241 Faoprperxoamxpilmea,tte8ol.py4regpoarfeso1d0i0ummLb,idciasrsboolnvaetaepipnro1x0i0mmatLeloyf1d0e.6igoofnsiowdzaiteuemrd.caMrbioxnawteellantdo ensure complete dissolution. 30 INSTRUMENTS, MATERIALS, AND APPARATUS The following or their equivalentsmaybe used. 31 HPLC pump(s), autosampler, and triple quadrupole mass spectrometer 32 Autosampler vials with inserts 33 Vortex mixers (e.g, touch mixer and IKA-Vibrax platform mixer) 34 Solvent-concentration apparatus (e.g., Zymark Turbo-Vap with sourceofnitrogen) 35 HPLCmobile phasefiltrationapparatus 36 Filters for HPLC mobile phase filtration apparatus (c.g, Nylon-66, 0.20 um) 000112 ANALYTICAL METHOD Pagedof 14 Method No.: BACG-3606 Title: `PDreetpearrmaitniaotnioannodf PAenrafllyusoirsohebxyanHesPuLlfConaMtaesisn MSopnekcteryomSeetrruym/Maansds UrSipneec:trSoammeptlrey (HPLC/MS/MS) --_---- 37 Analytical balance 38 Volumetric flasks (.g., 10 and 25 mL) 39 Disposable Pasteur pipettes 310 Micropipettor(s) with tips 3.1 Culturetubeswithteflon-linedcaps . 312 Cemifuge 313 Assorted glassware and syringes 3.14 Culture tubes (vials) for use with solvent-concentration apparatus 315 1m Plasticsyringeswith 0.2 pm PVDFsyringe filters 316 Variablespeedhorizontal platform shaker 317 pHumeter 40 PREPARATION OF STOCKS AND WORKING STOCKS oApfptrhoeprainaaltyescth.anAgcetusialntdihleuctoinocnsenwtirlatbieondsoocfutmheenstoleudtoionntshmeapyrebpearmaatdioenasthteheetsd,iscretion 41 Main Stock SolutionofPFHS ~1000 pg/mL. #411 Pacrceupraarteelaynwe~i1g0h00abpougt/m1L0msgoluPtFiHonSoifntPoFaHS10i-nmLdevioolnuimzeetdriocrgfalnasikc)-.freAeddwadteeiron(iez.egd, organic-free watertodissolve.Dilutetothemark. Altemativly, weigh the compound 000113 PageSof 14 ANALYTICAL METHOD Method No: BACG-3606 Title: DPreetpearrmaitniaotnioanondfPAenrafllyusoirsohebxyaneHsPulLfConaMtaesisn MSopnekcteryomSeetrruym/Maansds UrSipneec:trSoammeptlrey (HPLC/MS/MS) --mmm iwnattoear.naMpiprxowperlila.teTrveasnssefler(et.hge.scoulluttuiroenttuobae)claenadnavdedss1el0idmfeLsoifrdeedi.onized organic-free 42 Stock SolutionofInternal Standard (PROC), ~200 pg/mL, 421 `Pwreeipgahreaabonu~t21000mpgg/imnLtosoaluSt0io-nmoLfvPoFluOmCetirnidcefiloansikz)e.dAordgdandiec-iforneiezewdatoerrgaen.igc,.farceceurwaatteelry ttohdeiscsoomlpvoeaunndddiilnuttoetaotahneampaprrokpwriitathedevieosnsiezled(eo.rgg.a,niccu-ltfurreeewtautbeer).Aalntderaatdidve5l0y,mweLigohf deionized organic-free water. desired. Mix well. Transfer the solution to a clean vessel if 43 `Spiking solution of Internal Standard (PFOC), ~ S0pg/mL 43.1 2Pm repaoreftaL hne~25000gp/g/mmLLssoluotiloniounfttoPaFiOcuClotiunnrdeetiuobneizaenddoardgadni6cm-Lfroeefwdaetieornibzyepdipweattteirn.g Mix well. 44 `Working Stock Solutionsof PFHS 44.1 Ttoabpler.epParreepwaorrekiinn1gs0t-omcLksvoolluutmieotnrsi,cmfalkaesktshoerprotohpeerradpiplurtoipornisataessghlaoswsnwairnet.hIeffdoelsliorweidnga `modifieddilutionschemecanbe usedand documentedinthestudyrecords. 000114 ANALYTICAL METHOD Page6of 14 Method No.: BACG-3606 Title: mee DePtreepramriantaiotnioanonfdPeArnfalluyosrioshebxyaneHsPulLfConaMtaesisn (HPLC/MS/MS) `SMpoenckteryomSeetrruym/Maansds Urine: Sample Spectrometry FE ome E [ey `Approximate Concentration [ [c s ooa oesosmooowwolsm wcsm m mrwmomoammwa rmommmoooammomwo o mmoansommage|| | | | || 0 m0 ow 0 s g eoe] ] ] ] w] ] a ]]]n] (ng/mL) `Volume of PFHS solution Final Volume in deionizeodrganic free water (mL) 000115 Method No.: BACG-3606 ANALYTICAL METHOD Page Tof 14 Title: mes Determination of Preparation and `APnearlfylsuiosrohbeyxanHesPuLlfConaMtaesisn (HPLC/MS/MS) Monkey Serum and SpectrometryMass Urine:Sample Spectrometry 442 Summaryofconcentrationsofserum standards: Standard Level Volume and Spike Conc. Approximate `Concentration of 'PFHS in serum (ng/mL) [To otowtmoosom||rsrnooamgr|] : | [ |orein m|| gaaw m0e]] Tr [omosa|smsgmm] To| oirossorsomngn| | 0] ] iomo0 rioiwomngns] |20] CToowmeasn | |0] ] 000116 Method No: BACG-3606 ANALYTICAL METHOD Page8of14 Title: Determination of Preparation and PAenrafllyusoirsohebxyanHesPulLfConaMtaesisn Monkey Serum and Spectrometry/Mass Urine: Sample Spectromenry (HPLC/MS/MS) _--_--mnmm 50 PREPARATION OF SPIKED STANDARDS AND BLANKS oApfptrhoeprainaaltyescth.angesintheconcentrations ofthesolutionsmaybemadea thediscretion 51 bMaeunlaatlniyapzlleyedzw(eieditgfh.deeaasbciohruetsdte.htroefeu)nsketnsoowfmmsaatmrpilxesst.aAndamradtsraixnddouabmlaetbrliaxabkl(abnlkan(kIbS)l+maaIySn)aalkrseo 52 pIainpptpoertoip1nrd0iiakvtLie.duovafololr~ugma2ne0iac-s.mfdrecesueclwrtaiubtreeedtiiunnbsettshe,eapdtioapfbelttehbaelbaownvokermkfaiotnrrgiexsatc(ohec.ksgt,saon0ld.ua5tridmo.nL.)F.orPtihpeetbliannktsh,e oorfgianntiecm-aflrseteawnadtaerrdisntsotcekad()~a5n0duvgo/rmtle)xftoore~a5chsteucbonedse.xceptthe blankIS Addthe 10 I. (pipet 10 of 53 osForolgruastneiiorcnu,fmr1eemsawLamotpelfre.0s.aV2do5drMtt/eh0xo.fe2oa5lcMlhoctwauirbnbegotnfaootreea/abbcoihuctatrubboesn:eacto5en0bd0usf.Lfero,fatnhde1TmBLAoifodne-ipoaniirzienyg. `foclalrowbiongnatto ee/abchictaubbruebffo1enrmaLtnedo1fmTLBoAfdieoino-npiazireidnwgatseorl.utViFooonr,rteu1xrimenaeLcshtaomufpble1ef.so0rMaa/db1do.tu0htMe 5 seconds. 54 Asdettdin2g..5mLofethylacetateandextractonhorizontalmixerfor |hourat a low speed 55 Remtohevtubee `minutes. fomtheshakerandplacein acentrifuge (e.g, 2500 rpm) for abou5t 56 Re(m8o,v~e5t0hemtionputeetshiynlatcheetTautrebloay-eVraapndp)uwtitthiantgoenatclleesatnrteuabmeoafnnditervoagpeonraatnedtomdordyenreastse heat (e.g., 50C). 000117 ANALYTICAL METHOD Page9of 14 Method No.: BACG-3606 Title: Determination of Preparation and PAenrafllyusoirschebxyancHsPulLfConaMtaesisn Monkey Serum and Spectrometry/Mass Urine: Sample Spectrometry (HPLC/MS/MS) ---- 57 Rceocnotnasitniitnugt1e.t5h%e froersmidiuceacinid5a0n0dkvLorotfex5br%ie5flmytMo amimxm.oFnilituermthaecetsaatmep:l9es5%thmroeutghhan0o.l2 umPVDForNylonsyrifnilgteres intoautosamplervials. 60 PREPARATION OF SAMPLES 61 Avlilgoorwoeusalcy.hsPeruimaspnaamlepilqeuttototohfaewacthosraomopmlete(mep.egr,a0t.u5rmeL.)iVnotrtoeixnedaivcihdsuaalm~p2l0eb-rmiLefcluyl,tbuurte `teuxbpeesc.teIdcfonnceecnetsrsaatriyo,ndiolfuttheeatnestaartlicleiobefiqanngauynsaalomyzpteldewwiillthfalbllwaintkhimntahtreicxonscoentthraattitohne ratunbgeeaonfdthvoerstteaxfndoarrdaccuoruvpel.eoAfddsec1o0npdLs.ofinternalstandardstock (~ 50pg/mL)toeach 62 For serum solution, 1 smaLmoplfes0.a2d5dM/t0he.2f5oMllcoawribnognattoe/cbaicchartbuobnea:te50b0ufifeLro, fatnhde1 TBA mLof fon-pairing deionized organicfrocwater. following to each tVuobrete1xemacLhtoufbTefBoAraiboonu-ptai5rsiencgosnodlsu.tiFoon,r ur1inmeLsaomfpl1e.s0aMd/d1t.h0eM Scasercbonodns.ate/bicabrubfofenraatned 1mL ofdeionized : water. Vortex each tube for about 63 Add2.5 setting. mLofethyl acetateandextract on horizontal mixer for1 hour at a low speed 64 R`mineutesm.theotubvefreomtheshaankdpelarce in acentrifuge (e.g. 2500 rpm)for about 65 Re(moev~e5.t0hmeigtnoupt,eetshyilnatcheetaTtuerlbaoy-eVraapndp)uwtitithiatgoenatclleesanttubreoafnednietavraopgmeonraatnetdmooddreyrnaetses heat (e.g, 50C). 66 Rcoenctoanisntitnugt1e.t5h%e froersimdiuceaciind5a0n0dvuoLrtoefx5b%ri5efmltMyo maimx.moFniiltuermtahceetsaatmep:l9es5%thrmoeutghhan0c2l 1m PVDForNylonsyringe filters into autosampler vials. Capvials for analysis. 000118 Method No.: BACG-3606 ANALYTICAL METHOD Page 100f14 Title: DPreetpearrmaitniaotnioanondfPeAnrafllyusoirsohebxyaneHsPulLfConaMtaesisn MSopnekcetyroSmeertruymMaansds UrSipneec:trSoammeptlrey (HPLC/MS/MS) _--_--m 70 ASNPAELCYTSRIOSMBEYTHRIYG/HMAPSESRFSOPREMCATNRCOEMELTIQRUYI(DHCPHLCR/OMMSA/TMSO)GRAPHY MASS 71 Conditionsaretobeoptimized ifnecessary. 7.11 HPLCConditions Analytical Column: Keystone ScientificAquasil C18, 150mm x 2mmID,orequivalent Guard Column: Elution Flow rate: Injection volume: Mobile phase: Keystone Aquasil C18 600 pL/min. 10mx 2m mm suL AB::1.S5m%Mfoarmmmiocnaciiudmiancmeteattheabnuoflfer Gradient Profile: Temperature: 0-3min. 3-5min. S-8min. 8-10min. Ambient S50%A:S50%B 2800%B l% ineaA rgrad: ient 10%A:ste9pg0ra%dieBnt SO%A : SO%Bstep gradient 7.12 SPoEfStcwaireex:APPIE3S0c0i0exTTruiprlbeoQQuuaadnrupoleMass SpectrometerConditions TNotue: rVablSupeorsayliisStooeudruncnede table. r "MS /MS Acquisition Conditions" overri de p a r a m e t e r s in this AuxiliaryGas: Air (e.g., Grade 0.1)at 85popuersnquadreisnch Parameter Value 3 2000 000119 ANALYTICAL METHOD Page 11 of 14 Method No.: BACG-3606 _--_--m(HPLCMSIMS) Title: Determination ofPerfluorohexanesulfonate in Monkey Serum and Urine:Sample Preparation and Analysis by HPLC Mass Spectrometry/Mass Spectrometry Parameter Value Ne 0 TEM 450 OR -20 RNG "120 Qo 10 Q1 1 ST 15 RO1 11 Q2 20 RrOZ 50 ST3 60 RO3 52 DF 250 EM 1800 NEB 15 cur 6 CAD 5 QE 0 POL 1 vem ' : 000120 Page 120f 14 ANALYTICAL METHOD Method No: BACG-3606 Title: DPreetpearrmaitniaotnioannodf PAenrafllyusoirsohebxyaneHsPulLfConaMtaesisn MSopnekcteryomSeetrruym/Maansds UrSipneec:trSoammeptlrey (HPLC/MS/MS) --_--mnmm Parameter Value PE 0 Scan type: MRM Polarity: Acquisition mode: Pause time: Masses requested: prs: O9L8M9ass(unm) Negative Profile S milliseconds M398e9 s) PFOC(S) OL2M9as (unm) RDOa2me R0133 1 RsOtI 1 3Q6M8a9ss(ems) 3Ssar S35m I7 r3 1I8] 118 221 221 Duell2T0ieng) D2u0 Time(s) 000121 ANALYTICAL METHOD Page 130f 14 Method No. BACG-3606 Title: PDreetpearrmaitniaotnioannodfPeArnfalluyosrioshebxyaneHsPulLfConaMtaesisn Monkey Serum and Spectrometry/Mass Urine: Sample Spectrometry (HPLC/MS/MS) _--_--m 80 CALCULATIONS 81 Aptaectaochkpseiheaabnpldeeo.,faTnthdhepeaednaaatklayhtmeiiacgyahblteaunnsd,mrpeoevoaitkehwaeredeaaacdsheactpehprrrmooimpnraaittaiotogenr.aomfFttohoreetqneussautnratreitttiahctlireoeant,nednuttsiheoentIhtSeimfaoerne,. profiles at thefollowingmass-to-charge ratios: PAnFaHlySte PFOC I3o9n8Pr9o1f0i3l9e89 4129103689 82 PflrootmthaelpleasltaanrdeaarrdsesvpeornssuesofthPeFHcSondcievnitdreatdiboyntohfeptehaekafersetaraertsipcolensienoftthehesItSan(dParFdOs,C) Aqlfiuttaedomrfaattthiievcedfliatyt),a.t(hNeeo.pgt.ee,:aqTkuhhaederibagethsittcscmfuiatrywvebeiefiguthstmeeaddyiwnbisetthedae1dp/ocefonnpdceeenanttkraoarntetiahosne.orfaOtnhgebeotfettsththeabearetssitctialencduonarrrvdea cucornvceenatnradtiitonmraayngbeseunseicnegstshaeryfotlolohwianvge: morethanonestandardcurve forvarious y=al+bx+c . where y= PethaekIhSe(iPgFhtOCr)einsstpanoodafrndPssF.HoSdividedbypeakheightresponosef x= b,c =CCoonstnancts edeorfnitvehtdefPrrFoHmaSthietnrsetgiarnedosasridnosn.analysis. 83 Uthseinregsutlhtesostfasnadmarpdlecsurfvoer,acanlyoudlialutteitonhse.level ofPFE in each unkuown sample. Correct NOTE: Dfruoemttohuenmraetsroilxv,aebxlteienrtnearlsfetraenndcaersdwiqtuahntthietatteisotnarmtaicylbeaenuds/eordiantttehrenadlissctraentdiaornd ofthe supervising mass spectrometrist. 000122 Page 140f 14 ANALYTICAL METHOD Method No: BACG-3606 Title: DPreetpearrmaitniaotnionaonfdPeArnfalluyosrioshebxayneHsuPlLfConaMtaesisn MSopnekcetryoSmeertruymMaansds UrSipneec:trSoammeptlrey (HPLC/MS/MS) --_--mm 90 ACCEPTANCE AND REJECTION CRITERIA 91 Refer to SOP SRI 91-3 for acoeptancelrejection standards is 80-120%oftheoretical. criteria except acceptable accuracy for 100 REPORTING 10.1 Reasreulttosbeoffalleldanianltyhseeaspaprreoptrabiualtaetesdt,uadnydftilhee. rawdata,originalchromatograms, and reports Author(s): on - l St. Research Associste Bioanalytical Chemistry Group Approved by: Greg PhD. `MBainoaangaelyrtical Chemistry Group Date"2/72/63 9/5/03 Date 000123 ANALYTICAL METHOD Page1of13 Method No.: BACG-3607 Title: PDreetpearrmaitniaotnioannodf PAemrafllyusoirsoocbtyaneHsPulLfConaMteasisn MSopnekcetyroSmeerturmyMaansdsUrSipneec:trSoammeptlrey (FHPLC/MS/MS) _--_--mnm 10 PRINCIPLE PeiSrseflrfouuromtriofiooecrdtawunireitsnhuelafnsoanimanpttleee(msPalFOasrSte)a.nodTbahtradeisn(1eSde), fPrroeorrmfuulrucimoynrneo(oocmetogal.ngeu0cs.a5rbmmooLxna)lkcaetoyesnttraeait(endPiFwOniStgh) esamxpltes rawrieatthhceetnthymliiaxceeotdatnwei.tThhaenetihoynl-paacieitantgelraeaygeernits,rbeumfofveerda,nedvawpaotreart,(ePdfOotCold)lro.ywneedTshbse,y Sracepecetocanttsret,oimtfeuittletrdeyr/eiMdn,a9sas5nSd%ptemrceattnrhsofamenerotrlredyco(tnoHtPaaLiuCntio/nsMgaSm/1p.Ml5Se)r%.vifaolrsm,iacnadciadn,a5ly%zedSbmyMHaPmLmConMiaass, fSraommpalbeosucto2nt0ationi1n0g,P0F00OSnga/tmcL.oofnPcFeOSnitnrsgearretautimearoTtnhhndeafsnrroa1nm0g,e0o100f0rtn oel5ia0bg 0lnemrae/ gsyubl/tiem sndemixultrL ueiLtnnededs. iretlihabcle oresnubltltsapnrrkimoraottroliaxnasloystihsa.ttheconcentration ofPROSwillbewithintherange of tTh`ThehfeeomriaomnsastsipsorpaneyocsftoruoortmcheeetrvrpoyolottfeangPteiFiaOsllSsyeiatnanttder-Pf2Fe0rO0i0Cnvgoilisotanscswecxhotmirpcalhcitssehdelodfwinetnrthoheuegnohemgattaortgmiirxve.eatiloynrmeodduec.e inCucnAliuUvdeTirInsgaOlNblp:oroeSdci,anupctleaisoptnrnsia.maantRedessfeemrrauytmo,cSaarrOrePy 9ambnueumcmbobenersriSdoRefIrzeo2do-an5s-ob5sieofsoh,raazalaldruednsspcarrniedpstheiarovnneddletidswsiuets,, procedurestobeusedwhenhandlingunpreserved primatetissue, of safety 20 REAGENTS AND SOLUTIONS The listed reagents or their equivalents may be used. 21 Neat Reagents 211 Water, deionizedandorgani fre (fromin-housepurificationsyste;e.g, Ingalls210N) 212 Methanol, HPLC grade 000124 ANALYTICAL METHOD Page2of13 Method No.: BACG-3607 Title: PDreetpearrmaitniaotnioannodf (HPLCMS/MS) PAenrafllyusoirsoo cbtyan eHsPulLfCon aMteasisn MSopnekcetryomSeetrruym/ Maansds UrSipneec:tSraommeptlrey _--_--m 213 214 215 2.16 217 218 219 2.1.10 211 2112 21.13 22 221 2211 222 Perfluorooctanesulfonate (analyte),asprovided by the client Perfluorooctanecarboxalate (internal standard), 97% Ammonium acetate, HPLC grade `Blank control monkey serum Sodium Carbonate, Certified ACSGradeorequivalent SodiumBicarbonate, Certified ACS Grade orequivalent Ethyl Acetate, HPLC grade `Tetrabutylammonium Hydrogen Sulfate, 97% Sodium Hydroxide 50% solution, Certified grade or equivalent `Blankcontrol monkeyurine Formic Acid, 88% Prepared Solutions Appropriatechangesinthesolutionsmaybemadeatthediscretion ofth analyst 5 mMAmmoniumacetatein organic free water Siltration apparatus. For example, toprepare 4liters, measureout ammonium acetate (e.g.1, .542g)andadd in organic-free water (e.g., 4 L). Mix well and filter through HPLC mobilephase `TBA lon-Pairing Solution (0.5 M tetrabutylammonium hydroxide) 000125 Method No: Title: _--_-- ANALYTICAL METHOD Page3of 13 BACG-3607 DPreetpearrmaitniaotnioannodf PAenrafllyusoirsoocbtyaneHsPulLfConaMteasisn MSopnekcetryomSeetrruym/Maansds UrSipneec:trSoammeptlrey (HPLCMS/MS) 222.1 223 223.1 224 224.1 30 31 32 33 34 35 36 iFnordeexioanmipzleed,watotperreapnadraed2j5usmtLt,hdeispsHolvtoe 41.02w4igtohft5e0t%rsNbautOyHlasmolmuotnioinu.m hydrogen sulfite Note: 2 more adjustments. dilute solutionof NaOH in water maybe used to effect smaller pH Cabonate/Bicarbonate Buffer SolutionforSerum (0.25M/0.25M) F`oraexapmplpe, rt2o.p1or0epgxaorefis1o0dm0imuLam,bidtciasrseboolvnleataepyiprnox1i0m0amteLlyo2f.d6e5iognoifzsedodwiatuemr,caMrbioxnawteellantdo ensure complete dissolution. Carbonate/Bicarbonate Buffer Solution for Urine (1.0M/1.0M) Faoprpreoxximaatemltypop8.l4reepgoar,feso1d0i0ummL,bidicsasroblvoenaapitprenox1i0m0amtLeloyf1d0.e6igoofnsoidwziautemedrc.aMrbioxnwaetellantdo ensure complete dissolution. INSTRUMENTS, MATERIALS, AND APPARATUS The following or their equivalentsmaybe used. "HPLC pump(s), autosampler, and triple quadrupole mass spectrometer Autosampler vials with inserts Vortex mixers (e.g. touch mixer and IKA-Vibrax platform mixer) Solvent-concentration apparatus (e.g., Zymark Turbo-Vap with sourceofnitrogen) HPLC mobile phase filtration apparatus Filters for HPLC mobile phase filtration apparatus (e.g, Nylon-66, 0.20 um) 000126 Page dof 13 ANALYTICAL METHOD Method No.: BACG-3607 Title: Determination of (PrHePpaLrCatMiSon/MaSn)d Perfluorooctanesulfonate in Analysis by HPLC Mass Monkey Serum and Spectrometry/Mass Urine: Sample Spectrometry _--mmmm---------------- 37 Analytical balance 38 Volumetric flasks (.g., 10 and 25mL) 39 Disposable Pasteur pipettes 3.10 Micropipettor(s) with tips 311 Culture tubes with teflon-lined caps 312 Centrifuge 3.13 Assorted glassware and syringes 3.14 Culture tubes (vials) for use with solvent-concentration apparatus 315 1 mL Plasticsyringeswith 0.2 pm PVDFsyrifnilgteers 3.16 Variable speed horizontalplatformshaker 37 PH meter 4.0 PREPARATION OF STOCKS AND "WORKING STOCKS a1 ApoMpfatrihoneprSaintaaoltcyekscthS.aolnAugctteiusoainlnodtiflhuPetcFiooOnncSsew~nit1lr0la0tb0ieodnposgoc/fumtmLhe.entsoeldutoinotnshmeapryebpearmaatidoensahteehtesd,iscretion 411 oParcrgceaupnraiarcte-eflaryenewe~wi1ag0the0r0atbopoudtigss1mo0lmvsego.lDPuitFliOuotnSeotifonttPohReaOmSa1r0ki-.nmLdAelvitooelrnuuimazeietvdreilocyr,gflawanseikic).g-fhrAteddwadteeiron(iea.egg, he compovad 000127 Page Sof 13 ANALYTICAL METHOD Method No.: BACG-3607 Title: PDreetpearrmaitniaotnioanondf PAenrafllyusoirsoocbtyaneHsPulLfConaMteasisn MSopnekcetryoSmeetrruym/MaansdsUrSipneec:trSoammeptlrey (HPLC/MS/MS) _----- iwnattoera.n Mapipxrowperlila.teTrvaensssefler(ct.hge.scoulluttuiroenttuobae)claenadnavdedss1el0mifdLeosfirdeedi.onized organic-ree 42 Stock SolutionofInternal Standard (FOC), ~200 pg/mL 421 P`wreeipgahroabaonu~t21000mpggfiunltosoaluSt0io-nmoLfvPolOumCetirnidcefiloansikz).edoArdgadnidce.iforneiezweadotregra(nei.cg..farceceurwaatteelsy tthoedcisosmoplvoeuannddidnittoetaoatnheampaprroiprwiiatthedevieosnseilze(dco.rgg,acnuicl-tfurreeetwautbeer).aAnltdeamadtdive5l0y,mweLioghf deionized desired. organic-free water. Mix well. Transfer the solution to a clean vessel if 43 Spiking solutionofInternal Standard (PFOC), ~ S0pig/mL 431 P2rmepLaorfetahne~20500ggi/lm.LssoloutliounoitfntPioFoaOcnCulitnurdeetiuonbiezaenddoragdadn6cm-Lfroeefdweioanbizytepdiwpeaettterirng Mix well. 44 `Working Stock Solutions ofPFOS 44. Ttoablper.ePpraerpeawroerikinng10s-tomcLkvsoolluumtieotnrsi,cmfalkasektshoeroptrhoepreradpiplruotpiroinasatesgslhaosswwnairnet.hIeffdoelsloiwrien5dg `modified dilution scheme can be used and documented in the study records. AWpoprrkoixnigmSattoecCkoLnecveenltr(aWtiSoLn)| (ug/ml) Volume ofPFOS solution| Final Volume in deionized organic free water (mL) salotiooougnt |10| sulotstoooorgmt | 10 | 000128 Page6 of 13 ANALYTICAL METHOD Method No.: BACG-3607 meesosomosonswonollllsssmmrmmowmmumeateomrooomsmmmmrmnwmoeamesoatom|[ | | ||[mm| n0 mm0 0 e r5us] e] m] e] ] ] ] ]eaa `Title: PDreetpearrmaitniaotnioannodfPeArvfalluyosriosocbtyaneHsuPlLfConaMteasisn Monkey Serum and Spectrometry/Mass Urine:Sample Spectrometry (HPLC/MS/MS) 442 Summaryofconcentrationsofserum standards: Standard Level Volume and Spike Conc.| Approximate Concentration of PFOS in serum (ng/mL) o Tiowumomgn [=5]Lio[onwovamassaes||| wo| o o ||ozo Page 7 of 13 ANALYTICAL METHOD Method No.: BACG-3607 Title: mes DeterminationofPerfluorooctanesulfonate in Monkey Serum and Urine:Sample Preparation and Analysis by HPLC Mass Spectrometry/Mass Spectrometry (HPLC/MS/MS) [(F_ oom | sm] TooTo[ouonssommero||0nwn] ws] CTioowoprommmm|| 0] ] CcTom momgnr 5] 5.0 PREPARATION OF SPIKED STANDARDS AND BLANKS Appropriate changesinthe concentratoifotnhse solutionsmaybemadeatthediscretion of the analyst. 5.1 Multiple(e.g.,aboutthree)sets ofmatrix standardsand amatrixblank(blank +IS)are analyzed with each set ofunknown samples. A matrix double blank(blank-IS) `may also be analyzed ifdesired. 52 Into individual ~20-mL culture tubes, pipet blank matrix (eg, 05mL). Pipet in the appropriate volume as described in the table above foreachstandard. For `the blanks, o`pfipientte1r0naklLsotafnodragradnisct-ofcrke(ew~a50teprgi/nmsLte)atdooef atchhetwuobrekeixncgespttotchkesbollauntki-oInS.(Apdipdetth1e0 10p iL uL of organic-free`waterinstead)andvortexfor ~5 seconds. 53 For serum samples add the following to each tube: 500 Lofthe TBA ion-pairing solution, 1mLof0.25M/0.25M carbonate/bicarbonate `buffer, and 1 mLofdeionized `organicfreewater. Vortex eachtube for about 5 seconds. Forurine samples add the following to each tube 1 mL of TBA ion-pairing solution, 1 mL of 1.0M/1.0M carbonate/bicabrufbfoernaantd1e mLof deionizedwater. Vortexeachtu fob rabe out 5 seconds. 000130 Page8of 13 ANALYTICAL METHOD Method No: BACG-3607 Title: DPreetpearrmaitniaotnioannodf PAenrafliyusoirsoocbtyancHsPulLfConaMtaesisn MSopnekcetyroSmeerturmyMaansds UrSipneec:trSoammeptlrey (HPLC/MS/MS) _--mmmm--m--m--m-- 54 sAedttdin2g.,5mLofethylacetateandextractonhorizontalmixerfor | hourat lowspeed 55 Remove thetubefrom theshakerandplacein `minutes. acentrifuge (e.g., 2500 rpm) forabout 56 `Takeoffthetop ethylacetatelayerand putitinto acleantubeandevaporatetodryness (e.8,~50. `minutes in the Turbo-Vap ) with a. `gentle streamofnitrogen and moderate heat (e.g., 50 C). 57 Reconstitute the residue in 500 uL of 5% 5 mM ammonium acetate: 95% methanol `containing 1.5% formic acid and vortex briefly to mix. Filter um PVDF or Nylon syringe filters into `autosampler vials. the `samples through 0.2 6.0 PREPARATION OFSAMPLES 61 Avlilgoorwouesalcy.hsPeirpuemtsaanmaplilqeutoototfhaewacthosaromopmlete(mep.ge.r,a0t.u5rme.L)Voirnttoeixnediavcihdsuaalmp~l2e0b-rmieLflcyuf,btuurte etxupbeecs.tedIcfonnceecenstsraartyi,ondoifluttheeatnetaalritqiucolteboeifnagnaynaslaymzpeldewiwlitfhalbllwainthkimnatthreicxonscoenttrhaatttiohne `rangeof the standardcurve.Add10 WL ofinternalstandardstock tubeandvortex for acoupleof seconds. (~ 50 pg/mL)to each 62 For serum samples add the following to each tube: 500 uLofthe TBA ion-pairing solution, 1 mL of 0.25M/0.25M carbonate/bicarbonate `buffer, and 1 mLofdeionized cfoarorglbalononiwacitnfegr/ebteiocwaaertabecorhn.attVeuobbreutfef1xermeaaLncdho1tfumbTeLBofAfordeiaiobnoo-nuptiazi5eridsnewgcaotsneordl.su.tiVFooonr,rtue1rximenaeLcshaotmfupbl1ee.sf0oaMrd/a1db.ot0uhMte 5 seconds. 63 Asdetdtin2g..5ml. ofethylacetateandextracton horizontalmixerfor 1 hourat low speed 000131 ANALYTICAL METHOD Page9of 13 Method No.: BACG-3607 Title: DPreetpearrmaitniaotnio n of and. Perfluoro Analysis octa by neHsPulLfConaMteasisn Monkey Serum and SpectrometryMass Urine: Sample Spectrometry (HPLC/MS/MS) _--_--mnmmm 64 R`emminouvtees.thetubefromtheshakerandplacein a centrifuge (e.8., 2500rp form abou) t5 heat eg. 50C). 65 `Takeoffthetopethylacetatelayerandput itinto aclean tube and evaporatetodryness (e.g, ~50.`minutes in the Turbo-Vap ) with a gentle streamofnitrogen and moderate 6.6 7.0 7.1 711 Recconatnasitniitnugte1t.h5e%rfeosrimdiuce iacnid5a0n0duvoLrotfex5b%rie5fmlyMtoammixm.onFiilutemratcheetsataem:pl9e5s%thmreotuhgahn0o.l2 + wm PVDF or Nylon syringe filters into `autosampler vials. Cap vials for `analysis. ANALYSIS BY HIGH PERFORMANCE LIQUID CHROMATOGRAPHY MASS SPECTROMETRY/MASS SPECTROMETRY(HPLC/MS/MS) Conditionsaretobe optimizedifnecessary. HPLCConditions Analytical Columa: KeystoneScieutificAquasil C18, 150mm x 2mmID,orequivalent Guard Column: Elution Flow rate: Injection volume: Mobile phase: Gradient Profile: Temperature: Keystone Aquasil C18 10mx2m mm 400 pl/min. Sul BA:: 1S.m5M%foarmmmiocnaiciudm iancemteattheabnuoflfer 0-3min 3 - Smin. 5-8min. 8-10min. Ambient 50%A:SO%B 20% A : 80% Blineargradient 10%A : 90% Bstepgradient 50%A. : 50%Bstepgradient 712 SPoEftSwcaireex:APPEI 3S0ci0e0xTTruiprlbeoQQuuaadnrupole Mass Spectrometer Conditions 000132 Page 10013 ANALYTICAL METHOD Method No: BACG-3607 Title: DPreetpearrmaitniaotnioannodf PAenrafllyusoirsoocbtyaneHsPulLfConatMeasisn MSopnekcetyroSmeerturmyMaansds UrSipneec:trSoammeptlrey (HPLC/MS/MS) ------------------------eeee TNuortbeo:ioVnalSupersayliSsoteudrucned:er "MS/MS Acqision Conditions" override parameters in is Auxiliary Gas: Parameter I] NC TEM Or RNG Q@ Q1 sT ROI Q2 RO2 sT3 RO3 DF CEM Air (8, Grade0.1)at 85popuersnquadreisnch Value 2000 0 450 20 -120 10 1 15 1 20 50 60 52 250 1800 000133 MethodNo: Tite: _--_-- Page 110f13 ANALYTICAL METHOD BACG-3607 DP(reHetPpeLarrCmai/tnMiaoStn/ioManSn)odf PAenrafllyusoirsoocbtyaneHsPulLfConaMteasisn MSopnekcetyroSmeerturmyMaansds UrSipnee:ctrSoammepilrey PNaEraBmeter V1aslue Cur 6 cap 5 QE 0 , POL 1 vem 0 PE 0 s SPoclaamts.: MRM Negative APcqausisttiimoe:nmo$dmiel:liseconPdrosfile Massesrequested: OP9Lr8oM9sa:s arm) Q989M) Du2e0l Time(s) OPL9RMOaCsS)am) Q36M89wsem) DRoZoce 3San 3Ssop sROm} nsousw (R Q3t) Z B 1 o1s De0llTime(s) 000134 Page 120f 13 ANALYTICAL METHOD Method No. BACG-3607 Title: PDreetpearrmatiinoant.ioanndo.f PAenrafllyusoirsoocbtyaneHsPulLfConaMteasisn MSopnekcetryoSmeetrruym/MaansdsUrSipneec:trSoammeptlrey (HPLC/MS/MS) _--mmm ROi)I 21 21 80 CALCULATIONS 81 Apaetcactekhpsetheaabnpldeeo.,faTnthdhepeeadanatakalhymetaiicgyahbltearunnsd,mrpoeevoaitkehawerdceaaacdshecatpheprrrmooipmnraaiatttioeog.nroafmFttohoreetqneussautnartrietttiahctelieroaent,nednuttsiehoenthtISeeaior,ne, profiles at the following mass-to-charge ratios: AnPaFlOySte PFOC I4o9n8P.r9o1f0il4e989 4129103689 82 PfAlrltooemtrntaahlteilpvesetalakyn,atdrhaereapdrseveaeksrhespiugsoohttfhnsPemRsaOcyoeSnbdceeinvutisrdeaedtdiibnoysntotehfaedtophefaepketaeaskrtaeaarrreteaissc.ploeOnisnebotfhttethhseetbIaaSensd(aPrFdsO,C) qiutaodfrtahtiecdfaitl)a. (Neo.tge,:qTuhaedrbaetsitccfuitrvweeifgithtmeadywbiethde1p/econndceennttoanttiohneroftahenotfgesttheaertsitctialencodunrarrvd5e cu`crovnceeantnrdatiitonmraanygbeseunseicnegstshaeryftololohwainvge:morethan one standard curve forvarious y=altbrte where y= PtheeakISh(eiPgFhOtCr)esipnosntsaendoafrPdsR.OS divided by peak height response of x= b,c =CoCnocnesnttarnattsiodneorfivtehdefPrFoOmSthienrsetgarnedsasridso.n analysis. 000135 ANALYTICAL METHOD Page 130f 13 Method No.: BACG-3607 -------- Title: DPreetpearrmaitniaotnioannodf PAenrafllyusoirsoocbtyaneHsPulLfConaMteasisn MSopnekcetyroSmeerturmyMaansds UrSipneec:tSraommeptlrey (HPLC/MS/MS) 83 Utshienrgetsuhletssotfansdaamrpdlceusrvfeo,rcaalncyudlialtuettihonesl.evel ofPFHCineachunknown sample. Correct NOTE: `Dueto unresolvableinterferenceswiththe testarticleand/orinternalstandard offrotmhtehseumpaetrvriisxi,negxmtearsnsalsspteacntrdoamredtqruiasntt.itationmaybe used atthediscretion 92.0 ACCEPTANCE AND REJECTION CRITERIA 9.1 R`setfaenrdatrodsSiOs P80S-R1I209%1o-f3tfhoeroraectciecpatla.nce/rejection criteria except acceptable accuracy for 10.0 REPORTING 10.1 Reasreultotbseoffialeldainnaltyhseeasapreptarboulpatrsetdiu,adanydtfitlehee. rawdata, original chromatograms,andreports rubor: C br nAn Lori Coward, BS BSir.oaRneasleytairccahlACshseomciisattery Group Approve: 8 FAD. Manager "Lolo Date 5/5/60) Date 000136