Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub
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1 SUPPLEMENTAL MATERIAL Sistik P, Turjap M, Iordache AM, Saldanha H, Lemr K, Bednar P. Quantification of selected antidepressants and antipsychotics in clinical samples using chromatographic methods combined with mass spectrometry: A review ( (doi: /bp Supplemental Table 1 part 1 preparation (recovery mobile phase (ratio, v/v (detection mode, amisulpride, aripiprazole, zotepine (+ another 44 analytes Amisulpride (+ another 5 analytes (+ another 5 analytes Brain tissue Rat acetonitrile: methanol LLE, sample + sodium borate buffer, ph 10.2; extracted with tert-butyl methyl ether LLE, sample + 1M K 2 CO 3 ; extracted with diisopropylethe: dichloromethane, 1:1; (recovery: 82 85% LLE, sample + sat. aq. soln. Na 2 CO 3 extracted with methylene dichloride:pentane, 2:8 (recovery 82% LLE, sample + 0.5M Na 2 HPO 4, ph 10.69, extracted with isopropyl ether (recovery: % for all analytes LLE, sample + 0.5M Na 2 HPO 4, ph 10.7; extracted with isopropyl ether; (recovery 77% clonidine, methyl risperidone, methabenzthiazurone, A: MeOH B: 5mM acetate buffer, ph 3,9 N- methyl ziprasidone, 2mM NH 4 Ac in ACN : water (9:1 sulpride INS-RSP midazolam midazolam, 5 mm ammonium acetate (30:70, 0.65 mm ammonium acetate in water : MeOH : ACN (10:45:45, A: 5mM aqueous ammonium formate (ph 6.1 A: 5mM aqueous ammonium formate (ph 6.1 Chromolith Speed ROD C 18 ( mm, 5 µm, ambient temperature Symmetry C 8 ( mm, 5 µm Phenomenex Synergy Polar-RP ( mm, 4 µm Luna-C 18 ( mm, 5 µm, (37 C Atlantis TM dc-18 ( mm, 3 µm, (25 C Waters Atlantis TM dc-18 ( mm, 3 µm (CID mode, Q 3 (CID mode, Q 3 LC-APCI(+-MS/MS, (CAD mode, Q 3 (CAD, Q , internal standard; MS, mass spectrometry; PPT, protein precipitation; LLE, liquid-liquid extraction; ESI(+, electrospray ionization (positive ionization mode; APCI(+, atmospheric pressure chemical ionization (positive ionization mode; LC-MS/MS, liquid chromatography coupled with tandem mass spectrometry; CID, collision-induced dissociation; MRM, multiple reaction monitoring; CAD, collision-activated dissociation; Q 1, single-quadrupole mass spectrometer; Q 3, triple-quadrupole mass spectrometer. 1
2 Supplemental Table 1 - part 2. preparation (recovery Aripiprazole (+ another 3 analytes Ranolazine Diltiazem and 2 metabolites Aripiprazole, dehydro-aripiprazole Aripirazole, dehydro-aripirazole (+ another 9 analytes Aripriprazole In vitro sample Rat, brain tissue Dried sample dissolved in 1-chlorobutane: triethylamine, 5:0.5 (recovery % LLE, sample + 0.5M Na 2 HPO 4, ph 10.7; extracted with isopropyl: methylchloride, 80:20 (v/v (recovery 81% zaleplon midazolam mobile phase (ratio, v/v, acetonitril :30 mm ammonium acetate (62:38, A: 0,02% aqueous soln. of ammonium (ph = 7.2 methanol aripiprazole, MeOH : 1% aqueous formic acid (65:35 LLE, sample + methyl-t-butyl ether (recovery 74.1% LLE, sample + aqueous ammonium; extracted with methyl-t-butylether:ether, 1:1 (v/v (recovery % ziprasidone papaverine, 10 mm ammonium acetate : ACN (25:75, MeOH : ammonium acetate (70:30 Oasis MCX (recovery % remoxipride, A: 20 mm ammonium acetate (ph = 8.1 LLE, sample + 1M NaOH;extracted with n-butyl chloride: acetonitrile, 4:1(v/v haloperidol-d4 A: 0,1% formic acid BEH C18 ( mm, 1.7 µm, (40 C Agilent Elipse XDB C-8 ( , 5 µm, (25 C Peerless Cyano ( mm, 3 µm Acquity UPLC BEH C 18 ( mm, 1.7 µ m, (45 C RP BDS Phenyl column ( mm, 5 µm, (30 C Xbridge C18 ( mm, 3.5 µm YMC ODS-AQ S ( mm, 3 µm (detection mode (SRM mode, Q 3 LC-ESI(+-MS, (SIM mode, Q 1 (SRM mode, Q , internal standard; MS, mass spectrometry; PPT, protein precipitation; LLE, liquid-liquid extraction; solid phase extraction; ESI(+, electrospray ionization (positive ionization mode; LC-MS/MS, liquid chromatography coupled with tandem mass spectrometry; MRM, multiple reaction monitoring; SIM, single ion monitoring; SRM, selected reaction monitoring; Q1, single-quadrupole mass spectrometer; Q3, triple-quadrupole mass spectrometer. 2
3 Supplemental Table 1 - part 3. preparation (recovery mobile phase (ratio, v/v (detection mode Zotepin (+ another 12 analytes Lurasidone Aripiprazole, amisulpride (+ another 95 analytes and metabolites Rat PPT with acetonitrile type not given (recovery 81.3% zinc sulphate, methanol (recovery 70% PPT with acetonitrile Oasis HLB imipramine carbamazepine ziprasidone-d 8 ziprasidone d 3 -clomipramine, d 5 -amphetamine, A: 10 mm ammonium formate + 10% ACN B: 10 mm ammonium formate + 90% ACN, 15 mm NH 4 Ac and 0.12% acetic acid in water : MeOH (50:50, B: 0.1% formic acid in MeOH, B: 0.1% formic acid in ACN B: 0.1% formic acid in ACN Tosoh ODS-100V (50 2 mm, 5 µm, (40 C Acquity UPLC BEH C 18 ( mm, 1.7 µm, (40 C Zorbax SB-C 8 column ( mm, 1.8 µm, (60 C Gemini C 18 (50 2 mm, 5 µm, (25 C Hypersil gold ( mm, 1.9 µm, (40 C LC-EC/ESI-MS/MS, (SRM mode, Q 3 LC-ESI-MS, (QTRAP , internal standard; MS, mass spectrometry; PPT, protein precipitation; solid phase extraction; ESI(+, electrospray ionization (positive ionization mode; LC-MS/MS, liquid chromatography coupled with tandem mass spectrometry; MRM, multiple reaction monitoring; SRM, selected reaction monitoring; Q3, triple-quadrupole mass spectrometer; QTRAP, combined ion trap - triple quadrupole mass spectrometer. 3
4 Supplemental Table 1 - part 4., aripiprazole (+ another 16 analytes, aripiprazole, amisulpride (+ another 14 analytes Agomelatine Asenapine (ASE, N-desmethyl asenapine (DMA, asenapine-n + -glucuronide (ASG Aripiprazole, dehydroaripirazole brain tissue Rat Bile, urine urine preparation (recovery acetonitrile:methanol, 9:1 (v/v formic acid in acetonitrile, HybridSPE precipitation cartridges clonidine haloperidole-d 4 LLE, lurasidone sample + acetic acid and ZnSO 4 ; extracted with hexane LLE with ethyl acetate (recovery 67% Oasis HLB acetonitrile fluoxetine mobile phase (ratio, v/v A: 0.2% AcA in ACN B: 0.2% AcA in water A: ACN B: ammonium formate in water (ph 8.2 ACN: 0.1% formic acid (80:20 0.1% acetic acid in water : ACN (20:80 A: 0.1 M ammonium acetate (ph 4.2 dansyl-norvaline B: 100% ACN Chromolith Speed ROD C 18 (50 2 mm, 5 µm Zorbax Eclipse plus C 8 ( mm, 5 µm, (30 C Gemini C 6 Phenyl ( mm, 5 µm Betasil C 18 (100 4 mm, 5 µm for ASE a DMA: Discovery C 8 ( mm, 5 µm for ASG: Luna C18 (30 2 mm,5 µm Luna C18 ( mm, 5 µm (detection mode (SIM mode (CAD mode, Q , internal standard; MS, mass spectrometry; PPT, protein precipitation; LLE, liquid-liquid extraction; solid phase extraction; ESI(+, electrospray ionization; LC-MS/MS, liquid chromatography coupled with tandem mass spectrometry; MRM, multiple reaction monitoring; SIM, single ion monitoring; CAD, collision-activated dissociation; Q3, triple-quadrupole mass spectrometer. 4
5 Supplemental Table 1 - part 5. Asenapine (ASE, N-desmethyl asenapine (DMA, asenapine-n + - glucuronide (ASG, 11-O-sulfate-asenapine (OSA preparation (recovery On-line Symbiosis Pharma System (recovery 69-97% for ASG [ 13 C 2 H 3 ]-ASE, [ 13 C 2 H 3 ]-ASG, Org 5649 for DMA, Org 8444 for OSA mobile phase (ratio, v/v A1: 0.01 M ammonium acetate (ph 4.2 for ASE, DMA, OSA A2: 0.1 M ammonium acetate (ph 4.2 for ASG CM 156 Rat LLE with chloroform aripiprazole 10 mm ammonium formate in 0.1% formic acid : ACN (10:90 Aripiprazole Aripiprazole (+ another 1 analyte Rat and brain Evolute CX LLE with ethyl acetate (recovery 71% midazolam propranolol, zidovudine 0.1% formic acid in water : ACN (10:90 for ASE, DMA, OSA: Discovery C 8 ( mm, 5 µm, (30 C, for ASG: Luna C 18 ( mm, 5 µm, (40 C Acquity UPLC BEH HILIC ( mm, 1.7 µm, (25 C Agilent Eclipse plus C 18 ( mm, 1.8 µm Phenomenex C18 ( mm, 5 µm (detection mode (CAD mode, Q 3 (SIM mode, Q Aripiprazole, dehydroaripiprazole, amisulpride (+ another 7 analytes human,, saliva, blood LLE with butyl acetate: butanol, 9:1 (v/v (recovery ARP %, d-arp %, AMS 43-48% aripiprazole-d8, amisulpride-d5 50 mm ammonium acetate in MeOH (ph 6.0 Waters Spherisorb S5SCX ( mm, 5 µm LC-APCI(+-MS/MS, (SRM mode, Q 3 62, internal standard; MS, mass spectrometry; LLE, liquid-liquid extraction; solid phase extraction; ESI(+, electrospray ionization; APCI(+, atmospheric pressure chemical ionization; LC-MS/MS, liquid chromatography coupled with tandem mass spectrometry; SIM, single ion monitoring; MRM, multiple reaction monitoring; SRM, selected reaction monitoring; CAD, collision-activated dissociation; Q3, triple-quadrupole mass spectrometer. 5
6 Supplemental Table 1 - part 6. Target compounds AZ66 Amisulpride, asenapine, iloperidone (+ another 7 analytes Iloperidone + 2 metabolites Asenapine (+ 1 analyte preparation (recovery Rat LLE with chloroform, (av. recovery 98% acetonitrile (recovery AMS 95-96%, ASE 46-50%, ILO 81-83% LLE with ethyl acetate (ILO >71% LLE with methyl-tert-butyl ether (recovery >81.3% aripiprazole amisulpride-d 5, asenapine- 13 C,d 3, iloperidone-d 3 pioglitazone gliclazide mobile phase (ratio, v/v Acquity UPLC BEH 10 mm ammonium acetate containing 0.1% Shield RP18 formic acid : MeOH (40:60 ( mm, 1.7 µm A: 10 mm ammonium formate buffer (ph 3.0 ACN:5 mm ammonium formate contaning 0.3% formic acid, ph 4.8, (25:75 10 mm ammonium formate : ACN, (5:95 Acquity UPLC BEH Shield RP18 ( mm, 1.7 µm, 40 C CAPCELL PAK C18 MG III column ( mm, 5 µm, 40 C Phenomenex C18 ( mm, 5 µm, 40 C (detection mode (MRM mode, QTRAP , internal standard; MS, mass spectrometry; PPT, protein precipitation; LLE, liquid-liquid extraction; ESI(+, electrospray ionization; LC-MS/MS, liquid chromatography coupled with tandem mass spectrometry; MRM, multiple reaction monitoring; Q3, triple-quadrupole mass spectrometer; QTRAP, QTRAP, combined ion trap - triple quadrupole mass spectrometer. 6
7 Supplemental Table 1 - part 7. preparation (recovery mobile phase (ratio, v/v (work temperature, run time (detection mode Aripiprazole Strata X (recovery >96% aripiprazole-d8 MeOH : 100 mm ammonium formate, ph 4, (85:15 BEH C18 ( mm, 1.7 µm, (30 C 41 Iloperidone, asenapine, aripiprazole, dehydroaripiprazole amisulpride (+ 19 another analytes LLE, sample + 1M carbonate buffer, ph 9.5; extracted with methyl-tert-butyl ether amisulpride-d5, aripiprazole-d8, dehydro-aripiprazole-d8, iloperidone-d3, asenapine-13cd3 A:10 mm ammonium acetate, ph 3.7 B:ACN Agilent SB C18 ( mm, 1.7 µm, (40 C 64 Agomelatine (screening for another 131 drugs Whole blood acetonitrile trimipramine-d3, nimodipine-d7 A:25 mm ammonium acetate, ph 7.5 B:ACN Kinetex XB C18 ( mm, 5 µm, (60 C (MRM mode,qtrap 56, internal standard; MS, mass spectrometry; PPT, protein precipitation; LLE, liquid-liquid extraction; solid phase extraction; ESI(+, electrospray ionization; LC-MS/MS, liquid chromatography coupled with tandem mass spectrometry; MRM, multiple reaction monitoring; Q3, triple-quadrupole mass spectrometer; QTRAP, QTRAP, combined ion trap - triple quadrupole mass spectrometer 7
8 Supplemental Table 1 - part 8. Target compounds preparation (recovery Vilazodone Dog LLE, sample + sat. Na 2 CO 3 ; extracted with ethyl acetate Agomelatine LLE with n-hexane: dichloro methane:2-propanol, 20:10:1 (v/v/v, (recovery >90.0% Vilazodone Rat LLE, + 1M Na 2 CO 3 + water; extraction with diethyl ether (recovery >82.0% omeprazole diazepam mobile phase (ratio, v/v, ACN : 10 mm ammoniu acetate (50:50 5 mm ammonium acetate contaning 0.1% formic acid : MeOH (30:70 escitalopram ACN : 5 mm ammoniu acetate : formic acid, (35:65:0.1 Luna C18 ( mm, 5 µm, (35 C Zorbax SB-C18 ( mm, 5 µm, (35 C Agela C18 ( mm, 3 µm, (30 C (detection mode LC-ESI(--MS/MS, (SIM mode, Q , internal standard; MS, mass spectrometry; LLE, liquid-liquid extraction; ESI(+, electrospray ionization; LC-MS/MS, liquid chromatography coupled with tandem mass spectrometry; MRM, multiple reaction monitoring; Q3, triple-quadrupole mass spectrometer. Supplemental Table 1 - part 9. preparation (recovery mobile phase (ratio, v/v (detection mode Agomelatine, amisulpride, aripiprazole (+ 37 another analytes Whole blood acetonitrile venlafaxine-d6, amisulpride-d5, aripiprazole-d8 Gradient elution A-50 mm ammonium formate + 0.3% formic acid B- ACN + 0.1% formic acid Synergy Polar RP (100 2 mm, 2.5 µm (MRM mode, QTRAP 65 Gradient elution A-10 mm ammonium formate (ph 3.5 B-ACN + 0.1% acetic acid Halo Phenyl Hexyl column ( mm, 2.7 µm Microflow-LC- ESI(+ MS/MS, (MRM mode, QTRAP, internal standard; MS, mass spectrometry; PPT, protein precipitation; ESI(+, electrospray ionization; LC-MS/MS, liquid chromatography coupled with tandem mass spectrometry; MRM, multiple reaction monitoring; Q3, triple-quadrupole mass spectrometer; QTRAP, combined ion trap - triple quadrupole mass spectrometer 8
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