715
Views
5
CrossRef citations to date
0
Altmetric
Research Article

A Highly Selective and Sensitive LC–MS/HRMS Assay for Quantifying Coproporphyrins as Organic Anion-Transporting Peptide Biomarkers

, , &
Pages 1787-1806 | Received 23 Aug 2017, Accepted 13 Sep 2017, Published online: 05 Oct 2017

References

  • Rodrigues AD , TaskarKS, KusuharaH, SugiyamaY. Endogenous probes for drug transporters: balancing vision with reality. Clin. Pharmacol. Ther. doi: 10.1002/cpt.749 (2017) ( Epub ahead of print).
  • Sohlenius-Sternbeck AK , MeyersonG, HagbjorkAL, JuricS, TereliusY. A strategy for early-risk predictions of clinical drug–drug interactions involving the GastroPlusTM DDI module for time-dependent CYP inhibitors. Xenobiotica doi: https://doi.org/10.1080/00,498254.2017.13,23136 1–9 (2017) ( Epub ahead of print).
  • Fowler S , MorcosPN, ClearyYet al. Progress in prediction and interpretation of clinically relevant metabolic drug–drug interactions: a minireview illustrating recent developments and current opportunities. Curr. Pharmacol. Rep. 3 (1), 36–49 (2017).
  • Kumar S , SharmaR, RoychowdhuryA. Modulation of cytochrome-P450 inhibition (CYP) in drug discovery: a medicinal chemistry perspective. Curr. Med. Chem. 19 (21), 3605–3621 (2012).
  • Yoshida K , ZhaoP, ZhangLet al. In vitro-Ii vivo extrapolation of metabolism- and transporter-mediated drug–drug interactions – overview of basic prediction methods. J. Pharm. Sci. 106 (9), 2209–2213 (2017).
  • Vaidyanathan J , YoshidaK, AryaV, ZhangL. Comparing various in vitro prediction criteria to assess the potential of a new molecular entity to inhibit organic anion transporting polypeptide 1B1. J. Clin. Pharmacol. 56 (Suppl. 7), S59–S72 (2016).
  • Bednarczyk D , BoiselleC. Organic anion transporting polypeptide (OATP)-mediated transport of coproporphyrins I and III. Xenobiotica46 (5), 457–466 (2016).
  • Hayashi Y , UdagawaM. High-pressure liquid chromatography combined with fluorescence detection and solvent extraction for simultaneous determination of coproporphyrins I and III in human urine. Talanta30 (5), 368–370 (1983).
  • Sakai T , NiinumaY, YanagiharaS, UshioK. Liquid-chromatographic separation and determination of coproporphyrins I and III in urine. Clin. Chem. 29 (2), 350–353 (1983).
  • Shen H , ChenW, DrexlerDMet al. Comparative evaluation of plasma bile acids, dehydroepiandrosterone sulfate, hexadecanedioate, and tetradecanedioate with coproporphyrins I and III as markers of OATP inhibition in healthy subjects. Drug Metab. Dispos. 45 (8), 908–919 (2017).
  • Shen H , DaiJ, LiuTet al. Coproporphyrins I and III as functional markers of OATP1B activity: in vitro and in vivo evaluation in preclinical species. J. Pharmacol. Exp. Ther. 357 (2), 382–393 (2016).
  • Lai Y , MandlekarS, ShenHet al. Coproporphyrins in plasma and urine can be appropriate clinical biomarkers to recapitulate drug–drug interactions mediated by organic anion transporting polypeptide inhibition. J. Pharmacol. Exp. Ther. 358 (3), 397–404 (2016).
  • Minato K , SuzukiM, NagaoH, SuzukiR, OchiaiH. Development of analytical method for simultaneous determination of five rodent unique bile acids in rat plasma using ultra-performance liquid chromatography coupled with time-of-flight mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 1002, 399–410 (2015).
  • Ito S , KusuharaH, KumagaiYet al. N-methylnicotinamide is an endogenous probe for evaluation of drug–drug interactions involving multidrug and toxin extrusions (MATE1 and MATE2-K). Clin. Pharmacol. Ther. 92 (5), 635–641 (2012).
  • Lechner C , IshiguroN, FukuharaAet al. Impact of experimental conditions on the evaluation of interactions between multidrug and toxin extrusion proteins and candidate drugs. Drug Metab. Dispos. 44 (8), 1381–1389 (2016).
  • Omae K , SakuraiH, HigashiT, HosodaK, TeruyaK, SuzukiY. Reevaluation of urinary excretion of coproporphyrins in lead-exposed workers. Int. Arch. Occup. Environ. Health60 (2), 107–110 (1988).
  • Garcia-Vargas GG , Hernandez-ZavalaA. Urinary porphyrins and heme biosynthetic enzyme activities measured by HPLC in arsenic toxicity. Biomed. Chromatogr. 10 (6), 278–284 (1996).
  • Abe K , KonakaR. Quantification of urinary porphyrins by liquid chromatography after oxidation of porphyrinogens. Clin. Chem. 35 (8), 1619–1622 (1989).
  • Bozek P , HuttaM, HrivnakovaB. Rapid analysis of porphyrins at low ng/l and microg/l levels in human urine by a gradient liquid chromatography method using octadecylsilica monolithic columns. J. Chromatogr. A1084 (1–2), 24–32 (2005).
  • Respaud R , Benz-De BretagneI, BlascoH, HulotJS, LechatP, Le GuellecC. Quantification of coproporphyrin isomers I and III in urine by HPLC and determination of their ratio for investigations of multidrug resistance protein 2 (MRP2) function in humans. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 877 (30), 3893–3898 (2009).
  • Jacob K , DossMO. Composition of urinary coproporphyrin isomers I-IV in human porphyrias. Eur. J. Clin. Chem. Clin. Biochem. 31 (10), 617–624 (1993).
  • Jacob K , EgelerE, GrossU, DossMO. Investigations on the formation of urinary coproporphyrin isomers I-IV in 5-aminolevulinic acid dehydratase deficiency porphyria, acute lead intoxication and after oral 5-aminolevulinic acid loading. Clin. Biochem. 32 (2), 119–123 (1999).
  • To-Figueras J , OzallaD, MateuCH. Long-standing changes in the urinary profile of porphyrin isomers after clinical remission of porphyria cutanea tarda. Ann. Clin. Lab. Sci. 33 (3), 251–256 (2003).
  • Cohen C , KirschRE, MooreMR. Porphobilinogen deaminase and the synthesis of porphyrin isomers in the Dubin-Johnson syndrome. S. Afr. Med. J. 70 (1), 36–39 (1986).
  • Jacob K , EgelerE, HennelB, LuppaP. Coproporphyrin isomers II and IV are normal constituents of human urine. J. Clin. Chem. Clin. Biochem. 27 (9), 659–661 (1989).
  • Jacob K , EgelerE, HennelB, LuppaP, NeumeierD. The isomer ratios of urinary coproporphyrins I–IV are pH-dependent. Eur. J. Clin. Chem. Clin. Biochem. 29 (2), 115–119 (1991).
  • Xia YQ , LauJ, OlahT, JemalM. Targeted quantitative bioanalysis in plasma using liquid chromatography/high-resolution accurate mass spectrometry: an evaluation of global selectivity as a function of mass resolving power and extraction window, with comparison of centroid and profile modes. Rapid Commun. Mass Spectrom. 25 (19), 2863–2878 (2011).
  • Wei C , GraceJEJr., ZvyagaTA, DrexlerDM. Utility of high-resolution accurate MS to eliminate interferences in the bioanalysis of ribavirin and its phosphate metabolites. Bioanalysis4 (15), 1895–1905 (2012).
  • Huang MQ , LinZJ, WengN. Applications of high-resolution MS in bioanalysis. Bioanalysis5 (10), 1269–1276 (2013).
  • Ramanathan R , JemalM, RamagiriSet al. It is time for a paradigm shift in drug discovery bioanalysis: from SRM to HRMS. J. Mass Spectrom. 46 (6), 595–601 (2011).
  • Gomez-Perez ML , Romero-GonzalezR, Martinez VidalJL, Garrido FrenichA. Analysis of veterinary drug and pesticide residues in animal feed by high-resolution mass spectrometry: comparison between time-of-flight and Orbitrap. Food Addit. Contam. Part A Chem. Anal. Control Expo. Risk Assess. 32 (10), 1637–1646 (2015).
  • Lee MS , ZhuM. Mass Spectrometry in Drug Metabolism and Disposition: Basic Principles and Applications. Wiley, Hoboken, NJ, USA (2011).
  • Hopfgartner G , TonoliD, VaresioE. High-resolution mass spectrometry for integrated qualitative and quantitative analysis of pharmaceuticals in biological matrices. Anal. Bioanal. Chem. 402 (8), 2587–2596 (2012).
  • Andrews GL , SimonsBL, YoungJB, HawkridgeAM, MuddimanDC. Performance characteristics of a new hybrid quadrupole time-of-flight tandem mass spectrometer (TripleTOF 5600). Anal. Chem. 83 (13), 5442–5446 (2011).
  • FDA C . Guidance for Industry: Bioanalytical Method Validation. US Department of Health and Human Services. Food and Drug Administration, Center for Drug Evaluation and Research (CDER), Center for Veterinary Medicine (CVM), Rockville, MD, USA (2001).
  • Yuan L , LuoY, KandoussiH, JiQC. A simple, fast, sensitive and robust LC–MS/MS bioanalytical assay for evaluating 7alpha-hydroxy-4-cholesten-3-one biomarker in a clinical program. Bioanalysis8 (23), 2445–2455 (2016).
  • Korfmacher WA . Foundation review: principles and applications of LC–MS in new drug discovery. Drug Discov. Today10 (20), 1357–1367 (2005).
  • Korfmacher WA . Principles and applications of LC–MS in new drug discovery. Drug Discov. Today10 (20), 1357–1367 (2005).
  • Penner N , RamanathanR, Zgoda-PolsJ, ChowdhuryS. Quantitative determination of hippuric and benzoic acids in urine by LC–MS/MS using surrogate standards. J. Pharm. Biomed. Anal. 52 (4), 534–543 (2010).
  • Thakare R , ChhonkerYS, GautamN, AlamoudiJA, AlnoutiY. Quantitative analysis of endogenous compounds. J. Pharm. Biomed. Anal. 128, 426–437 (2016).
  • Jones BR , SchultzGA, EcksteinJA, AckermannBL. Surrogate matrix and surrogate analyte approaches for definitive quantitation of endogenous biomolecules. Bioanalysis4 (19), 2343–2356 (2012).
  • Li W , CohenLH. Quantitation of endogenous analytes in biofluid without a true blank matrix. Anal. Chem. 75 (21), 5854–5859 (2003).
  • Food and Drug Administration . Guidance for Industry-Bioanalytical Method Validation. (2001). www.fda.gov/downloads/Drugs/Guidance/ucm070107.pdf
  • Nedderman AN . Metabolites in safety testing: metabolite identification strategies in discovery and development. Biopharm. Drug Dispos. 30 (4), 153–162 (2009).
  • Bower J , FastD, GarofoloFet al. 8th GCC: consolidated feedback to US FDA on the 2013 draft FDA guidance on bioanalytical method validation. Bioanalysis6 (22), 2957–2963 (2014).
  • Food and Drug Administration . Guidance for industry M3(R2). Nonclinical safety studies for the conduct of human clinical trials and marketing authorization for pharmaceuticals (2010). www.fda.gov/downloads/drugs/guidances/ucm073246.pdf
  • Zimmer D . New US FDA draft guidance on bioanalytical method validation versus current FDA and EMA guidelines: chromatographic methods and ISR. Bioanalysis6 (1), 13–19 (2014).
  • Cummings J , RaynaudF, JonesL, SugarR, DiveC. Fit-for-purpose biomarker method validation for application in clinical trials of anticancer drugs. Br. J. Cancer103 (9), 1313–1317 (2010).
  • Booth B , ArnoldME, DesilvaBet al. Workshop report: Crystal City V – quantitative bioanalytical method validation and implementation: the 2013 revised FDA guidance. AAPS J. 17 (2), 277–288 (2015).
  • Song A , LeeA, GarofoloFet al. 2016 White Paper on recent issues in bioanalysis: focus on biomarker assay validation (BAV): (Part II - hybrid LBA/LCMS and input from regulatory agencies). Bioanalysis8 (23), 2457–2474 (2016).
  • Chambers E , Wagrowski-DiehlDM, LuZ, MazzeoJR. Systematic and comprehensive strategy for reducing matrix effects in LC/MS/MS analyses. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 852 (1–2), 22–34 (2007).
  • Jiang H , CaoH, ZhangY, FastDM. Systematic evaluation of supported liquid extraction in reducing matrix effect and improving extraction efficiency in LC–MS/MS based bioanalysis for 10 model pharmaceutical compounds. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 891–892, 71–80 (2012).
  • Ranasinghe A , RamanathanR, JemalM, D’arienzoCJ, HumphreysWG, OlahTV. Integrated quantitative and qualitative workflow for in vivo bioanalytical support in drug discovery using hybrid Q-TOF-MS. Bioanalysis4 (5), 511–528 (2012).
  • Ramanathan R , KorfmacherW. The emergence of high-resolution MS as the premier analytical tool in the pharmaceutical bioanalysis arena. Bioanalysis4 (5), 467–469 (2012).
  • Aratyn-Schaus Y , RamanathanR. Advances in high resolution mass spectrometry and hepatocyte models solve a long-standing metabolism challenge: the loratadine story. Bioanalysis8 (16), 1645–1662 (2016).
  • Grafmuller L , WeiC, RamanathanR, BarlettaF, SteenwykR, TweedJ. Unconjugated payload quantification and DAR characterization of antibody-drug conjugates using high resolution mass spectrometry (HRMS). Bioanalysis8 (16), 1663–1678 (2016).
  • Ramanathan R , KorfmacherW. HRMS or HRAMS. Bioanalysis8 (16), 1639–1640 (2016).
  • Xia YQ , LauJ, OlahT, JemalM. Targeted quantitative bioanalysis in plasma using liquid chromatography/high-resolution accurate mass spectrometry: an evaluation of global selectivity as a function of mass resolving power and extraction window, with comparison of centroid and profile modes. Rapid Commun. Mass Spectrom. 25 (19), 2863–2878 (2011).
  • Sturm RM , JonesBR, MulvanaDE, LowesS. HRMS using a Q-Exactive series mass spectrometer for regulated quantitative bioanalysis: how, when, and why to implement. Bioanalysis8 (16), 1709–1721 (2016).
  • Hamelin EI , BraggW, ShanerRL, SwaimLL, JohnsonRC. Comparison of high-resolution and tandem mass spectrometry for the analysis of nerve agent metabolites in urine. Rapid Commun. Mass Spectrom. 27 (15), 1697–1704 (2013).
  • Van De Merbel NC , BronsemaKJ, Van HoutMW, NilssonR, SillenH. A validated liquid chromatography-tandem mass spectrometry method for the quantitative determination of 4beta-hydroxycholesterol in human plasma. J. Pharm. Biomed. Anal. 55 (5), 1089–1095 (2011).
  • Tu J , BennettP. Parallelism experiments to evaluate matrix effects, selectivity and sensitivity in ligand-binding assay method development: pros and cons. Bioanalysis9 (14), 1107–1122 (2017).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.