133
Views
0
CrossRef citations to date
0
Altmetric
Review

Analytical Techniques for Monitoring of Toluene and Xylene Exposure Biomarkers Hippuric Acid and Methylhippuric Acid in Human Urine Samples

, , , , , , & ORCID Icon show all
Pages 1569-1584 | Received 22 Aug 2021, Accepted 06 Oct 2021, Published online: 26 Oct 2021

References

  • Lyu Y , LiC, DuXet al. Catalytic removal of toluene over manganese oxide-based catalysts: a review. Environ. Sci. Pollut. Res. Int.27(3), 2482–2501 (2020).
  • Kuranchie FA , AngnunavuriPN, AttiogbeF, Nerquaye-TettehEN, YunGY. Occupational exposure of benzene, toluene, ethylbenzene and xylene (BTEX) to pump attendants in Ghana: implications for policy guidance. Cogent Environmental Sci.5(1), 1603418 (2019).
  • Yadav A , BasuA, ChakarbartiA. Method for estimation of hippuric acid as a biomarker of toluene exposure in urine by high-performance liquid chromatography after extraction with ethyl acetate. Environmental Dis.4(1), 17 (2019).
  • Szucs S , TothL, LegozaJ, SarvaryA, AdanyR. Simultaneous determination of styrene, toluene, and xylene metabolites in urine by gas chromatography/mass spectrometry. Arch. Toxicol.76(10), 560–569 (2002).
  • CM Filley WH , Kleinschmidt-DemastersBK. The effects of toluene on the central nervous system. J. Neuropathol. Exp. Neurol.63(1), 1–12 (2004).
  • Yavari F , van ThrielC, NitscheMA, KuoMF. Effect of acute exposure to toluene on cortical excitability, neuroplasticity, and motor learning in healthy humans. Arch. Toxicol.92(10), 3149–3162 (2018).
  • Mauro M , LeperaJS, BorsariB, CapelaJMV, de MoraesNV. Effect of inhalation exposure to toluene on the activity of organic anion transporting polypeptide (Oatp) using pravastatin as a probe drug in rats. Xenobiotica48(7), 734–738 (2017).
  • Shan X , TanS, ShiYet al. Activated carbon/diatomite-based magnetic nanocomposites for magnetic solid-phase extraction of S-phenylmercapturic acid from human urine. Biomed. Chromatogr.34(7), e4834 (2020).
  • Maziejuk M , SzczurekA, MaciejewskaM, PietruchaT, SzyposzynskaM. Determination of benzene, toluene and xylene concentration in humid air using differential ion mobility spectrometry and partial least squares regression. Talanta152, 137–146 (2016).
  • Win-Shwe TT , FujimakiH. Neurotoxicity of toluene. Toxicol. Lett.198(2), 93–99 (2010).
  • Barros N , CarvalhoM, SilvaCet al. Environmental and biological monitoring of benzene, toluene, ethylbenzene and xylene (BTEX) exposure in residents living near gas stations. J. Toxicol. Environ. Health A82(9), 550–563 (2019).
  • Behbahani M , BagheriS, OmidiF, AminiMM. An amino-functionalized mesoporous silica (KIT-6) as a sorbent for dispersive and ultrasonication-assisted micro solid phase extraction of hippuric acid and methylhippuric acid, two biomarkers for toluene and xylene exposure. Mikrochim. Acta185(11), 505 (2018).
  • Ukai H , KawaiT, InoueOet al. Comparative evaluation of biomarkers of occupational exposure to toluene. Int. Arch. Occup. Environ. Health81(1), 81–93 (2007).
  • Hajizadeh Y , TeiriH, NazmaraS, ParsehI. Environmental and biological monitoring of exposures to VOCs in a petrochemical complex in Iran. Environ. Sci. Pollut. Res. Int.25(7), 6656–6667 (2018).
  • Jakubowski M . Biological monitoring versus air monitoring strategies in assessing environmental-occupational exposure. J. Environ. Monit.14(2), 348–352 (2012).
  • Hopf NB , BolognesiC, DanuserB, WildP. Biological monitoring of workers exposed to carcinogens using the buccal micronucleus approach: a systematic review and meta-analysis. Mutat. Res. Rev. Mutat. Res.781, 11–29 (2019).
  • Soleimani E . Benzene, toluene, ethylbenzene, and xylene: current analytical techniques and approaches for biological monitoring. Rev. Analytical Chem.39(1), 168–187 (2020).
  • Ramesh Kumar A , SivaperumalP. Analytical methods for the determination of biomarkers of exposure to phthalates in human urine samples. TrAC Trends Analytical Chem.75, 151–161 (2016).
  • Heibati B , GodriPollitt KJ, CharatiJYet al. Biomonitoring-based exposure assessment of benzene, toluene, ethylbenzene and xylene among workers at petroleum distribution facilities. Ecotoxicol. Environ. Saf.149, 19–25 (2018).
  • Arabi M , GhaediM, OstovanA. Water compatible molecularly imprinted nanoparticles as a restricted access material for extraction of hippuric acid, a biological indicator of toluene exposure, from human urine. Microchim. Acta184(3), 879–887 (2017).
  • Hu C , YangZ, YanF, SunB. Extraction of the toluene exposure biomarkers hippuric acid and methylhippuric acid using a magnetic molecularly imprinted polymer, and their quantitation by LC-MS/MS. Mikrochim. Acta186(3), 135 (2019).
  • Chaiklieng S , SuggaravetsiriP, KaminskiN, AutrupH. Exposure to benzene and toluene of gasoline station workers in Khon Kaen, Thailand and adverse effects. Human Ecological Risk Assessment27(7), 1823–1837 (2021).
  • Dogan CS , AksoyGK, DemircanKA, YildirimS. A teenager presenting with anuric acute renal failure and metabolic acidosis with a high anion gap: answers. Pediatr. Nephrol.35(12), 2257–2258 (2020).
  • Gonzalez JL , PellA, Lopez-MesasM, ValienteM. Simultaneous determination of BTEX and their metabolites using solid-phase microextraction followed by HPLC or GC/MS: an application in teeth as environmental biomarkers. Sci. Total Environ.603–604, 109–117 (2017).
  • Hubkova B , RaczO, BodyG, FrismanE, MarekovaM. Toluene abuse markers in marginalized populations. Interdiscip. Toxicol.11(1), 22–26 (2018).
  • Chiu C-H , ChenC-T, ChengM-Het al. Use of urinary hippuric acid and o-/p-/m-methyl hippuric acid to evaluate surgical smoke exposure in operating room healthcare personnel. Ecotoxicol. Environmental Safety217, 112231 (2021).
  • Yuan Y , HanY, YangC, HanD, YanH. Deep eutectic solvent functionalized graphene oxide composite adsorbent for miniaturized pipette-tip solid-phase extraction of toluene and xylene exposure biomarkers in urine prior to their determination with HPLC-UV. Mikrochim. Acta187(7), 387 (2020).
  • Kwon JW , ParkHW, KimWJ, KimMG, LeeSJ. Exposure to volatile organic compounds and airway inflammation. Environ. Health17(1), 65 (2018).
  • Kwon NH , LeeYR, KimHS, CheongJC, KimJY. Hybrid solid-phase extraction for selective determination of methamphetamine and amphetamine in dyed hair by using gas chromatography–mass spectrometry. Molecules24(13), 2501 (2019).
  • Sagu ST , HuschekG, HomannT, RawelHM. Effect of sample preparation on the detection and quantification of selected nuts allergenic proteins by LC-MS/MS. Molecules26(15), 4698 (2021).
  • Boscari CN , MazzuiaGR, WisniewskiC, BorgesKB, FigueiredoEC. Molecularly imprinted probe for solid-phase extraction of hippuric and 4-methylhippuric acids directly from human urine samples followed by MEKC analysis. Electrophoresis38(7), 1083–1090 (2017).
  • Gonzalez JL , PellA, Lopez-MesasM, ValienteM. Hollow fibre supported liquid membrane extraction for BTEX metabolites analysis in human teeth as biomarkers. Sci. Total Environ.630, 323–330 (2018).
  • Bahrami A , GhamariF, YaminiY, GhorbaniShahna F, KoolivandA. Ion-pair-based hollow-fiber liquid-phase microextraction combined with high-performance liquid chromatography for the simultaneous determination of urinary benzene, toluene, and styrene metabolites. J. Sep. Sci.41(2), 501–508 (2018).
  • Ghamari F , BahramiA, YaminiY, ShahnaFG, MoghimbeigiA. Hollow-fiber liquid-phase microextraction based on carrier-mediated transport for determination of urinary methyl hippuric acids. Toxicol. Environ. Chem.99(5-6), 760–771 (2017).
  • Bahrami A , GhamariF, YaminiY, GhorbaniShahna F, MoghimbeigiA. Hollow fiber supported liquid membrane extraction combined with HPLC-UV for simultaneous preconcentration and determination of urinary hippuric acid and mandelic acid. Membranes7(1), 8 (2017).
  • Rimnacova L , MoosM, OpekarSet al. Ethyl chloroformate mediated gas chromatographic-mass spectrometric biomonitoring of acidic biomarkers of occupational exposure and endogenous metabolites in human urine. J. Chromatogr. A1656, 462547 (2021).
  • Omidi F , BehbahaniM, KhademM, GolbabaeiF, ShahtaheriSJ. Application of ultrasonication for facilitating the extraction of hippuric acid and methyl hippuric acid in real samples using Fe3O4@SiO2@sodium dodecyl sulfate: experimental design methodology. Analytical Methods10(37), 4588–4595 (2018).
  • Pirmohammadi Z , BahramiA, NematollahiDet al. Determination of urinary methylhippuric acids using MIL-53-NH2 (Al) metal-organic framework in microextraction by packed sorbent followed by HPLC-UV analysis. Biomed. Chromatogr.34(1), e4725 (2020).
  • Ye H , ShaoJ, ShiYet al. Magnetic molecularly imprinted polymers for extraction of S-phenylmercapturic acid from urine samples followed by high-performance liquid chromatography. J. Mol. Recogn. n/a(n/a), e2930 (2021).
  • Choi Y-B , JeonW-Y, KimH-H. A simple interfacial platform for homogeneous electrochemical immunoassays using a poly(vinylimidazole)-modified electrode. Sensors17(12), 54 (2016).
  • Vitali L , GoncalvesS, RodriguesV, FavereVT, MickeGA. Development of a fast method for simultaneous determination of hippuric acid, mandelic acid, and creatinine in urine by capillary zone electrophoresis using polymer multilayer-coated capillary. Anal. Bioanal. Chem.409(7), 1943–1950 (2017).
  • Du Y , LiX, ZhengH, LvX, JiaQ. Design of a calix [4]arene-functionalized metal-organic framework probe for highly sensitive and selective monitor of hippuric acid for indexing toluene exposure. Anal. Chim. Acta1001, 134–142 (2018).
  • Doddawad VG , AyasM, GurupadayyaBM. Occupational exposure to petroleum workers by assessing urinary methyl hippuric acid and micronuclei in oral mucosa cell. Indian J. Public Health Res. Develop.10(12), 272 (2019).
  • M Ayas VD , GurupadayyaBM. Evaluation of occupational exposure to xylene in petroleum workers by assessing urinary methyl hippuric acid and cellular changes of exfoliated epithelial eells in buccal mucosa smears. Internat. J. Recent Technol. Engin.8(2), 1323–1328 (2019).
  • Qin S-J , HaoJ-N, XuX-Y, LianX, YanB. Highly sensing probe for biological metabolite of benzene series pollutants based on recyclable Eu3+ functionalized metal-organic frameworks hybrids. Sensors Actuators B: Chemical.253, 852–859 (2017).
  • Zhu Z-X , WangC-J, LuoDet al. Six new lanthanide metal–organic frameworks as luminescent sensors for the detection of 1-N, TDGA, UA, and HA in urine. J. Coordination Chem.72(22–24), 3526–3543 (2019).
  • Geraldino BR , NunesRFN, GomesJBet al. Evaluation of exposure to toluene and xylene in gasoline station workers. Adv. Prev. Med.2021, 5553633 (2021).
  • Hormozi M , MirzaeiR, NakhaeeAet al. Quantification of urinary metabolites of toluene and xylene isomers as biological indices of occupational exposure in printing industry workers. Health Scope ( In Press) (2019).
  • Choi CY , ChoN, ParkSYet al. Urine methyl hippuric acid levels in acute pesticide poisoning: estimation of ingested xylene volume and association with clinical outcome parameters. J. Korean Med. Sci.32(12), 2051–2057 (2017).
  • Sharma P , RaoVSSatyanS, BenegaV. Hippuric acid quantification by HPLC among inhalant users. J. Addict. Recovery3(1), 1023 (2020).
  • Pruneda-Alvarez T R-V LG , Ochoa-MartínezAC, Pérez-MaldonadoIN. Urinary trans-trans muconic acid (exposure biomarker to benzene) and hippuric acid (exposure biomarker to toluene) concentrations in Mexican women living in high-risk scenarios of air pollution. Arch. Environ. Occup. Health72(6), 1–27 (2017).
  • Nguyen CH , FuC-C, ChenZ-Het al. Enhanced and selective adsorption of urea and creatinine on amine-functionalized mesoporous silica SBA-15 via hydrogen bonding. Microporous Mesoporous Material.311, 110733 (2021).
  • Li X , LiX, ZhengHet al. Design of a ruthenium(III) immobilized affinity material based on a beta-cyclodextrin-functionalized poly(glycidyl methacrylate-ethylene dimethacrylate) monolith for the enrichment of hippuric acid. J. Sep. Sci.40(18), 3696–3702 (2017).
  • Sun XD , WuHL, LiuZet al. Target-based metabolomics for fast and sensitive quantification of eight small molecules in human urine using HPLC-DAD and chemometrics tools resolving of highly overlapping peaks. Talanta201, 174–184 (2019).
  • Mut L , GroboschT, Binscheck-DomassT, FrenzelW. Toxicological screening of human plasma by on-line SPE-HPLC-DAD: identification and quantification of acidic and neutral drugs. Biomed. Chromatogr.30(3), 343–362 (2016).
  • Roman-Hidalgo C , Martin-ValeroMJ, Fernandez-TorresR, Callejon-MochonM, Bello-LopezMA. New nanostructured support for carrier-mediated electromembrane extraction of high polar compounds. Talanta162, 32–37 (2017).
  • Cristina RH , MariaJesus MV, RutFT, MiguelAngel BL. Use of polymer inclusion membranes (PIMs) as support for electromembrane extraction of non-steroidal anti-inflammatory drugs and highly polar acidic drugs. Talanta179, 601–607 (2018).
  • Román-Hidalgo C , López-PérezG, Martín-ValeroMJ, Bello-LópezMÁ. Chitosan tailor-made membranes as biopolymeric support for electromembrane extraction. Talanta199, 290–295 (2019).
  • Belal SF , ShaalanRA, RagabMAA, El-AttarEA, AgamiM. Liquid chromatography-mass spectrometry for muconic, mandelic, hippuric and methylhippuric acids analysis in human urine as metabolites for fuel exposure. Microchem. J.149, 103992 (2019).
  • Fabresse N , UteemI, LamyEet al. Quantification of free and protein bound uremic toxins in human serum by LC-MS/MS: comparison of rapid equilibrium dialysis and ultrafiltration. Clin. Chim. Acta507, 228–235 (2020).
  • Andre C , BennisY, Titeca-BeauportDet al. Two rapid, accurate liquid chromatography tandem mass spectrometry methods for the quantification of seven uremic toxins: an application for describing their accumulation kinetic profile in a context of acute kidney injury. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci.1152, 122234 (2020).
  • Jokioja J , PercivalJ, PhiloMet al. Phenolic metabolites in the urine and plasma of healthy men after acute intake of purple potato extract rich in methoxy substituted monoacylated anthocyanins. Mol. Nutr. Food Res.65(9), e2000898 (2021).
  • Prokopienko AJ , WestRE3rd, StubbsJR, NolinTD. Development and validation of a UHPLC-MS/MS method for measurement of a gut-derived uremic toxin panel in human serum: an application in patients with kidney disease. J. Pharm. Biomed. Anal.174, 618–624 (2019).
  • Kuang H , LiY, JiangWet al. Simultaneous determination of urinary 31 metabolites of VOCs, 8-hydroxy-2′-deoxyguanosine, and trans-3′-hydroxycotinine by UPLC-MS/MS: (13)C- and (15)N-labeled isotoped internal standards are more effective on reduction of matrix effect. Anal. Bioanal. Chem.411(29), 7841–7855 (2019).
  • Kim JH , AhnR-M, KimT-J, LeeK, SonB-S. Human exposure assessment of airborne pollutants for residents in gwangyang city near industrial plants (I). Toxicol. Environmental Health Sci.10(1), 31–41 (2018).
  • Baghdady YZ , SchugKA. A novel diagnostic in situ derivatization kit for the simultaneous determination of 14 biomarkers of exposure to benzene, toluene, ethyl benzene and xylenes in human urine by isotope dilution liquid chromatography tandem mass spectrometry and kit optimization using response surface methodology. Anal. Chim. Acta1036, 195–203 (2018).
  • Kim SY , SonBS, ParkHJet al. Impact of environmental volatile organic compounds on otitis media in children: correlation between exposure and urinary metabolites. Int. J Pediatr Otorhinolaryngol.93, 157–162 (2017).
  • Boyle EB , VietSM, WrightDJet al. Assessment of exposure to VOCs among pregnant women in the national children's study. Int. J. Environ. Res. Public Health13(4), 376 (2016).
  • Decharat S . Urinary hippuric acid and toluene levels in workers of printing factories in Thailand. Int. J. Occup. HYG8(2), 85–92 (2016).
  • P Kongtip JV , PruktharathikulV. Modified method for determination of hippuric acid and methylhippuric acid in urine by gas chromatography. J. Chromatogr. B751, 199–203 (2001).
  • Takeuchi A , NameraA, SakuiNet al. Direct methyl esterification with 2,2-dimethoxypropane for the simultaneous determination of urinary metabolites of toluene, xylene, styrene, and ethylbenzene by gas chromatography-mass spectrometry. J. Occup. Health61(1), 82–90 (2019).
  • Marchand A , Aranda-RodriguezR, TardifR, NongA, HaddadS. Evaluation and modeling of the impact of coexposures to VOC mixtures on urinary biomarkers. Inhal. Toxicol.28(6), 260–273 (2016).
  • Osman D , AliO, ObadaM, El-MezayenH, El-SaidH. Chromatographic determination of some biomarkers of liver cirrhosis and hepatocellular carcinoma in Egyptian patients. Biomed. Chromatogr.31(6), e3893 (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.