288
Views
6
CrossRef citations to date
0
Altmetric
Bioanalytical

Efficient Detection of Phthalate Esters in Human Saliva via Fluorescence Spectroscopy

, , &
Pages 479-495 | Received 15 Mar 2018, Accepted 26 Apr 2018, Published online: 23 Jul 2018

References

  • Anal, A. K., and H. Singh. 2007. Recent advances in microencapsulation of probiotics for industrial applications and targeted delivery. Trends in Food Science and Technology 18 (5):240–251. doi: 10.1016/j.tifs.2007.01.004
  • Asamoah, A., D. K. Essumang, J. Muff, S. V. Kucheryavskiy, and E. G. Søgaard. 2018. Assessment of PCBs and exposure risk to infants in breast milk of primiparae and multiparae mothers in an electronic waste hot spot and non-hot spot areas in Ghana. Science of the Total Environment 612:1473–1479. doi: 10.1016/j.scitotenv.2017.08.177.
  • Beija, M., C. A. M. Afonso, and J. M. G. Martinho. 2009. Synthesis and applications of rhodamine derivatives as fluorescent probes. Chemical Society Reviews 38 (8):2410–2433. doi: 10.1039/b901612k.
  • Boberg, J., H. K. L. Johansson, N. Hadrup, K. Dreisig, L. Berthelsen, K. Almstrup, A. M. Vinggaard, and U. Hass. 2015. Perinatal exposure to mixtures of anti-androgenic chemicals causes proliferative lesions in rat prostate. The Prostate 75 (2):126–140. doi: 10.1002/pros.22897.
  • Bowman, J. D., and M. Choudhury. 2016. Phthalates in neonatal health: friend or foe? Journal of Developmental Origins of Health and Disease 7 (06):652–664. doi: 10.1017/S2040174416000349.
  • Braun, J. M. 2017. Early-life exposure to EDCs: role in childhood obesity and neurodevelopment. Nature Reviews Endocrinology 13 (3):161–173. doi: 10.1038/nrendo.2016.186.
  • Carvalho, J. J., M. G. Weller, U. Panne, and R. J. Schneider. 2012. Monitoring caffeine in human saliva using a newly developed ELISA. Analytical Letters 45 (17):2549–2561. doi: 10.1080/00032719.2012.696226.
  • Chai, S., J. Wang, S. Y. Zhu, and S. L. Cong. 2015. Hydrogen-bonding dynamics of photoexcited coumarin 138 and 339 in protic methanol solution: time-dependent density functional theory study. Computational and Theoretical Chemistry 1061:6–11. doi: 10.1016/j.comptc.2015.03.005.
  • Cheng, D., W. Zhao, H. Yang, Z. Huang, X. Liu, and A. Han. 2016. Detection of Hg2+ by a FRET ratiometric fluorescent probe based on a novel BODIPY-RhB system. Tetrahedron Letters 57 (24):2655–2659. doi: 10.1016/j.tetlet.2016.05.015.
  • Chingin, K., H. Chen, G. Gamez, L. Zhu, and R. Zenobi. 2009. Detection of diethyl phthalate in perfumes by extractive electrospray ionization mass spectrometry. Analytical Chemistry 81 (1):123–129. doi: 10.1021/ac801572d.
  • Dekant, W., and J. Bridges. 2016. Assessment of reproductive and developmental effects of DINP, DnHP and DCHP using quantitative weight of evidence. Regulatory Toxicology and Pharmacology 81: 397–406. doi: 10.1016/j.yrtph.2016.09.032.
  • DiScenza, D. J., and M. Levine. 2016a. Selective detection of non-aromatic pesticides via cyclodextrin-promoted fluorescence modulation. New Journal of Chemistry 40 (1):789–793. doi: 10.1039/C5NJ02357B.
  • DiScenza, D. J., and M. Levine. 2016b. Sensitive and selective detection of alcohols via fluorescence modulation. Supramolecular Chemistry 28 (11–12):881–891. doi: 10.1080/10610278.2016.1140897.
  • DiScenza, D. J., E. Culton, M. Verderame, J. Lynch, N. Serio, and M. Levine. 2017. Towards rational chemosensor design through improved understanding of experimental parameter variation and tolerance in cyclodextrin-promoted fluorescence detection. Chemosensors 5 (4):34–49. doi: 10.3390/chemosensors5040034.
  • DiScenza, D. J., J. Lynch, J. Miller, M. Verderame, and M. Levine. 2017. Detection of organochlorine pesticides in contaminated marine environments via cyclodextrin-promoted fluorescence modulation. ACS Omega 2 (12):8591–8599. doi: 10.1021/acsomega.7b00991.
  • DiScenza, D. J., J. Lynch, M. Verderame, N. Serio, L. Prignano, L. Gareau, and M. Levine. 2018. Efficient fluorescence detection of aromatic toxicants and toxicant metabolites in human breast milk. Supramolecular Chemistry 30 (4):267–277. doi: 10.1080/10610278.2017.1343947.
  • DiScenza, D. J., L. Gareau, N. Serio, J. Roque, L. Prignano, M. Verderame, and M. Levine. 2016. Cyclodextrin-promoted detection of aromatic toxicants and toxicant metabolites in urine. Analytical Chemistry Letters 6 (4):345–353. doi: 10.1080/22297928.2016.1210021.
  • DiScenza, D. J., M. Verderame, and M. Levine. 2016. Detection of benzene and alkylated benzene derivatives in fuel contaminated environments. Clean - Soil, Air, Water 44 (12):1621–1627. doi: 10.1002/clen.201600206.
  • Dodson, R. F., M. Nishioka, L. J. Standley, L. J. Perovich, J. G. Brody, and R. A. Rudel. 2012. Endocrine disruptors and asthma-associated chemicals in consumer products. Environmental Health Perspectives 120 (7):935–943. doi: 10.1289/ehp.1104052.
  • Edetsberger, M., M. Knapp, E. Gaubitzer, C. Miksch, K. E. Gvichiya, and G. Kohler. 2011. Effective staining of tumor cells by coumarin-6 depends on the stoichiometry of cyclodextrin complex formation. Journal of Inclusion Phenomena and Macrocyclic Chemistry 70 (3–4):327–331. doi: 10.1007/s10847-010-9894-1.
  • Elmongy, H., and M. Abdel-Rehim. 2016. Saliva as an alternative specimen to plasma for drug bioanalysis. A review. TrAC Trends in Analytical Chemistry 83:70–79. doi: 10.1016/j.trac.07010.
  • Gallart-Ayala, H., O. Nunez, and P. Lucci. 2013. Recent advances in LC-MS analysis of food-packaging contaminants. TrAC Trends in Analytical Chemistry 42:99–124. doi: 10.1016/j.trac.2012.09.017.
  • Gerald, I., D. Arthur, E., and A. Adedayo. 2014. Determination of caffeine in beverages: a review. American Journal of Engineering Research 3 (8):124–137. ISSN: 2320-0847.
  • Gowda, G. A., and D. Djukovic. 2014. Overview of mass spectrometry-based metabolomics: opportunities and challenges. Methods in Molecular Biology 1198:3–12. doi: 10.1007/978-1-4939-1258-2_1.
  • Gu, Z. H., D. S. Guo, M. Sun, and Y. Liu. 2010. Effective enlargement of fluorescence resonance energy transfer of poly-porphyrin mediated by β-cyclodextrin dimers. The Journal of Organic Chemistry 75 (11):3600–3607. doi: 10.1021/jo100351f.
  • Hartler, J., R. Tharakan, H. C. Kofeler, D. R. Graham, and G. G. Thallinger. 2013. Bioinformatics tools and challenges in structural analysis of lipidomics MS/MS data. Briefings in Bioinformatics 14 (3):375–390. doi: 10.1093/bib/bbs030.
  • Hattori, K., and S. Murai. 1999. Inclusion of environmental contaminants with β-cyclodextrin, and adsorption and removal by β-cyclodextrin polymer. Proceedings of the Ninth International Symposium on Cyclodextrins, 587–590. doi: 10.1007/978-94-011-4681-4_139.
  • Hines, E. P., A. M. Calafat, M. J. Silva, P. Mendola, and S. E. Fenton. 2009. Concentrations of phthalate metabolites in milk, urine, saliva, and serum of lactating North Carolina women. Environmental Health Perspectives 117 (1):86–92. doi: 10.1289/ehp.11610.
  • Jung, G., S. Gerharz, and A. Schmitt. 2009. Solvent-dependent steady-state fluorescence spectroscopy for searching ESPT-dyes: solvatochromatism of HPTS revisited. Physical Chemistry Chemical Physics 11 (9):1416–1426. doi: 10.1039/B816695A.
  • Junghoon, K., E. Garcia-Esquinas, A. Navas-Acien, and Y. H. Choi. 2017. Blood and urine cadmium concentrations and walking speed in middle-aged and older U.S. adults. Environmental Pollution 232:97–104. doi: 10.1016/j.envpol.2017.09.022.
  • Kim, J., E. Garcia-Esquinas, A. Navas-Acien, and Y.-H. Choi. 2018. Blood and urine cadmium concentrations and walking speed in Middle-aged and older U.S. adults. Environmental Pollution 232 :97–104. doi: 10.1016/j.envpol.2017.09.022.
  • Karunamoorthi, K., and S. Sabesan. 2010. Laboratory evaluation of dimethyl phthalate treated wristbands against three predominant mosquito (diptera: Culicidae) vectors of disease. European Review for Medical and Pharmacological Sciences 14 (5):443–448. PMID: 20556923.
  • Katerinopoulos, H. E. 2004. The coumarin moiety as chromophore of fluorescent ion indicators in biological systems. Current Pharmaceutical Design 10 (30):3835–3852. doi: 10.2174/1381612043382666.
  • Kim, H. N., W. X. Ren, J. S. Kim, and J. Yoon. 2012. Fluorescent and colorimetric sensors for detection of lead, cadmium, and mercury ions. Chemical Society Reviews 41 (8):3210–3244. doi: 10.1039/C1CS15245A.
  • Kintz, P., and N. Samyn. 2002. Use of alternative specimens: drugs of abuse in saliva and doping agents in hair. Therapeutic Drug Monitoring 24 (2):239–246. ISSN: 0163-4356.
  • Koniecki, D., R. Wang, R. P. Moody, and J. Zhu. 2011. Phthalates in cosmetic and personal care products: concentrations and possible dermal exposure. Environmental Research 111 (3):329–336. doi: 10.1016/j.envres.2011.01.013.
  • Kumar, A. R., and P. Sivaperumal. 2016. Analytical methods for the determination of biomarkers of exposure to phthalates in human urine samples. TrAC Trends in Analytical Chemistry 75:151–161. doi: 10.1016/j.trac.2015.06.008.
  • Kwapniewski, R., S. Kozaczka, R. Hauser, M. J. Silva, A. M. Calafat, and S. M. Duty. 2008. Occupational exposure to dibutyl phthalate among manicurists. Journal of Occupational and Environmental Medicine 50 (6):705–711. doi: 10.1097/JOM.0b013e3181651571.
  • Ma, P., B. Yan, Q. Zeng, X. Liu, Y. Wu, M. Jiao, C. Liu, J. Wu, and X. Yang. 2014. Oral exposure of kunming mice to diisononyl phthalate induces hepatic and renal tissue injury through the accumulation of ROS. Protective effect of melatonin. Food and Chemical Toxicology 68:247–256. doi: 10.1016/j.fct.2014.03.027.
  • Martinez, V., S. Salleres, J. Banuelos, and F. L. Arbeloa. 2006. Application of polarized fluorescence to evaluate the orientation of dyes adsorbed in layered materials. Journal of Fluorescence 16 (2):233–240. doi: 10.1007/s10895-005-0042-z.
  • Mauriello, M. C., C. Sbordone, P. Montuori, R. Alfano, M. Triassi, I. Iavicoli, and M. Manno. 2017. Biomonitoring of toxic metals in incinerator workers: a systematic review. Toxicology Letters 272:8–28. doi: 10.1016/j.toxlet.2017.02.021.
  • Michelsen, V. B., G. Moe, M. B. Strom, E. Jensen, and H. Lygre. 2008. Quantitative analysis of TEGDMA and HEMA eluted into saliva from two dental composites by use of GC/MS and tailor-made internal standards. Dental Materials 24 (6):724–731. doi: 10.1016/j.dental.2007.08.002.
  • National Service Center for Environmental Publications (NSCEP). 1978. Phthalate esters ambient water criteria. https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=910000MZ.txt (accessed March 1, 2018).
  • Net, S., R. Sempéré, A. Delmont, A. Paluselli, and B. Ouddane. 2015. Occurrence, fate, behavior and ecotoxicological state of phthalates in different environmental matrices. Environmental Science & Technology 49 (7):4019–4035. doi: 10.1021/es505233b.
  • Nyssen, G. A., E. T. Miller, T. F. Glass, C. R. Quinn, J. Underwood, and D. J. Wilson. 1987. Solubilities of hydrophobic compounds in aqueous-organic solvent mixtures. Environmental Monitoring and Assessment 9 (1):1–11. doi: 10.1007/BF00394211.
  • Okoli, C. P., G. O. Adewuyi, Q. Zhang, P. N. Diagboya, and Q. Guo. 2014. Mechanism of dialkyl phthalates removal from aqueous solution using γ-cyclodextrin and starch based polyurethane polymer adsorbents. Carbohydrate Polymers 114 :440–449. doi: 10.1016/j.carbpol.2014.08.016.
  • Pinkas, A., C. L. Goncalves, and M. Aschner. 2017. Neurotoxicity of fragrance compounds: a review. Environmental Research 158:342–349. doi: 10.1016/j.envres.2017.06.035.
  • Russo, M. V., P. Avino, L. Perugini, and I. Notardonato. 2015. Extraction and GC-MS analysis of phthalate esters in food matrices: a review. RSC Advances 5 (46):37023–37043. doi: 10.1039/C5RA01916H.
  • Saokham, P., and T. Loftsson. 2017. γ-cyclodextrin. International Journal of Pharmaceutics 516 (1-2):278–292. doi: 10.1016/j.ijpharm.2016.10.062.
  • Schneider, H. J. 2015. Dispersive interactions in solution complexes. Accounts of Chemical Research 48 (7):1815–1822. doi: 10.1021/acs.accounts.5b00111.
  • Serio, N., D. F. Moyano, V. M. Rotello, and M. Levine. 2015. Array-based detection of persistent organic pollutants via cyclodextrin promoted energy transfer. Chemical Communications 51(58):11615–11618. doi: 10.1039/C5CC04153H.
  • Serio, N., J. Roque, A. Badwal, and M. Levine. 2015. Rapid and efficient pesticide detection via cyclodextrin-promoted energy transfer. The Analyst 140 (22):7503–7507. doi: 10.1039/C5AN01471A.
  • Serio, N., K. Miller, and M. Levine. 2013. Efficient detection of polycyclic aromatic hydrocarbons and polychlorinated biphenyls via three-component energy transfer. Chemical Communications 49(42):4821–4823. doi: 10.1039/C3CC40534F.
  • Shepherd, J. L., E. Chung, C. W. Sinclar, M. S. Workentin, and D. Bizzotto. 2004. Selective reductive desorption of a SAM-coated gold electrode revealed using fluorescence microscopy. Journal of the American Chemical Society 126 (26):8329–8335. doi: 10.1021/ja0494095.
  • Soini, H. A., I. Klouckova, D. Wiesler, E. Oberzaucher, K. Grammer, S. J. Dixon, Y. Xu, R. G. Brereton, D. J. Penn, and M. V. Novotny. 2010. Analysis of volatile organic compounds in human saliva by static sorptive extraction method and gas chromatography-mass spectrometry. Journal of Chemical Ecology 36 (9):1035–1042. doi: 10.1007/s10886-010-9846-7.
  • Tarasov, A. E., G. V. Malkov, M. L. Bubnova, Y. I. Estrin, and E. R. Badamshina. 2015. Influence of curing conditions and dibutyl phthalate concentration on the properties of cured epoxy resin. Russian Journal of Applied Chemistry 88 (12):2015–2020. doi: 10.1134/S10704272150120174.
  • Wensing, M., E. Uhde, and T. Salthammer. 2005. Plastic additives in the indoor environment – flame retardants and plasticizers. Science of the Total Environment 339 (1–3):19–40. doi: 10.1016/j.scitotenv.2004.10.028.
  • Wooten, K. J., and P. N. Smith. 2013. Canine toys and training devices as sources of exposure to phthalates and bisphenol a: quantitation of chemicals in leachate and in vitro screening for endocrine activity. Chemosphere 93 (10):2245–2253. doi: 10.1016/j.chemosphere.2013.07.075.
  • Yeguas, V., M. Altarsha, G. Monard, R. Lopez, and M. F. Ruiz-Lopez. 2011. Peptide binding to β-cyclodextrins: structure, dynamics, energetics, and electronic effects. The Journal of Physical Chemistry A 115 (42):11810–11817. doi: 10.1021/jp2053037.
  • Zhang, Q., Y. Cai, X. J. Wang, J. L. Xu, Z. Ye, S. Wang, P. H. Seeberger, and J. Yin. 2016. Targeted photodynamic killing of breast cancer cells employing heptamannosylated β-cyclodextrin-mediated nanoparticle formation of an adamantane-functionalized BODIPY photosensitizer. ACS Applied Materials & Interfaces 8 (49):33405–33411. doi: 10.1021/acsami.6b13612.

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.