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Magnetic organic porous polymer as a solid-phase extraction adsorbent for enrichment and quantitation of gastric cancer biomarkers (P-cresol and 4-hydroxybenzoic acid) in urine samples by UPLC

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Abstract

A novel magnetic organic porous polymer (denoted as Fe3O4@PC-POP) was developed for magnetic solid-phase extraction (MSPE) of two gastric cancer biomarkers (P-cresol and 4-hydroxybenzoic acid) from urine samples prior to high-performance liquid chromatographic analysis. The adsorbent was characterized by scanning electron microscope, transmission electron microscope, FTIR, powder X-ray diffraction, and other techniques. The result of dynamic light scattering shows that the particle size of the adsorbent is mainly distributed around 400 nm. Based on the design concept of the Fe3O4@PC-POP, the proposed material can effectively capture the target analytes through electrostatic and hydrophobic interaction mechanism. Furthermore, the enrichment conditions were optimized by the response surface method, and the method was utilized for the determination of P-cresol and 4-hydroxybenzoic acid in real urine samples from health and gastric cancer patients with high enrichment factors (34.8 times for P-cresol and 38.7 times for 4-hydroxybenzoic acid), low limit of detection (0.9–5.0 μg L−1), wide linear ranges (3.0–1000 μg L−1), satisfactory relative standard deviation (2.5%–8.5%), and apparent recoveries (85.3–112% for healthy people’s and 86.0–112% for gastric cancer patients’ urine samples). This study provides a guided principle for design of the versatile polymer with specific capturing of the target compounds from complex biological samples.

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References

  1. Wittekmd C, Compton CC, Greene FL et al (2002) TNM residual tumorclassification revisited. Cancer 94:2511–2516

    Article  Google Scholar 

  2. Ychou M, Boige V, Pignon JP, Conroy T, Bouché O, Lebreton G, Ducourtieux M, Bedenne L, Fabre JM, Saint-Aubert B, Genève J, Lasser P, Rougier P (2011) Perioperative chemotherapy compared with surgery alone for resectable gastroesophageal adenocarcinoma: an FNCLCC and FFCD multicenter phase III trial. J Clin Oncol 29:1715–1721

    Article  CAS  Google Scholar 

  3. Jayanthi VSPKS, Das AB, Saxena U (2017) Recent advances in biosensor development for the detection of cancer biomarkers. Biosens Bioelectron 91:15–23

    Article  CAS  Google Scholar 

  4. Siegel RL, Miller KD, Jemal A (2015) Cancer statistics, 2015. CA Cancer J Clin 65:5–29

    Article  Google Scholar 

  5. Abbas M, Habib M, Naveed M, Karthik K, Dhama K, Shi M, Dingding C (2017) The relevance of gastric cancer biomarkers in prognosis and pre- and post-chemotherapy in clinical practice. Biomed Pharmacother 95:1082–1090

    Article  CAS  Google Scholar 

  6. Dunn WB, Broadhurst DI, Atherton HJ, Goodacre R, Griffin JL (2011) ChemInform abstract: systems level studies of mammalian metabolomes: the roles of mass spectrometry and nuclear magnetic resonance spectroscopy. Chem Soc Rev 40:387–426

    Article  CAS  Google Scholar 

  7. Chen JL, Fan J, Lu XJ (2014) CE-MS based on moving reaction boundary method for urinary metabolomic analysis of gastric cancer patients. Electrophoresis 35:1032–1039

    Article  CAS  Google Scholar 

  8. Liang Q, Wang C, Li B (2015) Metabolomic analysis using liquid chromatography/mass spectrometry for gastric cancer. Appl Biochem Biotechnol 176:2170–2184

    Article  CAS  Google Scholar 

  9. Chen Y, Zhang J, Guo L, Liu L, Wen J, Xu L, Yan M, Li Z, Zhang X, Nan P, Jiang J, Ji J, Zhang J, Cai W, Zhuang H, Wang Y, Zhu Z, Yu Y (2016) A characteristic biosignature for discrimination of gastric cancer from healthy population by high throughput GC-MS analysis. Oncotarget 7:87496–87510

    Article  Google Scholar 

  10. Pijls KE, Smolinska A, Jonkers DM et al (2016) A profile of volatile organic compounds in exhaled air as a potential non-invasive biomarker for liver cirrhosis. Sci Rep 6:19903

    Article  CAS  Google Scholar 

  11. Luo P, Yin PY, Hua R et al (2018) A large-scale, multicenter serum metabolite biomarker identification study for the early detection of hepatocellular carcinoma. Hepatology 67:662–675

    Article  CAS  Google Scholar 

  12. Wang J, Zhang T, Shen X, Liu J, Zhao D, Sun Y, Wang L, Liu Y, Gong X, Liu Y, Zhu ZJ, Xue F (2016) Serum metabolomics for early diagnosis of esophageal squamous cell carcinoma by UHPLC-QTOF/MS. Metabolomics 12:116

    Article  Google Scholar 

  13. Lu YH, Li N, Gao L et al (2016) Acetylcarnitine is a candidate diagnostic and prognostic biomarker of hepatocellular carcinoma. Cancer Res 76:2912–2920

    Article  CAS  Google Scholar 

  14. Tian Y, Liu X, Duan J et al (2018) Prediction of chemotherapeutic efficacy in non-small cell lung cancer by serum metabolomic profiling. Clin Cancer Re 24:2100–2109

    Article  CAS  Google Scholar 

  15. Kashani FZ, Ghoreishi SM, Khoobi A, Enhessari M (2019) A carbon paste electrode modified with a nickel titanate nanoceramic for simultaneous voltammetric determination of ortho- and para-hydroxybenzoic acids. Microchim Acta 186:12

    Article  Google Scholar 

  16. Belenguer-Sapia C, Pellicer-Castell E, Vila C et al (2019) A poly (glycidyl-co-ethylene dimethacrylate) nanohybrid modified with β-cyclodextrin as a sorbent for solid-phase extraction of phenolic compounds. Microchim Acta 186:1–11

    Article  Google Scholar 

  17. Shi Y, Zhang JY, He J et al (2019) A method of detecting two tumor markers (p-hydroxybenzoic acid and p-cresol) in human urine using a porous magnetic <beta >−cyclodextrine polymer as solid phase extractant, an alternative for early gastric cancer diagnosis. Talanta 191:133–140

    Article  CAS  Google Scholar 

  18. Wu D, Xu F, Sun B, Fu R, He H, Matyjaszewski K (2012) Design and preparation of porous polymers. Chem Rev 112:3959–4015

    Article  CAS  Google Scholar 

  19. Jiang JX, Cooper A (2010) Microporous organic polymers: design, synthesis, and function. Topics Curr Chem 293:1–33

    CAS  Google Scholar 

  20. Budd PM, Butler A, Selbie J, Mahmood K, McKeown NB, Ghanem B, Msayib K, Book D, Walton A (2007) The potential of organic polymer-based hydrogen storage materials. Phys Chem Chem Phys 9:1802–1808

    Article  CAS  Google Scholar 

  21. Li Z, Yang YW (2017) Creation and bioapplications of porous organic polymer materials. J Mater Chem B 5:9278–9290

    Article  CAS  Google Scholar 

  22. Zhang W, Aguila B, Ma S (2017) Potential applications of functional porous organic polymer materials. J Mater Chem A 5:8795–8824

    Article  CAS  Google Scholar 

  23. He J, Xu FJ, Chen Z et al (2017) AuNPs/POPs as a new type of SERS substrate for sensitive recognition of polyaromatic hydrocarbons. Chem Commun 53:11044–11047

    Article  CAS  Google Scholar 

  24. Qian L, Jian BS, Jian TS et al (2011) Graphene and graphene oxide sheets supported on silica as versatile and high-performance adsorbents for solid-phase extraction. Angew Chem 50:5913–5917

    Article  Google Scholar 

  25. Jiang B, Wu Q, Deng N, Chen Y, Zhang L, Liang Z, Zhang Y (2016) Hydrophilic GO/Fe3O4/Au/PEG nanocomposites for highly selective enrichment of glycopeptides. Nanoscale 8:4894–4897

    Article  CAS  Google Scholar 

  26. Zhang C, Li G, Zhang Z (2015) A hydrazone covalent organic polymer based micro-solid phase extraction for online analysis of trace Sudan dyes in food samples. J Chromatogr A 1419:1–9

    Article  CAS  Google Scholar 

  27. Wei W, Lu R, Xie H, Zhang Y, Bai X, Gu L, da R, Liu X (2015) Selective adsorption and separation of dyes from an aqueous solution on organic–inorganic hybrid cyclomatrix polyphosphazene submicro-spheres. J Mater Chem A 3:4314–4322

    Article  CAS  Google Scholar 

  28. He G, Peng H, Liu T, Yang M, Zhang Y, Fang Y (2009) A novel picric acid film sensor via combination of the surface enrichment effect of chitosan films and the aggregation-induced emission effect of siloles. J Mater Chem 19:7347–7353

    Article  CAS  Google Scholar 

  29. Hu X, Long Y, Fan M et al (2018) Two-dimensional covalent organic frameworks as self -template derived nitrogen-doped carbon nanosheets for eco-friendly metal-free catalysis. Appl Catal B Environ 244:25–35

    Article  Google Scholar 

  30. Ma HC, Kan JL, Chen GJ, Chen CX, Dong YB (2017) Pd NPs-loaded homochiral covalent organic framework for heterogeneous asymmetric catalysis. Chem Mater 29:6518–6524

    Article  CAS  Google Scholar 

  31. Wang H, Wang C, Yang Y, Zhao M, Wang Y (2017) H3PW12O40 /mpg-C3N4 as an efficient and reusable bifunctional catalyst in one-pot oxidation-Knoevenagel condensation tandem reaction. Catal Sci Technol 7:405–417

    Article  Google Scholar 

  32. Shcherban ND, Mäki-Arvela P, Aho A, Sergiienko SA, Yaremov PS, Eränen K, Murzin DY (2018) Melamine-derived graphitic carbon nitride as a new effective metal-free catalyst for Knoevenagel condensation of benzaldehyde with ethylcyanoacetate. Catal Sci Technol 8:2928–2937

    Article  CAS  Google Scholar 

  33. Fine AK, Schmidt MP, Martínez et al (2018) Nitrogen-rich compounds constitute an increasing proportion of organic matter with depth in O-i-O-e-O-a -A horizons of temperate forests. Geoderma 323:1–12

    Article  CAS  Google Scholar 

  34. Dong H, Guo X, Yang C, Ouyang Z (2018) Synthesis of g-C3N4, by different precursors under burning explosion effect and its photocatalytic degradation for tylosin. Appl Catal B Environ 230:65–76

    Article  CAS  Google Scholar 

  35. Faisal M, Ismail AA, Harraz FA, al-Sayari SA, el-Toni AM, al-Assiri MS (2016) Synthesis of highly dispersed silver doped g-C3N4 nanocomposites with enhanced visible-light photocatalytic activity. Mater Des 98:223–230

    Article  CAS  Google Scholar 

  36. Leng Y, Li J, Zhang C, Jiang P, Li Y, Jiang Y, du S (2017) N-doped carbon encapsulated molybdenum carbide as an efficient catalyst for oxidant-free dehydrogenation of alcohols. J Mater Chem A 5:17580–17588

    Article  CAS  Google Scholar 

  37. Ravindran S, Williams MAK, Ward RL, Gillies G (2018) Understanding how the properties of whey protein stabilized emulsions depend on pH, ionic strength and calcium concentration, by mapping environmental conditions to zeta potential. Food Hydrocoll 79:572–578

    Article  CAS  Google Scholar 

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Funding

This work was supported by the National Natural Science Foundation of China (NSFC) Fund (No. 21575055) and the Henan Key Laboratory of Biomolecular Recognition and Sensing (HKLBRSK1901).

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Correspondence to Xiaoyan Liu.

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Li, S., Zhang, Y., Mu, S. et al. Magnetic organic porous polymer as a solid-phase extraction adsorbent for enrichment and quantitation of gastric cancer biomarkers (P-cresol and 4-hydroxybenzoic acid) in urine samples by UPLC. Microchim Acta 187, 388 (2020). https://doi.org/10.1007/s00604-020-04362-z

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