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Analytical and Bioanalytical Chemistry

, Volume 378, Issue 8, pp 1898–1902 | Cite as

Synthetic polymers adsorbing bisphenol A and its analogues prepared by covalent molecular imprinting using bisphenol A dimethacrylate as a template molecule

  • Takashi Ikegami
  • Woo-Sang Lee
  • Hiroyuki Nariai
  • Toshifumi TakeuchiEmail author
Original Paper

Abstract

Synthetic polymers which can adsorb bisphenol A (BPA) and related compounds were prepared by a covalent molecular imprinting technique. BPA dimethacrylate, used as template molecule, was polymerized with a crosslinker, triethylene glycol dimethacrylate (TEGDMA) or trimethylol propane trimethacrylate (TRIM). After the polymerization treatment with dilute NaOH was used to cleave BPA from the polymers. For high recovery of BPA with low polymer matrix degradation, the hydrolysis conditions were determined to be treatment with 1.0 mol L−1 NaOH for 48 h. The binding sites generated by the hydrolysis were evaluated by determination of the retentivity of BPA, BPA analogues, and other endocrine disruptors. The polymers strongly adsorbed compounds with two hydroxyl groups at the 4,4′-positions. Generally the TEGDMA-based polymers had stronger affinity than the TRIM-based polymers, although the TRIM-based polymer adsorbed steroidal hormones with two hydroxyl groups, for example 17α-estradiol and 17β-estradiol, more strongly than the TEGDMA-based polymer, meaning that the crosslinkers affected the properties of the binding sites and, depending upon the target molecules, suitable crosslinkers should be chosen in this system.

Keywords

Covalent molecular imprinting Bisphenol A dimethacrylate Bisphenol A Endocrine disruptors Hydrogen bonding 

Notes

Acknowledgments

This work has supported by Japan Society for the promotion of Science and Ministry of Education, Culture, Sports, Science and Technology (Grants-in-Aid for Scientific Research).

References

  1. 1.
    Markey CM, Michaelson CL, Sonnenschein C, Soto AM (2001) In: Manfred M (ed) The handbook of environmental chemistry, endocrine disruptors, part 1, alkylphenols and bisphenol A as environmental estrogens. Springer, Berlin Heidelberg New York 129–153Google Scholar
  2. 2.
    Komiyama M, Takeuchi T, Mukawa T, Asanuma H (2002) Molecular Imprinting. Wiley–VCH, WeinheimGoogle Scholar
  3. 3.
    Sellergren B (2001) (ed) Molecularly imprinted polymers. Elsevier, AmsterdamGoogle Scholar
  4. 4.
    Bartsch RA, Maeda M (1998) (eds) Molecular and ionic recognition with imprinted polymers, ACS Symp Ser 703. American Chemical Society, Washington, DCGoogle Scholar
  5. 5.
    Wulff G (1995) Angew Chem Int Ed Engl 34:1812–1832Google Scholar
  6. 6.
    Takeuchi T, Haginaka J (1999) J Chromatogr B 728:1–20Google Scholar
  7. 7.
    Haupt K, Mosbach K (2000) Chem Rev 100:2495–2504CrossRefPubMedGoogle Scholar
  8. 8.
    Tarbin JAM, Sharman M (1999) Anal Commun 36:105–107CrossRefGoogle Scholar
  9. 9.
    Kanekiyo Y, Naganawa R, Tao H (2002) Chem Commun 2698–2699Google Scholar
  10. 10.
    Kubo T, Hosoya K, Watabe Y, Ikegami T, Tanaka N, Sano T, Kaya K (2003) J Chromatogr A 987:389–394CrossRefPubMedGoogle Scholar
  11. 11.
    Sanbe H, Haginaka J (2003) J Pharm Biomed Anal 30:1835–1844CrossRefPubMedGoogle Scholar
  12. 12.
    Umpleby II RJ, Bode M, Shimizu KD (2000) Analyst 125:1261–1265CrossRefGoogle Scholar
  13. 13.
    Joshi VP, Karmalkar RN, Kulkarni MG, Mashelkar RA (1999) Ind Eng Chem Res 38:4417–4423CrossRefGoogle Scholar
  14. 14.
    Ikegami T, Mukawa T, Nariai H, Takeuchi T (2004) Anal Chim Acta 504:131–135CrossRefGoogle Scholar
  15. 15.
    Wulff G, Vietmeier J, Poll HG (1987) Makromol Chem 188:731–740CrossRefGoogle Scholar
  16. 16.
    Ikegami T, Lee W-S, Nariai H, Takeuchi T (2004) J Chromatogr B, in pressGoogle Scholar

Copyright information

© Springer-Verlag 2004

Authors and Affiliations

  • Takashi Ikegami
    • 1
  • Woo-Sang Lee
    • 2
  • Hiroyuki Nariai
    • 2
  • Toshifumi Takeuchi
    • 2
    • 3
    Email author
  1. 1.Graduate School of Information SciencesHiroshima City UniversityHiroshima 731-3194Japan
  2. 2.Graduate School of Science and TechnologyKobe UniversityKobe 657-8501Japan
  3. 3.PrestoJapan Science and Technology Corporation (JST)Saitama 332-0012Japan

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