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Preparation and photoactivity of thermosensitive polymer supported metallophthalocyanine

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Abstract

A novel reactive metallophthalocyanine derivative, zinc tetra(2,4-dichloro-1,3,5-triazine)aminophthalocyanine (Zn-TDTAPc), was prepared and immobilized on poly(N-isopropylacrylamide) (PNIPAAm) by covalent bonding to obtain a thermosensitive polymer (Zn-TDTAPc-g-PNIPAAm). Compared with zinc tetraaminophthalocyanine (Zn-TAPc), Zn-TDTAPc-g-PNIPAAm exhibits excellent solubility in water and in most organic solvents. Furthermore, it has a special thermosensitive property in water and the lower critical solution temperature (LCST) is 34.1°C. It was found that both dissolved and precipitated Zn-TDTAPc-g-PNIPAAm present high photoactivity evidenced by the experiment of photocatalytic degradation of 1, 3-diphenylisobenzofuran (DPBF) in the presence of Zn-TDTAPc-g-PNIPAAm. These properties suggest that it can be used potentially in photodynamic therapy (PDT).

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References

  1. Gan F X, Hou L S, Wang G B. Optical and recording properties of short wavelength optical storage materials. Mater Sci Eng B, 2002, 76(1): 63–68

    Article  Google Scholar 

  2. Lee H K, Doi K, Kanazawa A, Shiono T, Ikeda T, Fujisawa T, Aizawa M, Lee B. Light-scattering-mode optical switching and image storage in polymer/liguid crystal composite films by means of photochemical phase transition. Polymer, 2000, 41(5): 1757–1763

    Article  CAS  Google Scholar 

  3. Elöise M, Rosalyn K, Edith A, Tebello N. Photocatalysis of 4-nitrophenol using zinc phthalocyanine complexes. J Mol Cata A-Chem, 2007, 261(1): 36–42

    Article  CAS  Google Scholar 

  4. Chen W X, Chen S L, Lü S S, Yao Y Y, Xu M H. Photocatalytic oxidation of phenol in aqueous solutions with oxygen catalyzed by supported metallophthalocyanine catalyst. Sci China Ser B-Chem, 2007, 50(3): 379–384

    Article  CAS  Google Scholar 

  5. Young F, Shtein M, Forrest S R. Controlled growth of a molecular bulk heterojunction photovoltaic cell. Nat Mater, 2005, 4(1): 37–41

    Article  CAS  Google Scholar 

  6. Mahmut D, Tebello N. Synthesis, photophysical and photochemical properties of aryloxy tetra-substituted gallium and indium phthalocyanine derivatives. Tetrahedron, 2007, 63(6): 1385–1394

    Article  CAS  Google Scholar 

  7. Stefano B, Enrico C, Loredana B, Raffaella R, Marzia G, Elena M. Zinc phthalocyanines-mediated photodynamic therapy induces cell death in adenocarcinoma cells. J Orgmet Chem, 2007, 692(6): 1269–1276

    Article  CAS  Google Scholar 

  8. Vanya M, Veselin K, Ivan A, Ekaterina B. Latchezar A, Günter S. and Dieter W. Photodynamic activity of water-soluble phthalocyanine zinc (II) complexes against pathogenic microorganisms. Bioorg Med Chem, 2007, 15(14): 4829–4835

    Article  CAS  Google Scholar 

  9. Ben-Hur E, Rosenthal I. Photosensitized inactivation of Chinese hamster cells by phthalocyanines. J Photochem Photobiol, 1985, 42(2): 129–133

    Article  CAS  Google Scholar 

  10. Huang J D, Lo P C, Chen Y M, Janice C L, Fong W P, Dennis K P N. Preparation and in vitro photodynamic activity of novel silicon (IV) phthalocyanines conjugated to serum albumins. J Inorg Biochem, 2006, 100(5–6): 946–951

    Article  CAS  Google Scholar 

  11. Eleni A, Dido Y, Spyros L. A confocal microscopy study of the very early cellular response to oxidative stress induced by zinc phthalocyanine sensitization. Free Radic Biol Med 2005, 39(9): 1119–1127

    Article  CAS  Google Scholar 

  12. Haywood-Small S L, Vernon D I, Griffiths J, Schofield J, Brown S B. Phthalocyanine-mediated photodynamic therapy induces cell death and a G0/G1 cell cycle arrest in cervical cancer cells. Biochem Biophys Res Commun, 2006, 339(2): 569–576

    Article  CAS  Google Scholar 

  13. Anne C E M. Signaling pathways in cell death and survival after photodynamic therapy. J Photochem Photobio B-Bio, 2000, 57(1): 1–13

    Article  Google Scholar 

  14. Ramiro D A, Bruno J M, Arsélio P C, Carlos B D. Intracellular signaling mechanisms in photodynamic therapy. Biochim Biophys Acta, 2004, 1704(2): 59–86

    Google Scholar 

  15. Hopper C. Photodynamic therapy: a clinical reality in the treatment of cancer. Lancet Oncol, 2000, 1: 212–219

    Article  CAS  Google Scholar 

  16. Fujimoto F, Iwasaki C, Arai C, Kuwako M, Yasugi E. Control of cell death by the smart polymeric vehicle. Biomacromolecules, 2000, 1(4): 515–518

    Article  CAS  Google Scholar 

  17. Molinaro G, Adam A, Zignani M, Taillefer J, Schwach-Abdellaoui K, Gurny R, Leroux J C. Evaluation of the local and systemic inflammatory responses induced by the subcutaneous injection of different biopolymers. Proc Intern Symp Control Relat Bioact Mater, 1999, 26: 611–612

    Google Scholar 

  18. Schild H G, Tirrell D A. Microcalorimetric detection of lower critical solution temperatures in aqueous polymer solutions. J Phys Chem, 1990, 94(10): 4352–4356

    Article  CAS  Google Scholar 

  19. Xia H P, Nogami M. Copper phthalocyanine bonding with gel and their optical limiting properties. Opt Mater, 2000, 15(2): 93–98

    Article  CAS  Google Scholar 

  20. Gil E S, Hudson S M. Stimuli-reponsive polymers and their bioconjugates. Prog Polym Sci, 2004, 29(12): 1173–1222

    Article  CAS  Google Scholar 

  21. Wilson T. Excited Singlet Molecular Oxygen in Photooxidation. J Am Chem Soc, 1966, 88(13): 2898–2902

    Article  CAS  Google Scholar 

  22. Luca B, Alessandro A, Mirko L, Michele C, Riccardo T, Francesco M, Silvia B. and Giorgio A P. New π-extended water-soluble squaraines as singlet oxygen generators. Org Lett 2005, 7(19): 4257–4260

    Article  CAS  Google Scholar 

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Correspondence to WenXing Chen.

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Supported by the National Natural Science Foundation of China (Grant No. 20574061), the Program for New Century Excellent Talents in University (Grant No. 040559) and the Program for Changjiang Scholars and Innovative Research Team in University (Grant No. 0654)

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Chen, W., Liu, F., Lü, W. et al. Preparation and photoactivity of thermosensitive polymer supported metallophthalocyanine. Sci. China Ser. B-Chem. 51, 570–576 (2008). https://doi.org/10.1007/s11426-008-0048-x

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  • DOI: https://doi.org/10.1007/s11426-008-0048-x

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