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Biomimetic star-shaped porphyrin-cored poly(l-lactide)-b-glycopolymer block copolymers for targeted photodynamic therapy

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Abstract

Porphyrin-cored poly(l-lactide) (SPPLA) was successfully synthesized from ring-opening polymerization (ROP) of l-lactide initiated with porphyrin core. Then, SPPLA was coupled with benzylsulfanylthiocarbonylsufanylpropionic acid (BSPA), and a macro-reversible addition-fragmentation chain transfer (macroRAFT) polymerization agent SPPLA-BSPA was obtained. Finally, star-shaped porphyrin-cored poly(l-lactide)-b-poly(gluconamidoethyl methacrylate) (SPPLA-b-PGAMA) block copolymers were synthesized via RAFT of unprotected gluconamidoethyl methacrylate (GAMA) in 1-methyl-2-pyrrolidinone (NMP) solution at 70 °C. The structure of this block copolymer was thoroughly studied by nuclear magnetic resonance spectroscopy (NMR), gel permeation chromatography (GPC), and differential scanning calorimetry (DSC). Under the irradiation, such SPPLA-b-PGAMA copolymer exhibits efficient singlet oxygen generation and indicates high fluorescence quantum yields. Notably, with UV–vis and dynamic light scattering (DLS) analysis, SPPLA-b-PGAMA showed a very specific recognition with concanavalin A (ConA). Particularly, MTT shows that the cytotoxicity of SPPLA-b-PGAMA against COS-7 cells was very low and, when given a longer irradiation time, more BEL-7402 cancer cells died, which will be investigated in this study.

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Acknowledgments

The authors are greatly grateful for the financial support of the National Natural Science Foundation of China (21004031), the Natural Science Foundation of Jiangsu Province (BK2011459), the National Postdoctoral Foundation of China (20090461065), the National Postdoctoral Foundation of Jiangsu Province (1001034B), Open Foundation of Stake Key Laboratory of Natural and Biomimetic Drugs, Peking University (K20110105), and the social development Foundation of Zhen jiang (SH2012024).

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Authors and Affiliations

  1. Department of Chemical Engineering, School of Chemistry and Chemical Technology, Jiangsu University, Zhenjiang, 212013, People’s Republic of China

    Xiao-Hui Dai, Zhi-Ming Wang, Jian-Ming Pan, Si-Song Yuan & Yong-sheng Yan

  2. State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing, 100191, People’s Republic of China

    Xiao-Hui Dai & Yong-sheng Yan

  3. Department of Polymer Science and Engineering, School of Chemistry and Chemical Technology, Shanghai Jiao Tong University, Shanghai, 200240, People’s Republic of China

    Wei Liu & Chang-Ming Dong

  4. Hospital Affiliated to Jiangsu University, Zhenjiang, 212013, People’s Republic of China

    Dong-Ming Liu

  5. CSR Qingdao Sifang Co. Ltd., Qingdao, Shandong, 266111, China

    Lin Sun

Authors
  1. Xiao-Hui Dai
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  2. Zhi-Ming Wang
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  3. Wei Liu
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  4. Chang-Ming Dong
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  5. Jian-Ming Pan
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  6. Si-Song Yuan
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  7. Yong-sheng Yan
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  8. Dong-Ming Liu
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  9. Lin Sun
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Corresponding author

Correspondence to Xiao-Hui Dai.

Additional information

Mr Pan has done a prominent work in the study of singlet oxygen research and Fluorescence quantum yield.

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Dai, XH., Wang, ZM., Liu, W. et al. Biomimetic star-shaped porphyrin-cored poly(l-lactide)-b-glycopolymer block copolymers for targeted photodynamic therapy. Colloid Polym Sci 292, 2111–2122 (2014). https://doi.org/10.1007/s00396-014-3244-6

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  • DOI: https://doi.org/10.1007/s00396-014-3244-6

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