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Click synthesis of glycosylated porphyrin-cored PAMAM dendrimers with specific recognition and thermosensitivity

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Abstract

Glycoporphyrin dendrimers have received increasing attentions due to their distinct physical and chemistry properties, such as fluorescence and water solubility. They also acted as a promising photodynamic therapy (PDT) sensitizer and used in the study of carbohydrate-protein interaction. In this study, different generations of porphyrin-cored dendrimers consisting of glycosylated siloxane-poly (amido amine) typed dendron (PP-Si-PAMAM-Dm-Lac, m = 1, 2, and 3), multifunctional specific-targeting sensitizers, had been synthesized via click reaction. The structure of PP-Si-PAMAM-Dm-Lac was characterized by 1H NMR, GPC, FT-IR, UV-vis and fluorescence analyses. This glycoporphyrin dendrimers, not only obtained high fluorescence quantum yield and singlet oxygen production efficiency, but also showed specific recognition of lectin and remarkable temperature-responsive property (20–80 °C). These properties proved a facile click synthetic strategy of glycosylated siloxane-poly (amido amine) typed dendrimers with multiple functions as a promising tumor-selective photsensitizer (PS) for PDT and also allow applications in highly sensitive fluorescent probes over a larger temperature window.

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Acknowledgements

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 Practice Innovation Program of Jiang Su (SJZZ-0138), and Jiangsu University Science and Technology Project for Youth Support Fund.

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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

    Dan-Dan Chang, Wei-He Yang, Xiao-Hui Dai, Ji-Xiang Wang, Li Chen, Jian-Ming Pan & Yong-Sheng Yan

  2. Institute of Green Chemistry and Chemical Technology, Jiangsu University, Zhenjiang, 212013, People’s Republic of China

    Xiao-Hui Dai, Li Chen & Yong-Sheng Yan

  3. Hospital Affiliated to Human Agricultural University, Zhenjiang, 212013, People’s Republic of China

    Yi-Rong Dai

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  1. Dan-Dan Chang
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  2. Wei-He Yang
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  4. Ji-Xiang Wang
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Correspondence to Xiao-Hui Dai or Li Chen.

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Chang, DD., Yang, WH., Dai, XH. et al. Click synthesis of glycosylated porphyrin-cored PAMAM dendrimers with specific recognition and thermosensitivity. J Polym Res 25, 257 (2018). https://doi.org/10.1007/s10965-018-1640-1

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