Nitrophenyl-engaged photocleavage of an amphiphilic copolymer for spatiotemporally controlled drug release

  • Liuwei Zhang
  • Ming Qian
  • Jingyun WangEmail author
  • Jing Xia
  • Hongyan Cui
  • Qixian ChenEmail author
Materials for life sciences


Photo-responsive nitrophenyl moieties were proposed to conjugate as pendants of the pullulan backbone through labile carbamate linkage to yield amphiphilic pullulan derivatives. Note that the hydrophobicity of the conjugated nitrophenyl components in the amphiphiles enable facile their self-assembly with the hydrophobic chemotherapeutic drug (doxorubicin) as the internal drug reservoirs, whereas the hydrophilic pullulan segments existed as the biocompatible surroundings. Upon photo-illumination, the carbamate linkage was susceptible to cleavage for departure of the nitrophenyl components from the pullulan backbone owing to the photo-responsive nitrophenyl moieties. Simultaneously, the nitrophenyl components transformed into water-soluble aldehyde-terminalized nitrosophenyl derivatives, leadingly accounting for structural disassembly and liberation of the cytotoxic doxorubicin payloads. Therefore, our proposed photo-responsive strategy could address the reluctant intracellular drug release drawbacks of the conventional amphiphile-based drug delivery systems. Notably, markedly lower IC50 (half maximal inhibitory concentration) index of our constructed doxorubicin delivery systems was determined to be approximately 1.0 μg/mL upon photo-illumination, in contrast to IC50 index of 5.6 μg/mL in the absence of photo-illumination (approximate fivefold), thereby representing as a facile spatiotemporal artifice to execute on-demand drug release to the photo-imposed cells.



This research was funded by National Natural Science Foundation of China (Nos. 21878041, U1608222), Fundamental Research Funds for the Central Universities [No. DUT17RC(3)059] and Talent Project of Revitalizing Liaoning (XLYC1807184).

Compliance with ethical standards

Conflict of interest

The authors declare no competing financial interest.

Supplementary material

10853_2019_3831_MOESM1_ESM.docx (812 kb)
Supplementary material 1 (DOCX 812 kb)


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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.State Key Laboratory of Fine ChemicalsDalian University of TechnologyDalianChina
  2. 2.School of BioengineeringDalian University of TechnologyDalianChina

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