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Acid and light dual- stimuli-cleavable polymeric micelles

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Abstract

In this study, acid and light dual- stimuli-responsive amphiphilic AB-type methoxy poly(ethylene glycol)-acetal-ONB-poly(4-substituted-ε-caprolactone) (MPEG-a-ONB-PXCL) diblock copolymers were synthesized using ring-opening polymerization and nucleophilic substitution reactions. The prepared copolymer features an acid-cleavable acetal group and photocleavable o-nitrobenzyl linkage between the hydrophilic MPEG and hydrophobic PXCL blocks. The design enables the diblock copolymers to respond to both acid and ultraviolet (UV) light while ensuring the minimum number of stimuli-reactive moieties in the copolymer structure. The disruption of the copolymeric micelles in aqueous solution was examined under the action of pH or UV light alone or under the combined stimulation pH and UV light. Under the combined stimulation of UV irradiation and pH, the micellar nanoparticles could dissociate; therefore, the loaded molecules could be released from the assemblies more efficiently than under either stimulus alone. The nanoparticles exhibited nonsignificant toxicity against human cervical cancer (HeLa) cells at concentrations ≤300 μg mL−1. Doxorubicin (DOX)-loaded micelles facilitated the uptake of DOX by the HeLa cells at the initial stage. The dual stimuli-cleavable polymeric micelles show promising potential as new nanocarrier for precisely controlled release of encapsulated drug.

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References

  1. Song N, Ding M, Pan Z, Li J, Zhou L, Tan H, Fu Q (2013) Biomacromolecules 14:4407–4419

    Article  CAS  Google Scholar 

  2. Cao Z, Wu H, Dong J, Wang G (2014) Macromolecules 47:8777–8783

    Article  CAS  Google Scholar 

  3. Yang S, Zhu F, Wang Q, Liang F, Qu X, Gan Z, Yang Z (2015) J Mater Chem B 3:4043–4051

    Article  CAS  Google Scholar 

  4. Discher DE, Eissenberg A (2002) Science 297:967–973

    Article  CAS  Google Scholar 

  5. Zhou Z, Li Z, Ren Y, Hillmyer MA, Lodge TP (2003) J Am Chem Soc 125:10182–10183

    Article  CAS  Google Scholar 

  6. Klaikherd A, Nagamani C, Thayumanavan S (2009) J Am Chem Soc 131:4830–4838

    Article  CAS  Google Scholar 

  7. Yuan W, Shen T, Wang J, Zou H (2015) Polym Chem 5:3968–3971

    Article  Google Scholar 

  8. Jiang X, Zhao B (2008) Macromolecules 41:9366–9375

    Article  CAS  Google Scholar 

  9. Mori H, Kato I, Endo T (2009) Macromolecules 42:4985–4992

    Article  CAS  Google Scholar 

  10. Agut W, Brûlet A, Schatz C, Taton D, Lecommandoux S (2010) Langmuir 26:10546–10554

    Article  CAS  Google Scholar 

  11. Chen J, Qiu X, Ouyang J, Kong J, Zhong W, Xing MMQ (2011) Biomacromolecules 12:3601–3611

    Article  CAS  Google Scholar 

  12. Pan YJ, Chen YY, Wang DR, Wei C, Guo J, Lu DR, Chu CC, Wang CC (2012) Biomaterials 33:6570–6579

    Article  CAS  Google Scholar 

  13. Remant Bahadur KC, Thapa B, Xu P (2012) Mol Pharm 9:2719–2729

    Article  Google Scholar 

  14. Shao W, Miao K, Liu H, Ye C, Du J, Zhao Y (2013) Polym Chem 4:3398–3410

    Article  CAS  Google Scholar 

  15. Chen W, Zhong P, Meng F, Cheng R, Deng C, Feijen J, Zhong Z (2013) J Control Release 169:171–179

    Article  CAS  Google Scholar 

  16. Yu S, He C, Ding J, Cheng Y, Song W, Zhuang X, Chen X (2013) Soft Matter 9:2637–2645

    Article  CAS  Google Scholar 

  17. Wu Y, Kuang H, Xie Z, Chen X, Jing X, Huang Y (2014) Polym Chem 5:4488–4498

    Article  CAS  Google Scholar 

  18. Zhang Y, He J, Cao D, Zhang M, Ni P (2014) Polym Chem 5:5124–5138

    Article  CAS  Google Scholar 

  19. Miao K, Shao W, Liu H, Zhao Y (2014) Polym Chem 5:1191–1201

    Article  CAS  Google Scholar 

  20. Liu H, Li C, Tang D, An X, Guo Y, Zhao Y (2015) J Mater Chem B 3:3959–3971

    Article  CAS  Google Scholar 

  21. Zhou L, Li J, Luo Q, Zhu J, Zou H, Gao Y, Wang L, Xu J, Dong Z, Liu J (2013) Soft Matter 9:4635–4641

    Article  CAS  Google Scholar 

  22. Yang F, Cao Z, Wang G (2015) Polym Chem 6:7995–8002

    Article  CAS  Google Scholar 

  23. Han D, Tong X, Zhao Y (2012) Langmuir 28:2327–2331

    Article  CAS  Google Scholar 

  24. Xiao W, Zeng X, Lin H, Han K, Jia HZ, Zhang XZ (2015) Chem Commun 51:1475–1478

    Article  CAS  Google Scholar 

  25. Huang F, Cheng R, Meng F, Deng C, Zhong Z (2015) Biomacromolecules 16:2228–2236

    Article  CAS  Google Scholar 

  26. Xuan J, Han D, Xia H, Zhao Y (2014) Langmuir 30:410–417

    Article  CAS  Google Scholar 

  27. Paramonov SE, Bachelder EM, Beaudette TT, Standley SM, Lee CC, Dashe J, Fréchet JMJ (2008) Bioconjug Chem 19:911–919

    Article  CAS  Google Scholar 

  28. Kharkar PM, Kiick KL, Kloxin AM (2015) Polym Chem 6:5565–5574

    Article  CAS  Google Scholar 

  29. Lee RS, Wang SW, Li YC, Fang JY (2015) RSC Adv 5:497–512

    Article  CAS  Google Scholar 

  30. Lee RS, Hung CB (2007) Polymer 48:2605–2612

    Article  CAS  Google Scholar 

  31. Kuang H, Wu S, Xie Z, Meng F, Jing X, Huang Y (2012) Biomacromolecules 13:3004–3012

    Article  CAS  Google Scholar 

  32. Provencher SW, Hendrix J (1978) J Phys Chem 69:4237–4276

    Article  Google Scholar 

  33. Griffin DR, Schlosser JL, Lam SF, Nguyen TH, Maynard HD, Kasko AM (2013) Biomacromolecules 14:1199–1207

    Article  CAS  Google Scholar 

  34. Torchilin VP (2001) J Contr Rel 73:137–172

    Article  CAS  Google Scholar 

  35. Fairley N, Hoang B, Allen C (2008) Biomacromolecules 9:2283–2291

    Article  CAS  Google Scholar 

  36. Ranjan R, Brittain WJ (2007) Macromol Rapid Commun 28:2084–2089

    Article  CAS  Google Scholar 

  37. Lv C, Wang Z, Wang P, Tang X (2012) Langmuir 28:9387–9394

    Article  CAS  Google Scholar 

  38. Hao Y, He J, Li S, Liu J, Zhang M, Ni P (2014) J Mater Chem B 2:4237–4249

    Article  CAS  Google Scholar 

  39. Wang H, He J, Cao D, Zhang M, Li F, Tam C, Ni P (2015) Polym Chem 6:4809–4818

    Article  CAS  Google Scholar 

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Acknowledgements

The research was supported by grants from Ministry of Science and Technology (MOST 104-2221-E-182-061) and Chang Gung Memorial Hospital (CMRPD5F0011).

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Authors and Affiliations

  1. Graduate Institute of Natural Products, Chang Gung University, Tao-Yuan, Taiwan

    Jia-You Fang

  2. Department of Traditional Chinese Medicine, Chang Gung Memorial Hospital at Keelung, Keelung, Taiwan

    Yin-Ku Lin

  3. Division of Natural Science, Center of General Education, Chang Gung University, 259 Wen-Hwa 1st Road, Guishan Dist, Tao-Yuan, 33302, Taiwan

    Shiu-Wei Wang, Yung-Ching Yu & Ren-Shen Lee

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  1. Jia-You Fang
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  2. Yin-Ku Lin
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  3. Shiu-Wei Wang
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  5. Ren-Shen Lee
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Correspondence to Ren-Shen Lee.

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Fang, JY., Lin, YK., Wang, SW. et al. Acid and light dual- stimuli-cleavable polymeric micelles. J Polym Res 24, 3 (2017). https://doi.org/10.1007/s10965-016-1166-3

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  • DOI: https://doi.org/10.1007/s10965-016-1166-3

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