Synthesis of Self-assemble pH-responsive Cyclodextrin Block Copolymer for Sustained Anticancer Drug Delivery

Bei-bei Lu; Lu-lu Wei; Gui-hua Meng; Jun Hou; Zhi-yong Liu; Xu-hong Guo

doi:10.1007/s10118-017-1947-0

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Synthesis of Self-assemble pH-responsive Cyclodextrin Block Copolymer for Sustained Anticancer Drug Delivery

Papers | Updated：2021-02-18

- Synthesis of Self-assemble pH-responsive Cyclodextrin Block Copolymer for Sustained Anticancer Drug Delivery
- Chinese Journal of Polymer Science Vol. 35, Issue 8, Pages: 924-938(2017)
- Affiliations：
  
  a.School of Chemistry & Chemical Engineering, Shihezi University/Key Laboratory of Materials-Oriented Chemical Engineering of Xinjiang Uygur Autonomous Region/Engineering Research Center of Materials-Oriented Chemical Engineering of Xinjiang Bingtuan, Shihezi 832003, China
  b.Department of Immunology, Shihezi University School of Medicine/Department of Pathology and Key Laboratories for Xinjiang Endemic and Ethnic Diseases, Shihezi University School of Medicine, Shihezi 832003, China
  c.State Key Laboratory of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China
- Author bio：
  
  Zhi-yong Liu (刘志勇), E-mail:lzyongclin@sina.com
- Funds：
- DOI：10.1007/s10118-017-1947-0
  CLC：
- Received：14 January 2017，
  
  Revised：2017-2-28，
  
  Accepted：01 March 2017，
  
  Published：2017-08
- Accepted：
Scan QR Code
Bei-bei Lu, Lu-lu Wei, Gui-hua Meng, et al. Synthesis of Self-assemble pH-responsive Cyclodextrin Block Copolymer for Sustained Anticancer Drug Delivery[J]. Chinese Journal of Polymer Science, 2017, 35(8): 924-938.
DOI：

Bei-bei Lu, Lu-lu Wei, Gui-hua Meng, et al. Synthesis of Self-assemble pH-responsive Cyclodextrin Block Copolymer for Sustained Anticancer Drug Delivery[J]. Chinese Journal of Polymer Science, 2017, 35(8): 924-938. DOI： 10.1007/s10118-017-1947-0.

摘要

Abstract

Well-defined pH-responsive poly(

-caprolactone)-graft-

-cyclodextrin-graft-poly(2-(dimethylamino)ethyl-methacrylate)-

-poly(ethylene glycol) methacrylate amphiphilic copolymers (PCL-

-CD-

-P(DMAEMA-

-PEGMA)) were synthesized using a combination of atom transfer radical polymerization (ATRP)

ring opening polymerization (ROP) and "click" chemistry. Successful synthesis of polymers was confirmed by Fourier transform infrared spectroscopy (FTIR)

proton nuclear magnetic resonance (

H-NMR)

and gel permeation chromatography (GPC). Then

the polymers could self-assemble into micelles in aqueous solution

which was demonstrated by dynamic light scattering (DLS) and transmission electron microscopy (TEM). The pH-responsive self-assembly behavior of these copolymers in water was investigated at different pH values of 7.4 and 5.0 for controlled doxorubicin (DOX) release

and these results revealed that the release rate of DOX could be effectively controlled by altering the pH

and the release of drug loading efficiency (DLE) was up to 88% (

W/W

). CCK-8 assays showed that the copolymers had low toxicity and possessed good biodegradability and biocompatibility

whereas the DOX-loaded micelles remained with high cytotoxicity for HeLa cells. Moreover

confocal laser scanning microscopy (CLSM) images revealed that polymeric micelles could actively target the tumor site and the efficient intracellular DOX release from polymeric micelles toward the tumor cells further confirmed the anti-tumor effect. The DOX-loaded micelles could easily enter the cells and produce the desired pharmacological action and minimize the side effect of free DOX. These results successfully indicated that pH-responsive polymeric micelles could be potential hydrophobic drug delivery carriers for cancer targeting therapy with sustained release.

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references

F. Liu , M.W. Urban . . Prog. Polym. Sci , 2010 . 35 3 DOI: 10.1016/j.progpolymsci.2009.10.002 http://doi.org/10.1016/j.progpolymsci.2009.10.002 .

M.W. Urban . . Prog. Polym. Sci. , 2009 . 34 679 DOI: 10.1016/j.progpolymsci.2009.03.004 http://doi.org/10.1016/j.progpolymsci.2009.03.004 .

S. Mura , J. Nicolas , P. Couvreur . . Nat. Mater. , 2013 . 12 991 DOI: 10.1038/nmat3776 http://doi.org/10.1038/nmat3776 .

N.H. Aloorkar , A.S. Kulkarni , R.A. Patil , D.J. Ingale . . Int. J. Pharm. Sci. Nanotech. , 2012 . 5 1675 .

Q. Zhang , N.R. Ko , J.K. Oh . . Chem. Commun. , 2012 . 48 7542 DOI: 10.1039/c2cc32408c http://doi.org/10.1039/c2cc32408c .

L. Li , B.B. Lu , Q.K. Fan , L.L. Wei , J.N. Wu , J. Hou , X.H. Guo , Z.Y. Liu . . RSC Adv. , 2016 . 6 27102 DOI: 10.1039/C6RA01504B http://doi.org/10.1039/C6RA01504B .

Y.J. Zhang , P. Li , H. Pan , L.L. Liu , M.Y. Ji , N. Sheng , C. Wang , L.T. Cai , Y.F. Ma . . Biomaterials , 2016 . 83 219 DOI: 10.1016/j.biomaterials.2016.01.023 http://doi.org/10.1016/j.biomaterials.2016.01.023 .

B.B. Lu , L. Li , L.L. Wei , X.H. Guo , J. Hou , Z.Y. Liu . . RSC Adv. , 2016 . 6 50993 DOI: 10.1039/C6RA08108H http://doi.org/10.1039/C6RA08108H .

A. Hervault , M. Lim , C. Boyer , A.E. Dunn , D. Mott , S. Maenosono , N.T.K. Thanh . . Nanoscale , 2016 . 8 12152 DOI: 10.1039/C5NR07773G http://doi.org/10.1039/C5NR07773G .

H.T. Zhang , W. Tian , R.T. Suo , Y. Yue , X.D. Fan , Z. Yang , H. Li , W.B. Zhang , Y. Bai . . J. Mater. Chem. B , 2015 . 3 8528 DOI: 10.1039/C5TB01665G http://doi.org/10.1039/C5TB01665G .

Z.R. Guo , Y.J. Feng , D.W. Zhu , S. He , H.B. Liu , X.R. Shi , J. Sun , M.Z. Qu . . Adv. Funct. Mater. , 2013 . 23 5010 DOI: 10.1002/adfm.v23.40 http://doi.org/10.1002/adfm.v23.40 .

W. Wang , H.B. Liu , M. Mu , H.Y. Yin , Y.J. Feng . . Polym. Chem. , 2015 . 6 2900 DOI: 10.1039/C5PY00053J http://doi.org/10.1039/C5PY00053J .

H.Y. Yin , Y.J. Feng , H.B. Liu , M. Mu , C.H. Fei . . Langmuir , 2014 . 30 9911 DOI: 10.1021/la501461n http://doi.org/10.1021/la501461n .

S. Lee , K. Saito , H.R. Lee , M.J. Lee , Y. Shibasaki , Y. Oishi , B.S. Kim . . Biomacromolecules , 2012 . 13 1190 DOI: 10.1021/bm300151m http://doi.org/10.1021/bm300151m .

X. Liu , P.H. Ni , J.L. He , M.Z. Zhang . . Macromolecules , 2010 . 43 4771 DOI: 10.1021/ma902658n http://doi.org/10.1021/ma902658n .

K. Ulbrich , Holá , . K , V. Šubr , A. Bakandritsos , J. Tuček , R. Zbořil . . Chem. Rev. , 2016 . 116 5338 DOI: 10.1021/acs.chemrev.5b00589 http://doi.org/10.1021/acs.chemrev.5b00589 .

Y.Y. Durmaz , Y.L. Lin , M.E.H. ElSayed . . Adv. Funct. Mater. , 2013 . 23 3885 DOI: 10.1002/adfm.v23.31 http://doi.org/10.1002/adfm.v23.31 .

J.M. Ren , T.G. McKenzie , Q. Fu , E.H.H. Wong , J.T. Xu , Z.S. An , S. Shanmugam , T.P. Davis , C. Boyer , G.G. Qiao . . Chem. Rev. , 2016 . 116 6743 DOI: 10.1021/acs.chemrev.6b00008 http://doi.org/10.1021/acs.chemrev.6b00008 .

O. Altintas , A.P. Vogt , C.B. Kowollik , U. Tunca . . Polym. Chem. , 2012 . 3 34 DOI: 10.1039/C1PY00249J http://doi.org/10.1039/C1PY00249J .

J.J. Wang , J.L. Zhang , S.L. Yu , W. Wu , X.Q. Jiang . . ACS Macro Lett. , 2013 . 2 82 DOI: 10.1021/mz300538u http://doi.org/10.1021/mz300538u .

D.J.A. Cameron , M.P. Shaver . . Chem. Soc. Rev. , 2011 . 40 1761 DOI: 10.1039/C0CS00091D http://doi.org/10.1039/C0CS00091D .

K. Ren , M.Z. Zhang , J.L. He , Y.X. Wu , P.H. Ni . . ACS Appl. Mater. Interfaces , 2015 . 7 11263 DOI: 10.1021/acsami.5b01410 http://doi.org/10.1021/acsami.5b01410 .

C. Boyer , N.A. Corrigan , K. Jung , D. Nguyen , T.K. Nguyen , N.N.M. Adnan , S. Oliver , S. Shanmugam , J. Yeow . . Chem. Rev. , 2016 . 116 1803 DOI: 10.1021/acs.chemrev.5b00396 http://doi.org/10.1021/acs.chemrev.5b00396 .

T. Higashiharaa , M. Hayashib , A. Hirao . . Prog. Polym. Sci. , 2011 . 36 323 DOI: 10.1016/j.progpolymsci.2010.08.001 http://doi.org/10.1016/j.progpolymsci.2010.08.001 .

C. Boyer , A. Derveaux , P.B. Zetterlund , M.R. Whittaker . . Polym. Chem. , 2012 . 3 117 DOI: 10.1039/C1PY00384D http://doi.org/10.1039/C1PY00384D .

Y. Hao , J.L. He , S. Li , J. Liu , M.Z. Zhang , P.H. Ni . . J. Mater. Chem. B , 2014 . 2 4237 DOI: 10.1039/C4TB00334A http://doi.org/10.1039/C4TB00334A .

N.J. Warren , S.P. Armes . . J. Am. Chem. Soc. , 2014 . 136 10174 DOI: 10.1021/ja502843f http://doi.org/10.1021/ja502843f .

P.F. Shi , Q.L. Li , X. He , S.T. Li , P.C. Sun , W.Q. Zhang . . Macromolecules , 2014 . 47 7442 DOI: 10.1021/ma501598k http://doi.org/10.1021/ma501598k .

P.L. Golas , K. Matyjaszewski . . Chem. Soc. Rev. , 2010 . 39 1338 DOI: 10.1039/B901978M http://doi.org/10.1039/B901978M .

K. Kempe , A. Krieg , C.R. Becer , U.S. Schubert . . Chem. Soc. Rev. , 2012 . 41 176 DOI: 10.1039/C1CS15107J http://doi.org/10.1039/C1CS15107J .

W.Z. Yuan , X.F. Li , S.Y. Gua , A. Cao , J. Ren . . Polymer , 2011 . 52 658 DOI: 10.1016/j.polymer.2010.12.052 http://doi.org/10.1016/j.polymer.2010.12.052 .

F. Manakker , T. Vermonden , C.F. Nostrum , W.E. Hennink . . Biomacromolecules , 2009 . 10 3157 DOI: 10.1021/bm901065f http://doi.org/10.1021/bm901065f .

G.S. Chen , M. Jiang . . Chem. Soc. Rev. , 2011 . 40 2254 DOI: 10.1039/c0cs00153h http://doi.org/10.1039/c0cs00153h .

J.X. Zhang , P.X. Ma . . Adv. Drug Deliver. Rev. , 2013 . 65 1215 DOI: 10.1016/j.addr.2013.05.001 http://doi.org/10.1016/j.addr.2013.05.001 .

H. Wei , C.Y. Yu . . Biomater. Sci. , 2015 . 3 1050 DOI: 10.1039/C4BM00417E http://doi.org/10.1039/C4BM00417E .

M.E. Davis , M.E. Brewster . . Nat. Rev. Drug Discov. , 2004 . 3 1023 DOI: 10.1038/nrd1576 http://doi.org/10.1038/nrd1576 .

K. Uekama , F. Hirayama , T. Irie . . Chem. Rev. , 1998 . 98 2045 DOI: 10.1021/cr970025p http://doi.org/10.1021/cr970025p .

Y.Y. Yuan , Q. Du , Y.C. Wang , J. Wang . . Macromolecules , 2010 . 43 1739 DOI: 10.1021/ma9023763 http://doi.org/10.1021/ma9023763 .

J.C. Chen , M.Z. Liu . . RSC Adv. , 2014 . 4 9684 DOI: 10.1039/c3ra47026a http://doi.org/10.1039/c3ra47026a .

Q. He , W. Wu , K.M. Xiu , Q. Zhang , F.J. Xu , J.S. Li . . Int. J. Pharm. , 2013 . 443 110 DOI: 10.1016/j.ijpharm.2012.12.042 http://doi.org/10.1016/j.ijpharm.2012.12.042 .

J.J. Yin , S.P. Shumyak , C. Burgess , Z.W. Zhou , Z.X. He , X.J. Zhang , S.T. Pan , T.X. Yang , W. Duan , J.X. Qiu , S.F. Zhou . . Int. J. Pharm. , 2015 . 10 4717 .

J. Liu , Y. Xu , Q. Yang , C. Li , W.E. Hennink , R. Zhuo , X. Jiang . . Acta Biomater. , 2013 . 9 7758 DOI: 10.1016/j.actbio.2013.04.046 http://doi.org/10.1016/j.actbio.2013.04.046 .

M.M. Wang , Y. Wang , K. Hu , N.M. Shao , Y.Y. Cheng . . Biomater. Sci. , 2015 . 3 480 DOI: 10.1039/C4BM00365A http://doi.org/10.1039/C4BM00365A .

T.M. Allen , P.R. Cullis . . Science , 2004 . 303 1818 DOI: 10.1126/science.1095833 http://doi.org/10.1126/science.1095833 .

K. Tungala , P. Adhikary , S. Krishnamoorthi . . Carbohyd. Polym. , 2013 . 95 295 DOI: 10.1016/j.carbpol.2013.02.074 http://doi.org/10.1016/j.carbpol.2013.02.074 .

Z.S. Ge , S.Y. Liu . . Chem. Soc. Rev. , 2013 . 42 7289 DOI: 10.1039/c3cs60048c http://doi.org/10.1039/c3cs60048c .

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