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Synthesis of β‐Cyclodextrin Containing Copolymer via “Click” Chemistry and Its Self‐Assembly in the Presence of Guest Compounds
dc.contributor.authorZhang, Jianxiangen_US
dc.contributor.authorEllsworth, Kristinen_US
dc.contributor.authorMa, Peter X.en_US
dc.date.accessioned2012-05-21T15:48:39Z
dc.date.available2013-06-11T19:15:52Zen_US
dc.date.issued2012-04-23en_US
dc.identifier.citationZhang, Jianxiang; Ellsworth, Kristin; Ma, Peter X. (2012). "Synthesis of β‐Cyclodextrin Containing Copolymer via “Click” Chemistry and Its Self‐Assembly in the Presence of Guest Compounds." Macromolecular Rapid Communications 33(8): 664-671. <http://hdl.handle.net/2027.42/91173>en_US
dc.identifier.issn1022-1336en_US
dc.identifier.issn1521-3927en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/91173
dc.description.abstractWe report the synthesis of a hydrophilic copolymer with one polyethylene glycol (PEG) block and one β‐cyclodextrin (β‐CD) containing block by a “click” reaction between azido‐substituted β‐CD and propargyl flanking copolymer. 1 H NMR study suggested a highly efficient conjugation of β‐CD units by this approach. The obtained copolymer was used as a host macromolecule to construct assemblies in the presence of hydrophobic guests. For assemblies containing a hydrophobic polymer, their size can be simply adjusted by simply changing the content of hydrophobic component. By serving as a guest molecule, hydrophobic drugs can also be loaded accompanying the formation of nanoparticles, and the drug payload is releasable. Therefore, the copolymer synthesized herein can be employed as a carrier for drug delivery. The synthesis of β‐cyclodextrin containing block copolymer via a “click” reaction is reported. The self‐assembly of this newly synthesized copolymer in the presence of guest compounds can lead to the formation of core–shell structured nanoparticles. These assemblies can be employed as novel delivery vehicles for therapeutics.en_US
dc.publisherWILEY‐VCH Verlagen_US
dc.subject.otherSelf‐Assemblyen_US
dc.subject.otherNanoparticlesen_US
dc.subject.otherHost–Guest Interactionen_US
dc.subject.otherDrug Deliveryen_US
dc.subject.otherClick Chemistryen_US
dc.subject.otherCopolymeren_US
dc.subject.otherβ‐Cyclodextrinen_US
dc.titleSynthesis of β‐Cyclodextrin Containing Copolymer via “Click” Chemistry and Its Self‐Assembly in the Presence of Guest Compoundsen_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelChemistryen_US
dc.subject.hlbsecondlevelMaterials Science and Engineeringen_US
dc.subject.hlbsecondlevelBiological Chemistryen_US
dc.subject.hlbsecondlevelChemical Engineeringen_US
dc.subject.hlbtoplevelHealth Sciencesen_US
dc.subject.hlbtoplevelScienceen_US
dc.subject.hlbtoplevelEngineeringen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumDepartment of Biologic and Materials Sciences, University of Michigan, Ann Arbor, MI 48109, USA; Fax: +1 734 647 2110.en_US
dc.contributor.affiliationumDepartment of Materials Science and Engineering, University of Michigan, Ann Arbor, MI 48109, USAen_US
dc.contributor.affiliationumMacromolecular Science and Engineering Center, University of Michigan, Ann Arbor, MI 48109, USAen_US
dc.contributor.affiliationumDepartment of Biomedical Engineering, University of Michigan, Ann Arbor, MI 48109, USAen_US
dc.contributor.affiliationumDepartment of Biologic and Materials Sciences, University of Michigan, Ann Arbor, MI 48109, USA; Fax: +1 734 647 2110en_US
dc.contributor.affiliationotherDepartment of Pharmaceutics, College of Pharmacy, Third Military Medical University, Chongqing 400038, P.R. Chinaen_US
dc.identifier.pmid22318939en_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/91173/1/marc_201100814_sm_suppl.pdf
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/91173/2/664_ftp.pdf
dc.identifier.doi10.1002/marc.201100814en_US
dc.identifier.sourceMacromolecular Rapid Communicationsen_US
dc.identifier.citedreferenceI. Baussanne, J. M. Benito, C. O. Mellet, J. M. G. Fernández, H. Law, J. Defaye, Chem. Commun. 2000, 1489.en_US
dc.identifier.citedreferencea) S. Liu, R. Maheshwari, K. L. Kiick, Macromolecules 2009, 42, 3; b) D. K. Kim, J. Dobson, J. Mater. Chem. 2009, 19, 6294; c) C. Khemtong, C. W. Kessinger, J. M. Gao, Chem. Commun. 2009, 24, 3497; d) J. X. Zhang, S. H. Li, X. H. Li, Recent Pat. Nanotech. 2009, 3, 225; e) A. S. Hoffman, J. Controlled Release 2009, 132, 153.en_US
dc.identifier.citedreferencea) S. Ganta, H. Devalapally, A. Shahiwala, M. Amiji, J. Controlled Release 2008, 126, 187; b) J. H. Park, S. Lee, J. H. Kim, K. Park, K. Kim, I. C. Kwon, Prog. Polym. Sci. 2008, 33, 113; c) D. E. Discher, V. Ortiz, G. Srinivas, M. L. Klein, Y. Kim, C. A. David, S. S. Cai, P. Photos, F. Ahmed, Prog. Polym. Sci. 2007, 32, 838; d) D. Sutton, N. Nasongkla, E. Blanco, J. M. Gao, Pharm. Res. 2007, 24, 1029; e) A. N. Lukyanov, V. P. Torchilin, Adv. Drug Deliv. Rev. 2004, 56, 1273; f) H. Otsuka, Y. Nagasaki, K. Kataoka, Adv. Drug Deliv. Rev. 2003, 55, 403; g) A. V. Kabanov, E. V. Batrakova, Y. Y. Alakhov, J. Controlled Release 2002, 82, 189.en_US
dc.identifier.citedreferencea) K. Itaka, K. Kataoka, Eur. J. Pharm. Biopharm. 2009, 71, 475; b) A. V. Kabanov, H. E. Gendelman, Prog. Polym. Sci. 2007, 32, 1054.en_US
dc.identifier.citedreferenceJ. X. Zhang, P. X. Ma, Nano Today 2010, 5, 337.en_US
dc.identifier.citedreferencea) L. X. Ren, F. Y. Ke, Y. M. Chen, D. H. Liang, J. Huang, Macromolecules 2008, 41, 5295; b) C. C. Tsai, W. B. Zhang, C. L. Wang, R. M. van Horn, M. J. Graham, J. Huang, Y. M. Chen, M. M. Guo, S. Z. D. Cheng, J. Chem. Phys. 2010, 132, 204903.en_US
dc.identifier.citedreferenceM. E. Davis, Mol. Pharm. 2009, 6, 659.en_US
dc.identifier.citedreferenceF. van de Manakker, T. Vermonden, C. F. van Nostrum, W. E. Hennink, Biomacromolecules 2009, 10, 3157.en_US
dc.identifier.citedreferenceR. de la Rica, R. M. Fratila, A. Szarpak, J. Huskens, A. H. Velders, Angew. Chem. Int. Ed. 2011, 50, 5704.en_US
dc.identifier.citedreferencea) X. J. Liao, G. S. Chen, X. X. Liu, W. X. Chen, F. Chen, M. Jiang, Angew. Chem. Int. Ed. 2010, 49, 4409; b) W. Deng, H. Yamaguchi, Y. Takashima, A. Harada, Angew. Chem. Int. Ed. 2007, 46, 5144.en_US
dc.identifier.citedreferenceS. Angelos, Y. W. Yang, K. Patel, J. F. Stoddart, J. I. Zink, Angew. Chem. Int. Ed. 2008, 47, 2222.en_US
dc.identifier.citedreferenceJ. X. Zhang, K. Ellsworth, P. X. Ma, J. Controlled Release 2010, 145, 116.en_US
dc.identifier.citedreferenceC. Kim, S. S. Agasti, Z. J. Zhu, L. Isaacs, V. M. Rotello, Nat. Chem. 2010, 2, 962.en_US
dc.identifier.citedreferencea) J. X. Zhang, P. X. Ma, Polymer 2011, 52, 4928; b) J. X. Zhang, K. Feng, M. Cuddihy, N. A. Kotov, P. X. Ma, Soft Matter 2010, 6, 610; c) J. Huang, L. X. Ren, Y. M. Chen, Polym. Int. 2008, 57, 714; d) J. Huang, L. X. Ren, H. Zhu, Y. M. Chen, Macromol. Chem. Phys. 2006, 207, 1764.en_US
dc.identifier.citedreferencea) W. Wang, A. E. Kaifer, Adv. Polym. Sci. 2009, 222, 205; b) J. Lagona, P. Mukhopadhyay, S. Chakrabarti, L. Isaacs, Angew. Chem. Int. Ed. 2005, 44, 4844; c) M. E. Davis, M. E. Brewster, Nat. Rev. Drug Discov. 2004, 3, 1023.en_US
dc.identifier.citedreferenceJ. X. Zhang, P. X. Ma, Angew. Chem. Int. Ed. 2009, 48, 964.en_US
dc.identifier.citedreferenceH. Q. Dong, Y. Y. Li, S. J. Cai, R. X. Zhuo, X. Z. Zhang, L. J. Liu, Angew. Chem. Int. Ed. 2008, 47, 5573.en_US
dc.identifier.citedreferencea) H. Wang, S. T. Wang, H. L. Su, K. J. Chen, A. L. Armijo, W. Y. Lin, Y. J. Wang, J. Sun, K. I. Kamei, J. Czernin, C. G. Radu, H. R. Tseng, Angew. Chem. Int. Ed. 2009, 48, 4344; b) J. X. Zhang, H. L. Sun, P. X. Ma, ACS Nano 2010, 4, 1049; c) J. X. Zhang, Y. Jia, X. D. Li, Y. Q. Hu, X. H. Li, Adv. Mater. 2011, 23, 3035; d) Y. X. Zhu, L. Che, H. M. He, Y. Jia, J. X. Zhang, X. H. Li, J. Controlled Release 2011, 152, 317.en_US
dc.identifier.citedreferencea) H. K. Lee, K. M. Park, Y. J. Jeon, D. Kim, D. H. Oh, H. S. Kim, C. K. Park, K. Kim, J. Am. Chem. Soc. 2005, 127, 5006; b) P. Falvey, C. W. Lim, R. Darcy, T. Revermann, U. Karst, M. Giesbers, A. T. M. Marcelis, A. Lazar, A. W. Coleman, D. N. Reinhoudt, B. J. Ravoo, Chem. Eur. J. 2005, 11, 1171; c) I. Bohm, K. Isenbugel, H. Ritter, R. Branscheid, U. Kolb, Angew. Chem. Int. Ed. 2011, 50, 7896.en_US
dc.identifier.citedreferencea) D. Patra, F. Ozdemir, O. R. Miranda, B. Samanta, A. Sanyal, V. M. Rotello, Langmuir 2009, 25, 13852; b) Y. L. Wu, J. Li, Angew. Chem. Int. Ed. 2009, 48, 3842; c) C. Li, G. F. Luo, H. Y. Wang, J. Zhang, Y. H. Gong, S. X. Cheng, R. X. Zhuo, X. Z. Zhang, J. Phys. Chem. C 2011, 115, 17651; d) D. Kim, E. Kim, J. Kim, K. M. Park, K. Baek, M. Jung, Y. H. Ko, W. Sung, H. S. Kim, J. H. Suh, C. G. Park, O. S. Na, D. K. Lee, K. E. Lee, S. S. Han, K. Kim, Angew. Chem. Int. Ed. 2007, 46, 3471.en_US
dc.identifier.citedreferencea) X. H. Guo, J. Wang, L. Li, D. T. Pham, P. Clements, S. F. Lincoln, B. L. May, Q. C. Chen, L. Zheng, R. K. Prud'homme, Macromol. Rapid Commun. 2010, 31, 300; b) L. X. Ren, L. H. He, T. C. Sun, X. Dong, Y. M. Chen, J. Huang, C. Wang, Macromol. Biosci. 2009, 9, 902.en_US
dc.identifier.citedreferencea) M. Klink, H. Ritter, Macromol. Rapid Commun. 2008, 29, 1208; b) J. Shi, Y. Chen, Q. Wang, Y. Liu, Adv. Mater. 2010, 22, 2575; c) K. Isenbugel, H. Ritter, R. Branscheid, U. Kolb, Macromol. Rapid Commun. 2010, 31, 2121.en_US
dc.identifier.citedreferenceH. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004.en_US
dc.identifier.citedreferencea) P. Lundberg, C. J. Hawker, A. Hult, M. Malkoch, Macromol. Rapid Commun. 2008, 29, 998; b) W. H. Binder, R. Sachsenhofer, Macromol. Rapid Commun. 2008, 29, 952; c) J. A. Johnson, M. G. Finn, J. T. Koberstein, N. J. Turro, Macromol. Rapid Commun. 2008, 29, 1052; d) M. Meldal, Macromol. Rapid Commun. 2008, 29, 1016; e) P. Lecomte, R. Riva, C. Jerome, R. Jerome, Macromol. Rapid Commun. 2008, 29, 982; f) G. Temel, B. Aydogan, N. Arsu, Y. Yagci, Macromolecules 2009, 42, 6098; g) A. Saha, S. Ramakrishnan, Macromolecules 2009, 42, 4028; h) Y. Peng, H. Liu, X. Zhang, S. Liu, Y. Li, Macromolecules 2009, 42, 6457; i) H. Misaka, R. Kakuchi, C. Zhang, R. Sakai, T. Satoh, T. Kakuchi, Macromolecules 2009, 42, 5091; j) T. P. Lodge, Macromolecules 2009, 42, 3827; k) J. N. Hoskins, S. M. Grayson, Macromolecules 2009, 42, 6406.en_US
dc.identifier.citedreferencea) M. Munteanu, S. W. Choi, H. Ritter, Macromolecules 2008, 41, 9619; b) J. M. Bryson, W. J. Chu, J. H. Lee, T. M. Reineke, Bioconjugate Chem. 2008, 19, 1505; c) S. Srinivasachari, K. M. Fichter, T. M. Reineke, J. Am. Chem. Soc. 2008, 130, 4618; d) Y. Zhang, Z. Guo, J. Ye, Q. Xu, X. Liang, A. Lei, J. Chromatogr. A 2008, 1191, 188; e) M. Munteanu, S. W. Choi, H. Ritter, Macromolecules 2009, 42, 3887; f) J. Xu, S. Liu, J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 404.en_US
dc.identifier.citedreferenceW. H. Daly, D. Poche, Tetrahedron Lett. 1988, 29, 5859.en_US
dc.identifier.citedreferenceA. Harada, K. Kataoka, Macromolecules 1995, 28, 5294.en_US
dc.identifier.citedreferenceK. Miyata, M. Oba, M. Nakanishi, S. Fukushima, Y. Yamasaki, H. Koyama, N. Nishiyama, K. Kataoka, J. Am. Chem. Soc. 2008, 130, 16287.en_US
dc.identifier.citedreferenceE. Peggion, M. Terbojevich, A. Cosani, C. Colombini, J. Am. Chem. Soc. 1966, 88, 3630.en_US
dc.identifier.citedreferenceW. F. Dong, A. Kishimura, Y. Anraku, S. Chuanoi, K. Kataoka, J. Am. Chem. Soc. 2009, 131, 3804.en_US
dc.identifier.citedreferenceM. Nakanishi, J. S. Park, W. D. Jang, M. Oba, K. Kataoka, React. Funct. Polym. 2007, 67, 1361.en_US
dc.identifier.citedreferencea) E. Renard, A. Deratani, G. Volet, B. Sebille, Eur. Polym. J. 1997, 33, 49; b) S. H. Pun, N. C. Bellocq, A. Liu, G. Gensen, T. Machemer, E. Quijano, T. Schluep, S. Wen, H. Engler, J. Heidel, M. E. Davis, Bioconjugate Chem. 2004, 15, 831; c) G. P. Tang, H. Y. Guo, F. Alexis, X. Wang, S. Zeng, T. M. Lim, J. Ding, Y. Y. Yang, S. Wang, J. Gene Med. 2006, 8, 736.en_US
dc.identifier.citedreferenceS. Schmitz, H. Ritter, Angew. Chem. Int. Ed. 2005, 44, 5658.en_US
dc.identifier.citedreferenceV. J. Stella, R. A. Rajewski, Pharm. Res. 1997, 14, 556.en_US
dc.identifier.citedreferencea) Z. L. Tyrrell, Y. Q. Shen, M. Radosz, Prog. Polym. Sci. 2010, 35, 1128; b) N. Wiradharma, Y. Zhang, S. Venkataraman, J. L. Hedrick, Y. Y. Yang, Nano Today 2009, 4, 302; c) F. H. Meng, Z. Y. Zhong, J. Feijen, Biomacromolecules 2009, 10, 197.en_US
dc.identifier.citedreferenceM. Motornov, Y. Roiter, I. Tokarev, S. Minko, Prog. Polym. Sci. 2010, 35, 174.en_US
dc.identifier.citedreferenceN. Nishiyama, Y. Morimoto, W. D. Jang, K. Kataoka, Adv. Drug Delivery Rev. 2009, 61, 327.en_US
dc.identifier.citedreferenceA. V. Kabanov, S. V. Vinogradov, Angew. Chem. Int. Ed. 2009, 48, 5418.en_US
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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