메뉴 건너뛰기




Volumn 22, Issue 12, 2011, Pages 2519-2530

Synthesis and characterization of biodegradable and thermosensitive polymeric micelles with covalently bound doxorubicin-glucuronide prodrug via click chemistry

Author keywords

[No Author keywords available]

Indexed keywords

BIODEGRADABLE POLYMERS; BLOCK COPOLYMERS; CONTROLLED DRUG DELIVERY; ENZYMES; FUNCTIONAL POLYMERS; MOTION PICTURE EXPERTS GROUP STANDARDS; POLYETHYLENE GLYCOLS; SYNTHESIS (CHEMICAL); TARGETED DRUG DELIVERY;

EID: 84555220701     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc2003499     Document Type: Article
Times cited : (58)

References (49)
  • 1
    • 0017178490 scopus 로고
    • Effect of adriamycin on DNA, RNA, and protein synthesis in cell free systems and intact cells
    • Momparler, R. L., Karon, M., Siegel, S. E., and Avila, F. (1976) Effect of adriamycin on DNA, RNA, and protein synthesis in cell free systems and intact cells Cancer Res. 36, 2891-2895
    • (1976) Cancer Res. , vol.36 , pp. 2891-2895
    • Momparler, R.L.1    Karon, M.2    Siegel, S.E.3    Avila, F.4
  • 3
    • 49249105457 scopus 로고    scopus 로고
    • Doxorubicin, cardiac risk factors, and cardiac toxicity in elderly patients with diffuse B-cell non-Hodgkins lymphoma
    • Hershman, D. L., McBride, R. B., Eisenberger, A., Wei, Y. T., Grann, V. R., and Jacobson, J. S. (2008) Doxorubicin, cardiac risk factors, and cardiac toxicity in elderly patients with diffuse B-cell non-Hodgkins lymphoma J. Clin. Oncol. 26, 3159-3165
    • (2008) J. Clin. Oncol. , vol.26 , pp. 3159-3165
    • Hershman, D.L.1    Mcbride, R.B.2    Eisenberger, A.3    Wei, Y.T.4    Grann, V.R.5    Jacobson, J.S.6
  • 6
    • 34249327294 scopus 로고    scopus 로고
    • Targeted pharmaceutical nanocarriers for cancer therapy and imaging
    • Torchilin, V. P. (2007) Targeted pharmaceutical nanocarriers for cancer therapy and imaging AAPS J. 9, E128-E147
    • (2007) AAPS J. , vol.9
    • Torchilin, V.P.1
  • 8
    • 67449084321 scopus 로고    scopus 로고
    • Preclinical and clinical studies of anticancer agent-incorporating polymer micelles
    • Matsumura, Y. and Kataoka, K. (2009) Preclinical and clinical studies of anticancer agent-incorporating polymer micelles Cancer Sci. 100, 572-579
    • (2009) Cancer Sci. , vol.100 , pp. 572-579
    • Matsumura, Y.1    Kataoka, K.2
  • 9
    • 75749149269 scopus 로고    scopus 로고
    • HPMA copolymers: Origins, early developments, present, and future
    • Kopecek, J. and Kopeckova, P. (2010) HPMA copolymers: Origins, early developments, present, and future Adv. Drug Delivery Rev. 62, 122-149
    • (2010) Adv. Drug Delivery Rev. , vol.62 , pp. 122-149
    • Kopecek, J.1    Kopeckova, P.2
  • 10
    • 75749134040 scopus 로고    scopus 로고
    • Improving the efficacy of combined modality anticancer therapy using HPMA copolymer-based nanomedicine formulations
    • Lammers, T. (2010) Improving the efficacy of combined modality anticancer therapy using HPMA copolymer-based nanomedicine formulations Adv. Drug Delivery Rev. 62, 203-230
    • (2010) Adv. Drug Delivery Rev. , vol.62 , pp. 203-230
    • Lammers, T.1
  • 11
    • 72949119112 scopus 로고    scopus 로고
    • Preclinical evaluation of linear HPMA-doxorubicin conjugates with pH-sensitive drug release: Efficacy, safety, and immunomodulating activity in murine model
    • Sirova, M., Mrkvan, T., Etrych, T., Chytil, P., Rossmann, P., Ibrahimova, M., Kovar, L., Ulbrich, K., and Rihova, B. (2010) Preclinical evaluation of linear HPMA-doxorubicin conjugates with pH-sensitive drug release: Efficacy, safety, and immunomodulating activity in murine model Pharm. Res. 27, 200-208
    • (2010) Pharm. Res. , vol.27 , pp. 200-208
    • Sirova, M.1    Mrkvan, T.2    Etrych, T.3    Chytil, P.4    Rossmann, P.5    Ibrahimova, M.6    Kovar, L.7    Ulbrich, K.8    Rihova, B.9
  • 13
    • 75749144204 scopus 로고    scopus 로고
    • Structural and chemical aspects of HPMA copolymers as drug carriers
    • Ulbrich, K. and Subr, V. (2010) Structural and chemical aspects of HPMA copolymers as drug carriers Adv. Drug Delivery Rev. 62, 150-166
    • (2010) Adv. Drug Delivery Rev. , vol.62 , pp. 150-166
    • Ulbrich, K.1    Subr, V.2
  • 14
    • 39349084237 scopus 로고    scopus 로고
    • Prodrug strategies in anticancer chemotherapy
    • Kratz, F., Muller, I. A., Ryppa, C., and Warnecke, A. (2008) Prodrug strategies in anticancer chemotherapy ChemMedChem 3, 20-53
    • (2008) ChemMedChem , vol.3 , pp. 20-53
    • Kratz, F.1    Muller, I.A.2    Ryppa, C.3    Warnecke, A.4
  • 15
    • 34447520330 scopus 로고    scopus 로고
    • Anticancer carrier-linked prodrugs in clinical trials
    • DOI 10.1517/13543784.16.7.1037
    • Kratz, F., Ajaj, K. A., and Warnecke, A. (2007) Anticancer carrier-linked prodrugs in clinical trials Expert Opin. Invest. Drug 16, 1037-1058 (Pubitemid 47074159)
    • (2007) Expert Opinion on Investigational Drugs , vol.16 , Issue.7 , pp. 1037-1058
    • Kratz, F.1    Ajaj, K.A.2    Warnecke, A.3
  • 16
    • 0001144402 scopus 로고    scopus 로고
    • Characterization of novel anthracycline prodrugs activated by human β-glucuronidase for use in antibody-directed enzyme prodrug therapy
    • DOI 10.1016/0006-2952(96)00248-1
    • Houba, P. H. J., Leenders, R. G. G., Boven, E., Scheeren, J. W., Pinedo, H. M., and Haisma, H. J. (1996) Characterization of novel anthracycline prodrugs activated by human β-glucuronidase for use in antibody-directed enzyme prodrug therapy Biochem. Pharmacol. 52, 455-463 (Pubitemid 26233589)
    • (1996) Biochemical Pharmacology , vol.52 , Issue.3 , pp. 455-463
    • Houba, P.H.J.1    Leenders, R.G.G.2    Boven, E.3    Scheeren, J.W.4    Pinedo, H.M.5    Haisma, H.J.6
  • 17
    • 7444241374 scopus 로고    scopus 로고
    • A methylester of the glucuronide prodrug DOX-GA3 for improvement of tumor-selective chemotherapy
    • DOI 10.1016/j.bcp.2004.08.004, PII S0006295204005817
    • Graaf, M. D., Nevalainen, T. J., Scheeren, H. W., Pinedo, H. M., Haisma, H. J., and Boven, E. (2004) A methylester of the glucuronide prodrug DOX-GA3 for improvement of tumor-selective chemotherapy Biochem. Pharmacol. 68, 2273-2281 (Pubitemid 39446154)
    • (2004) Biochemical Pharmacology , vol.68 , Issue.11 , pp. 2273-2281
    • Graaf, M.D.1    Nevalainen, T.J.2    Scheeren, H.W.3    Pinedo, H.M.4    Haisma, H.J.5    Boven, E.6
  • 18
    • 0035106974 scopus 로고    scopus 로고
    • A novel doxorubicin-glucuronide prodrug DOX-GA3 for tumour-selective chemotherapy: Distribution and efficacy in experimental human ovarian cancer
    • DOI 10.1054/bjoc.2000.1640
    • Houba, P. H. J., Boven, E., van Der Meulen-Muileman, I. H., Leenders, R. G. G., Scheeren, J. W., Pinedo, H. M., and Haisma, H. J. (2001) A novel doxorubicin-glucuronide prodrug DOX-GA3 for tumour-selective chemotherapy: Distribution and efficacy in experimental human ovarian cancer Br. J. Cancer 84, 550-557 (Pubitemid 32215885)
    • (2001) British Journal of Cancer , vol.84 , Issue.4 , pp. 550-557
    • Houba, P.H.J.1    Boven, E.2    Van Der Meulen-Muileman, I.H.3    Leenders, R.G.G.4    Scheeren, J.W.5    Pinedo, H.M.6    Haisma, H.J.7
  • 21
    • 36949004756 scopus 로고    scopus 로고
    • Polymeric micelles with transient stability: A novel delivery concept
    • van Nostrum, C. F., Neradovic, D., Soga, O., and Hennink, W. E. (2006) Polymeric micelles with transient stability: A novel delivery concept ACS Sympos. Ser. 923, 40-54
    • (2006) ACS Sympos. Ser. , vol.923 , pp. 40-54
    • Van Nostrum, C.F.1    Neradovic, D.2    Soga, O.3    Hennink, W.E.4
  • 24
    • 34447302274 scopus 로고    scopus 로고
    • Triggered destabilisation of polymeric micelles and vesicles by changing polymers polarity: An attractive tool for drug delivery
    • DOI 10.1016/j.jconrel.2007.03.023, PII S0168365907001903
    • Rijcken, C. J. F., Soga, O., Hennink, W. E., and van Nostrum, C. F. (2007) Triggered destabilisation of polymeric micelles and vesicles by changing polymers polarity: An attractive tool for drug delivery J. Controlled Release 120, 131-148 (Pubitemid 47058635)
    • (2007) Journal of Controlled Release , vol.120 , Issue.3 , pp. 131-148
    • Rijcken, C.J.F.1    Soga, O.2    Hennink, W.E.3    Van Nostrum, C.F.4
  • 25
    • 0034000453 scopus 로고    scopus 로고
    • Tumor vascular permeability and the EPR effect in macromolecular therapeutics: A review
    • DOI 10.1016/S0168-3659(99)00248-5, PII S0168365999002485
    • Maeda, H., Wu, J., Sawa, T., Matsumura, Y., and Hori, K. (2000) Tumor vascular permeability and the EPR effect in macromolecular therapeutics: A review J. Controlled Release 65, 271-284 (Pubitemid 30122932)
    • (2000) Journal of Controlled Release , vol.65 , Issue.1-2 , pp. 271-284
    • Maeda, H.1    Wu, J.2    Sawa, T.3    Matsumura, Y.4    Hori, K.5
  • 26
    • 36048953122 scopus 로고    scopus 로고
    • Photosensitiser-loaded biodegradable polymeric micelles: Preparation, characterisation and in vitro PDT efficacy
    • DOI 10.1016/j.jconrel.2007.09.002, PII S0168365907004932
    • Rijcken, C. J. F., Hofman, J. W., van Zeeland, F., Hennink, W. E., and van Nostrum, C. F. (2007) Photosensitiser-loaded biodegradable polymeric micelles: Preparation, characterisation and in vitro PDT efficacy J. Controlled Release 124, 144-153 (Pubitemid 350101885)
    • (2007) Journal of Controlled Release , vol.124 , Issue.3 , pp. 144-153
    • Rijcken, C.J.F.1    Hofman, J.-W.2    Van Zeeland, F.3    Hennink, W.E.4    Van Nostrum, C.F.5
  • 28
    • 63249128638 scopus 로고    scopus 로고
    • Superparamagnetic iron oxide nanoparticles encapsulated in biodegradable thermosensitive polymeric micelles: Toward a targeted nanomedicine suitable for image-guided drug delivery
    • Talelli, M., Rijcken, C. J. F., Lammers, T., Seevinck, P. R., Storm, G., Van Nostrum, C. F., and Hennink, W. E. (2009) Superparamagnetic iron oxide nanoparticles encapsulated in biodegradable thermosensitive polymeric micelles: Toward a targeted nanomedicine suitable for image-guided drug delivery Langmuir 25, 2060-2067
    • (2009) Langmuir , vol.25 , pp. 2060-2067
    • Talelli, M.1    Rijcken, C.J.F.2    Lammers, T.3    Seevinck, P.R.4    Storm, G.5    Van Nostrum, C.F.6    Hennink, W.E.7
  • 29
    • 35349022545 scopus 로고    scopus 로고
    • Hydrolysable core-crosslinked thermosensitive polymeric micelles: Synthesis, characterisation and in vivo studies
    • DOI 10.1016/j.biomaterials.2007.08.047, PII S0142961207007028
    • Rijcken, C. J., Snel, C. J., Schiffelers, R. M., van Nostrum, C. F., and Hennink, W. E. (2007) Hydrolysable core-crosslinked thermosensitive polymeric micelles: Synthesis, characterisation and in vivo studies Biomaterials 28, 5581-5593 (Pubitemid 47599643)
    • (2007) Biomaterials , vol.28 , Issue.36 , pp. 5581-5593
    • Rijcken, C.J.1    Snel, C.J.2    Schiffelers, R.M.3    Van Nostrum, C.F.4    Hennink, W.E.5
  • 32
    • 0348109450 scopus 로고    scopus 로고
    • The growing impact of click chemistry on drug discovery
    • DOI 10.1016/S1359-6446(03)02933-7, PII S1359644603029337
    • Kolb, H. C. and Sharpless, K. B. (2003) The growing impact of click chemistry on drug discovery Drug Discovery Today 8, 1128-1137 (Pubitemid 37547919)
    • (2003) Drug Discovery Today , vol.8 , Issue.24 , pp. 1128-1137
    • Kolb, H.C.1    Sharpless, K.B.2
  • 33
    • 0000096835 scopus 로고    scopus 로고
    • Click chemistry: Diverse chemical function from a few good reactions
    • Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Click chemistry: diverse chemical function from a few good reactions Angew. Chem., Int. Ed. 40, 2004-2021
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 34
    • 71249129936 scopus 로고    scopus 로고
    • Synthesis and applications of biomedical and pharmaceutical polymers via click chemistry methodologies
    • Van Dijk, M., Rijkers, D. T. S., Liskamp, R. M. J., Van Nostrum, C. F., and Hennink, W. E. (2009) Synthesis and applications of biomedical and pharmaceutical polymers via click chemistry methodologies Bioconjugate Chem. 20, 2001-2016
    • (2009) Bioconjugate Chem. , vol.20 , pp. 2001-2016
    • Van Dijk, M.1    Rijkers, D.T.S.2    Liskamp, R.M.J.3    Van Nostrum, C.F.4    Hennink, W.E.5
  • 35
    • 77949812304 scopus 로고    scopus 로고
    • Marrying click chemistry with polymerization: Expanding the scope of polymeric materials
    • Golas, P. L. and Matyjaszewski, K. (2010) Marrying click chemistry with polymerization: Expanding the scope of polymeric materials Chem. Soc. Rev. 39, 1338-1354
    • (2010) Chem. Soc. Rev. , vol.39 , pp. 1338-1354
    • Golas, P.L.1    Matyjaszewski, K.2
  • 38
    • 51049094897 scopus 로고    scopus 로고
    • Cu-catalyzed azide-alkyne cycloaddition
    • Meldal, M. and Tornoe, C. W. (2008) Cu-catalyzed azide-alkyne cycloaddition Chem. Rev. 108, 2952-3015
    • (2008) Chem. Rev. , vol.108 , pp. 2952-3015
    • Meldal, M.1    Tornoe, C.W.2
  • 39
    • 22844456871 scopus 로고    scopus 로고
    • Poly(N-isopropylacrylamide) with hydrolyzable lactic acid ester side groups: A new type of thermosensitive polymer
    • Neradovic, D., Hinrichs, W. L. J., Kettenes-van Den Bosch, J. J., and Hennink, W. E. (1999) Poly(N-isopropylacrylamide) with hydrolyzable lactic acid ester side groups: A new type of thermosensitive polymer Macromol. Rapid Commun. 20, 577-581 (Pubitemid 129717491)
    • (1999) Macromolecular Rapid Communications , vol.20 , Issue.11 , pp. 577-581
    • Neradovic, D.1    Hinrichs, W.L.J.2    Kettenes-Van Den Bosch, J.J.3    Hennink, W.E.4
  • 40
    • 0347760399 scopus 로고    scopus 로고
    • The effect of the processing and formulation parameters on the size of nanoparticles based on block copolymers of poly(ethylene glycol) and poly(N-isopropylacrylamide) with and without hydrolytically sensitive groups
    • DOI 10.1016/j.biomaterials.2003.09.024
    • Neradovic, D., Soga, O., van Nostrum, C. F., and Hennink, W. E. (2004) The effect of the processing and formulation parameters on the size of nanoparticles based on block copolymers of poly(ethylene glycol) and poly(N-isopropylacrylamide) with and without hydrolytically sensitive groups Biomaterials 25, 2409-2418 (Pubitemid 38102394)
    • (2004) Biomaterials , vol.25 , Issue.12 , pp. 2409-2418
    • Neradovic, D.1    Soga, O.2    Van Nostrum, C.F.3    Hennink, W.E.4
  • 41
    • 0026415708 scopus 로고
    • Poly(styrene-ethylene oxide) block copolymer micelle formation in water: A fluorescence probe study
    • Wilhelm, M., Zhao, C. L., Wang, Y., Xu, R., Winnik, M. A., Mura, J. L., Riess, G., and Croucher, M. D. (1991) Poly(styrene-ethylene oxide) block copolymer micelle formation in water: A fluorescence probe study Macromolecules 24, 1033-1040
    • (1991) Macromolecules , vol.24 , pp. 1033-1040
    • Wilhelm, M.1    Zhao, C.L.2    Wang, Y.3    Xu, R.4    Winnik, M.A.5    Mura, J.L.6    Riess, G.7    Croucher, M.D.8
  • 42
    • 66249130624 scopus 로고    scopus 로고
    • Covalent layer-by-layer functionalization of multiwalled carbon nanotubes by click chemistry
    • Zhang, Y., He, H., Gao, C., and Wu, J. (2009) Covalent layer-by-layer functionalization of multiwalled carbon nanotubes by click chemistry Langmuir 25, 5814-5824
    • (2009) Langmuir , vol.25 , pp. 5814-5824
    • Zhang, Y.1    He, H.2    Gao, C.3    Wu, J.4
  • 43
    • 34547179800 scopus 로고    scopus 로고
    • Graft copolymers by a combination of ATRP and two different consecutive click reactions
    • DOI 10.1021/ma070705m
    • Tsarevsky, N. V., Bencherif, S. A., and Matyjaszewski, K. (2007) Graft copolymers by a combination of ATRP and two different consecutive click reactions Macromolecules 40, 4439-4445 (Pubitemid 47110733)
    • (2007) Macromolecules , vol.40 , Issue.13 , pp. 4439-4445
    • Tsarevsky, N.V.1    Bencherif, S.A.2    Matyjaszewski, K.3
  • 44
    • 67651108679 scopus 로고    scopus 로고
    • Synthesis of well-defined macrocyclic poly(?-valerolactone) by "Click Cyclization
    • Hideki, M., Ryohei, K., Chunhong, Z., Ryosuke, S., Toshifumi, S., and Toyoji, K. (2009) Synthesis of well-defined macrocyclic poly(?-valerolactone) by "Click Cyclization Macromolecules 42, 5091-5096
    • (2009) Macromolecules , vol.42 , pp. 5091-5096
    • Hideki, M.1    Ryohei, K.2    Chunhong, Z.3    Ryosuke, S.4    Toshifumi, S.5    Toyoji, K.6
  • 45
    • 77955163407 scopus 로고    scopus 로고
    • Shell-cross-linked micelles from PNIPAM- b -(PLL)2 Y-shaped miktoarm star copolymer as drug carriers
    • Li, L. Y., He, W. D., Li, J., Zhang, B. Y., Pan, T. T., Sun, X. L., and Ding, Z. L. (2010) Shell-cross-linked micelles from PNIPAM- b -(PLL)2 Y-shaped miktoarm star copolymer as drug carriers Biomacromolecules 11, 1882-1890
    • (2010) Biomacromolecules , vol.11 , pp. 1882-1890
    • Li, L.Y.1    He, W.D.2    Li, J.3    Zhang, B.Y.4    Pan, T.T.5    Sun, X.L.6    Ding, Z.L.7
  • 46
    • 0001190920 scopus 로고
    • Micelles based on AB block copolymers of poly(ethylene oxide) and poly(β-benzyl L-aspartate)
    • Kwon, G., Naito, M., Yokoyama, M., Okano, T., Sakurai, Y., and Kataoka, K. (1993) Micelles based on AB block copolymers of poly(ethylene oxide) and poly(β-benzyl L-aspartate) Langmuir 9, 945-949
    • (1993) Langmuir , vol.9 , pp. 945-949
    • Kwon, G.1    Naito, M.2    Yokoyama, M.3    Okano, T.4    Sakurai, Y.5    Kataoka, K.6
  • 47
    • 33845388144 scopus 로고    scopus 로고
    • Micellar nanocarriers: Pharmaceutical perspectives
    • DOI 10.1007/s11095-006-9132-0
    • Torchilin, V. P. (2007) Micellar nanocarriers: Pharmaceutical perspectives Pharm. Res. 24, 1-16 (Pubitemid 44902565)
    • (2007) Pharmaceutical Research , vol.24 , Issue.1 , pp. 1-16
    • Torchilin, V.P.1
  • 48
    • 0033221068 scopus 로고    scopus 로고
    • Nano-engineering block copolymer aggregates for drug delivery
    • Allen, C., Maysinger, D., and Eisenberg, A. (1999) Nano-engineering block copolymer aggregates for drug delivery Colloids Surf., B 16, 3-27
    • (1999) Colloids Surf., B , vol.16 , pp. 3-27
    • Allen, C.1    Maysinger, D.2    Eisenberg, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.