메뉴 건너뛰기




Volumn 89, Issue , 2015, Pages 259-270

Effect of different chemical bonds in pegylation of zinc protoporphyrin that affects drug release, intracellular uptake, and therapeutic effect in the tumor

Author keywords

Antitumor effect; Intracellular uptake; PEG cleavability; PEG dilemma; PEG ZnPP; Tumor proteases

Indexed keywords

AMIDE; CYSTEINE PROTEINASE; ESTER; ESTERASE; ETHER; MACROGOL; PEGYLATED ZINC PROTOPORPHYRIN; PROTOPORPHYRIN ZINC; SERINE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; MACROGOL DERIVATIVE; METALLOPORPHYRIN;

EID: 84920202863     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2014.12.016     Document Type: Article
Times cited : (20)

References (35)
  • 2
    • 56949102614 scopus 로고    scopus 로고
    • The origins and evolution of "controlled" drug delivery systems
    • A.S. Hoffman The origins and evolution of "controlled" drug delivery systems J. Control. Release 132 2008 153 163
    • (2008) J. Control. Release , vol.132 , pp. 153-163
    • Hoffman, A.S.1
  • 3
    • 60749108001 scopus 로고    scopus 로고
    • Polymeric drugs for efficient tumor-targeted drug delivery based on EPR-effect
    • H. Maeda, G.Y. Bharate, and J. Daruwalla Polymeric drugs for efficient tumor-targeted drug delivery based on EPR-effect Eur. J. Pharm. Biopharm. 71 2009 409 419
    • (2009) Eur. J. Pharm. Biopharm. , vol.71 , pp. 409-419
    • Maeda, H.1    Bharate, G.Y.2    Daruwalla, J.3
  • 4
    • 0025341615 scopus 로고
    • Amphipathic polyethyleneglycols effectively prolong the circulation time of liposomes
    • A.L. Klibanov, K. Maruyama, V.P. Torchilin, and L. Huang Amphipathic polyethyleneglycols effectively prolong the circulation time of liposomes FEBS Lett. 268 1990 235 237
    • (1990) FEBS Lett. , vol.268 , pp. 235-237
    • Klibanov, A.L.1    Maruyama, K.2    Torchilin, V.P.3    Huang, L.4
  • 5
    • 34548482374 scopus 로고    scopus 로고
    • Stealth liposomes: Review of the basic science, rationale, and clinical applications, existing and potential
    • M.L. Immordino, F. Dosio, and L. Cattel Stealth liposomes: review of the basic science, rationale, and clinical applications, existing and potential Int. J. Nanomed. 1 2006 297 315
    • (2006) Int. J. Nanomed. , vol.1 , pp. 297-315
    • Immordino, M.L.1    Dosio, F.2    Cattel, L.3
  • 6
    • 0022858683 scopus 로고
    • A new concept for macromolecular therapeutics in cancer chemotherapy: Mechanism of tumoritropic accumulation of proteins and the antitumor agent smancs
    • Y. Matsumura, and H. Maeda A new concept for macromolecular therapeutics in cancer chemotherapy: mechanism of tumoritropic accumulation of proteins and the antitumor agent smancs Cancer Res. 46 1986 6387 6392
    • (1986) Cancer Res. , vol.46 , pp. 6387-6392
    • Matsumura, Y.1    Maeda, H.2
  • 7
    • 79953054576 scopus 로고    scopus 로고
    • The EPR effect: Unique features of tumor blood vessels for drug delivery, factors involved, and limitations and augmentation of the effect
    • J. Fang, H. Nakamura, and H. Maeda The EPR effect: unique features of tumor blood vessels for drug delivery, factors involved, and limitations and augmentation of the effect Adv. Drug Deliv. Rev. 63 2011 136 151
    • (2011) Adv. Drug Deliv. Rev. , vol.63 , pp. 136-151
    • Fang, J.1    Nakamura, H.2    Maeda, H.3
  • 9
    • 79953066932 scopus 로고    scopus 로고
    • A multifunctional envelope type nano device (MEND) for gene delivery to tumours based on the EPR effect: A strategy for overcoming the PEG dilemma
    • H. Hatakeyama, H. Akita, and H. Harashima A multifunctional envelope type nano device (MEND) for gene delivery to tumours based on the EPR effect: a strategy for overcoming the PEG dilemma Adv. Drug Deliv. Rev. 63 2011 152 160
    • (2011) Adv. Drug Deliv. Rev. , vol.63 , pp. 152-160
    • Hatakeyama, H.1    Akita, H.2    Harashima, H.3
  • 10
    • 33645234124 scopus 로고    scopus 로고
    • Novel PEG-matrix metalloproteinase-2 cleavable peptide-lipid containing galactosylated liposomes for hepatocellular carcinoma-selective targeting
    • T. Terada, M. Iwai, S. Kawakami, F. Yamashita, and M. Hashida Novel PEG-matrix metalloproteinase-2 cleavable peptide-lipid containing galactosylated liposomes for hepatocellular carcinoma-selective targeting J. Control. Release 111 2006 333 342
    • (2006) J. Control. Release , vol.111 , pp. 333-342
    • Terada, T.1    Iwai, M.2    Kawakami, S.3    Yamashita, F.4    Hashida, M.5
  • 11
    • 50949094102 scopus 로고    scopus 로고
    • Esterase-catalyzed dePEGylation of pH-sensitive vesicles modified with cleavable PEG-lipid derivatives
    • H. Xu, Y. Deng, D. Chen, W. Hong, Y. Lu, and X. Dong Esterase-catalyzed dePEGylation of pH-sensitive vesicles modified with cleavable PEG-lipid derivatives J. Control. Release 130 2008 238 245
    • (2008) J. Control. Release , vol.130 , pp. 238-245
    • Xu, H.1    Deng, Y.2    Chen, D.3    Hong, W.4    Lu, Y.5    Dong, X.6
  • 12
    • 14044252938 scopus 로고    scopus 로고
    • Toward synthetic viruses: Endosomal pH-triggered deshielding of targeted polyplexes greatly enhances gene transfer in vitro and in vivo
    • G.F. Walker, C. Fella, J. Pelisek, J. Fahrmeir, S. Boeckle, M. Ogris, and E. Wagner Toward synthetic viruses: endosomal pH-triggered deshielding of targeted polyplexes greatly enhances gene transfer in vitro and in vivo Mol. Ther. 11 2005 418 425
    • (2005) Mol. Ther. , vol.11 , pp. 418-425
    • Walker, G.F.1    Fella, C.2    Pelisek, J.3    Fahrmeir, J.4    Boeckle, S.5    Ogris, M.6    Wagner, E.7
  • 14
    • 33645815708 scopus 로고    scopus 로고
    • Injection of PEGylated liposomes in rats elicits PEG-specific IgM, which is responsible for rapid elimination of a second dose of PEGylated liposomes
    • T. Ishida, M. Ichihara, X. Wang, K. Yamamoto, J. Kimura, E. Majima, and H. Kiwada Injection of PEGylated liposomes in rats elicits PEG-specific IgM, which is responsible for rapid elimination of a second dose of PEGylated liposomes J. Control. Release 112 2006 15 25
    • (2006) J. Control. Release , vol.112 , pp. 15-25
    • Ishida, T.1    Ichihara, M.2    Wang, X.3    Yamamoto, K.4    Kimura, J.5    Majima, E.6    Kiwada, H.7
  • 15
    • 84861586806 scopus 로고    scopus 로고
    • Size-dependent induction of accelerated blood clearance phenomenon by repeated injections of polymeric micelles
    • H. Koide, T. Asai, H. Kato, H. Ando, K. Shiraishi, M. Yokoyama, and N. Oku Size-dependent induction of accelerated blood clearance phenomenon by repeated injections of polymeric micelles Int. J. Pharm. 432 2012 75 79
    • (2012) Int. J. Pharm. , vol.432 , pp. 75-79
    • Koide, H.1    Asai, T.2    Kato, H.3    Ando, H.4    Shiraishi, K.5    Yokoyama, M.6    Oku, N.7
  • 16
    • 40849138014 scopus 로고    scopus 로고
    • Accelerated blood clearance (ABC) phenomenon upon repeated injection of PEGylated liposomes
    • T. Ishida, and H. Kiwada Accelerated blood clearance (ABC) phenomenon upon repeated injection of PEGylated liposomes Int. J. Pharm. 354 2008 56 62
    • (2008) Int. J. Pharm. , vol.354 , pp. 56-62
    • Ishida, T.1    Kiwada, H.2
  • 17
    • 0036740180 scopus 로고    scopus 로고
    • Pegylated zinc protoporphyrin: A water-soluble heme oxygenase inhibitor with tumor-targeting capacity
    • S.K. Sahoo, T. Sawa, J. Fang, S. Tanaka, Y. Miyamoto, T. Akaike, and H. Maeda Pegylated zinc protoporphyrin: a water-soluble heme oxygenase inhibitor with tumor-targeting capacity Bioconjug. Chem. 13 2002 1031 1038
    • (2002) Bioconjug. Chem. , vol.13 , pp. 1031-1038
    • Sahoo, S.K.1    Sawa, T.2    Fang, J.3    Tanaka, S.4    Miyamoto, Y.5    Akaike, T.6    Maeda, H.7
  • 18
    • 1442326158 scopus 로고    scopus 로고
    • Antiapoptotic role of heme oxygenase (HO) and the potential of HO as a target in anticancer treatment
    • J. Fang, T. Akaike, and H. Maeda Antiapoptotic role of heme oxygenase (HO) and the potential of HO as a target in anticancer treatment Apoptosis 9 2004 27 35
    • (2004) Apoptosis , vol.9 , pp. 27-35
    • Fang, J.1    Akaike, T.2    Maeda, H.3
  • 19
    • 0024497521 scopus 로고
    • Heme oxygenase is the major 32-kDa stress protein induced in human skin fibroblasts by UVA radiation, hydrogen peroxide, and sodium arsenite
    • S.M. Keyse, and R.M. Tyrrell Heme oxygenase is the major 32-kDa stress protein induced in human skin fibroblasts by UVA radiation, hydrogen peroxide, and sodium arsenite Proc. Natl. Acad. Sci. USA 86 1989 99 103
    • (1989) Proc. Natl. Acad. Sci. USA , vol.86 , pp. 99-103
    • Keyse, S.M.1    Tyrrell, R.M.2
  • 20
    • 0032778341 scopus 로고    scopus 로고
    • Induction of haem oxygenase-1 nitric oxide and ischaemia in experimental solid tumours and implications for tumour growth
    • K. Doi, T. Akaike, S. Fujii, S. Tanaka, N. Ikebe, T. Beppu, S. Shibahara, M. Ogawa, and H. Maeda Induction of haem oxygenase-1 nitric oxide and ischaemia in experimental solid tumours and implications for tumour growth Br. J. Cancer 80 1999 1945 1954
    • (1999) Br. J. Cancer , vol.80 , pp. 1945-1954
    • Doi, K.1    Akaike, T.2    Fujii, S.3    Tanaka, S.4    Ikebe, N.5    Beppu, T.6    Shibahara, S.7    Ogawa, M.8    Maeda, H.9
  • 22
    • 0027516686 scopus 로고
    • The role of inorganic metals and metalloporphyrins in the induction of haem oxygenase and heat-shock protein 70 in human hepatoma cells
    • K. Mitani, H. Fujita, Y. Fukuda, A. Kappas, and S. Sassa The role of inorganic metals and metalloporphyrins in the induction of haem oxygenase and heat-shock protein 70 in human hepatoma cells Biochem. J. 290 Pt3 1993 819 825
    • (1993) Biochem. J. , vol.290 , pp. 819-825
    • Mitani, K.1    Fujita, H.2    Fukuda, Y.3    Kappas, A.4    Sassa, S.5
  • 25
    • 0035282719 scopus 로고    scopus 로고
    • Unique effects of zinc protoporphyrin on HO-1 induction and apoptosis
    • G. Yang, X. Nguyen, J. Ou, P. Rekulapelli, D.K. Stevenson, and P.A. Dennery Unique effects of zinc protoporphyrin on HO-1 induction and apoptosis Blood 97 2001 1306 1313
    • (2001) Blood , vol.97 , pp. 1306-1313
    • Yang, G.1    Nguyen, X.2    Ou, J.3    Rekulapelli, P.4    Stevenson, D.K.5    Dennery, P.A.6
  • 26
    • 0038418359 scopus 로고    scopus 로고
    • In vivo antitumor activity of pegylated zinc protoporphyrin: Targeted inhibition of heme oxygenase in solid tumor
    • J. Fang, T. Sawa, T. Akaike, T. Akuta, S.K. Sahoo, G. Khaled, A. Hamada, and H. Maeda In vivo antitumor activity of pegylated zinc protoporphyrin: targeted inhibition of heme oxygenase in solid tumor Cancer Res. 63 2003 3567 3574
    • (2003) Cancer Res. , vol.63 , pp. 3567-3574
    • Fang, J.1    Sawa, T.2    Akaike, T.3    Akuta, T.4    Sahoo, S.K.5    Khaled, G.6    Hamada, A.7    Maeda, H.8
  • 27
    • 34547666680 scopus 로고    scopus 로고
    • Polymeric micelles of zinc protoporphyrin for tumor targeted delivery based on EPR effect and singlet oxygen generation
    • A.K. Iyer, K. Greish, T. Seki, S. Okazaki, J. Fang, K. Takeshita, and H. Maeda Polymeric micelles of zinc protoporphyrin for tumor targeted delivery based on EPR effect and singlet oxygen generation J. Drug Target. 15 2007 496 506
    • (2007) J. Drug Target. , vol.15 , pp. 496-506
    • Iyer, A.K.1    Greish, K.2    Seki, T.3    Okazaki, S.4    Fang, J.5    Takeshita, K.6    Maeda, H.7
  • 28
    • 80054695837 scopus 로고    scopus 로고
    • Intracellular uptake and behavior of two types zinc protoporphyrin (ZnPP) micelles, SMA-ZnPP and PEG-ZnPP as anticancer agents; Unique intracellular disintegration of SMA micelles
    • H. Nakamura, J. Fang, B. Gahininath, K. Tsukigawa, and H. Maeda Intracellular uptake and behavior of two types zinc protoporphyrin (ZnPP) micelles, SMA-ZnPP and PEG-ZnPP as anticancer agents; unique intracellular disintegration of SMA micelles J. Control. Release 155 2011 367 375
    • (2011) J. Control. Release , vol.155 , pp. 367-375
    • Nakamura, H.1    Fang, J.2    Gahininath, B.3    Tsukigawa, K.4    Maeda, H.5
  • 29
    • 84863775348 scopus 로고    scopus 로고
    • HSP32 (HO-1) inhibitor, copoly(styrene-maleic acid)-zinc protoporphyrin IX, a water-soluble micelle as anticancer agent: In vitro and in vivo anticancer effect
    • J. Fang, K. Greish, H. Qin, L. Liao, H. Nakamura, M. Takeya, and H. Maeda HSP32 (HO-1) inhibitor, copoly(styrene-maleic acid)-zinc protoporphyrin IX, a water-soluble micelle as anticancer agent: in vitro and in vivo anticancer effect Eur. J. Pharm. Biopharm. 81 2012 540 547
    • (2012) Eur. J. Pharm. Biopharm. , vol.81 , pp. 540-547
    • Fang, J.1    Greish, K.2    Qin, H.3    Liao, L.4    Nakamura, H.5    Takeya, M.6    Maeda, H.7
  • 30
    • 84873268296 scopus 로고    scopus 로고
    • The EPR effect for macromolecular drug delivery to solid tumors: Improvement of tumor uptake, lowering of systemic toxicity, and distinct tumor imaging in vivo
    • H. Maeda, H. Nakamura, and J. Fang The EPR effect for macromolecular drug delivery to solid tumors: improvement of tumor uptake, lowering of systemic toxicity, and distinct tumor imaging in vivo Adv. Drug Deliv. Rev. 65 2013 71 79
    • (2013) Adv. Drug Deliv. Rev. , vol.65 , pp. 71-79
    • Maeda, H.1    Nakamura, H.2    Fang, J.3
  • 31
    • 84865396710 scopus 로고    scopus 로고
    • Species difference of esterase expression and hydrolase activity in plasma
    • F.G. Bahar, K. Ohura, T. Ogihara, and T. Imai Species difference of esterase expression and hydrolase activity in plasma J. Pharm. Sci. 101 2012 3979 3988
    • (2012) J. Pharm. Sci. , vol.101 , pp. 3979-3988
    • Bahar, F.G.1    Ohura, K.2    Ogihara, T.3    Imai, T.4
  • 32
    • 84883051099 scopus 로고    scopus 로고
    • Role of proteases in cancer: A review
    • S. Rakash Role of proteases in cancer: a review Biotechnol. Mol. Biol. Rev. 7 2012 90 101
    • (2012) Biotechnol. Mol. Biol. Rev. , vol.7 , pp. 90-101
    • Rakash, S.1
  • 33
    • 0028145291 scopus 로고
    • Cathepsin B and other proteases in human colorectal carcinoma
    • J.M. Jessup Cathepsin B and other proteases in human colorectal carcinoma Am. J. Pathol. 145 1994 253 262
    • (1994) Am. J. Pathol. , vol.145 , pp. 253-262
    • Jessup, J.M.1
  • 34
    • 80755159445 scopus 로고    scopus 로고
    • Amantadine amides prodrugs as hepatic delivery systems to enhance its activity against HCV
    • T. Aboul-Fadl, M. Sheha, A. El-Azab, and H. Abdel-Aziz Amantadine amides prodrugs as hepatic delivery systems to enhance its activity against HCV Dig. J. Nanomater. Biostruct. 6 2011 1675 1683
    • (2011) Dig. J. Nanomater. Biostruct. , vol.6 , pp. 1675-1683
    • Aboul-Fadl, T.1    Sheha, M.2    El-Azab, A.3    Abdel-Aziz, H.4
  • 35
    • 80054903598 scopus 로고    scopus 로고
    • Effects of different carboxylic ester spacers on chemical stability, release characteristics, and anticancer activity of mono-PEGylated curcumin conjugates
    • W. Wichitnithad, U. Nimmannit, P.S. Callery, and P. Rojsitthisak Effects of different carboxylic ester spacers on chemical stability, release characteristics, and anticancer activity of mono-PEGylated curcumin conjugates J. Pharm. Sci. 100 2011 5206 5218
    • (2011) J. Pharm. Sci. , vol.100 , pp. 5206-5218
    • Wichitnithad, W.1    Nimmannit, U.2    Callery, P.S.3    Rojsitthisak, P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.