Tumor targeting by pH-sensitive, biodegradable, cross-linked N-(2-hydroxypropyl) methacrylamide copolymer micelles

Biomaterials

Volumn 35, Issue 24, 2014, Pages 6622-6635

  Zhou, Zhou ^a   Li, Lian ^a   Yang, Yang ^a   Xu, Xiuli ^a   Huang, Yuan ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Biodegradable; Cross linked; HPMA copolymer conjugates; PH sensitive; Polymeric micelles; sitosterol

Indexed keywords

BIODEGRADABLE POLYMERS; BIODEGRADATION; CELL CULTURE; COPOLYMERS; CROSSLINKING; DRUG DELIVERY; HYDROPHOBICITY; MAMMALS; MOLECULAR WEIGHT; PH; SELF ASSEMBLY; TUMORS;

BIODEGRADABLE; CROSS-LINKED; HPMA COPOLYMER CONJUGATES; PH SENSITIVE; POLYMERIC MICELLE;

MICELLES;

ACRYLAMIDE DERIVATIVE; ALANINE AMINOTRANSFERASE; ANTINEOPLASTIC AGENT; ASPARTATE AMINOTRANSFERASE; BIOMATERIAL; CROSS LINKING REAGENT; DOXORUBICIN; FLUORESCEIN ISOTHIOCYANATE; MICELLE; N-(2-HYDROXYPROPYL)METHACRYLAMIDE; POLYMER; SITOSTEROL DERIVATIVE;

ANIMAL; BLOOD; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; ENDOCYTOSIS; FEMALE; HUMAN; LIVER; METABOLISM; MICELLE; MOUSE; NEOPLASMS; PATHOLOGY; PH; SYNTHESIS; TISSUE DISTRIBUTION; TRANSMISSION ELECTRON MICROSCOPY; TUMOR CELL LINE; TUMOR VOLUME;

ACRYLAMIDES; ALANINE TRANSAMINASE; ANIMALS; ANTINEOPLASTIC AGENTS; ASPARTATE AMINOTRANSFERASES; BIOCOMPATIBLE MATERIALS; CELL LINE, TUMOR; CROSS-LINKING REAGENTS; DOXORUBICIN; ENDOCYTOSIS; FEMALE; FLUORESCEIN-5-ISOTHIOCYANATE; HUMANS; HYDROGEN-ION CONCENTRATION; LIVER; MICE; MICELLES; MICROSCOPY, ELECTRON, TRANSMISSION; NEOPLASMS; POLYMERS; SITOSTEROLS; TISSUE DISTRIBUTION; TUMOR BURDEN; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84901444459     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2014.04.059     Document Type: Article

References (47)

1. Torchilin V.P. Structure and design of polymeric surfactant-based drug delivery systems. JControl Release 2001, 73:137-172.
2. Torchilin V.P. Targeted polymeric micelles for delivery of poorly soluble drugs. Cell Mol Life Sci 2004, 61:2549-2559.
3. Kataoka K., Harada A., Nagasaki Y. Block copolymer micelles for drug delivery: design, characterization and biological significance. Adv Drug Deliv Rev 2001, 47:113-131.
4. Nasongkla N., Bey E., Ren J., Ai H., Khemtong C., Guthi J.S., et al. Multifunctional polymeric micelles as cancer-targeted, MRI-ultrasensitive drug delivery systems. Nano Lett 2006, 6:2427-2430.
5. Kim B.-S., Park S.W., Hammond P.T. Hydrogen-bonding layer-by-layer-assembled biodegradable polymeric micelles as drug delivery vehicles from surfaces. ACS Nano 2008, 2:386-392.
6. Matsumura Y., Kataoka K. Preclinical and clinical studies of anticancer agent-incorporating polymer micelles. Cancer Sci 2009, 100:572-579.
7. Matsumura Y. Preclinical and clinical studies of NK012, an SN-38-incorporating polymeric micelles, which is designed based on EPR effect. Adv Drug Deliv Rev 2011, 63:184-192.
8. Plummer R., Wilson R., Calvert H., Boddy A., Griffin M., Sludden J., et al. Aphase I clinical study of cisplatin-incorporated polymeric micelles (NC-6004) in patients with solid tumours. Br J Cancer 2011, 104:593-598.
9. Kim T.-Y., Kim D.-W., Chung J.-Y., Shin S.G., Kim S.-C., Heo D.S., et al. Phase I and pharmacokinetic study of Genexol-PM, a cremophor-free, polymeric micelle-formulated paclitaxel, in patients with advanced malignancies. Clin Cancer Res 2004, 10:3708-3716.
10. Chai J., Buriak J.M. Using cylindrical domains of block copolymers to self-assemble and align metallic nanowires. ACS Nano 2008, 2:489-501.
11. Kim B.-S., Qiu J.-M., Wang J.-P., Taton T.A. Magnetomicelles: composite nanostructures from magnetic nanoparticles and cross-linked amphiphilic block copolymers. Nano Lett 2005, 5:1987-1991.
12. Wright E.R., Conticello V.P. Self-assembly of block copolymers derived fromelastin-mimetic polypeptide sequences. Adv Drug Deliv Rev 2002, 54:1057-1073.
13. Kopeček J., Kopečková P. HPMA copolymers: origins, early developments, present, and future. Adv Drug Deliv Rev 2010, 62:122-149.
14. Duncan R., Vicent M.J. Do HPMA copolymer conjugates have a future as clinically useful nanomedicines? A critical overview of current status and future opportunities. Adv Drug Deliv Rev 2010, 62:272-282.
15. Ulbrich K., Šubr V. Structural and chemical aspects of HPMA copolymers as drug carriers. Adv Drug Deliv Rev 2010, 62:150-166.
16. Fisher K.D., Seymour L.W. HPMA copolymers for masking and retargeting of therapeutic viruses. Adv Drug Deliv Rev 2010, 62:240-245.
17. Yuan F., Qin X., Zhou D., Xiang Q.-Y., Wang M.-T., Zhang Z.-R., et al. Invitro cytotoxicity, invivo biodistribution and antitumor activity of HPMA copolymer-5-fluorouracil conjugates. Eur J Pharm Biopharm 2008, 70:770-776.
18. Greish K., Ray A., Bauer H., Larson N., Malugin A., Pike D., et al. Anticancer and antiangiogenic activity of HPMA copolymer-aminohexylgeldanamycin-RGDfK conjugates for prostate cancer therapy. JControl Release 2011, 151:263-270.
19. Ray A., Larson N., Pike D.B., Grüner M., Naik S., Bauer H., et al. Comparison of active and passive targeting of docetaxel for prostate cancer therapy by HPMA copolymer-RGDfK conjugates. Mol Pharm 2011, 8:1090-1099.
20. Etrych T., Jelínková M., Říhová B., Ulbrich K. New HPMA copolymers containing doxorubicin bound via pH-sensitive linkage: synthesis and preliminary invitro and invivo biological properties. JControl Release 2001, 73:89-102.
21. Pan H., Yang J., Kopečková P., Kopeček Ji Backbone degradable multiblock N-(2-hydroxypropyl) methacrylamide copolymer conjugates via reversible addition-fragmentation chain transfer polymerization and thiol-ene coupling reaction. Biomacromolecules 2010, 12:247-252.
22. Etrych T., Strohalm J., Chytil P., Černoch P., Starovoytova L., Pechar M., et al. Biodegradable star HPMA polymer conjugates of doxorubicin for passive tumor targeting. Eur J Pharm Sci 2011, 42:527-539.
23. Etrych T., Chytil P., Mrkvan T., Šírová M., Říhová B., Ulbrich K. Conjugates of doxorubicin with graft HPMA copolymers for passive tumor targeting. JControl Release 2008, 132:184-192.
24. Chytil P., Etrych T., Koňák Č., Šírová M., Mrkvan T., Bouček J., et al. New HPMA copolymer-based drug carriers with covalently bound hydrophobic substituents for solid tumour targeting. JControl Release 2008, 127:121-130.
25. Chytil P., Etrych T., Kostka L., Ulbrich K. Hydrolytically degradable polymer micelles for anticancer drug delivery to solid tumors. Macromol Chem Phys 2012, 213:858-867.
26. Jäger E., Jäger A., Chytil P., Etrych T., Říhová B., Giacomelli F.C., et al. Combination chemotherapy using core-shell nanoparticles through the self-assembly of HPMA-based copolymers and degradable polyester. JControl Release 2013, 165:153-161.
27. Talelli M., Rijcken C., Van Nostrum C., Storm G., Hennink W. Micelles based on HPMA copolymers. Adv Drug Deliv Rev 2010, 62:231-239.
28. Kim S., Shi Y., Kim J.Y., Park K., Cheng J.-X. Overcoming the barriers in micellar drug delivery: loading efficiency, invivo stability, and micelle-cell interaction. Expert Opin Drug Deliv 2010, 7:49-62.
29. Liu J., Zeng F., Allen C. Invivo fate of unimers and micelles of a poly (ethylene glycol)-block-poly (caprolactone) copolymer in mice following intravenous administration. Eur J Pharm Biopharm 2007, 65:309-319.
30. Ulbrich K., Šubr V., Strohalm J., Plocova D., Jelinková M., Říhová B. Polymeric drugs based on conjugates of synthetic and natural macromolecules: I. Synthesis and physico-chemical characterisation. JControl Release 2000, 64:63-79.
31. Duncan R., Cable H.C., Lloyd J.B., Rejmanová P., Kopeček J. Polymers containing enzymatically degradable bonds, 7. Design of oligopeptide side-chains in poly [N-(2-hydroxypropyl) methacrylamide] copolymers to promote efficient degradation by lysosomal enzymes. Die Makromol Chem 1983, 184:1997-2008.
32. Liu X.-M., Quan L.-D., Tian J., Alnouti Y., Fu K., Thiele G.M., et al. Synthesis and evaluation of a well-defined HPMA copolymer-dexamethasone conjugate for effective treatment of rheumatoid arthritis. Pharm Res 2008, 25:2910-2919.
33. Lammers T., Peschke P., Kühnlein R., Subr V., Ulbrich K., Debus J., et al. Effect of radiotherapy and hyperthermia on the tumor accumulation of HPMA copolymer-based drug delivery systems. JControl Release 2007, 117:333-341.
34. Omelyanenko V., Kopečková P., Gentry C., Kopeček J. Targetable HPMA copolymer-adriamycin conjugates. Recognition, internalization, and subcellular fate. JControl Release 1998, 53:25-37.
35. Kim J.O., Kabanov A.V., Bronich T.K. Polymer micelles with cross-linked polyanion core for delivery of a cationic drug doxorubicin. JControl Release 2009, 138:197-204.
36. Zhang L., Nguyen T.U., Bernard J., Davis T.P., Barner-Kowollik C., Stenzel M.H. Shell-cross-linked micelles containing cationic polymers synthesized via the RAFT process: toward a more biocompatible gene delivery system. Biomacromolecules 2007, 8:2890-2901.
37. Zhang L., Liu W., Lin L., Chen D., Stenzel M.H. Degradable disulfide core-cross-linked micelles as a drug delivery system prepared from vinyl functionalized nucleosides via the RAFT process. Biomacromolecules 2008, 9:3321-3331.
38. Zhao Y., Bertrand J., Tong X., Zhao Y. Photo-cross-linkable polymer micelles in hydrogen-bonding-built layer-by-layer films. Langmuir 2009, 25:13151-13157.
39. Lammers T., Kühnlein R., Kissel M., Subr V., Etrych T., Pola R., et al. Effect of physicochemical modification on the biodistribution and tumor accumulation of HPMA copolymers. JControl Release 2005, 110:103-118.
40. Pearson J.P., Van Delden C., Iglewski B.H. Active efflux and diffusion are involved in transport of Pseudomonas aeruginosa cell-to-cell signals. JBacteriol 1999, 181:1203-1210.
41. Atobe K., Ishida T., Ishida E., Hashimoto K., Kobayashi H., Yasuda J., et al. Invitroefficacy of a sterically stabilized immunoliposomes targeted to membrane type 1 matrix metalloproteinase (MT1-MMP). Biol Pharm Bull 2007, 30:972-978.
42. Schnitzer J.E., Oh P., Pinney E., Allard J. Filipin-sensitive caveolae-mediated transport in endothelium: reduced transcytosis, scavenger endocytosis, andcapillary permeability of select macromolecules. JCell Biol 1994, 127:1217-1232.
43. Koivusalo M., Welch C., Hayashi H., Scott C.C., Kim M., Alexander T., et al. Amiloride inhibits macropinocytosis by lowering submembranous pH and preventing Rac1 and Cdc42 signaling. JCell Biol 2010, 188:547-563.
44. Kovář M., Kovář L., Šubr V., Etrych T., Ulbrich K., Mrkvan T., et al. HPMA copolymers containing doxorubicin bound by a proteolytically or hydrolytically cleavable bond: comparison of biological properties invitro. JControl Release 2004, 99:301-314.
45. Yang Y., Zhou Z., He S., Fan T., Jin Y., Zhu X., et al. Treatment of prostate carcinoma with (Galectin-3)-targeted HPMA copolymer-(G3-C12)-5-fluorouracil conjugates. Biomaterials 2012, 33:2260-2271.
46. Allmeroth M., Moderegger D., Biesalski B., Koynov K., Rösch F., Thews O., et al. Modifying the body distribution of HPMA-based copolymers by molecular weight and aggregate formation. Biomacromolecules 2011, 12:2841-2849.
47. Giannini E., Botta F., Fasoli A., Ceppa P., Risso D., Lantieri P.B., et al. Progressive liver functional impairment is associated with an increase in AST/ALT ratio. Dig Dis Sci 1999, 44:1249-1253.