Biodegradable star HPMA polymer conjugates of doxorubicin for passive tumor targeting

European Journal of Pharmaceutical Sciences

Volumn 42, Issue 5, 2011, Pages 527-539

  Etrych, Tomáš ^a   Strohalm, Jiří ^a   Chytil, Petr ^a   Černoch, Peter ^a   Starovoytova, Larisa ^a   Pechar, Michal ^a   Ulbrich, Karel ^a  

^a INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Czech Republic)

Author keywords

Dendrimer; Doxorubicin; Drug conjugates; HPMA copolymers; Tumor targeting

Indexed keywords

CATHEPSIN B; COPOLYMER; DENDRIMER; DOXORUBICIN; GLUTATHIONE; HYDRAZONE DERIVATIVE; N (2 HYDROXYPROPYL)METHACRYLAMIDE; POLYAMIDOAMINE;

ARTICLE; BIODEGRADABILITY; BLOOD PH; CELL PH; CHEMICAL BOND; CONTROLLED DRUG RELEASE; CONTROLLED STUDY; DRUG CONJUGATION; DRUG DESIGN; DRUG SYNTHESIS; ENZYMATIC DEGRADATION; GLOMERULUS FILTRATION; HUMAN; MOLECULAR STABILITY; MOLECULAR WEIGHT; PRIORITY JOURNAL; STEREOSPECIFICITY; TARGET ORGAN; TUMOR MICROENVIRONMENT;

ANTIBIOTICS, ANTINEOPLASTIC; BIOCOMPATIBLE MATERIALS; DENDRIMERS; DOXORUBICIN; DRUG CARRIERS; DRUG STABILITY; METHACRYLATES; MOLECULAR STRUCTURE; SOLUBILITY;

EID: 79954632423     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2011.03.001     Document Type: Article

References (51)

1. P. Chytil, T. Etrych, Č. Koňák, M. Šírová, T. Mrkvan, J. Bouček, B. Říhová, and K. Ulbrich New HPMA copolymer-based drug carriers with covalently bound hydrophobic substituents for solid tumour targeting Journal of Controlled Release 127 2008 121 130
2. R. Duncan Selective endocytosis of macromolecular drug carriers J.R. Robinson, V.H. Lee, Controlled Drug Delivery 1987 Marcel Dekker New York 581 607
3. R. Duncan The dawning era of polymer therapeutics Nature Reviews Drug Discovery 2 2003 347 360 (Pubitemid 37361705)
4. T. Dutta, N.K. Jain, N.A.J. McMillan, and H.S. Parekh Dendrimer nanocarriers as versatile vectors in gene delivery Nanomedicine: Nanotechnology Biology and Medicine 6 2010 25 34
5. M. Dvořák, P. Kopečková, and J. Kopeček High-molecular weight HPMA copolymer-adriamycin conjugates Journal of Controlled Release 60 1999 321 332 (Pubitemid 29335957)
6. G.L. Ellman Tissue sulfhydryl groups Archives of Biochemistry and Biophysics 82 1959 70 77
7. T. Etrych, P. Chytil, M. Jelínková, B. Ří hová, and K. Ulbrich Synthesis of HPMA copolymers containing doxorubicin bound via a hydrazone linkage. Effect of spacer on drug release and in vitro cytotoxicity Macromolecular Bioscience 2 2002 43 52 (Pubitemid 44790994)
8. T. Etrych, P. Chytil, T. Mrkvan, M. Šírová, B. Říhová, and K. Ulbrich Conjugates of doxorubicin with graft HPMA copolymers for passive tumor targeting Journal of Controlled Release 132 2008 184 192
9. T. Etrych, M. Jelínková, B. Říhová, and K. Ulbrich New HPMA copolymers containing doxorubicin bound via pH-sensitive linkage: synthesis and preliminary in vitro and in vivo biological properties Journal of Controlled Release 73 2001 89 102 (Pubitemid 32406104)
10. T. Etrych, T. Mrkvan, P. Chytil, Č. Koňák, B. Říhová, and K. Ulbrich N-(2-Hydroxypropyl)methacrylamide- based polymer conjugates with pH-controlled activation of doxorubicin. I. New synthesis, physicochemical characterization and preliminary biological evaluation Journal of Applied Polymer Science 109 2008 3050 3061
11. T. Etrych, J. Strohalm, L. Kovář, M. Kabešová , B. Říhová, and K. Ulbrich HPMA copolymer conjugates with reduced anti-CD20 antibody for cell-specific drug targeting. I. Synthesis and in vitro evaluation of binding efficacy and cytostatic activity Journal of Controlled Release 140 2009 18 26
12. T. Etrych, M. Šírová, L. Starovoytova, B. Říhová, and K. Ulbrich HPMA copolymer conjugates of paclitaxel and docetaxel with pH-controlled drug release Molecular Pharmaceutics 7 2010 1015 1026
13. E. Gianasi, M. Wasil, E.G. Evagorou, A. Keddle, G. Wilson, and R. Duncan HPMA copolymer platinates as novel antitumour agents: in vitro properties, pharmacokinetics and antitumour activity in vivo European Journal of Cancer 35 1999 994 1002 (Pubitemid 29277137)
14. R. Haag, and F. Kratz Polymer therapeutics: concepts and applications Angewandte Chemie, International Edition 45 2006 1198 1215 (in English) (Pubitemid 44097641)
15. R.C. Hedden, and B.J. Bauer Structure and dimensions of PAMAM/PEG dendrimer-star polymers Macromolecules 36 2003 1829 1835
16. J. Jakeš Regularized positive exponential sum (REPES) program - a way of inverting laplace transform data obtained by dynamic light scattering Collection of Czechoslovak Chemical Communications 60 1995 1781 1797 (Pubitemid 126015546)
17. J. Kopeček, and P. Kopečková HPMA copolymers: origins, early developments, present, and future Advanced Drug Delivery Reviews 62 2010 122 149
18. J. Kopeček, P. Kopečková, T. Minko, and Z.R. Lu HPMA copolymer-anticancer drug conjugates: design, activity, and mechanism of action European Journal of Pharmaceutics and Biopharmaceutics 50 2000 61 81 (Pubitemid 30326689)
19. J. Kopeček, P. Kopečková, T. Minko, Z.R. Lu, and C.M. Peterson Water soluble polymers in tumor targeted delivery Journal of Controlled Release 74 2001 147 158 (Pubitemid 32727617)
20. M. Kovář, T. Mrkvan, J. Strohalm, T. Etrych, K. Ulbrich, M. Štastný, and B. Říhová HPMA copolymer-bound doxorubicin targeted to tumor-specific antigen of BCL1 mouse B cell leukemia Journal of Controlled Release 92 2003 315 330 (Pubitemid 38372094)
21. H. Krakovičová, T. Etrych, and K. Ulbrich HPMA-based polymer conjugates with drug combination European Journal of Pharmaceutical Sciences 37 2009 405 412
22. F. Kratz, U. Beyer, and M.T. Schutte Drug-polymer conjugates containing acid-cleavable bonds Critical Reviews in Therapeutic Drug Carrier Systems 16 1999 245 288 (Pubitemid 29305204)
23. F. Kratz, I.A. Muller, C. Ryppa, and A. Warnecke Prodrug strategies in anticancer chemotherapy ChemMedChem 3 2008 20 53
24. H. Maeda The enhanced permeability and retention (EPR) effect in tumor vasculature: the key role of tumor-selective macromolecular drug targeting Advances in Enzyme Regulation 41 2001 189 207
25. D.Q. McNerny, P.R. Leroueil, and J.R. Baker Understanding specific and nonspecific toxicities: a requirement for the development of dendrimer-based pharmaceuticals Wiley Interdisciplinary Reviews: Nanomedicine and Nanobiotechnology 2 2010 249 259
26. A. Meister Glutathione deficiency produced by inhibition of its synthesis, and its reversal - applications in research and therapy Pharmacology & Therapeutics 51 1991 155 194
27. N. Nishiyama, Y. Morimoto, W.D. Jang, and K. Kataoka Design and development of dendrimer photosensitizer-incorporated polymeric micelles for enhanced photodynamic therapy Advanced Drug Delivery Reviews 61 2009 327 338
28. Y. Noguchi, J. Wu, R. Duncan, J. Strohalm, K. Ulbrich, T. Akaike, and H. Maeda Early phase tumor accumulation of macromolecules: a great difference in clearance rate between tumor and normal tissues Japanese Journal of Cancer Research 89 1998 307 314 (Pubitemid 28197296)
29. V. Omelyanenko, P. Kopečková, C. Gentry, J.G. Shiah, and J. Kopeček HPMA copolymer-anticancer drug-OV-TL16 antibody conjugates. 1. Influence of the method of synthesis on the binding affinity to OVCAR-3 ovarian carcinoma cells in vitro Journal of Drug Targeting 3 1996 357 373 (Pubitemid 26059826)
30. G. Pasut, and F.M. Veronese PEG conjugates in clinical development or use as anticancer agents: an overview Advanced Drug Delivery Reviews 61 2009 1177 1188
31. M. Pechar, A. Braunová, K. Ulbrich, M. Jelínková, and B. Říhová Poly(ethylene glycol) - doxorubicin conjugates with pH-controlled activation Journal of Bioactive and Compatible Polymers 20 2005 319 341 (Pubitemid 41104878)
32. D.B. Pike, and H. Ghandehari HPMA copolymer-cyclic RGD conjugates for tumor targeting Advanced Drug Delivery Reviews 62 2010 167 183
33. 123I-labelled N-(2-hydroxypropyl)methacrylamide copolymer-doxorubicin conjugates in mice with transplanted melanoma and mammary carcinoma Journal of Drug Targeting 3 1996 375 383
34. R. Pola, M. Studenovský, M. Pechar, K. Ulbrich, O. Hovorka, D. Větvička, and B. Říhová HPMA-copolymer conjugates targeted to tumor endothelium using synthetic oligopeptides Journal of Drug Targeting 17 2009 763 776
35. D. Putnam, and J. Kopeček Polymer conjugates with anticancer activity Biopolymers 122 1995 55 123
36. P. Rejmanová, J. Kopeček, J. Pohl, M. Baudyš, and V. Kostka Polymers containing enzymatically degradable bonds. 8. Degradation of oligopeptide sequences in N-(2-hydroxypropyl)methacrylamide co-polymers by bovine spleen cathepsin-B Makromolekulare Chemie-Macromolecular Chemistry and Physics 184 1983 2009 2020
37. P.C.A. Rodrigues, T. Roth, H.H. Fiebig, C. Unger, R. Mulhaupt, and F. Kratz Correlation of the acid-sensitivity of polyethylene glycol daunorubicin conjugates with their in vitro antiproliferative activity Bioorganic & Medicinal Chemistry 14 2006 4110 4117
38. B. Říhová, T. Etrych, M. Pechar, M. Jelínková, M. Šťastný, O. Hovorka, M. Kovář, and K. Ulbrich Doxorubicin bound to a HPMA copolymer carrier through hydrazone bond is effective also in a cancer cell line with a limited content of lysosomes Journal of Controlled Release 74 2001 225 232 (Pubitemid 32727624)
39. 2-targeted conjugates and combined therapy with immunomodulators Journal of Controlled Release 64 2000 241 261 (Pubitemid 30035323)
40. G. Saito, J.A. Swanson, and K.D. Lee Drug delivery strategy utilizing conjugation via reversible disulfide linkages: role and site of cellular reducing activities Advanced Drug Delivery Reviews 55 2003 199 215 (Pubitemid 36135916)
41. L.W. Seymour, Y. Miyamoto, H. Maeda, M. Brereton, J. Strohalm, K. Ulbrich, and R. Duncan Influence of molecular-weight on passive tumor accumulation of a soluble macromolecular drug carrier European Journal of Cancer 31A 1995 766 770
42. J.G. Shiah, M. Dvořák, P. Kopečková, Y. Sun, C.M. Peterson, and J. Kopeček Biodistribution and antitumour efficacy of long-circulating N-(2-hydroxypropyl)methacrylamide copolymer-doxorubicin conjugates in nude mice European Journal of Cancer 37 2001 131 139 (Pubitemid 32119370)
43. P.S. Steyger, D.F. Baban, M. Brereton, K. Ulbrich, and L.W. Seymour Intratumoural distribution as a determinant of tumour responsiveness to therapy using polymer-based macromolecular prodrugs Journal of Controlled Release 39 1996 35 46 (Pubitemid 26135550)
44. V. Šubr, and K. Ulbrich Synthesis and properties of new N-(2-hydroxypropyl)-methacrylamide copolymers containing thiazolidine-2-thione reactive groups Reactive & Functional Polymers 66 2006 1525 1538 (Pubitemid 44751599)
45. K. Ulbrich, T. Etrych, P. Chytil, M. Jelínková, and B. Říhová HPMA copolymers with pH-controlled release of doxorubicin: in vitro cytotoxicity and in vivo antitumor activity Journal of Controlled Release 87 2003 33 47 (Pubitemid 36258386)
46. K. Ulbrich, T. Etrych, P. Chytil, M. Jelínková, and B. Říhová Antibody-targeted polymer-doxorubicin conjugates with pH-controlled activation Journal of Drug Targeting 12 2004 477 489 (Pubitemid 40081303)
47. K. Ulbrich, J. Strohalm, V. Šubr, D. Plocová, R. Duncan, and B. Říhová Polymeric conjugates of drugs and antibodies for site-specific drug delivery Macromolecular Symposia 103 1996 177 192
48. K. Ulbrich, and V. Šubr Polymeric anticancer drugs with pH-controlled activation Advanced Drug Delivery Reviews 56 2004 1023 1050 (Pubitemid 38520207)
49. K. Ulbrich, and V. Šubr Structural and chemical aspects of HPMA copolymers as drug carriers Advanced Drug Delivery Reviews 62 2010 150 166
50. K. Ulbrich, V. Šubr, J. Strohalm, D. Plocová, M. Jelínková, and B. Říhová Polymeric drugs based on conjugates of synthetic and natural macromolecules. I. Synthesis and physico-chemical characterisation Journal of Controlled Release 64 2000 63 79 (Pubitemid 30035308)
51. D. Wang, P. Kopečková, T. Minko, V. Nanayakkara, and J. Kopeček Synthesis of starlike N-(2-hydroxypropyl)methacrylamide copolymers: potential drug carriers Biomacromolecules 1 2000 313 319