Polymer conjugates of doxorubicin bound through an amide and hydrazone bond: Impact of the carrier structure onto synergistic action in the treatment of solid tumours

European Journal of Pharmaceutical Sciences

Volumn 58, Issue 1, 2014, Pages 1-12

  Etrych, Tomáš ^a   Šubr, Vladimír ^a   Laga, Richard ^a   Říhová, Blanka ^b   Ulbrich, Karel ^a  

^a INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Czech Republic)

^b INSTITUTE OF MATHEMATICS   (Czech Republic)

Author keywords

Doxorubicin; Drug delivery; HPMA copolymer; In vivo efficacy; Synergistic effect

Indexed keywords

AMIDE; DOXORUBICIN; GLUTATHIONE; HYDRAZONE DERIVATIVE; N (2 HYDROXYPROPYL)METHACRYLAMIDE COPOLYMER; ACRYLAMIDE DERIVATIVE; ANTINEOPLASTIC ANTIBIOTIC; DRUG CARRIER; N-(2-HYDROXYPROPYL)METHACRYLAMIDE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; AQUEOUS SOLUTION; ARTICLE; B CELL LYMPHOMA; BIODEGRADABILITY; BREAST CANCER; CANCER CELL CULTURE; CANCER RESISTANCE; CELL DEATH; CONTROLLED STUDY; CYTOSTASIS; CYTOTOXICITY; DISULFIDE BOND; DRUG CONJUGATION; DRUG DISTRIBUTION; DRUG MECHANISM; DRUG POTENTIATION; DRUG STABILITY; FEMALE; GLOMERULUS FILTRATION; HYDRODYNAMICS; HYDROLYSIS; IN VITRO STUDY; IN VIVO STUDY; LUNG CARCINOMA; MALE; MOLECULAR WEIGHT; MOUSE; NANOMEDICINE; NONHUMAN; PH; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; T CELL LYMPHOMA; TUMOR GROWTH; TUMOR IMMUNITY; TUMOR MICROENVIRONMENT; ANIMAL; C57BL MOUSE; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; METABOLISM; NEOPLASMS; TUMOR CELL LINE;

ACRYLAMIDES; ANIMALS; ANTIBIOTICS, ANTINEOPLASTIC; CELL LINE, TUMOR; CELL SURVIVAL; DOXORUBICIN; DRUG CARRIERS; DRUG STABILITY; FEMALE; HYDRAZONES; HYDROGEN-ION CONCENTRATION; MICE; MICE, INBRED C57BL; NEOPLASMS;

EID: 84897373234     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2014.02.016     Document Type: Article

References (41)

1. M.B. Astor, M.E. Anderson, and A. Meister Relationship between intracellular GSH levels and hypoxic cell radiosensitivity Pharmacol. Therapeut. 39 1988 115 121
2. 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 J. Control. Release 127 2008 121 130
3. P. Chytil, T. Etrych, L. Kostka, and K. Ulbrich Hydrolytically degradable polymer micelles for anticancer drug delivery to solid tumors Macromol. Chem. Phys. 213 2012 858 867
4. R. Duncan N-(2-hydroxypropyl)methacrylamide copolymer conjugates G.S. Kwon, Drugs and the Pharmaceutiutical Sciences Polymeric Drug Delivery Systems vol. 148 2005 Taylor & Francis Boca Raton 1 92
5. M. Dvořák, P. Kopečková, and J. Kopeček High-molecular weight HPMA copolymer-adriamycin conjugates J. Control. Release 60 1999 321 332 (Pubitemid 29335957)
6. Y.W. Ebright, Y. Chen, P.S. Pendergrast, and R.H. Ebright Incorporation of an EDTA-metal complex at a rationally selected site within a protein: application to EDTA-iron DNA affinity cleaving with catabolite gene activator protein (CAP) and Cro Biochemistry (Mosc.) 31 1992 10664 10670
7. 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 J. Control. Release 73 2001 89 102 (Pubitemid 32406104)
8. 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 Macromol. Biosci. 2 2002 43 52 (Pubitemid 44790994)
9. T. Etrych, P. Chytil, T. Mrkvan, M. Šírová, B. Říhová, and K. Ulbrich Conjugates of doxorubicin with graft HPMA copolymers for passive tumor targeting J. Control. Release 132 2008 184 192
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 J. Appl. Polym. Sci. 109 2008 3050 3061
11. T. Etrych, L. Kovář, V. Šubr, A. Braunová, M. Pechar, P. Chytil, B. Říhová, and K. Ulbrich High-molecular-weight polymers containing biodegradable disulfide bonds: synthesis and in vitro verification of intracellular degradation J. Bioactive Compat. Polym. 25 2010 5 26
12. Etrych, T.; Ulbrich, K.; Hovorka, O.; Říhová, B.; 2010b. Polymeric composition with synergistic effect in treatment of tumour diseases. WO2010045896, Czech Republic.
13. T. Etrych, L. Kovář, J. Strohalm, P. Chytil, B. Říhová, and K. Ulbrich Biodegradable star HPMA polymer-drug conjugates: biodegradability, distribution and anti-tumor efficacy J. Control. Release 154 2011 241 248
14. T. Etrych, J. Strohalm, P. Chytil, P. Černoch, L. Starovoytova, M. Pechar, and K. Ulbrich Biodegradable star HPMA polymer conjugates of doxorubicin for passive tumor targeting Eur. J. Pharm. Sci. 42 2011 527 539
15. T. Etrych, V. Šubr, J. Strohalm, M. Šírová, B. Říhová, and K. Ulbrich Fate of HPMA based polymer-doxorubicin conjugates in organism: effect of the molecular weight of polymer carrier J. Control. Release 164 2012 346 354
16. D. Fraier, E. Frigerio, E. Pianezzola, M.S. Benedetti, J. Cassidy, and P. Vasey A sensitive procedure for the quantitation of free and N-(2-hydroxypropyl)methacrylamide polymer-bound doxorubicin (Pk1) and some of its metabolites, 13-dihydrodoxorubicin, 13-dihydrodoxorubicinone and doxorubicinone, in human plasma and urine by reversed-phase Hplc with fluorometric detection J. Pharm. Biomed. Anal. 13 1995 625 633
17. O. Hovorka, T. Etrych, V. Šubr, J. Strohalm, K. Ulbrich, and B. Říhová HPMA based macromolecular therapeutics: internalization, intracellular pathway and cell death depend on the character of covalent bond between the drug and the peptide spacer and also on spacer composition J. Drug Target. 14 2006 391 403 (Pubitemid 44203519)
18. J. Kopeček Polymer-drug conjugates: origins, progress to date and future directions Adv. Drug Deliv. Rev. 65 2013 49 59
19. H. Kostková, B. Říhová, T. Etrych, and K. Ulbrich Synergistic effect of HPMA copolymer-bound doxorubicin and dexamethasone in vivo on mouse lymphomas J. Bioactive Compat. Polym. 26 2011 270 286
20. H. Kostková, T. Etrych, B. Říhová, L. Kostka, L. Starovoytova, M. Kovář, and K. Ulbrich HPMA copolymer conjugates of DOX and mitomycin C for combination therapy: physicochemical characterization, cytotoxic effects, combination index analysis and anti-tumor afficacy Macromol. Biosci. 13 2013 1648 1660
21. G. Kroemer, L. Galluzzi, O. Kepp, and L. Zitvogel Immunogenic cell death in cancer therapy Annu. Rev. Immunol. 31 2013 51 72
22. H. Maeda Macromolecular therapeutics in cancer treatment: the EPR effect and beyond J. Control. Release 164 2012 138 144
23. 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
24. 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 (Pubitemid 17221789)
25. B. Říhová, and K. Kubáčková Clinical implications of N-(2-hydroxypropyl)methacrylamide copolymers Curr. Pharm. Biotechnol. 4 2003 311 322 (Pubitemid 37220863)
26. B. Říhová, T. Etrych, M. Pechar, M. Jelínková, M. Štastný, 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 J. Control. Release 74 2001 225 232 (Pubitemid 32727624)
27. B. Říhová, J. Strohalm, J. Prausová, K. Kubáčková, M. Jelínková, L. Rozprimová, M. Šírová, D. Plocová, T. Etrych, V. Šubr, T. Mrkvan, M. Kovář, and K. Ulbrich Cytostatic and immunomobilizing activities of polymer-bound drugs: experimental and first clinical data J. Control. Release 91 2003 1 16 (Pubitemid 37288875)
28. B. Říhová, T. Etrych, M. Šírová , L. Kovář, O. Hovorka, M. Kovář, A. Benda, and K. Ulbrich Synergistic action of doxorubicin bound to the polymeric carrier based on N-(2-hydroxypropyl)methacrylamide copolymers through an amide or hydrazone bond Mol. Pharmaceut. 7 2010 1027 1040
29. 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 Adv. Drug Deliv. Rev. 55 2003 199 215 (Pubitemid 36135916)
30. L.W. Seymour, D.R. Ferry, D.J. Kerr, D. Rea, M. Whitlock, R. Poyner, Ch. Boivin, S. Hesslewood, Ch. Twelves, R. Blackie, A. Schatzlein, D. Jodrell, D. Bissett, H. Calvert, M. Lind, A. Robbins, S. Burtles, R. Duncan, and J. Cassidy Phase II studies of polymer-doxorubicin (PK1, FCE28068) in the treatment of breast, lung and colorectal cancer Int. J. Oncol. 34 2009 1629 1636
31. M. Šírová, T. Mrkvan, T. Etrych, P. Chytil, P. Rossmann, M. Ibrahimová, L. Kovář, K. Ulbrich, and B. Říhová Preclinical evaluation of linear HPMA-doxorubicin conjugates with pH-sensitive drug release: efficacy, safety, and immunomodulating activity in murine model Pharm. Res. 27 2010 200 208
32. M. Šírová, M. Kabešová, L. Kovář, T. Etrych, J. Strohalm, K. Ulbrich, and B. Říhová Polymer-bound doxorubicin induces immunogenic tumor cell death Curr. Med. Chem. 20 2013 4815 4826
33. K. Ulbrich, and V. Šubr Structural and chemical aspects of HPMA copolymers as drug carriers Adv. Drug Deliv. Rev. 62 2010 150 166
34. 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 J. Control. Release 64 2000 63 79 (Pubitemid 30035308)
35. 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 J. Control. Release 87 2003 33 47 (Pubitemid 36258386)
36. K. Ulbrich, T. Etrych, P. Chytil, M. Jelínková, and B. Říhová Antibody-targeted polymer-doxorubicin conjugates with pH-controlled activation J. Drug Target. 12 2004 477 489 (Pubitemid 40081303)
37. K. Ulbrich, T. Etrych, P. Chytil, M. Pechar, M. Jelínková, and B. Říhová Polymeric anticancer drugs with pH-controlled activation Int. J. Pharm. 277 2004 63 72 (Pubitemid 38670421)
38. P.A. Vasey, R. Duncan, S.B. Kaye, and J. Cassidy Clinical phase I trial of PK1 (HPMA co-polymer doxorubicin) Eur. J. Cancer 31 1995 S193
39. P.A. Vasey, S.B. Kaye, R. Morrison, C. Twelves, P. Wilson, R. Duncan, A.H. Thomson, L.S. Murray, T.E. Hilditch, T. Murray, S. Burtles, D. Fraier, E. Frigerio, and J. Cassidy Phase I clinical and pharmacokinetic study of PK1 [N-(2-hydroxypropyl)methacrylamide copolymer doxorubicin]: first member of a new class of chemotherapeutic agents - drug-polymer conjugates Clin. Cancer Res. 5 1999 83 94 (Pubitemid 29045181)
40. M.J. Vicent, L. Dieudonneé, R.J. Carbajo, and A. Pineda-Lucena Polymer conjugates as therapeutics: future trends, challenges and opportunities Exp. Opin. Drug Deliv. 5 2008 593 614 (Pubitemid 351888105)
41. M.J. Vicent, H. Ringsdorf, and R. Duncan Polymer therapeutics: clinical applications and challenges for development Adv. Drug Deliv. Rev. 61 2009 1117 1120