Co-delivery of daunomycin and oxaliplatin by biodegradable polymers for safer and more efficacious combination therapy

Journal of Controlled Release

Volumn 163, Issue 3, 2012, Pages 304-314

  Xiao, Haihua ^a,b   Li, Wenliang ^a,b   Qi, Ruogu ^a,b   Yan, Lesan ^a,b   Wang, Rui ^a,b   Liu, Shi ^a   Zheng, Yonghui ^a   Xie, Zhigang ^a   Huang, Yubin ^a   Jing, Xiabin ^a  

^a CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Combination chemotherapy; Daunorubicin; Drug delivery; Oxaliplatin; Polymer conjugates

Indexed keywords

ACID HYDROLYSIS; AMPHIPHILICS; ANTICANCER DRUG; CANCER CELLS; CARBOXYL GROUPS; CO-ASSEMBLE; COMBINATION CHEMOTHERAPY; COMBINATION THERAPY; DAUNOMYCIN; DAUNORUBICIN; DRUG-CONJUGATES; HYDROPHOBIC DRUG; HYDROXYL GROUPS; IN-VITRO; OXALIPLATIN; PLATINUM DRUGS; POLYMER BACKBONES; POLYMER BASED; POLYMER CONJUGATE; SMALL MOLECULES; SYNERGISTIC EFFECT; WATERSOLUBLE;

BIODEGRADABLE POLYMERS; CHEMOTHERAPY; DRUG DELIVERY; HYDROPHOBICITY; MICELLES; PLATINUM;

CONJUGATED POLYMERS;

ALANINE AMINOTRANSFERASE; ASPARTATE AMINOTRANSFERASE; CARBOXYL GROUP; DAUNORUBICIN; HYDROXYL GROUP; OXALIPLATIN; POLYMER; UREA;

ALANINE AMINOTRANSFERASE BLOOD LEVEL; ANIMAL EXPERIMENT; ARTICLE; ASPARTATE AMINOTRANSFERASE BLOOD LEVEL; CONFOCAL LASER MICROSCOPY; CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG EFFICACY; DRUG POTENTIATION; DRUG RELEASE; ELECTROSPRAY MASS SPECTROMETRY; ENDOCYTOSIS; HYDROGEN BOND; HYDROLYSIS; IN VITRO STUDY; IN VIVO STUDY; LIVER CELL CARCINOMA; MICELLE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TUMOR XENOGRAFT; UREA NITROGEN BLOOD LEVEL; ZETA POTENTIAL;

ANTINEOPLASTIC AGENTS; ANTINEOPLASTIC COMBINED CHEMOTHERAPY PROTOCOLS; CELL LINE, TUMOR; CELL SURVIVAL; DAUNORUBICIN; DRUG CARRIERS; HUMANS; MICELLES; ORGANOPLATINUM COMPOUNDS; POLYMERS; PRODRUGS;

EID: 84866158450     PISSN: 01683659     EISSN: 18734995     Source Type: Journal    
DOI: 10.1016/j.jconrel.2012.06.004     Document Type: Article

References (46)

1. M.S. Aapro, F.H. van Wijk, G. Bolis, B. Chevallier, M.E.L. van der Burg, A. Poveda, C.F. Oliveira, S. Tumolo, V. Scotto, di Palumbo, M. Piccart, M. Franchi, F. Zanaboni, A.J. Lacave, R. Fontanelli, G. Favalli, P. Zola, J.P. Guastalla, R. Rosso, C. Marth, M. Nooij, M. Presti, C. Scarabelli, T.A. Splinter, E. Ploch, L.V. Beex, W. ten Bokkel Huinink, M. Forni, M. Melpignano, P. Blake, P. Kerbrat, C. Mendiola, A. Cervantes, A. Goupil, P.G. Harper, C. Madronal, M. Namer, G. Scarfone, J.E. Stoot, I. Teodorovic, C. Coens, I. Vergote, and J.B. Vermorken Doxorubicin versus doxorubicin and cisplatin in endometrial carcinoma: definitive results of a randomised study (55872) by the EORTC Gynaecological Cancer Group Ann. Oncol. 14 2003 441 448 (Pubitemid 36367423)
2. S.M. Lee, T.V. O'Halloran, and S.B.T. Nguyen Polymer-caged nanobins for synergistic cisplatin-doxorubicin combination chemotherapy J. Am. Chem. Soc. 132 2010 17130 17138
3. G. Scambia, R. De Vincenzo, F.O. Ranelletti, P.B. Panici, G. Ferrandina, G.D. Agostino, A. Fattorossi, E. Bombardelli, and S. Mancuso Antiproliferative effect of silybin on gynaecological malignancies: synergism with cisplatin and doxorubicin Eur. J. Cancer 32 1996 877 882
4. M. Bigioni, A. Benzo, C. Irrissuto, G. Lopez, B. Curatella, C.A. Maggi, S. Manzini, A. Crea, S. Caroli, F. Cubadda, and M. Binaschi Antitumor effect of combination treatment with Sabarubicin (MEN 10755) and cisplatin (DDP) in human lung tumour xenograft Chemother. Pharmacol. 62 2008 621 629
5. A. Martoni, A. Bellucco, N. Canova, and F. Pannuti Four-year analysis of platinum and anthracycline combination for ovarian cancer Oncology 46 1989 109 116 (Pubitemid 19075323)
6. D. Nielsen, P. Dombernowsky, S.K. Larsen, O.P. Hansen, and T. Skovsgaard Epirubicin or epirubicin and cisplatin as first-line therapy in advanced breast cancer. A phase III study Cancer Chemother. Pharmacol. 46 2000 459 466
7. J.T. Thigpen, M.F. Brady, H.D. Homesley, J. Malfetano, B. DuBeshter, R.A. Burger, and S. Liao Phase III trial of doxorubicin with or without cisplatin in advanced endometrial carcinoma: a gynecologic oncology group study J. Clin. Oncol. 22 2004 3902 3908 (Pubitemid 41079871)
8. H. Maeda The enhanced permeability and retention (EPR) effect in tumor vasculature: the key role of tumor-selective macromolecular drug targeting Adv. Enzyme Regul. 41 2001 189 207
9. 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
10. Z.G. Xie, H.L. Guan, L. Chen, H.Y. Tian, X.S. Chen, and X.B. Jing Novel biodegradable poly(ethylene glycol)-block-poly(2-methyl-2carboxyl-propylene carbonate) copolymers: synthesis, characterization, and micellization Polymer 46 2005 10523 10530
11. X.L. Hu, S. Liu, Y.B. Huang, X.S. Chen, and X.B. Jing Biodegradable block copolymer-doxorubicin conjugates via different linkages: preparation, characterization, and in vitro evaluation Biomacromolecules 11 2010 2094 2102
12. H.H. Xiao, R.G. Qi, S. Liu, X.L. Hu, T.C. Duan, Y.H. Zheng, Y.B. Huang, and X.B. Jing Biodegradable polymer-cisplatin(IV) conjugate as a pro-drug of cisplatin(II) Biomaterials 32 2011 7732 7739
13. F. Michelet, R. Gueguen, P. Leroy, M. Wellman, A. Nicolas, and G. Siest Blood and plasma glutathione measured in healthy subjects by HPLC: relation to sex, aging, biological variables, and life habits Clin. Chem. 41 1995 1509 1517
14. A. Eastman Cross-linking of glutathione to DNA by cancer chemotherapeutic platinum coordination complexes Chem. Biol. Interact. 61 1987 241 248 (Pubitemid 17071620)
15. 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)
16. H. Reiber, M. Ruff, and M. Uhr Ascorbate concentration in human cerebrospinal fluid (CSF) and serum. Intrathecal accumulation and CSF flow rate Clin. Chim. Acta 217 1993 163 173 (Pubitemid 23274406)
17. P. Washko, D. Rotrosen, and M. Levine Ascorbic acid in human neutrophils Am. J. Clin. Nutr. 54 1991 1221S 1227S
18. T. Boulikas, A. Pantos, E. Bellis, and P. Christofis Designing platinum compounds in cancer: structures and mechanisms Cancer Ther. 5 2007 537 583
19. E.R. Jamieson, and S.J. Lippard Structure, recognition, and processing of cisplatin-DNA adducts Chem. Rev. 99 1999 2467 2498
20. A. Grothey Clinical management of oxaliplatin-associated neurotoxicity Clin. Colorectal Cancer 1 Supp I 2005 38 46
21. R.J. Cersosimo Oxaliplatin-associated neuropathy: a review Ann. Pharmacother. 39 2005 128 135 (Pubitemid 40052388)
22. M. Montaña, and C. Batalla The rational design of anticancer platinum complexes: the importance of the structure-activity relationship Curr. Med. Chem. 16 2009 2235 2260
23. W.H. Ang, S. Pilet, R. Scopelliti, F. Bussy, L. Juillerat-Jeaneret, and P.J. Dyson Synthesis and characterization of platinum(IV) anticancer drugs with functionalized aromatic carboxylate ligands: influence of the ligands on drug efficacies and uptake J. Med. Chem. 48 2005 8060 8069 (Pubitemid 41798436)
24. W.H. Ang, I. Khalaila, C.S. Allardyce, L. Juillerat-Jeanneret, and P.J. Dyson Rational design of platinum(IV) compounds to overcome glutathione-S- transferase mediated drug resistance J. Am. Chem. Soc. 127 2005 1382 1383 (Pubitemid 40204507)
25. H.T.T. Duong, V.T. Huynh, P. de Souza, and M.H. Stenze Core-cross-linked micelles synthesized by clicking bifunctional Pt(IV) anticancer drugs to isocyanates Biomacromolecules 11 2010 2290 2299
26. S. Choi, C. Filotto, M. Bisanzo, S. Delaney, D. Lagasee, J.L. Whitworth, A. Jusko, C. Li, N.A. Wood, J. Willingham, A. Schwenker, and K. Spaulding Reduction and anticancer activity of platinum(IV) complexes Inorg. Chem. 37 1998 2500 2504 (Pubitemid 128487903)
27. M.D. Hall, H.R. Mellor, R. Callaghan, and T.W. Hambley Basis for design and development of platinum(IV) anticancer complexes J. Med. Chem. 50 2007 3403 3411 (Pubitemid 47195446)
28. S. Dhar, and S.J. Lippard Mitaplatin, a potent fusion of cisplatin and the orphan drug dichloroacetate PNAS 106 2009 22199 22204
29. M.D. Hall, and T.W. Hambley Platinum(IV) antitumor compounds: their bioinorganic chemistry Coord. Chem. Rev. 232 2002 49 67
30. A.F. Westendorf, A. Bodtke, and P.J. Bednarski Studies on the photoactivation of two cytotoxic trans, trans, trans-diazidodiaminodihydroxo- Oxa(IV) complexes Dalton Trans. 40 2011 5342 5351
31. K. Lemma, A.M. Sargeson, and L.I. Elding Kinetics and mechanism for reduction of oral anticancer platinum(IV) dicarboxylate compounds by L-ascorbate ions J. Chem. Soc. Dalton Trans. 2000 1167 1172
32. A. Iakovidis, and N. Hadjiliadis Complex compounds of platinum (II) and (IV) with amino acids, peptides and their derivatives Coord. Chem. Rev. 135-136 1994 17 63 (Pubitemid 124001835)
33. A. Eastman Glutathione-mediated activation of anticancer platinum IV complexes Biochem. Pharmacol. 36 1987 4177 4188
34. 3(5′-GMP)] by NMR spectroscopy and ESI-MS Inorg. Chim. Acta 300-302 2000 783 789
35. D.G. Sar, M. Montes-Bayon, E.B. Gonzalez, and A. Sanz-Medel Speciation studies of cis-platin adducts with DNA nucleotides via elemental specific detection (P and Pt) using liquid chromatography inductively coupled plasma-mass spectrometry and structural characterization by electrospray mass spectrometry J. Anal. At. Spectrom. 21 2006 861 868 (Pubitemid 44286291)
36. M.D. Hall, S. Amjadi, M. Zhang, P.J. Beale, and T.W. Hambley The mechanism of action of platinum(IV) complexes in ovarian cancer cell lines J. Inorg. Biochem. 98 2004 1614 1624 (Pubitemid 39349187)
37. T. Skovsgaard, and N.I. Nissen Membrane transport of anthracyclines Pharmacol. Ther. 18 1982 293 311 (Pubitemid 13139553)
38. D. Wang, and S.J. Lippard Cellular processing of platinum anticancer drugs Nat. Rev. Drug Discov. 4 2005 307 320 (Pubitemid 41130944)
39. L. Zhao, M.G. Wientjes, and J.L.S. Au Evaluation of combination chemotherapy integration of nonlinear regression, curve shift, isobologram, and combination index analyses Clin. Cancer Res. 10 2004 7994 8004 (Pubitemid 39587541)
40. T.C. Chou, and P. Talalay Analysis of combined drug effects:a new look at a very old problem Trends Pharmacol. Sci. 4 1983 450 454
41. M.C. Berenbaum What is synergy? Pharmacol. Rev. 41 1989 931 941
42. I.H.L. Hamelers, R.W.H.M. Staffhorst, J. Voortman, B. de Kruijff, J. Reedijk, P.M.P. van Bergen en Henegouwen, and Anton I.P.M. de Kroon High cytotoxicity of cisplatin nanocapsules in ovarian carcinoma cells depends on uptake by caveolae-mediated endocytosis Clin. Cancer Res. 15 2009 1259 1268
43. G. Sahay, E.V. Batrakova, and A.V. Kabanov Different internalization pathways of polymeric micelles and unimers and their effects on vesicular transport Bioconjug. Chem. 19 2008 2023 2029
44. S. Zhang, J. Li, G. Lykotrafitis, G. Bao, and S. Suresh Size-dependent endocytosis of nanoparticles Adv. Mater. 21 2009 419 424
45. L. Samuel, J. Cummings, and P. Shaw Daunorubicin cardiotoxicity in childhood cancer Lancet 352 1998 1150 1153
46. S.E. Shadle, B.P. Bammel, B.J. Cusack, R.A. Knighton, S.J. Olson, P.S. Mushlin, and R.D. Olson Daunorubicin cardiotoxicity: evidence for the importance of the quinone moiety in a free-radical-independent mechanism Biochem. Pharmacol. 60 2000 1435 1444