Demonstrating the importance of polymer-conjugate conformation in solution on its therapeutic output: Diethylstilbestrol (DES)-polyacetals as prostate cancer treatment

Journal of Controlled Release

Volumn 159, Issue 2, 2012, Pages 290-301

  Giménez, Vanessa ^a   James, Craig ^b   Armiñán, Ana ^a   Schweins, Ralf ^c   Paul, Alison ^b   Vicent, María J ^a  

^a CENTRO DE INVESTIGACIÓN PRÍNCIPE FELIPE   (Spain)

^b CARDIFF UNIVERSITY   (United Kingdom)

^c INSTITUT LAUE LANGEVIN   (France)

Author keywords

pH dependent degradation; Polyacetals; Polymer therapeutics; Prostate cancer; SANS; Solution conformation

Indexed keywords

PH-DEPENDENT; POLYMER THERAPEUTICS; PROSTATE CANCERS; SANS; SOLUTION CONFORMATIONS;

ACETAL RESINS; CONFORMATIONS; DEGRADATION; DISEASES; NANOCONJUGATES; NEUTRON SCATTERING;

FUNCTIONAL POLYMERS;

DIETHYLSTILBESTROL; NANOCONJUGATE; POLYACETYLENE DERIVATIVE;

ADVANCED CANCER; ARTICLE; CANCER CELL; CANCER CHEMOTHERAPY; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; DRUG RELEASE; ELECTRON SPIN RESONANCE; HUMAN; HUMAN CELL; NEUTRON SCATTERING; PH; PRIORITY JOURNAL; PROSTATE CANCER;

ACETALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; DIETHYLSTILBESTROL; DRUG CARRIERS; DRUG DESIGN; DRUG STABILITY; ENDOCYTOSIS; HUMANS; HYDROGEN-ION CONCENTRATION; MALE; MICROSCOPY, CONFOCAL; MOLECULAR CONFORMATION; MOLECULAR WEIGHT; POLYMERS; PROSTATIC NEOPLASMS; SOLUBILITY; SOLUTIONS; STEREOISOMERISM;

EID: 84861097955     PISSN: 01683659     EISSN: 18734995     Source Type: Journal    
DOI: 10.1016/j.jconrel.2011.12.035     Document Type: Article

References (56)

1. R. Duncan The dawning era of polymer therapeutics Nat. Rev. Drug Discov. 2 5 2003 347 360 (Pubitemid 37361705)
2. R. Duncan Polymer therapeutics as nanomedicines: new perspectives Current Opin. Biotechnol. 22 4 2011 492 501
3. M.J. Vicent, H. Ringsdorf, and R. Duncan Polymer therapeutics: clinical applications and challenges for development Preface Adv. Drug Deliv. Rev. 61 13 2009 1117 1120
4. M. Barz, R. Luxenhofer, R. Zentel, and M.J. Vicent Overcoming the PEG-addiction: well-defined alternatives to PEG, from structure-property relationships to better defined therapeutics Polym. Chem. 2 2011 1900 1918
5. F. Canal, J. Sanchis, and M.J. Vicent Polymer-drug conjugates as nano-sized medicines Current Opin. Biotechnol. 22 6 2011 894 900
6. J. Hardwicke, E.L. Ferguson, R. Moseley, P. Stephens, D.W. Thomas, and R. Duncan Dextrin-rhEGF conjugates as bioresponsive nanomedicines for wound repair J. Control. Release 130 3 2008 275 283
7. D. Hreczuk-Hirst, D. Chicco, L. German, and R. Duncan Dextrins as potential carriers for drug targeting: tailored rates of dextrin degradation by introduction of pendant groups Int. J. Pharm. 230 2001 11 20
8. A. Eldar-Boock, K. Miller, J. Sanchis, R. Lupu, M.J. Vicent, and R. Satchi-Fainaro Integrin-assisted drug delivery of nano-scaled polymer therapeutics bearing paclitaxel Biomaterials 32 15 2011 3862 3874
9. V.L. Galic, T.J. Herzog, J.D. Wright, and S.N. Lewin Paclitaxel poliglumex for ovarian cancer Expert Opin. Invest. Drugs 20 6 2011 813 821
10. L. Erdmann, B. Macedo, and K.E. Uhrich Degradable poly(anhydride ester) implants: effects of localized salicylic acid release on bone Biomaterials 21 24 2000 6 10
11. J.N. Hoskins, and S.M. Grayson Cyclic polyesters: synthetic approaches and potential applications Polym. Chem. 2 2 2011 289 299
12. R. Tomlinson, J. Heller, S. Brocchini, and R. Duncan Polyacetal- doxorubicin conjugates designed for pH-dependent degradation Bioconjugate Chem. 14 6 2003 1096 1106 (Pubitemid 37449036)
13. R. Tomlinson, M. Klee, S. Garrett, J. Heller, R. Duncan, and S. Brocchini Pendent chain functionalized polyacetals that display pH-dependent degradation: a platform for the development of novel polymer therapeutics Macromolecules 35 2 2002 473 480 (Pubitemid 34097190)
14. L.W. Seymour, D.R. Ferry, D.J. Kerr, D. Rea, M. Whitlock, R. Poyner, C. Boivin, S. Hesslewood, C. 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 6 2009 1629 1636
15. J. Heller, D.W.H. Penhale, and R.F. Helwing Preparation of polyacetals by the reaction of divinyl ethers and polyols J. Polym. Sci. Part C: Polym. Lett. 18 4 1980 5 11
16. M.J. Vicent, R. Tomlinson, S. Brocchini, and R. Duncan Polyacetal-diethylstilboestrol: a polymeric drug designed for pH-triggered activation J. Drug Target. 12 8 2004 491 501 (Pubitemid 40081304)
17. F. Boccardo Hormone therapy of prostate cancer: is there a role for antiandrogen monotherapy? Crit. Rev. Oncol. Hematol. 35 2000 121 132 (Pubitemid 30599435)
18. P. Gould Prostate cancer - diethylstilbestrol and docetaxel? Lancet Oncol. 8 9 2007 767-767
19. S.B. Malkowicz The Role of Diethylstilbestrol in the treatment of Prostate Cancer Urology 58 Suppl. 2A 2001 108 113 (Pubitemid 32743424)
20. N. Mottet, J. Bellmunt, M. Bolla, S. Joniau, M. Mason, V. Matveev, H.P. Schmid, T. Van der Kwast, T. Wiegel, F. Zattoni, and A. Heidenreich EAU guidelines on prostate cancer. Part II: Treatment of advanced, relapsing, and castration-resistant prostate cancer Eur. Urol. 59 4 2011 572 583
21. C. Serrate, Y. Loriot, T. De La Motte Rouge, M. Gross-Goupil, C. Massard, B. Escudier, A. Bossi, and K. Fizazi Diethylstilbestrol (DES) retains activity and is a reasonable option in patients previously treated with docetaxel for castration-resistant prostate cancer Ann. Oncol. 20 2009 965
22. F. Cornford Evolution of docetaxel-based therapy for metastatic castrate-resistant prostate cancer Br. J. Med. Surg. Urol. 3 2009 225 229
23. R. Duncan Polymer conjugates as anticancer nanomedicines Nat. Rev. Cancer 6 9 2006 688 701 (Pubitemid 44286001)
24. F. Greco, and M.J. Vicent Combination therapy: opportunities and challenges for polymer-drug conjugates as anticancer nanomedicines Adv. Drug Deliv. Rev. 61 13 2009 1203 1213
25. G. Degen, and J.A. McLachlan Non-estrogenic metabolites of diethylstilbestrol produced by prostaglandin synthetase mediated metabolism Steroids 42 1983 253 264
26. H.D. Tang, C.J. Murphy, B. Zhang, Y.Q. Shen, E.A. Van Kirk, W.J. Murdoch, and M. Radosz Curcumin polymers as anticancer conjugates Biomaterials 31 27 2010 7139 7149
27. P. Griffiths, A.Y.F. Cheung, J.A. Davies, A. Paul, C.N. Tipples, and A.L. Winnington Probing interactions within complex colloidal systems using PGSE-NMR Magn. Reson. Chem. 40 2002 S40 S50
28. V. Arrighi, and J.S. Higgins Structural investigation of polymers by neutron scattering Plast. Rubber Compos. Process. Appl. 33 8 2004 313 329 (Pubitemid 40573392)
29. P.C. Griffiths, A. Paul, B. Apostolovic, H.A. Klok, E. de Luca, S.M. King, and R.K. Heenan Conformational consequences of cooperative binding of a coiled-coil peptide motif to poly(N-(2-hydroxypropyl) methacrylamide) HPMA copolymers J. Control. Release 153 2 2011 173 179
30. A. Paul, C. James, R.K. Heenan, and R. Schweins Drug mimic induced conformational changes in model polymer-drug conjugates characterized by small-angle neutron scattering Biomacromolecules 11 8 2010 1978 1982
31. A. Paul, M.J. Vicent, and R. Duncan Using small-angle neutron scattering to study the solution conformation of N-(2-hydroxypropyl)methacrylamide copolymer-doxorubicin conjugates Biomacromolecules 8 5 2007 1573 1579 (Pubitemid 46865130)
32. K.W. Wan, B. Malgesini, L. Verpilio, P. Ferruti, P.C. Griffiths, A. Paul, A.C. Hann, and R. Duncan Poly(amidoamine) salt form: effect on pH-dependent membrane activity and polymer conformation in solution Biomacromolecules 5 3 2004 1102 1109 (Pubitemid 38702288)
33. J. Davies, and P. Griffiths A phenomological approach to separating the effects of obstruction and binding to the diffusion of small molecules in polymer solutions Macromolecules 36 2003 950 952
34. A. Paul, P. Griffiths, E. Pettersson, P. Stilbs, B.L. Bales, R. Zana, and R.K. Heenan Nuclear magnetic resonance and small-angle neutron scattering studies of anionic surfactants with macrocounterions: tetramethylammonium dodecyl sulfate J. Phys. Chem. B 109 33 2005 15775 15779 (Pubitemid 41321493)
35. D. Sgouras, and R. Duncan Methods for the evaluation of biocompatibility of soluble synthetic polymers which have the potential for bio-medical use.1. Use of the tetrazolium-based colorimetric assay (MTT) a a preliminary screen for evaluation of in vitro cytotoxicity J. Mater. Sci.-Mater. Med. 1 2 1990 61 68
36. R. Duncan Designing polymer conjugates as lysosomotropic nanomedicines Biochem. Soc. Trans. 35 2007 56 60
37. W.S. Cheow, and K. Hadinoto Enhancing encapsulation efficiency of highly water-soluble antibiotic in poly(lactic-co-glycolic acid) nanoparticles: modifications of standard nanoparticle preparation methods Colloids Surf. A Physicochem. Eng. Asp. 370 1-3 2011 79 86
38. F. Ren, R.D. Chen, Y. Wang, Y.B. Sun, Y.D. Jiang, and G.F. Li Paclitaxel-loaded poly(n-butylcyanoacrylate) nanoparticle delivery system to overcome multidrug resistance in ovarian cancer Pharm. Res. 28 4 2011 897 906
39. Z.-W. Laia, N.C. Fiorea, P.J. Hahnb, T.A. Gasiewiczc, and A.E. Silverstonea Differential effects of diethylstilbestrol and 2,3,7,8- tetrachlorodibenzo-p-dioxin on thymocyte differentiation, proliferation, and apoptosis in bcl-2 transgenic mouse fetal thymus organ culture Toxicol. Appl. Pharmacol. 168 1 2000 15 23
40. B. Hartley-Asp, J. Deinum, and M. Wallin Diethylstilbestrol induces metaphase arrest and inhibits microtubule assembly Mutat. Res. Lett. 143 4 1985 231 235 (Pubitemid 15012599)
41. M. Metzler, and E. Pfeiffer Effects of estrogens on microtubule polymerization in vitro: correlation with estrogenicity Environ. Health Perspect. 103 1995 21 23
42. R. Geier, S. Adler, G. Rashid, and A. Klein The synthetic estrogen diethylstilbestrol (DES) inhibits the telomerase activity and gene expression of prostate cancer cells Prostate 70 12 2010 1307 1312
43. D.C. Sharp, and J.M. Parry Diethylstilbestrol - the binding and effects of DES upon the polymerization and depolymerization of purified microtubule protein in vitro Carcinogenesis 6 6 1985 865 871 (Pubitemid 15064145)
44. J.J. Kalach, M.O. Joly-Pharaboz, J. Chantepie, B. Nicolas, F. Descotes, C. Mauduit, M. Benahmed, and J. André Divergent biological effects of estradiol and diethylstilbestrol in the prostate cancer cell line MOP J. Steroid Biochem. Mol. Biol. 96 2005 119 128
45. R.N. Day, and F. Schaufele Imaging molecular interactions in living cells Mol. Endocrinol. 19 2005 1675 1685
46. M.M. Frigault, J. Lacoste, J.L. Swift, and C.M. Brown Live-cell microscopy: tips and tools J. Cell Sci. 122 2009 753 763
47. D.J. Stephens, and V.J. Allan Light microscopy techniques for live cell imaging Science 300 2003 82 86 (Pubitemid 36423031)
48. P. Watson Live cell imaging for target and drug discovery Drug News Perspect. 22 2009 69 78
49. M. Barz, R. Luxenhofer, R. Zentel, and A.V. Kabanov The uptake of N-(2-hydroxypropyl)-methacrylamide based homo, random and block copolymers by human multi-drug resistant breast adenocarcinoma cells Biomaterials 30 29 2009 5682 5690
50. M.J. Vicent, F. Greco, R.I. Nicholson, A. Paul, P.C. Griffiths, and R. Duncan Polymer therapeutics designed for a combination therapy of hormone-dependent cancer Angew. Chem. Int. Ed. 44 26 2005 4061 4066 (Pubitemid 40886448)
51. E. Castro, P. Taboada, S. Barbosa, and V. Mosquera Size control of styrene oxide-ethylene oxide diblock copolymer aggregates with classical surfactants: DLS, TEM, and ITC study Biomacromolecules 6 3 2005 1438 1447 (Pubitemid 40775061)
52. B.J. Crawford, and R.D. Burke TEM and SEM methods Methods Cell Biol. 74 2004 411 441
53. B. Yue, C.Y. Huang, M.P. Nieh, C.J. Glinka, and J. Katsaras Highly stable phospholipid unilamellar vesicles from spontaneous vesiculation: a DLS and SANS study J. Phys. Chem. B 109 1 2005 609 616 (Pubitemid 40121007)
54. A.V. Kabanov, and V.Y. Alakhov Pluronic block copolymers in drug delivery: from micellar nanocontainers to biological response modifiers Crit. Rev. Ther. Drug Carrier Syst. 19 1 2002 1 72 (Pubitemid 34521248)
55. M. Saad, O.B. Garbuzenko, E. Ber, P. Chandna, J.J. Khandare, V.P. Pozharov, and T. Minko Receptor targeted polymers, dendrimers, liposomes: which nanocarrier is the most efficient for tumor-specific treatment and imaging? J. Control. Release 130 2 2008 107 114
56. S.M. Grayson, and W.T. Godbey The role of macromolecular architecture in passively targeted polymeric carriers for drug and gene delivery J. Drug Target. 16 5 2008 329 356 (Pubitemid 351940516)