Cyclodextrin/paclitaxel complex in biodegradable capsules for breast cancer treatment

Chemistry of Materials

Volumn 25, Issue 19, 2013, Pages 3867-3873

  Jing, Jing ^a,b   Szarpak Jankowska, Anna ^a,b   Guillot, Raphael ^c   Pignot Paintrand, Isabelle ^c   Picart, Catherine ^c   Auzély Velty, Rachel ^a,b  

^a CENTRE DE RECHERCHES SUR LES MACROMOLÉCULES VÉGÉTALES CERMAV CNRS   (France)

^b UNIV GRENOBLE ALPES   (France)

^c LABORATOIRE DES MATÉRIAUX ET DU GÉNIE PHYSIQUE   (France)

Author keywords

cyclodextrin; drug release; host guest complexation; hyaluronic acid; layer by layer capsules

Indexed keywords

BIODEGRADABLE CAPSULES; BREAST CANCER TREATMENT; DRUG RELEASE; HOST GUEST INTERACTIONS; HOST-GUEST COMPLEXATIONS; LAYER BY LAYER DEPOSITION; LAYER-BY-LAYERS; PHYSIOLOGICAL CONDITION;

AMINO ACIDS; BIOCOMPATIBILITY; CELLS; CYCLODEXTRINS; DRUG INTERACTIONS; HYALURONIC ACID; MOLECULES; TRANSPORT PROPERTIES;

DEPOSITION;

EID: 84885401608     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/cm4019925     Document Type: Article

References (38)

1. Agarwal, A.; Lvov, Y.; Sawant, R.; Torchilin, V. Stable nanocolloids of poorly soluble drugs with high drug content prepared using the combination of sonication and layer-by-layer technology J. Controlled Release 2008, 128, 255-260
2. Smith, R. C.; Riollano, M.; Leung, A.; Hammond, P. T. Layer-by-Layer Platform Technology for Small-Molecule Delivery Angew. Chem., Int. Ed. 2009, 48, 8974-8977
3. Wang, Y.; Yan, Y.; Cui, J.; Hosta-Rigau, L.; Heath, J. K.; Nice, E. C.; Caruso, F. Encapsulation of Water-Insoluble Drugs in Polymer Capsules Prepared Using Mesoporous Silica Templates for Intracellular Drug Delivery Adv. Mater. 2010, 22, 4293-4297
4. Duncan, R. Development of HPMA copolymer-anticancer conjugates: Clinical experience and lessons learnt Adv. Drug Delivery Rev. 2009, 61, 1131-1148
5. Farokhzad, O. C.; Langer, R. Impact of Nanotechnology on Drug Delivery ACS Nano 2009, 3, 16-20
6. Loomis, K.; McNeeley, K.; Bellamkonda, R. V. Nanoparticles with targeting, triggered release, and imaging functionality for cancer applications Soft Matter 2011, 7, 839-856
7. Uekama, K.; Hirayama, F.; Irie, T. Cyclodextrin Drug Carrier Systems Chem. Rev. 1998, 98, 2045-2076
8. Devi, N. K. D.; Rani, A. P.; Javed, M. M.; Kumar, K. S.; Kaushik, J.; Sowjanya, V. Cyclodextrins in pharmacy- an overview Pharmacophore 2010, 1, 155-165
9. Hayashi, K.; Ono, K.; Suzuki, H.; Sawada, M.; Moriya, M.; Sakamoto, W.; Yogo, T. High-Frequency, Magnetic-Field-Responsive Drug Release from Magnetic Nanoparticle/Organic Hybrid Based on Hyperthermic Effect ACS Appl. Mater. Interfaces 2010, 2, 1903-1911
10. Yan, Y.; Ochs Christopher, J.; Such Georgina, K.; Heath Joan, K.; Nice Edouard, C.; Caruso, F. Bypassing multidrug resistance in cancer cells with biodegradable polymer capsules Adv. Mater. 2010, 22, 5398-403
11. Cui, D.; Jing, J.; Boudou, T.; Pignot-Paintrand, I.; De Koker, S.; De Geest, B. G.; Picart, C.; Auzély-Velty, R. Hydrophobic Shell Loading of Biopolyelectrolyte Capsules Adv. Mater. 2011, 23, H200-H204
12. Luo, G.-F.; Xu, X.-D.; Zhang, J.; Yang, J.; Gong, Y.-H.; Lei, Q.; Jia, H.-Z.; Li, C.; Zhuo, R.-X.; Zhang, X.-Z. Encapsulation of an Adamantane-Doxorubicin Prodrug in pH-Responsive Polysaccharide Capsules for Controlled Release ACS Appl. Mater. Interfaces 2012, 4, 5317-5324
13. Xiao, W.; Chen, W.-H.; Zhang, J.; Li, C.; Zhuo, R.-X.; Zhang, X.-Z. Design of a Photoswitchable Hollow Microcapsular Drug Delivery System by Using a Supramolecular Drug-Loading Approach J. Phys. Chem. B 2011, 115, 13796-13802
14. Wang, Z.; Feng, Z.; Gao, C. Stepwise Assembly of the Same Polyelectrolytes Using Host-Guest Interaction To Obtain Microcapsules with Multiresponsive Properties Chem. Mater. 2008, 20, 4194-4199
15. Mergy, J.; Fournier, A.; Hachet, E.; Auzély-Velty, R. Modification of polysaccharides via thiol-ene chemistry: A versatile route to functional biomaterials J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 4019-4028
16. Szarpak, A.; Cui, D.; Dubreuil, F.; De Geest, B. G.; De Cock, L. J.; Picart, C.; Auzély-Velty, R. Designing Hyaluronic Acid-Based Layer-by-Layer Capsules as a Carrier for Intracellular Drug Delivery Biomacromolecules 2010, 11, 713-720
17. Volodkin, D. V.; Larionova, N. I.; Sukhorukov, G. B. Protein Encapsulation via Porous CaCO3Microparticles Templating Biomacromolecules 2004, 5, 1962-1972
18. Richert, L.; Lavalle, P.; Payan, E.; Shu, X. Z.; Prestwich, G. D.; Stoltz, J.-F.; Schaaf, P.; Voegel, J.-C.; Picart, C. Layer by Layer Buildup of Polysaccharide Films: Physical Chemistry and Cellular Adhesion Aspects Langmuir 2004, 20, 448-458
19. Schneider, A.; Vodouhe, C.; Richert, L.; Francius, G.; Le Guen, E.; Schaaf, P.; Voegel, J.-C.; Frisch, B.; Picart, C. Multifunctional polyelectrolyte multilayer films: combining mechanical resistance, biodegradability, and bioactivity Biomacromolecules 2007, 8, 139-145
20. Auzenne, E.; Ghosh, S. C.; Khodadadian, M.; Rivera, B.; Farquhar, D.; Price, R. E.; Ravoori, M.; Kundra, V.; Freedman, R. S.; Klostergaard, J. Hyaluronic acid-paclitaxel: antitumor efficacy against CD44(+) human ovarian carcinoma xenografts Neoplasia 2007, 9, 479-486
21. Draffin, J. E.; McFarlane, S.; Hill, A.; Johnston, P. G.; Waugh, D. J. J. CD44 Potentiates the Adherence of Metastatic Prostate and Breast Cancer Cells to Bone Marrow Endothelial Cells Cancer Res. 2004, 64, 5702-5711
22. Luo, Y.; Prestwich, G. D. Synthesis and Selective Cytotoxicity of a Hyaluronic Acid-Antitumor Bioconjugate Bioconjugate Chem. 1999, 10, 755-763
23. Qhattal, H. S. S.; Liu, X. Characterization of CD44-Mediated Cancer Cell Uptake and Intracellular Distribution of Hyaluronan-Grafted Liposomes Mol. Pharmaceutics 2011, 8, 1233-1246
24. Luo, Y.; Ziebell, M. R.; Prestwich, G. D. A Hyaluronic Acid-Taxol Antitumor Bioconjugate Targeted to Cancer Cells Biomacromolecules 2000, 1, 208-218
25. Surace, C.; Arpicco, S.; Dufay-Wojcicki, A.; Marsaud, V.; Bouclier, C.; Clay, D.; Cattel, L.; Renoir, J.-M.; Fattal, E. Lipoplexes Targeting the CD44 Hyaluronic Acid Receptor for Efficient Transfection of Breast Cancer Cells Mol. Pharmaceutics 2009, 6, 1062-1073
26. Hyung, W.; Ko, H.; Park, J.; Lim, E.; Park, S. B.; Park, Y.-J.; Yoon, H. G.; Suh, J. S.; Haam, S.; Huh, Y.-M. Novel hyaluronic acid (HA) coated drug carriers (HCDCs) for human breast cancer treatment Biotechnol. Bioeng. 2007, 99, 442-454
27. Hamada, H.; Ishihara, K.; Masuoka, N.; Mikuni, K.; Nakajima, N. Enhancement of water-solubility and bioactivity of paclitaxel using modified cyclodextrins J. Biosci. Bioeng. 2006, 102, 369-371
28. Sharma, U. S.; Balasubramanian, S. V.; Straubinger, R. M. Pharmaceutical and Physical Properties of Paclitaxel (Taxol) Complexes with Cyclodextrins J. Pharm. Sci. 1995, 84, 1223-30
29. Gelderblom, H.; Verweij, J.; Nooter, K.; Sparreboom, A. the drawbacks and advantages of vehicle selection for drug formulation Eur. J. Cancer 2001, 37, 1590-1598
30. Auzély-Velty, R.; Djedaïni-Pilard, F.; Desert, S.; Perly, B.; Zemb, T. Micellization of Hydrophobically Modified Cyclodextrins. 1. Micellar Structure Langmuir 2000, 16, 3727-3734
31. Charlot, A.; Heyraud, A.; Guenot, P.; Rinaudo, M.; Auzély-Velty, R. Controlled Synthesis and Inclusion Ability of a Hyaluronic Acid Derivative Bearing β-Cyclodextrin Molecules Biomacromolecules 2006, 7, 907-913
32. Picart, C.; Mutterer, J.; Richert, L.; Luo, Y.; Prestwich, G. D.; Schaaf, P.; Voegel, J. C.; Lavalle, P. Molecular basis for the explanation of the exponential growth of polyelectrolyte multilayers Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 12531-12535
33. Frasci, G.; Comella, P.; D'Aiuto, G.; Budillon, A.; Barbarulo, D.; Thomas, R.; Capasso, I.; Casaretti, R.; Daponte, A.; Caponigro, F.; Gravina, A.; Maiorino, L.; Carateni, G.; Gentile, A.; Comella, G. Weekly paclitaxel-cisplatin administration with G-CSF support in advanced breast cancer. A phase II study Breast Cancer Res. Treat. 1998, 49, 13-26
34. Boudou, T.; Kharkar, P.; Jing, J.; Guillot, R.; Pignot-Paintrand, I.; Auzély-Velty, R.; Picart, C. Polyelectrolyte multilayer nanoshells with hydrophobic nanodomains for delivery of Paclitaxel J. Controlled Release 2012, 159, 403-412
35. Menzel, E. J.; Farr, C. Hyaluronidase and its substrate hyaluronan: biochemistry, biological activities and therapeutic uses Cancer Lett. 1998, 131, 3-11
36. Tan, J.-X.; Wang, X.-Y.; Li, H.-Y.; Su, X.-L.; Wang, L.; Ran, L.; Zheng, K.; Ren, G.-S. HYAL1 overexpression is correlated with the malignant behavior of human breast cancer Int. J. Cancer 2010, 128, 1303-1315
37. Li, Y.; Li, L.; Brown, T. J.; Heldin, P. Silencing of hyaluronan synthase 2 suppresses the malignant phenotype of invasive breast cancer cells Int. J. Cancer 2007, 120, 2557-2567
38. Yeung, T. K.; Germond, C.; Chen, X.; Wang, Z. The Mode of Action of Taxol: Apoptosis at Low Concentration and Necrosis at High Concentration Biochem. Biophys. Res. Commun. 1999, 263, 398-404