In situ precipitation of amorphous calcium phosphate and ciprofloxacin crystals during the formation of chitosan hydrogels and its application for drug delivery purposes

Langmuir

Volumn 28, Issue 45, 2012, Pages 15937-15946

  Nardecchia, Stefania ^a   Gutiérrez, María C ^a   Serrano, M Concepción ^a   Dentini, Mariella ^b   Barbetta, Andrea ^b   Ferrer, M Luisa ^a   Del Monte, Francisco ^a  

^a INSTITUTO DE CIENCIA DE MATERIALES DE MADRID   (Spain)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMORPHOUS CALCIUM PHOSPHATE; BIOCOMPATIBLE POLYMER; BONE TISSUE ENGINEERING; CHITOSAN HYDROGEL; CIPROFLOXACIN; COIMMOBILIZATION; DIVERSE SOLIDS; ENHANCED PROPERTIES; IN-SITU PRECIPITATION; INDIVIDUAL COMPONENTS; OSTEOGENESIS; PHASE-SEPARATED STRUCTURES; SELF ASSEMBLY PROCESS;

ANTIBIOTICS; BIOLOGICAL MATERIALS; BIOMATERIALS; CALCIUM PHOSPHATE; CHITOSAN; DRUG DELIVERY; MORPHOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SEPARATION;

SCAFFOLDS (BIOLOGY);

CALCIUM PHOSPHATE; CHITOSAN; CIPROFLOXACIN;

ARTICLE; CHEMISTRY; CRYSTALLIZATION; DRUG DELIVERY SYSTEM; FLOW KINETICS; HYDROGEL; PARTICLE SIZE; SURFACE PROPERTY; SYNTHESIS;

CALCIUM PHOSPHATES; CHITOSAN; CIPROFLOXACIN; CRYSTALLIZATION; DRUG DELIVERY SYSTEMS; HYDROGELS; PARTICLE SIZE; RHEOLOGY; SURFACE PROPERTIES;

EID: 84869045355     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la3033435     Document Type: Article

References (60)

1. Langer, R.; Tirrell, D. A. Designing materials for biology and medicine Nature 2004, 428, 487-492
2. Panyam, J.; Labhasetwar, V. Biodegradable nanoparticles for drug and gene delivery to cells and tissue Adv. Drug Delivery Rev. 2003, 55, 329-347
3. Liu, Z.; Sun, X.; Nakayama-Ratchford, N.; Dai, H. Supramolecular chemistry on water-soluble carbon nanotubes for drug loading and delivery ACS Nano 2007, 1, 50-56
4. des Rieux, A.; Fievez, V.; Garinot, M.; Schneider, Y.-J.; Préat, V. Nanoparticles as potential oral delivery systems of proteins and vaccines: A mechanistic approach J. Controlled Release 2006, 116, 1-27
5. Anton, N.; Benoit, J.-P.; Saulnier, P. Design and production of nanoparticles formulated from nano-emulsion templates-A review J. Controlled Release 2008, 128, 185-199
6. Cohen, S.; Coué, G.; Beno, D.; Korenstein, R.; Engbersen, J. F. J. Bioreducible poly(amidoamine)s as carriers for intracellular protein delivery to intestinal cells Biomaterials 2012, 33, 614-623
7. Abarrategi, A.; Gutiérrez, M. C.; Moreno-Vicente, C.; Hortigüela, M. J.; Ramos, V.; López-Lacomba, J. L.; Ferrer, M. L.; del Monte, F. Multiwall carbon nanotube scaffolds for tissue engineering purposes Biomaterials 2008, 29, 94-102
8. Cölfen, H.; Mann, S. Higher-order organization by mesoscale self-assembly and transformation of hybrid nanostructures Angew. Chem., Int. Ed. 2003, 42, 2350-2365
9. Morissette, S. L.; Soukasene, S.; Levinson, D.; Cima, M. J.; Almarsson, Ö. Elucidation of crystal form diversity of the HIV protease inhibitor ritonavir by high-throughput crystallization Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 2180-2184
10. Chou, Y.-F.; Chiou, W.-A.; Xu, Y.; Dunn, J. C. Y.; Wu, B. M. The effect of pH on the structural evolution of accelerated biomimetic apatite Biomaterials 2004, 25, 5323-5331
11. Wang, L.; Nancollas, G. H. Calcium orthophosphates: Crystallization and dissolution Chem. Rev. 2008, 108, 4628-4669
12. Skrtic, D.; Antonucci, J. M.; Eanes, E. D.; Eichmiller, F. C.; Schumacher, G. E. Physicochemical evaluation of bioactive polymeric composites based on hybrid amorphous calcium phosphates J. Biomed. Mater. Res. 2000, 53, 381-391
13. Lowenstam, H. A.; Weiner, S. On biomineralization; Oxford University Press: New York, 1989.
14. Baeuerlein, E. Biomineralization. From biology to biotechnology and medical application; Wiley-VCH: Weinheim, 2000.
15. Ozin, G. A. Morphogenesis of biomineral and morphosynthesis of biomimetic forms Acc. Chem. Res. 1997, 30, 17-27
16. Mann, S. The Chemistry of Form Angew. Chem., Int. Ed. 2000, 39, 3392-3406
17. Zayats, M.; Baron, R.; Popov, I.; Willner, I. Biocatalytic growth of Au nanoparticles: From mechanistic aspects to biosensors design Nano Lett. 2005, 5, 21-25
18. Shankar, S. S.; Rai, A.; Ankamwar, B.; Singh, A.; Ahmad, A.; Sastry, M. Biological synthesis of triangular gold nanoprisms Nat. Mater. 2004, 3, 482-488
19. Dickerson, M. B.; Sandhage, K. H.; Naik, R. R. Protein- and peptide-directed syntheses of inorganic materials Chem. Rev. 2008, 108, 4935-4978
20. Shan, N.; Zaworotko, M. J. The role of cocrystals in pharmaceutical science Drug Discovery Today 2008, 13, 440-446
21. Shimizu, K.; Cha, J.; Stucky, G. D.; Morse, D. E. Silicatein ∞: Cathepsin L-like protein in sponge biosilica Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 6234-6238
22. Sumper, M.; Brunner, E. Learning from diatoms: Nature's tools for the production of nanostructured silica Adv. Funct. Mater. 2006, 16, 17-26
23. Cha, J. N.; Shimizu, K.; Zhou, Y.; Christiansen, S. C.; Chmelka, B. F.; Stucky, G. D.; Morse, D. E. Silicatein filaments and subunits from a marine sponge direct the polymerization of silica and silicones in vitro Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 361-365
24. Gutiérrez, M. C.; Ferrer, M. L.; del Monte, F. Ice templated materials: sophisticated structures exhibiting enhanced functionalities obtained after unidirectional freezing and ice segregation induced self-assembly Chem. Mater. 2008, 20, 634-648
25. Nardecchia, S.; Serrano, M. C.; Gutiérrez, M. C.; Portolés, M. T.; Ferrer, M. L.; del Monte, F. Osteoconductive performance of carbon nanotube scaffolds homogeneously mineralized by flow-through electrodeposition. Adv. Funct. Mater. 2012, DOI: 10.1002/adfm.201200684.
26. Gutiérrez, M. C.; Jobbágy, M.; Ferrer, M. L.; del Monte, F. Enzymatic assisted synthesis of amorphous calcium phosphate/chitosan nanocomposites and its processing into hierarchical structures Chem. Mater. 2008, 20, 11-13
27. Aranaz, I.; Gutiérrez, M. C.; Yuste, L.; Rojo, F.; Ferrer, M. L.; del Monte, F. Controlled formation of the anhydrous polymorph of ciprofloxacin crystals embedded within chitosan scaffolds: study of the kinetic release dependence on crystal size J. Mater. Chem. 2009, 19, 1576-1582
28. Gutiérrez, M. C.; García-Carvajal; Jobbágy, M.; Rubio, F.; Ferrer, M. L.; del Monte, F. PVA scaffolds with tailored morphologies for drug delivery and controlled release Adv. Funct. Mater. 2007, 17, 3505-3513
29. Dash, M.; Chiellini, F.; Ottenbrite, R. M.; Chiellini, E. Chitosan-A versatile semi-synthetic polymer in biomedical applications Prog. Polym. Sci. 2011, 36, 981-1014
30. Tadic, D.; Peters, F.; Epple, M. Continuous synthesis of amorphous carbonated apatites Biomaterials 2002, 23, 2553-2559
31. Boskey, A. L.; Posner, A. S. Conversion of amorphous calcium phosphate to microcrystalline hydroxyapatite. A pH-dependent, solution-mediated, solid-solid conversion J. Phys. Chem. 1973, 77, 2313-2317
32. Pan, H.; Liu, X. Y.; Tang, R.; Xu, H. Y. Mystery of the transformation from amorphous calcium phosphate to hydroxyapatite Chem. Commun. 2010, 46, 7415-7417
33. Posner, A. S.; Betts, F. Synthetic amorphous calcium phosphate and its relation to bone mineral structure Acc. Chem. Res. 1975, 8, 273-281
34. Hortigüela, M. J.; Gutiérrez, M. C.; Aranaz, I.; Jobbágy, M.; Abarrategi, A.; Moreno-Vicente, C.; Civantos, A.; Ramos, V.; López-Lacomba, J. L.; Ferrer, M. L.; del Monte, F. Urea assisted hydroxyapatite mineralization on MWCNT/CHI Scaffolds J. Mater. Chem. 2008, 18, 5933-5940
35. Yesinowski, J. P.; Eckert, H. Hydrogen environments in calcium phosphates: proton MAS NMR at high spinning speeds J. Am. Chem. Soc. 1987, 109, 6274-6282
36. Vyalikh, A.; Simon, P.; Kollmann, T.; Kniep, R.; Scheler, U. Local environment in biomimetic hydroxyapatite-gelatin nanocomposites as probed by NMR spectroscopy J. Phys. Chem. C 2011, 115, 1513-1519
37. Tropp, J.; Blumenthal, N. C.; Waugh, J. S. Phosphorus NMR study of solid amorphous calcium phosphate J. Am. Chem. Soc. 1983, 105, 22-26
38. Aue, W. P.; Roufosse, A. H.; Glimcher, M. J.; Griffin, R. G. Solid state 31P-NMR studies of synthetic solid phases of calcium phosphate: Potential models of bond mineral Biochemistry 1984, 23, 6110-6114
39. Jäger, C.; Welzel, T.; Meyer-Zaika, W.; Epple, M. A solid-state NMR investigation of the structure of nanocrystalline hydroxyapatite Magn. Reson. Chem. 2006, 44, 573-580
40. Bradley, J. V.; Bridgland, L. N.; Colyer, D. E.; Duer, M. J.; Friščić, T.; Gallagher, J. R.; Reid, D G.; Skepper, J. N.; Trasler, C. M. NMR of biopolymer-apatite composites: Developing a model of the molecular structure of the mineral-matrix interface in calcium phosphate biomaterials Chem. Mater. 2010, 22, 6109-6116
41. Nassif, N.; Martineau, F.; Syzgantseva, O.; Gobeaux, F.; Willinger, M.; Coradin, T.; Cassaignon, S.; Azaïs, T.; Giraud-Guille, M. M. In vivo inspired conditions to synthesize biomimetic hydroxyapatite Chem. Mater. 2010, 22, 3653-3663
42. Li, J.; Chen, Y.; Yin, Y.; Yao, F.; Yao, K. Modulation of nano-hydroxyapatite size via formation on chitosan-gelatin network film in situ Biomaterials 2007, 28, 781-790
43. Dorozhkin, S. V.; Epple, M. Biological and medical significance of calcium phosphates Angew. Chem., Int. Ed. 2002, 41, 3130-3146
44. Moura, M. J.; Figueiredo, M. M.; Gil, M. H. Rheological study of genipin cross-linked chitosan hydrogels Biomacromolecules 2007, 8, 3823-3829
45. Zhang, H.; Hussain, I.; Brust, M.; Butler, M. F.; Rannard, S. P.; Cooper, A. I. Aligned two- and three-dimensional structures by directional freezing of polymers and nanoparticles Nat. Mater. 2005, 4, 787-793
46. Shi, Q.; Liang, H.; Feng, D.; Wang, J.; Stucky, G. D. Porous carbon and carbon/metal oxide microfibers with well-controlled pore structure and interface J. Am. Chem. Soc. 2008, 130, 5034-5035
47. Deville, S.; Saiz, E.; Nalla, R. K.; Tomsia, A. P. Freezing as a path to build complex composites Science 2006, 311, 515-518
48. Galaev, I. Y.; Mattiasson, B. "Smart" polymers and what they could do in biotechnology and medicine Trends Biotechnol. 1999, 17, 335-340
49. Bandi, S.; Schiraldi, D. A. Glass transition behavior of clay aerogel/poly(vinyl alcohol) composites Macromolecules 2006, 39, 6537-6545
50. 2 cryogel fibers through unidirectional freezing of hydrogel followed by freeze-drying Chem. Mater. 2004, 16, 4987-4991
51. Gutiérrez, M. C.; Hortigüela, M. J.; Jiménez, R.; Amarilla, J. M.; Ferrer, M. L.; del Monte, F. Macroporous 3D architectures of self-assembled MWCNTs surface decorated with Pt nanoparticles as anodes for a direct methanol fuel cell J. Phys. Chem. C 2007, 111, 5557-5560
52. Hortigüela, M. J.; Aranaz, I.; Gutiérrez, M. C.; Ferrer, M. L.; del Monte, F. Chitosan gelation induced by the in situ formation of gold nanoparticles and its processing into macroporous scaffolds Biomacromolecules 2011, 12, 179-186
53. Kirsebom, H.; Mattiasson, B. Cryostructuration as a tool for preparing highly porous polymer materials Polym. Chem. 2011, 2, 1059-1062
54. Shi, Q.; An, Z.; Tsung, C.-K.; Liang, H.; Zheng, N.; Hawker, C. J.; Stucky, G. D. Ice-templating of silica/poly(N-isopropylacrylamide) core/shell microgel fibers through "brick-and-mortar" assembly Adv. Mater. 2007, 19, 4539-4543
55. Gutiérrez, M. C.; García-Carvajal, Z. Y.; Jobággy, M.; Catalina, F.; Abrusci, C.; Yuste, L.; Rojo, F.; Ferrer, M. L.; del Monte, F. Hydrogel scaffolds with immobilized bacteria for 3D cultures Chem. Mater. 2007, 19, 1968-1973
56. Gutiérrez, M. C.; García-Carvajal, Z. Y.; Hortigüela, M. J.; Yuste, L.; Rojo, F.; Ferrer, M. L.; del Monte, F. Biocompatibility of MWCNT Scaffolds for immobilization and proliferation of E. coli J. Mater. Chem. 2007, 17, 2992-2995
57. Ferrer, M. L.; Esquembre, R.; Ortega, I.; Mateo, C. R.; del Monte, F. Freezing of binary colloidal systems for the formation of hierarchy assemblies Chem. Mater. 2006, 18, 554-559
58. Liao, J.-D.; Lin, S.-P.; Wu, Y.-T. Dual Properties of the deacetylated sites in chitosan for molecular immobilization and biofunctional effects Biomacromolecules 2005, 6, 392-399
59. Zemljič, L. F.; Peršin, Z.; Stenius, P. Improvement of chitosan adsorption onto cellulosic fabrics by plasma treatment Biomacromolecules 2009, 10, 1181-1187
60. Li, X.; Zhi, F.; Hu, F. Investigation of excipient and processing on solid phase transformation and dissolution of ciprofloxacin Int. J. Pharm. 2007, 328, 177-182