Inkjet printing of layer-by-layer assembled poly(lactide) stereocomplex with encapsulated proteins

Langmuir

Volumn 30, Issue 6, 2014, Pages 1669-1676

  Akagi, Takami ^a   Fujiwara, Tomoko ^b   Akashi, Mitsuru ^a  

^a OSAKA UNIVERSITY   (Japan)

^b University of Memphis   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG CARRIER; NANOPARTICLE; OLIGOPEPTIDE; OVALBUMIN; POLYESTER; POLYLACTIDE;

ARTICLE; CHEMISTRY; DELAYED RELEASE FORMULATION; DRUG FORMULATION; KINETICS; METHODOLOGY; MICROTECHNOLOGY; PRINTING;

DELAYED-ACTION PREPARATIONS; DRUG CARRIERS; DRUG COMPOUNDING; KINETICS; MICROTECHNOLOGY; NANOPARTICLES; OLIGOPEPTIDES; OVALBUMIN; POLYESTERS; PRINTING;

EID: 84894230197     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la404162h     Document Type: Article

References (58)

1. Calvert, P. Inkjet printing for materials and devices Chem. Mater. 2001, 13, 3299-3305 (Pubitemid 32999277)
2. deGans, B.-J.; Duineveld, P. C.; Schubert, U. S. Inkjet printing of polymers: State of the art and future developments Adv. Mater. 2004, 22, 203-213
3. Boland, T.; Xu, T.; Damon, B.; Cui, X. Application of inkjet printing to tissue engineering Biotechnol. J. 2006, 1, 910-917
4. Sumerel, J.; Lewis, J.; Doraiswamy, A.; Deravi, L.; Sewell, S.; Gerdon, A.; Wright, D.; Narayan, R. Piezoelectric ink jet processing of materials for medical and biological applications Biotechnol. J. 2006, 1, 976-987
5. Saunders, R. E.; Gough, J. E.; Derby, B. Delivery of human fibroblast cells by piezoelectric drop-on-demand inkjet printing Biomaterials 2008, 29, 193-203 (Pubitemid 350016297)
6. Tekin, E.; Smith, P. J.; Schubert, U. S. Inkjet printing as a deposition and patterning tool for polymers and inorganic particles Soft Matter 2008, 4, 703-713 (Pubitemid 351434075)
7. Delaney, J.; Smith, P.; Schubert, U. Inkjet printing of proteins Soft Matter 2009, 5, 4866-4877
8. Singh, M.; Haverinen, H. M.; Dhagat, P.; Jabbour, G. E. Inkjet printing-process and its applications Adv. Mater. 2010, 22, 673-685
9. Zheng, Q.; Lu, J.; Chen, H.; Huang, L.; Cai, J.; Xu, Z. Application of inkjet printing technique for biological material delivery and antimicrobial assays Anal. Biochem. 2011, 410, 171-176
10. Minemawari, H.; Yamada, T.; Matsui, H.; Tsutsumi, J.; Haas, S.; Chiba, R.; Kumai, R.; Hasegawa, T. Inkjet printing of single-crystal films Nature 2011, 475, 364-367
11. Andres, C. M.; Kotov, N. A. Inkjet deposition of layer-by-layer assembled films J. Am. Chem. Soc. 2010, 132, 14496-14502
12. Suntivich, R.; Shchepelina, O.; Choi, I.; Tsukruk, V. V. Inkjet-assisted layer-by-layer printing of encapsulated arrays ACS Appl. Mater. Interfaces 2012, 4, 3102-3110
13. Zhang, H.; Xie, A.; Shen, Y.; Qiu, L.; Tian, X. Layer-by-layer inkjet printing of fabricating reduced graphene-polyoxometalate composite film for chemical sensors Phys. Chem. Chem. Phys. 2012, 14, 12757-12763
14. Decher, G. Fuzzy nanoassemblies: toward layered polymeric multicomposites Science 1997, 277, 1232-1237 (Pubitemid 27449063)
15. Becker, A. L.; Johnston, A. P. R.; Caruso, F. Layer-by-layer-assembled capsules and films for therapeutic delivery Small 2010, 6, 1836-1852
16. Panyam, J.; Labhasetwar, V. Biodegradable nanoparticles for drug and gene delivery to cells and tissue Adv. Drug Delivery Rev. 2003, 55, 329-347 (Pubitemid 36297053)
17. Mundargi, R. C.; Babu, V. R.; Rangaswamy, V.; Patel, P.; Aminabhavi, T. M. Nano/micro technologies for delivering macromolecular therapeutics using poly(D,L-lactide-co-glycolide) and its derivatives J. Controlled Release 2008, 125, 193-209
18. Kumari, A.; Yadav, S. K.; Yadav, S. C. Biodegradable polymeric nanoparticles based drug delivery systems Colloids Surf., B 2010, 75, 1-18
19. Tamber, H.; Johansen, P.; Merkle, H. P.; Gander, B. Formulation aspects of biodegradable polymeric microspheres for antigen delivery Adv. Drug Delivery Rev. 2005, 57, 357-376 (Pubitemid 39555502)
20. Li, M.; Rouaud, O.; Poncelet, D. Microencapsulation by solvent evaporation: state of the art for process engineering approaches Int. J. Pharm. 2008, 363, 26-39
21. Okada, H.; Doken, Y.; Ogawa, Y.; Toguchi, H. Preparation of three-month depot injectable microspheres of leuprorelin acetate using biodegradable polymers Pharm. Res. 1994, 11, 1143-1147 (Pubitemid 24259854)
22. Okada, H. One- and three-month release injectable microspheres of the LH-RH superagonist leuprorelin acetate Adv. Drug Delivery Rev. 1997, 28, 43-70 (Pubitemid 27497673)
23. O'Hagan, D. T.; Jeffery, H.; Davis, S. S. The preparation and characterization of poly(lactide-co-glycolide) microparticles: III. Microparticle/polymer degradation rates and the in vitro release of a model protein Int. J. Pharm. 1994, 103, 37-45
24. Li, X.; Deng, X.; Yuan, M.; Xiong, C.; Huang, Z.; Zhang, Y.; Jia, W. In vitro degradation and release profiles of poly-DL-lactide-poly(ethylene glycol) microspheres with entrapped proteins J. Appl. Polym. Sci. 2000, 78, 140-148
25. Liggins, R. T.; Burt, H. M. Paclitaxel loaded poly(L-lactic acid) microspheres: properties of microspheres made with low molecular weight polymers Int. J. Pharm. 2001, 222, 19-33 (Pubitemid 32525785)
26. Ikada, Y.; Jamshidi, K.; Tsuji, H.; Hyon, S. H. Stereocomplex formation between enantiomeric poly(lactides) Macromolecules 1987, 20, 904-906
27. Brizzolara, D.; Cantow, H. J.; Diederichs, K.; Keller, E.; Domb, A. J. Mechanism of the stereocomplex formation between enantiomeric poly(lactide)s Macromolecules 1996, 29, 191-197 (Pubitemid 126548663)
28. Tsuji, H.; Ikada, Y. Stereocomplex formation between enantiomeric poly(lactic acid)s. XI. Mechanical properties and morphology of solution-cast films Polymer 1999, 40, 6699-6708 (Pubitemid 29404809)
29. Tsuji, H. Poly(lactide) stereocomplexes: Formation, structure, properties, degradation, and applications Macromol. Biosci. 2005, 5, 569-597
30. Anderson, K. S.; Hillmyer, M. A. Melt preparation and nucleation efficiency of polylactide stereocomplex crystallites Polymer 2006, 47, 2030-2035 (Pubitemid 43344379)
31. Furuhashi, Y.; Kimura, Y.; Yoshie, N.; Yamane, H. Higher-order structures and mechanical properties of stereocomplex-type poly(lactic acid) melt spun fibers Polymer 2006, 47, 5965-5972 (Pubitemid 44041596)
32. He, Y.; Xu, Y.; Wei, J.; Fan, Z.; Li, S. Unique crystallization behavior of poly(l-lactide)/poly(d-lactide) stereocomplex depending on initial melt states Polymer 2008, 49, 5670-5675
33. Andersson, S. R.; Hakkarainen, M.; Inkinen, S.; Sodergard, A.; Albertsson, A. C. Polylactide stereocomplexation leads to higher hydrolytic stability but more acidic hydrolysis product pattern Biomacromolecules 2010, 11, 1067-1073
34. Akagi, T.; Fujiwara, T.; Akashi, M. Rapid fabrication of polylactide stereocomplex using layer-by-layer deposition by inkjet printing Angew. Chem., Int. Ed. 2012, 51, 5493-5496
35. Ajiro, H.; Akashi, M. Inkjet approaches contributed the facile isotactic-poly(methyl methacrylate)/syndiotacitc-poly(methyl methacrylate) stereocomplex surface preparation Macromol. Chem. Phys. 2013, 214, 1590-1595
36. Matsusaki, M.; Sakaue, K.; Kadowaki, K.; Akashi, M. Three-dimensional human tissue chips fabricated by rapid and automatic inkjet cell printing Adv. Healthcare Mater. 2013, 2, 534-539
37. Akagi, T.; Kaneko, T.; Kida, T.; Akashi, M. Preparation and characterization of biodegradable nanoparticles based on poly(γ-glutamic acid) with L-phenylalanine as a protein carrier J. Controlled Release 2005, 108, 226-236 (Pubitemid 41608656)
38. Akagi, T.; Shima, F.; Akashi, M. Intracellular degradation and distribution of protein-encapsulated amphiphilic poly(amino acid) nanoparticles Biomaterials 2011, 32, 4959-4967
39. Tsuji, H.; Hyon, S. H.; Ikada, Y. Stereocomplex formation between enantiomeric poly(1actic acid)s. 3. Calorimetric studies on blend films cast from dilute solution Macromolecules 1991, 24, 5651-5656 (Pubitemid 21737943)
40. Tsuji, H.; Hyon, S. H.; Ikada, Y. Stereocomplex formation between enantiomeric poly(1actic acid)s. 4. Differential scanning calorimetric studies on precipitates from mixed solutions of poly(D-lactic acid) and poly(L-lactic acid) Macromolecules 1991, 24, 5657-5662 (Pubitemid 21737942)
41. Tsuji, H.; Yamamoto, S. Enhanced stereocomplex crystallization of biodegradable enantiomeric poly(lactic acid)s by repeated casting Macromol. Mater. Eng. 2011, 296, 583-589
42. Sah, H. Stabilization of proteins against methylene chloride/water interface induced denaturation and aggregation J. Controlled Release 1999, 58, 143-151 (Pubitemid 29112885)
43. Panyam, J.; Dali, M. M.; Sahoo, S. K.; Ma, W.; Chakravarthi, S. S.; Amidon, G. L.; Levy, R. J.; Labhasetwar, V. Polymer degradation and in vitro release of a model protein from poly(D,L-lactide-co-glycolide) nano- and microparticles J. Controlled Release 2003, 92, 173-187 (Pubitemid 37130131)
44. Fu, K.; Klibanov, A. M.; Langer, R. Protein stability in controlled-release systems Nat. Biotechnol. 2000, 18, 24-25 (Pubitemid 30041164)
45. Morlock, M.; Koll, H.; Winter, G.; Kissel, T. Microencapsulation of rh-erythropoietin, using biodegradable poly(D,Llactide-co-glycolide): Protein stability and the effects of stabilizing excipients Eur. J. Pharm. Biopharm. 1997, 43, 29-36 (Pubitemid 28298807)
46. Griebenow, K.; Klibanov, A. M. On protein denaturation in aqueous-organic mixtures but not in pure organic solvents J. Am. Chem. Soc. 1996, 118, 11695-11700 (Pubitemid 26417457)
47. King, T. W.; Patrick, C. W. Development and in vitro characterization of vascular endothelial growth factor (VEGF)-loaded poly(DL-lactic-co-glycolic acid)/poly(ethylene glycol) microspheres using a solid encapsulation/single emulsion/solvent extraction technique J. Biomed. Mater. Res. 2000, 51, 383-390 (Pubitemid 30452141)
48. Scoutaris, N.; Alexander, M. R.; Gellert, P. R.; Roberts, C. J. Inkjet printing as a novel medicine formulation technique J. Controlled Release 2011, 156, 179-185
49. Lee, B. K.; Yun, Y. H.; Choi, J. S.; Choi, Y. C.; Kim, J. D.; Cho, Y. W. Fabrication of drug-loaded polymer microparticles with arbitrary geometries using a piezoelectric inkjet printing system Int. J. Pharm. 2012, 427, 305-310
50. Serizawa, T.; Yamashita, H.; Fujiwara, T.; Kimura, Y.; Akashi, M. Stepwise assembly of enantiomeric poly(lactide)s on surfaces Macromolecules 2001, 34, 1996-2001 (Pubitemid 34216575)
51. Tsuji, H. In vitro hydrolysis of blends from enantiomeric poly(lactide)s Part 1. Well-stereo-complexed blend and non-blended films Polymer 2000, 41, 3621-3630 (Pubitemid 30116864)
52. Yang, Y. Y.; Chung, T. S.; Ng, N. P. Morphology, drug distribution, and in vitro release profiles of biodegradable polymeric microspheres containing protein fabricated by double-emulsion solvent extraction/evaporation method Biomaterials 2001, 22, 231-241
53. van de Weert, M.; Hennink, W. E.; Jiskoot, W. Protein instability in poly(lactic-co-glycolic acid) microparticles Pharm. Res. 2000, 17, 1159-1167
54. Akagi, T.; Wang, X.; Uto, T.; Baba, M.; Akashi, M. Protein direct delivery to dendritic cells using nanoparticles based on amphiphilic poly(amino acid) derivatives Biomaterials 2007, 28, 3427-3436 (Pubitemid 46729729)
55. Yang, Y. Y.; Chia, H. H.; Chung, T. S. Effect of preparation temperature on the characteristics and release profiles of PLGA microspheres containing protein fabricated by double-emulsion solvent extraction/evaporation method J. Controlled Release 2000, 69, 81-96
56. Dunne, M.; Corrigan, I.; Ramtoola, Z. Influence of particle size and dissolution conditions on the degradation properties of polylactide-co-glycolide particles Biomaterials 2000, 21, 1659-1668 (Pubitemid 30347308)
57. Wischke, C.; Borchert, H. H. Influence of the primary emulsification procedure on the characteristics of small protein-loaded PLGA microparticles for antigen delivery J. Microencapsulation 2006, 23, 435-448 (Pubitemid 44132551)
58. Zhang, H.; Bei, J.; Wang, S. Multi-morphological biodegradable PLGE nanoparticles and their drug release behavior Biomaterials 2009, 30, 100-107