Preparation of microparticles composed of amphiphilic poly(γ-glutamic acid) through hydrophobic interactions

Polymer Journal

Volumn 46, Issue 3, 2014, Pages 184-188

  Shima, Fumiaki ^a,c   Schulte, Bjoern ^b,c   Keul, Helmut ^b,c   Moeller, Martin ^b,c   Akashi, Mitsuru ^a,c  

^a OSAKA UNIVERSITY   (Japan)

^b RWTH AACHEN UNIVERSITY   (Germany)

^c JAPAN SOCIETY FOR THE PROMOTION OF SCIENCE   (Japan)

Author keywords

amphiphilic copolymer; drug delivery; hydrophobic interaction; microparticles; poly(g glutamic acid); self assembly

Indexed keywords

AMPHIPHILIC CO-POLYMERS; AMPHIPHILIC GRAFT COPOLYMERS; CARBOXYLIC GROUP; COUPLING REAGENTS; HYDROPHOBIC INTERACTIONS; MICRO-PARTICLES; POLY(G-GLUTAMIC ACID); VACCINE CARRIERS;

AMINO ACIDS; CATIONIC SURFACTANTS; COPOLYMERS; DRUG DELIVERY; GRAFTING (CHEMICAL); HYDROPHOBIC CHROMATOGRAPHY; PROTEINS; SELF ASSEMBLY;

HYDROPHOBICITY;

EID: 84897731119     PISSN: 00323896     EISSN: 13490540     Source Type: Journal    
DOI: 10.1038/pj.2013.74     Document Type: Article

References (28)

1. Cruz, J. L., Tacken, J. P., Fokkink, R., Joosten, B., Stuart, C. M., Albericio, F., Torensma, R. & Figdor, G. C. Targeted PLGA nano-but not microparticles specifically deliver antigen to human dendritic cells via DC-SIGN in vitro. J. Control Release 144, 118-126 (2010).
2. Kanchan, V. & Panda, K. A. Interactions of antigen-loaded polylactide particles with macrophages and their correlation with the immune response. Biomaterials 28, 5344-5357 (2007).
3. Ozawa, Y., Sawada, S., Morimoto, N. & Akiyoshi, K. Self-assembled nanogel of hydrophobized dendritic dextrin for protein delivery. Macromol. Biosci. 9, 694-701 (2009).
4. Yokoyama, M., Kwon, S. G., Okano, T., Sakurai, Y., Seto, T. & Kataoka, K. Preparation of micelle-forming polymer-drug conjugates. Bioconjugate Chem. 3, 295-301 (1992).
5. Brewer, M. J., Pollock, J. G. K., Tetley, L. & Russell, G. D. Vesicle size influences the trafficking, processing, and presentation of antigens in lipid vesicles. J. Immunol. 173, 6143-6150 (2004).
6. Dash, C.B., Réthoré, G., Monaghan, M., Fitzgerald, K., Gallagher, W. & Pandit, A. The influence of size and charge of chitosan/polyglutamic acid hollow spheres on cellular internalization, viability and blood compatibility. Biomaterials 31, 8188-8197 (2010).
7. Chiu, L. Y., Ho, C. Y., Chen, M. Y., Peng, F. S., Ke, J. C., Chen, J. K., Mi, L. F. & Sung, W. H. The characteristics, cellular uptake and intracellular trafficking of nanoparticles made of hydrophobically-modified chitosan. J. Control Release 146, 152-159 (2010).
8. Chen, S., Cheng, X. S. & Zhuo, X. R. Self-assembly strategy for the preparation of polymer-based nanoparticles for drug and gene delivery. Macromol. Biosci. 11, 576-589 (2011).
9. Mundargi, C. R., Babu, R. V., Rangaswamy, V., Patel, P. & Aminabhavi, M. T. Nano/micro technologies for delivering macromolecular therapeutics using poly(D, L-lactideco-glycolide) and its derivatives. J. Control Release 125, 193-209 (2008).
10. Song, S., Zheng, Q., Song, A. & Hao, J. Self-assembled aggregates originated from the balance of hydrogen-bonding, electrostatic, and hydrophobic interactions. Langmuir 28, 219-226 (2012).
11. Molla, R. M. & Ghosh, S. Hydrogen-bonding-mediated vesicular assembly of functionalized naphthalene-diimide-based bolaamphiphilic and guest-induced gelation in water. Chem. Eur. J. 18, 9860-9869 (2012).
12. Torchilin, P. V. Recent advances with liposomes as pharmaceutical carriers. Nat. Rev. Drug Discov. 4, 145-160 (2005).
13. Saha, R., Verma, K. P., Mitra, K. R. & Pal, K. S. Structural and dynamical characterization of unilamellar AOT vesicles in aqueous solutions and their efficacy as potential drug delivery vehicle. Colloid. Surf. B 88, 324-353 (2011).
14. Maria, A., Ribeiro, C., Yoshida, S. L., Sesso, A. & Chaimovich, H. Permeabilities and stabilities of large dihexadecylphosphate and dioctadecyldimethylammonium chloride vesicles. J. Colloid Interface Sci. 100, 433-443 (1984).
15. Berkland, C., King, M., Cox, A., Kim, K. K. & Pack, W. D. Precise control of PLG microsphere size provides enhanced control of drug release rate. J. Control Release 82, 137-147 (2002).
16. Matsusaki, M., Hiwatari, K., Higashi, M., Kaneko, T. & Akashi, M. Stably-dispersed and surface-functional bionanoparticles prepared by self-assembling amphipathic polymers of hydrophilic poly(g-glutamic acid) bearing hydrophobic amino acids. Chem. Lett. 33, 398-399 (2004).
17. Akagi, T., Baba, M. & Akashi, M. Preparation of nanoparticles by the self-organization of polymers consisting of hydrophobic and hydrophilic segments: potential applications. Polymer (Guildf). 48, 6729-6747 (2007).
18. Kim, H., Akagi, T. & Akashi, M. Preparation of size tunable amphiphilic poly(amino acid) nanoparticles. Macromol. Biosci. 9, 825-932 (2009).
19. Akagi, T., Piyapakorn, P. & Akashi, M. Formation of unimer nanoparticles by controlling the self-association of hydrophobically modified poly(amino acid)s. Langmuir 28, 5249-5256 (2012).
20. 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 28, 3427-3436 (2007).
21. Akagi, T., Shima, F. & Akashi, M. Intracellular degradation and distribution of protein-encapsulated amphiphilic poly(amino acid) nanoparticles. Biomaterials 32, 4959-4967 (2011).
22. Akagi, T., Kaneko, T., Kida, T. & Akashi, M. Multifunctional conjugation of proteins on/into bio-nanoparticles prepared by amphiphilic poly(g-glutamic acid). J. Biomater. Sci. Polym. Ed. 17, 875-892 (2006).
23. Backes, M., Messager, L., Mourran, A., Keul, H. & Moeller, M. Synthesis and thermal properties of well-defined amphiphilic block copolymers based on polyglycidol. Macromolecules 43, 3238-3248 (2010).
24. Tian, B., Tao, X., Ren, T., Weng, Y., Lin, X., Zhang, Y. & Tang, X. Polypeptide-based vesicles: formation, properties and application for drug delivery. J. Mater. Chem. 22, 17404-17414 (2012).
25. Shih, L. I. & Van, T. Y. The production of poly-(γ-glutamic acid) from microorganisms and its various applications. Bioresour. Technol. 79, 207-225 (2001).
26. Ginkel, G. C., Pomper, A. M., Stroo, A. C. & Kroon, M. G. A. Biodegradation of fatty amides: utilization of the alkyl chain by isolated micro-organisms. Tenside Surf. Deterg 32, 355-359 (1995).
27. Kim, K. M., Zhao, H., Lee, H. C. & Kim, D. D. Formulation of a reservoir-type testosterone transdermal delivery system. Int. J. Pharm. 219, 51-59 (2001).
28. Bian, S., Doh, J. H., Zheng, J., Kim, S. J., Lee, H. C. & Kim, D. D. In vitro evaluation of patch formulations for topical delivery of gentisic acid in rats. Eur. J. Pharm. Sci. 18, 141-147 (2003).