New self-assembling polyaspartylhydrazide copolymer micelles for anticancer drug delivery

International Journal of Pharmaceutics

Volumn 396, Issue 1-2, 2010, Pages 219-228

  Licciardi, Mariano ^a   Cavallaro, Gennara ^a   Di Stefano, Mauro ^a   Pitarresi, Giovanna ^a   Fiorica, Calogero ^a   Giammona, Gaetano ^a,b  

^a UNIVERSITY OF PALERMO   (Italy)

^b CNR   (Italy)

Author keywords

Polyaspartylhydrazide (PAHy); Polymeric micelles; Self assembling copolymer; Tamoxifen

Indexed keywords

COPOLYMER; HYDRAZIDE; MACROGOL 2000; PALMITIC ACID; POLYASPARTYLHYDRAZIDE; PYRENE; TAMOXIFEN; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; DRUG CARRIER; MACROGOL DERIVATIVE; MICELLE; PEPTIDE; POLY(ASPARTYLHYDRAZIDE);

ANTINEOPLASTIC ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN MCF 7; CELL VIABILITY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG SOLUBILITY; ENCAPSULATION; HUMAN; HUMAN CELL; HYDRODYNAMICS; HYDROPHILICITY; HYDROPHOBICITY; MICELLE; MICELLIZATION; NUCLEAR OVERHAUSER EFFECT; PARTICLE SIZE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TRANSMISSION ELECTRON MICROSCOPY; ZETA POTENTIAL; BREAST TUMOR; CELL SURVIVAL; CHEMICAL PHENOMENA; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG FORMULATION; FEMALE; FLUORESCENCE; LIGHT; MEDICINAL CHEMISTRY; NANOTECHNOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PATHOLOGY; PHARMACEUTICS; PROCEDURES; RADIATION SCATTERING; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL SURVIVAL; CHEMISTRY, PHARMACEUTICAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG CARRIERS; DRUG COMPOUNDING; FEMALE; FLUORESCENCE; HUMANS; HYDROPHOBICITY; LIGHT; MAGNETIC RESONANCE SPECTROSCOPY; MICELLES; MICROSCOPY, ELECTRON, TRANSMISSION; NANOTECHNOLOGY; PALMITIC ACID; PARTICLE SIZE; PEPTIDES; POLYETHYLENE GLYCOLS; SCATTERING, RADIATION; TAMOXIFEN; TECHNOLOGY, PHARMACEUTICAL; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS;

EID: 77955054177     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2010.06.021     Document Type: Article

References (43)

1. Allen C., Maysinger D., Eisenberg A. Nano-engineering block copolymer aggregates for drug delivery. Colloids Surf. B: Biointerfaces 1999, 16:1-35.
2. Atkins P.W. Physical Chemistry 2002, Oxford University Press, Oxford. 7th ed.
3. Bae Y.H., Yin H. Stability issues of polymeric micelles. J. Control. Release 2008, 131:2-4.
4. Caliceti P., Quarta S.M., Veronese F.M., Cavallaro G., Pedone E., Giammona G. Synthesis and biopharmaceutical characterization of new poly(hydroxyethyl)aspartamide copolymers as drug carriers. Biochem. Biophys. Acta 2001, 1528:177-186.
5. Cao T., Munk P., Ramireddy C., Tuzar Z., Webber S.E. Fluorescence studies of amphiphilic poly(methacrylic acid)-block-polystyrene-block-poly(methacrylic acid) micelles. Macromolecules 1991, 24:6300-6305.
6. Carlsen A., Lecommandoux S. Self-assembly of polypeptide-based block copolymer amphiphiles. Curr. Opin. Colloid Interface Sci. 2009, 14:329-339.
7. Cavallaro G., Licciardi M., Mandracchia D., Pitarresi G., Giammona G. Hydrophilic and hydrophobic copolymers of a polyasparthylhydrazide bearing positive charges as vector for gene therapy. Polym. Int. 2008, 57:708-713.
8. Cavallaro G., Maniscalco L., Licciardi M., Giammona G. Tamoxifen-loaded polymeric micelles: preparation, physico-chemical characterization and in vitro evaluation studies. Macromol. Biosci. 2004, 4:1028-1038.
9. Cavallaro G., Palumbo F.S., Licciardi M., Giammona G. Novel cationic copolymers of a polyasparthylhydrazide: synthesis and characterization. Drug Deliv. 2005, 12:377-384.
10. Chawla J.S., Amiji M.M. Biodegradable poly(e{open}-caprolactone) nanoparticles for tumor-targeted delivery of tamoxifen. Int. J. Pharm. 2002, 249:127-138.
11. Chen J., Jiang M., Zhang Y., Zhou H. Fluorescence studies on hydrophobic associations of fluorocarbon-modified poly(acrylic acid) solutions. Macromolecules 1999, 32:4861-4866.
12. Civiale C., Licciardi M., Cavallaro G., Giammona G., Mazzone M.G. Polyhydroxyethylaspartamide-based micelles for ocular drug delivery. Int. J. Pharm. 2009, 378:177-186.
13. Gao S., Singh J. In vitro percutaneous absorption enhancement of a lipophilic drug tamoxifen by terpenes. J. Control. Release 1998, 51:193-199.
14. Gao Z., Eisenberg A. A model of micellization for block copolymers in solutions. Macromolecules 1993, 26:7353-7360.
15. Giammona G., Carlisi B., Cavallaro G., Pitarresi G., Spampinato S. A new water-soluble synthetic-polymer, alpha,-beta-polyasparthydrazide, as potential plasma expander and drug carrier. J. Control. Release 1994, 29:63-72.
16. Gjerde M.I., Nerdal W., Hoiland H. A NOESY NMR study of the interaction between sodium dodecyl sulphate and poly(ethylene oxide). J. Colloid Interface Sci. 1996, 183:285-288.
17. Gref R., Lück M., Quellec P., Marchand M., Dellacherie E., Harnisch S., et al. Stealth corona-core nanoparticles surface modified by polyethylene glycol (PEG): influence of corona (PEG chain length and surface density) and of the core composition on phagocytic uptake and plasma protein adsorption. Colloids Surf. B: Biointerfaces 2000, 18:301-313.
18. Gref R., Minamitake Y., Peracchia M.T., Trubetskoy V., Torchilin V., Langer R. Biodegradable long-circulating polymeric nanospheres. Science 1994, 28:1600-1603.
19. Halperin A., Alexander S. Polymeric micelles: their relaxation kinetics. Macromolecules 1989, 22:2403-2412.
20. Iyer A.K., Khaled G., Fang J., Maeda H. Exploiting the enhanced permeability and retention effect for tumor targeting. Drug Discov. Today 2006, 11:812-818.
21. Jacobsen N.E. NMR Spectroscopy Explained: Simplified Theory, Applications and Examples for Organic Chemistry and Structural Biology 2007, Wiley-Interscience, Hoboken, NJ.
22. Kwon G.S., Okano T. Polymeric micelles as new drug carriers. Adv. Drug Deliv. Rev. 1996, 21:107-116.
23. Lavasanifar A., Samuel J., Kwon G.S. The effect of alkyl core structure on micellar properties of poly(ethylene oxide)-block-poly(l-aspartamide) derivatives. Colloids Surf. B: Biointerfaces 2001, 22:115-126.
24. Lee M.Y., Kim S.H., Ganapathy H.S., Kim S.W., Lim K.T. Characterization of micellar film morphologies of semifluorinated block copolymers by AFM. Ultramicroscopy 2008, 108:1210-1214.
25. Licciardi M., Giammona G., Du J., Armes S.P., Tang Y., Lewis A.L. New folate-functionalized biocompatible block copolymer micelles as potential anti-cancer drug delivery systems. Polymer 2006, 47:2946-2955.
26. Ma Y., Tang Y., Billingham N.C., Armes S.P., Lewis A.L., Lloyd A.W. Well-defined biocompatible block copolymers via atom transfer radical polymerization of 2-methacryloyloxyethyl phosphorylcholine in protic media. Macromolecules 2003, 36:3475-3484.
27. Matsumura Y. Poly(amino acid) micelle nanocarriers in preclinical and clinical studies. Adv. Drug Deliv. Rev. 2008, 60:899-914.
28. Mendichi R., Giacometti Schieroni A., Cavallaro G., Licciardi M., Giammona G. Molecular characterization of α,β-poly(N-2-hydroxyethyl)-dl-aspartamide derivatives as potential self-assembling copolymers forming polymeric micelles. Polymer 2003, 44:4871-4879.
29. Mo H.P., Pochapsky T.C. Intermolecular interactions characterized by nuclear Overhauser effects. Prog. Nucl. Magn. Reson. Spectrosc. 1997, 30:1-38.
30. Paolino D., Cosco D., Licciardi M., Giammona G., Fresta M., Cavallaro G. Polyasparthylhidrazide copolymer-based supramolecular vesicular aggregates as delivery devices for anticancer drugs. Biomacromolecules 2008, 9:1117-1130.
31. Pitarresi G., Cavallaro G., Carlisi B., Giammona G., Bulone D., San Biagio P.L. Novel hydrogels based on a polyasparthydrazide. Synthesis and characterization. Macromol. Chem. Phys. 2000, 201:2542-2549.
32. Pommier R.F., Woltering E.A., Milo G., Fletcher W.S. Cytotoxicity of dimethyl sulfoxide and antineoplastic combinations against human tumors. Am. J. Surg. 1988, 155:672-676.
33. Rijcken C.J.F., Schiffelers R.M., van Nostrum C.F., Hennink W.E. Long circulating biodegradable polymeric micelles: towards targeted drug delivery. J. Control. Release 2008, 132:e33-e35.
34. Rösler A., Vandermeulen G.W.M., Klok H.-A. Advanced drug delivery devices via self-assembly of amphiphilic block copolymers. Adv. Drug Deliv. Rev. 2001, 53:95-108.
35. Sezgin Z., Yüksel N., Baykara T. Preparation and characterization of polymeric micelles for solubilization of poorly soluble anticancer drugs. Eur. J. Pharm. Biopharm. 2006, 64:261-268.
36. Savić R., Luo L., Eisenberg A., Maysinger D. Micellar nanocontainers distribute to defined cytoplasmic organelles. Science 2003, 300:615-618.
37. Torchilin V.P. Structure and design of polymeric surfactant-based drug delivery systems. J. Control. Release 2001, 73:137-172.
38. Torchilin V.P. PEG-based micelles as carriers of contrast agents for different imaging modalities. Adv. Drug Deliv. Rev. 2002, 54:235-252.
39. Torchilin V.P. Nanocarriers. Pharm. Res. 2007, 24:2333-2334.
40. Voets I.K., de Keizer A., Cohen Stuart M.A. Core and corona structure of mixed polymeric micelles. Macromolecules 2006, 39:5952-5955.
41. Wilhelm M., Zhao C.-L., Wang Y., Xu R., Winnik M.A., Mura J.-L., et al. Poly(styrene-ethylene oxide) block copolymer micelle formation in water: a fluorescence probe study. Macromolecules 1991, 24:1033-1040.
42. Wüthrich K. NMR of Proteins and Nucleic Acid 1986, Wiley, New York.
43. Yokoyama M., Mitauchi M., Yamada N., Okano T., Sakurai Y., Kataoka K., et al. Polymer micelles as novel drug carrier: adriamycin-conjugated poly(ethylene glycol)-poly(aspartic acid) block copolymer. J. Control. Release 1990, 11:269-278.