Abstract
Preparation methods of cyanoacrylic nanocapsules or nanoparticles containing phthalocyanines and naphthalocyanines are described. Nanocapsules were obtained by interfacial polymerization in an oil-in-water emulsion. Drug encapsulation efficiency depended upon drug concentration, ethanol concentration, and phthalocyanine sulfonation degree and reached 100% in some cases. Nanocapsules size ranged from 150 to 250 nm and varied with phthalocyanine sulfonation degree and pH of the aqueous phase. Nanoparticles were prepared by the addition of monomer to an aqueous phase containing hydrophilic phthalocyanine derivatives. Depending upon the pH, sizes ranged from 10 to 380 nm. Drug binding was between 75 and 80%. These new preparations could prove useful in the photodynamic treatment of tumors.
Similar content being viewed by others
REFERENCES
D. Kessel (ed.). Photodynamic Therapy of Neoplastic Disease. Vol. I. Clinical and Pre-Clinical Studies, CRC Press, Boca Raton, FL, 1990.
J. E. van Lier and J. D. Spikes. In G. Bock and S. Harnett (eds.), Ciba Foundation Symposium, 146: Photosensitizing Compounds: Their Chemistry, Biology and Clinical Use, Wiley, Chichester, 1989, pp. 17–26.
N. Brasseur, H. Ali, R. Langlois, and J. E. van Lier. Biological activities of phthalocyanines-IX. Photosensitization of V-79 Chinese hamster cells and EMT-6 mouse mammary tumor by selectively sulfonated zinc phthalocyanines. Photochem. Photobiol. 47:705–711 (1988).
C. Milanesi, R. Biolo, E. Reddi, and G. Jori. Ultrastructural studies on the mechanism of the photodynamic therapy of tumors. Photochem. Photobiol. 46:675–681 (1987).
M. C. Finkelstein and G. Weissman. Enzyme replacement via liposomes. Variations in lipid composition determine liposomal integrity in biological fluids. Biophys. Acta 587:202–206 (1979).
P. Couvreur, B. Kante, V. Lenaerts, V. Scailteur, M. Roland, and P. Speiser. Tissue distribution of antitumor drugs associated with polyalkylcyanoacrylate nanoparticles. J. Pharm. Sci. 69:199–202 (1980).
V. Lenaerts, P. Couvreur, D. Christiaens-Leyh, E. Joiris, M. Roland, B. Rollman, and P. Speiser. Degradation of poly (isobutylcyanoacrylate) nanoparticles. Biomaterials 5:65–68 (1984).
C. Verdun, P. Couvreur, H. Vranckx, V. Lenaerts, and M. Roland. Development of a nanoparticle controlled-release formulation for human use. J. Control. Rel. 3:205–220 (1986).
J. H. Weber and D. H. Bush. Complexes derived from strong field ligands. XIX magnetic properties of transition metal derivatives of 4,4′,4″,4‴-tetrasulfophthalocyanines. Inorg. Chem 4:469–471 (1965).
H. Ali, R. Langlois, J. R. Wagner, N. Brasseur, B. Paquette, and J. E. van Lier. Biological activities of phthalocyanines. X. Synthesis and analysis of sulfonated phthalocyanines. Photochem. Photobiol. 47:713–717 (1988).
R. P. Hinstead and F. T. Weiss. Linstead phthalocyanines and related compounds. XX. Further investigations on tetrabenzoporphine and allied substances. J. Chem. Soc. 2975–2981 (1950).
F. Chouinard, F. W. K. Kan, C. Foucher, J. C. Leroux, V. Lenaerts. Preparation and purification of polyisohexylcyanoacrylate nanocapsules. Int. J. Pharm. (in press) (1991).
N. Al Khoury Fallouh, L. Roblot-Treupel, H. Fessi, J. P. Devissaguet, and F. Puisieux. Development of a new process for the manufacture of polyisobutylcyanoacrylate nanocapsules. Int. J. Pharm. 28:125–132.
P. Couvreur, L. Grislain, V. Lenaerts, F. Brasseur, P. Guiot, and A. Biernacki. Biodegradable polymeric nanoparticles as drug carrier for antitumor agents. In P. Guiot and P. Couvreur (eds.), Polymeric Nanoparticles and Microspheres, CRC Press, Boca Raton, FL, 1986, pp. 27–93.
E. F. Donnely, D. S. Jonston, D. C. Pepper, and D. J. Dunn. Ionic and zwitterionic polymerization of alkyl-2-cyanoacrylates. J. Polym. Sci. Polym. Lett. ed. 13:399–405 (1977).
N. Ammouri, H. Fessi, J. P. Devissaguet, F. Puisieux, and S. Benita. Indomethacin-loaded poly (d,l-lactide) nanocapsules: Drug release kinetics and kinetic model evaluation. In R. Pearlman and J. A. Miller (eds.), Proceedings of the 16th International Symposium on Controlled Release of Bioactive Materials, Controlled Release Society Inc., Lincolnshire, 1989, pp. 75–76.
V. Lenaerts, J. F. Nagelkerke, T. J. C. Van Berkel, P. Couvreur, L. Grislain, M. Roland, and P. Speiser. In vivo uptake of polyisobutyl cyanoacrylate nanoparticles by rat liver Kupffer, endothelial and parenchymal cells. J. Pharm. Sci. 73:980–982 (1984).
E. Wisse. Scanning electron microscopical study of liver sinusoids. In E. Wisse and D. L. Knook (eds.), Kupffer Cells and Other Liver Simosoidal Cells, Elsevier North-Holland, Amsterdam, 1977, 33–60.
B. L. Wheeler, G. Nagasubramanian, A. J. Bard, L. A. Schechtman, D. R. Dininny, and M. E. Kenney. A silicon phthalocyanince and a silicon naphthalocyanine: Synthesis, electrochemistry and electrogenerated chemiluminescence. J. Am. Chem. Soc. 106:7404–7410.
D. Leyh, P. Couvreur, V. Lenaerts, M. Roland, and P. Speiser. Étude du mécanisme de dégradation des nanoparticules de polycyanoacrylate d'alkyle. Labo-Pharma-Probl. Tech. 32:100–104 (1984).
M. M. Gallardo, L. Roblot-Treupel, L. Mahuteau, I. Grenin, P. Couvreur, P. Plat, and F. Puisieux. Nanocapsules et nanosphères d'alkylcyanoacrylate: Interaction principe actif/polymère. Proceedings of the 5th International Symposium on Pharmaceutical Technology, APGI, Paris, pp. 36–45.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Labib, A., Lenaerts, V., Chouinard, F. et al. Biodegradable Nanospheres Containing Phthalocyanines and Naphthalocyanines for Targeted Photodynamic Tumor Therapy. Pharm Res 8, 1027–1031 (1991). https://doi.org/10.1023/A:1015809124895
Issue Date:
DOI: https://doi.org/10.1023/A:1015809124895