Preparation and characterization of sterile sub-200 nm meso-tetra(4-hydroxylphenyl)porphyrin-loaded nanoparticles for photodynamic therapy

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 55, Issue 1, 2003, Pages 115-124

  Konan, Yvette Niamien ^a   Cerny, Radovan ^a   Favet, Joselyne ^a   Berton, Myriam ^a   Gurny, Robert ^a   Allémann, Eric ^a,b  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b Bracco Suisse SA   (Switzerland)

Author keywords

Meso tetra(p hydroxyphenyl)porphyrin; Nanoparticles; P THPP; Photosensitizer; Poly(D,L lactide); Poly(D,L lactide co glycolide); Sterile filtration

Indexed keywords

COPOLYMER; MESO TETRAKIS(4 HYDROXYLPHENYL)PORPHYRIN; NANOPARTICLE; PHOTOSENSITIZING AGENT; POLYESTER; POLYGLACTIN; POLYLACTIDE; POLYMER; PORPHYRIN DERIVATIVE; RESOMER; TREHALOSE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIUM CONTAMINATION; CROSSFLOW FILTRATION; DIFFUSION; DISINFECTION; DISPERSION; DRUG PURIFICATION; EMULSION; FILTRATION; FREEZE DRYING; MEMBRANE; MOLECULAR WEIGHT; PARTICLE SIZE; PHOTODYNAMIC THERAPY; REPRODUCIBILITY; SURFACE PROPERTY; SUSPENSION; THEORETICAL STUDY;

EID: 0037241588     PISSN: 09396411     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0939-6411(02)00128-5     Document Type: Article

References (45)

1. Pandey R.K., Sumlin A.B., Constantine S., Aoudia M., Potter W.R., Bellnier D.A., Henderson B.W., Rodgers M.A., Smith K.M., Dougherty T.J. Alkyl ether analogs of chlorophyll-a derivatives: Part I. Synthesis, photophysical properties and photodynamic efficacy. Photochem. Photobiol. 64:1996;194-204.
2. Henderson B.W., Bellnier D.A., Greco W.R., Sharma A., Pandey R.K., Vaughan L.A., Weishaupt K.R., Dougherty T.J. An in vivo quantitative structure-activity relationship for a congeneric series of pyropheophorbide derivatives as photosensitizers for photodynamic therapy. Cancer Res. 57:1997;4000-4007.
3. Rovers J.P., Saarnak A.E., de Jode M., Sterenborg H.J.C.M., Terpstra O.T., Grahn M.F. Biodistribution and bioactivity of tetra-pegylated meta-tetra(hydroxyphenyl)chlorin compared to native meta-tetra(hydroxyphenyl)chlorin in a rat liver tumor model. Photochem. Photobiol. 71:2000;210-217.
4. Kopecek J., Kopeckova P., Minko T., Lu Z.-R., Peterson C.M. Water soluble polymers in tumor targeted delivery. J. Control. Rel. 74:2001;147-158.
5. Richter A.M., Waterfield E., Jain A.K., Canaan J.A., Allison B.A., Levy J.G. Liposomal delivery of a photosensitizer benzoporphyrin derivative monoacid ring A (BPD), to tumor tissue in a mouse tumor model. Photochem. Photobiol. 57:1993;1000-1006.
6. Isele U., van Hoogevest P., Hilfiker R., Capraro H.G., Schieweck K., Levy J.G., Leuenberger H. Large-scale production of liposomes containing monomeric zinc phthalocyanine by controlled dilution of organic solvents. J. Pharm. Sci. 83:1994;1608-1616.
7. Morgan A.R., Garbo G.M., Keck R.W., Selman S.H. New photosensitizers for photodynamic therapy: combined effect of metallopurpurin derivatives and light on transplantable bladder tumors. Cancer Res. 48:1988;194-198.
8. Garbo G.M., Fingar V.H., Wienman T.J., Noakes E.B. III, Haydon P.S., Cerrito P.B., Kessel D.H., Morgan A.R. In vivo and in vitro photodynamic studies with benzochlorin imimium salts delivered by a lipid emulsion. Photochem. Photobiol. 64:1998;561-568.
9. Taillefer J., Jones M.-C., Brasseur N., Van Lier J.E., Leroux J.C. Preparation and characterization of pH-responsive polymeric micelles for the delivery of photosensitizing anticancer drugs. J. Pharm. Sci. 89:2000;52-62.
10. Brasseur N., Brault D., Couvreur P. Adsorption of hematoporphyrin onto polyalkylcyanoacrylate nanoparticles: carrier capacity and drug release. Int. J. Pharm. 70:1991;129-135.
11. Lenaerts V., Labib A., Chouinard F., Rousseau J., Ali H., Van Lier J.E. Nanocapsules with a reduced liver uptake: targeting of phthalocyanines to EMT-6 mouse mammary tumour in vivo. Eur. J. Pharm. Biopharm. 41:1995;38-43.
12. Allémann E., Brasseur N., Benrezzak O., Rousseau J., Kudrevich S.V., Boyle R.W., Leroux J.C., Gurny R., Van Lier J.E. PEG-coated poly(lactic acid) nanoparticles for the delivery of hexadecafluoro zinc phthalocyanine to EMT-6 mouse mammary tumours. J. Pharm. Pharmacol. 47:1995;382-387.
13. Kristl J., Allémann E., Gurny R. Formulation and evaluation of zinc-phthalocyanine-loaded poly(D,L-lactic acid) nanoparticles. Acta Pharm. 46:1996;1-12.
14. Bourdon O., Mosqueira V., Legrand Ph., Blais J. A comparative study of the cellular uptake, localization and phototoxicity of meta-tetra(hydroxyphenyl)chlorin encapsulated in surface-modified submicronic oil/water carriers in HT29 tumor cells. J. Photochem. Photobiol. B Biol. 55:2000;164-171.
15. Yoo H.S., Lee K.H., Oh J.E., Park T.G. In vitro and in vivo anti-tumor activities of nanoparticles based on doxorubicin-PLGA conjugates. J. Control. Rel. 68:2000;419-431.
16. Barratt G.M. Therapeutic applications of colloidal drug carriers. Pharm. Sci. Technol. Today. 3:2000;163-171.
17. Juliano R.L. Factors affecting the clearance kinetics and tissue distribution of liposomes, microspheres and emulsions. Adv. Drug Deliv. Rev. 2:1988;31-54.
18. Maruyama K., Ishida O., Takizama T., Moribe K. Possibility of active targeting to tumor tissues with liposomes. Adv. Drug Deliv. Rev. 40:1999;89-102.
19. Poste G., Kirsh R., Allison B.A. Site-specific (targeted) drug delivery in cancer therapy. Biotechnology. 1:1983;869-878.
20. Kong G., Braun R.D., Dewhirst M.W. Hyperthermia enables tumor-specific nanoparticle delivery: effect of particle size. Cancer Res. 60:2000;4440-4445.
21. Konan Y.N., Gurny R., Allémann E. Preparation and characterization of sterile and freeze-dried sub-200 nm nanoparticles. Int. J. Pharm. 233:2002;239-252.
22. Leroux J.C., Allémann E., Doelker E., Gurny R. New approach for the preparation of nanoparticles by an emulsification-diffusion method. Eur. J. Pharm. Biopharm. 41:1995;14-18.
23. Govender T., Stolnik S., Garnett M.C., Illum I., Davis S.S. PLGA nanoparticles prepared by nanoprecipitation: drug loading and release studies of a water soluble drug. J. Control. Rel. 57:1999;171-185.
24. Berenbaum M.C., Akande S.L., Bonnett R., Kaur H., Ioannou S. meso-Tetra(hydroxyphenyl)porphyrins, a new class of potent tumour photosensitizers with favourable selectivity. Br. J. Cancer. 54:1986;717-725.
25. Bonnett R., White R.D., Winfield U.-J., Berenbaum M.C. Hydroporphyrins of the meso-tetra(hydroxyphenyl)porphyrin series as tumour photosensitizers. Biochem. J. 261:1989;277-280.
26. Anderson J.M., Shive M.S. Biodegradation and biocompatibility of PLA and PLGA microspheres. Adv. Drug Deliv. Rev. 28:1997;5-24.
27. Dunn R.L., English J.P., Strobel J.D., Cowsar D.R., Tice T.R. Preparation and evaluation of lactide/glycolide copolymers for drug delivery. Migliaresi C. Polymers in Medicine III. 1988;149-160 Elsevier Science Publishers BV, Amsterdam.
28. Allémann E., Doelker E., Gurny R. Drug loaded poly(lactic acid) nanoparticles produced by a reversible salting-out process: purification of an injectable dosage form. Eur. J. Pharm. Biopharm. 39:1993;13-18.
29. Sakurada I. Chemical Reactions of Polyvinyl Alcohol, International Fiber Science and Technology Series: Polyvinyl Alcohol Fibers. 1985;137-159 Marcel Dekker, Inc, New York.
30. Anderson J.M., Shive M.S. Biodegradation and biocompatibility of PLA and PLGA microspheres. Adv. Drug Deliv. Rev. 28:1997;5-24.
31. Tsai D.C., Howard S.A., Hogan T.F., Malanga C.J., Kandzari S.J., Ma J.K.H. Preparation and in vitro evaluation of polylactic acid-mitomycin C microscapsules. J. Microencapsul. 3:1986;191-193.
32. Allémann E., Gurny R., Doelker E. Preparation of aqueous polymeric nanodispersions by a reversible salting-out process: influence of process parameters on particle size. Int. J. Pharm. 87:1992;247-253.
33. Lee S.C., Oh J.T., Jang M.H., Chung S.I. Quantitative analysis of polyvinyl alcohol on the surface of poly(D,L-lactide-co-glycolide) microparticles prepared by solvent evaporation method: effect of particle size and PVA concentration. J. Control. Rel. 59:1999;123-132.
34. Mallapragada S., McCarthy-Schroeder S. Poly(vinyl alcohol) as a drug delivery carrier. Wise D.L. Handbook of Pharmaceutical Controlled Release Technology. 2000;31-46 Marcel Dekker, Inc, New York.
35. Yamaoko T., Tabata Y., Ikada Y. Comparison of body distribution of poly(vinyl alcohol) with other water-soluble polymers after intravenous administration. J. Pharm. Pharmacol. 47:1995;479-486.
36. Tabata Y., Murakami Y., Ikada Y. Tumor accumulation of poly(vinyl alcohol) of different sizes after intravenous injection. J. Control. Rel. 50:1998;123-133.
37. Quintanar-Guerrero D., Fessi H., Allémann E., Doelker E. Influence of stabilizing agents and preparative variables on the formation of poly(D,L-lactic acid) nanoparticles by an emulsification-diffusion technique. Int. J. Pharm. 143:1996;133-141.
38. Görner T., Gref R., Michelot D., Sommer F., Tran M.N., Dellacherie E. Lidocaine-loaded biodegradable nanospheres. I. Optimatization of the drug incorporation into the polymer matrix. J. Control. Rel. 57:1999;259-268.
39. Snowman J.W. Freeze drying of sterile products. Groves M.J., Olson W.P., Anisfeld M.H. Sterile Pharmaceutical Manufacturing: Applications for the 1990's. 1991;79-108 Interpharm Press, Buffalo Grove.
40. Carpenter J.F., Pikal M.J., Chang B.S., Randolph T.W. Rational design of stable lyophilized protein formulations: some practical advice. Pharm. Res. 14:1997;969-974.
41. De Jaeghere F., Allémann E., Leroux J.C., Stevels W., Feijen J., Doelker E., Gurny R. Formulation and lyoprotection of poly(lactic acid-co-ethylene oxide) nanoparticles: influence on physical stability and in vitro cell uptake. Pharm. Res. 16:1999;859-866.
42. Murakami H., Kawashima Y., Niwa T., Hino T., Takeuchi H., Kobayashi M. Influence of the degree of hydrolyzation and polymerization of poly(vinyl alcohol) on the preparation and properties of poly(D,L-lactide-co-glycolide) nanoparticle. Int. J. Pharm. 149:1997;43-49.
43. Tonnesen H.H. Formulation and stability testing of photolabile drugs. Int. J. Pharm. 225:2001;1-14.
44. Jeffery H., Davis S.S., O'Hagan D.T. The preparation and characterization of poly(lactide-co-glycolide) microparticles. II: The entrapment of a model protein using a (water-in-oil)-in-water emulsion solvent evaporation technique. Pharm. Res. 10:1993;362-368.
45. Jain R., Shah N.H., Malick A.W., Rhodes C.T. Controlled drug delivery by biodegradable poly(ester) devices: different preparative approaches. Drug Dev. Ind. Pharm. 24:1998;703-727.