Biodegradation of Poly(alkylcyanoacrylates)
Dr. Christine Vauthier
- [email protected]
- +33-1-46835386 | Fax: +33-1-46619334
Université de Paris XI, Laboratoire de Physico-chimie, Pharmacotechnie et Biopharmacie, UMR CNRS 8612, 5 Rue Jean Baptiste Clément, Chatenay-Malabry Cedex, France, 92 296
Search for more papers by this authorProf. Patrick Couvreur
- [email protected]
- 33-1-46835396 | Fax: +33-1-46619334
Université de Paris XI, Laboratoire de Physico-chimie, Pharmacotechnie et Biopharmacie, UMR CNRS 8612, 5 Rue Jean Baptiste Clément, Chatenay-Malabry Cedex, France, 92 296
Search for more papers by this authorDr. Christine Vauthier
- [email protected]
- +33-1-46835386 | Fax: +33-1-46619334
Université de Paris XI, Laboratoire de Physico-chimie, Pharmacotechnie et Biopharmacie, UMR CNRS 8612, 5 Rue Jean Baptiste Clément, Chatenay-Malabry Cedex, France, 92 296
Search for more papers by this authorProf. Patrick Couvreur
- [email protected]
- 33-1-46835396 | Fax: +33-1-46619334
Université de Paris XI, Laboratoire de Physico-chimie, Pharmacotechnie et Biopharmacie, UMR CNRS 8612, 5 Rue Jean Baptiste Clément, Chatenay-Malabry Cedex, France, 92 296
Search for more papers by this authorAbstract
- Introduction
- Historical Outline
- Synthesis and Purification of Alkylcyanoacrylate Monomers
- Polymer Synthesis
- General Considerations
- Bulk Polymerization
- Polymerization in Organic Solvents
- Emulsion Polymerization: Preparation of Matricial PACA Nanoparticles (Nanospheres)
- Interfacial Polymerization: Preparation of Reservoir-Type PACA Nanoparticles (Nanocapsules)
- Synthesis of Amphiphilic Block Copolymers Containing PACA Segments
- World Market
- Characterization and Methods of Analysis
- Stability and Mechanism of Degradation
- Toxicity
- Application of PACA in the Design of Drug Delivery Systems
- Use of “Conventional” PACA Nanoparticles
- Treatment of Cancer
- Controlled Delivery of Peptides and Proteins
- Delivery of Oligonucleotides
- Delivery of Anti-Infectious Agents
- PACA Nanospheres in Ocular Therapy
- From “Conventional” to Targeted Systems
- Use of “Conventional” PACA Nanoparticles
- Patent Overview
- Outlook and Perspectives
References
-
Aboubakar, M.,
Puisieux, F.,
Couvreur, P.,
Deyme, M.,
Vauthier, C.
(1999)
Study of the mechanism of insulin encapsulation in poly(isobutylcyanoacrylate) nanocapsules obtained by interfacial polymerization,
J. Biomed. Mater. Res. 47,
568–576.
10.1002/(SICI)1097-4636(19991215)47:4<568::AID-JBM14>3.0.CO;2-X CAS PubMed Web of Science® Google Scholar
- Aboubakar, M., Couvreur, P., Pinto-Alphandary, H., Gouritin, B., Lacour, B., Farinotti, R., Puisieux, F., Vauthier, C. (2000) Insulin-loaded nanocapsules for oral administration: in vitro and in vivo investigation, Drug Dev. Res. 49, 109–117.
-
Al Khoury-Fallouh, N.,
Roblot-Treupel, L.,
Fessi, H.,
Devissaguet, J. P.,
Puisieux, F.
(1986)
Development of a new process for the manufacture of poly(isobutylcyanoacrylate) nanocapsules,
Int. J. Pharm. 28,
125–136.
10.1016/0378-5173(86)90236-X Google Scholar
- Alonso, M. J., Sanchez, A., Torres, D., Seijo, B., Vila-Jato, J. L. (1990) Joint effect of monomer and stabilizer concentrations on the physico-chemical characteristics of poly(butyl-2-cyanoacrylate) nanoparticles, J. Microencapsulation 7, 517–526.
- Ammoury, N., Fessi, H., Devissaguet, J. P., Puisieux, F., Benita, S. (1989) Physicochemical characterization of polymeric nanocapsules and in vitro release of indomethacin as a drug model, S.T.P. Pharma 5, 642–646.
- Andrade, J. D., Hlady, V. (1986) Protein adsorption and materials biocompatibility: A tutorial review and suggested hypotheses, Adv. Polym. Sci. 79, 1–63.
- Anger, S., Caldwell, K., Niehus, H., Muller, R. H. (1999) High resolution size determination of 20 nm colloidal gold particles by SedFFF, Pharm. Res. 16, 1743–1747.
- Arias, J. L., Gallardo, V., Gõmez-Lopera, S. A., Plaza, R. C., Delgado, A. V. (2001) Synthesis and characterization of poly(ethyl-2-cyanoacrylate nanoparticles with a magnetic core, J. Controlled. Rel. 77, 309–321.
- Aynié, I., Vauthier, C., Foulquier, M., Malvy, C., Fattal, E., Couvreur, P. (1996) Development of a quantitative polyacrylamide gel electrophoresis analysis using a multichannel radioactivity, Anal. Biochem. 240, 202–209.
- Balland, O., Pinto-Alphandary, H., Pecquet, S., Andremont, A., Couvreur, P. (1994) The uptake of ampicillin-loaded nanoparticles by murine macrophages infected with Salmonella typhimurium, J. Antimicrob. Chemother. 33, 509–522.
- Barratt, G. (1999) Characterization of colloidal drug carrier systems with zeta potential measurements, Pharmaceutical Technology Europe January, 25–32.
-
Barratt, G.,
Couarraze, G.,
Couvreur, P.,
Dubernet, C.,
Fattal, E.,
Gref, R.,
Labarre, D.,
Legrand, P.,
Ponchel, G.,
Vauthier, C.
(2001)
Polymeric micro and nanoparticles as drug carriers, in: Polymeric Biomaterials, Second Edition ( S. Dumitriu Ed.), New York: Marcel Dekker, Chapter 28,
753–782.
10.1093/nar/29.3.753 Google Scholar
- Bennis, S., Chapey, C., Couvreur, P., Robert, J. (1993) Enhanced cytotoxicity of doxorubicin encapsulated in polyisohexylcyanoacrylate nanospheres against multidrug-resistant tumor cells in culture, Eur. J. Cancer 30A, 89–96.
- Bevington, J. C., Jemmett, J. A. L. (1973) Polymerization of methyl α-cyanoacrylate. I. Initiation by benzoyl peroxide, J. Chem. Soc. Farady Trans. I. 69, 1866–1871.
- Bevington, J. C., Jemmett, J. A. L., Onyon, P. F. (1976) Polymerization of methyl α-cyanoacrylate. II. Conditions for radical polymerization, Eur. Polym. J. 12, 255–257.
- Birkinshaw, C., Pepper, D. C. (1986) The thermal degradation of polymers of n-butylcyanoacrylate prepared using tertiary phosphine and amine initiators, Polym. Degrad. Stab. 16, 241–259.
- Blunk, T., Hochstrasser, D. F., Sanchez, J. C., Muller, B. W., Muller, R. H. (1993) Colloidal carriers for i.v. drug targeting: plasma protein adsorption patterns on surface modified latex particles evaluated by two-dimensional polyacrylamide gel electrophoresis, Electrophoresis 14, 1382–1387.
- Brasseur, F., Couvreur, P., Kante, B., Deckers-Passau, L., Roland, M., Deckers, C., Speiser, P. (1986) Actinomycin D adsorbed on polymethylcyanoacrylate nanoparticles: increased efficiency against an experimental tumor, Eur. J. Cancer 16, 1441– 1445.
- Brasseur, F., Verdun, C., Couvreur, P., Deckers, C., Roland, M. (1987) Therapeutic efficacy of doxorubicin associated with poly(alkylcyanoacrylate), Chim. Oggi. 9, 17–21.
- Brigger, I., Chaminade, P., Desmaële, D., Peracchia, M. T., D'Angelo, J., Gurny, R., Renoir, M., Couvreur, P. (2000) Near infrared with principal component analysis as a novel analytical approach for nanoparticle technology, Pharm. Res. 17 1124–1132.
- Brigger, I., Chaminade, P., Marsaud, V., Appel, M., Besnard, M., Gurny, R., Renoir, M., Couvreur, P. (2001) Tamoxifen encapsulation within polyethylene glycol-coated nanospheres. A new antiestrogen formulation, Int. J. Pharm. 214, 37–42.
- Burns, D. T., Brown, J. K., Dinsmore, A., Harvey, K. (1998) Base-activated latent fingerprints fumed with a cyanoacrylate monomer. A quantitative study using Fourier-transformed infra-red spectroscopy, Anal. Chim. Acta 362, 171–176.
- Calvo, P., Gouritin, B., Chacun, H., Desmaële, D., D'Angelo, J., Noël, J. P., Georgin, D., Fattal, E., Andreux, J. P., Couvreur, P. (2001a) Long-circulating polycyanoacrylate nanoparticles as new drug carrier for brain delivery, Pharm. Res. 18, 1157–1166.
- Calvo, P., Gouritin, B., Brigger, I., Lasmezas, C., Deslys, J. P., Williams, A., Andreux, J. P., Dormont, D., Couvreur, P. (2001b) PEGylated polycyanoacrylate nanoparticles as vector for drug delivery in prion diseases, J. Neurosci. Methods 111, 151–155.
- Canale, A. J., Goode, W. E., Kinsinger, J. B., Panchak, J. R., Kelso, R. L., Graham, R. K. (1960) Methyl α-cyanoacrylate. I. Free-radical homopolymerization, J. Appl. Polym. Sci. 4, 231–236.
- Cartensen, H., Muller, B. W., Muller, R. H. (1991) Adsorption of ethoxylated surfactants on nanoparticles. I. Characterization by hydrophobic interaction chromatography, Int. J. Pharm. 67, 29–37.
- Chauvet, A., Masse, J., Egea, M. A., Valero, J., Garcia, M. L. (1993) Analyse thermique de nanoparticules à base de poly(alkylcyanoacrylate) et évaluation quantitative des différents constituants, Thermochim. Acta 220, 151–168.
- Chavany, C., Le Doan, T., Couvreur, P., Puisieux, F., Helene, C. (1992) Polyalkylcyanoacrylate nanoparticles as polymeric carriers for antisense oligonucleotides, Pharm. Res. 9, 441–449
- Chavany, C., Saison-Behmoaras, T., Le Doan, T., Puisieux, F., Couvreur, P., Helene, C. (1994) Adsorption of oligonucleotides onto polyisohexylcyanoacrylate nanoparticles protects them against nucleases and increases their cellular uptake, Pharm. Res. 11, 1370–1378.
- Chiannikulchai, N., Driouich, Z., Benoit, J. P., Parodi, A. L., Couvreur, P. (1989) Doxorubicin-loaded nanoparticles: increased efficiency in murine hepatic metastases, Select. Cancer Ther. 5, 1–11.
- Chiannikulchai, N., Ammoury, N., Caillou, B., Devissaguet, J. P., Couvreur, P. (1990) Hepatic tissue distribution of doxorubicin-loaded nanoparticles after i.v. administration in M5076 metastasis-bearing mice, Cancer Chemother. Pharmacol. 26, 122–126.
- Choi, Y. K., Kim, Y. H., Kim, S. W. (1995) Block copolymer nanoparticles of ethylene oxide and isobutyl cyanoacrylate, Macromolecules 28, 8419–8421.
- Chouinard, F., Kan, F. W. F., Leroux, J. C., Foucher, C., Lenaerts, V. (1991) Preparation and purification of polyisohexylcyanoacrylate nanocapsules, Int. J. Pharm. 71, 211–217.
- Ciapetti, G., Stea, S., Cenni, E., Sudanese, A., Marraro, D., Toni, A., Pizzoferrato, A. (1994a) Cytotoxicity testing of cyanoacrylates using direct contact assay on cell culture, Biomaterials, 15, 63–67.
- Ciapetti, G., Stea, S., Cenni, E., Sudanese, A., Marraro, D., Toni, A., Pizzoferrato, A. (1994b) Toxicity of cyanoacrylates in vitro using extract dilution assay on cell cultures, Biomaterials 15, 92–96.
- Colin de Verdière, A., Dubernet, C., Nemati, F., Poupon, M. F., Puisieux, F., Couvreur, P. (1994) Uptake of doxorubicin from loaded nanoparticles in multidrug-resistant leukemic murine cells, Cancer Chemother. Pharmacol. 33, 504–508.
- Colin de Verdière, A., Dubernet, C., Nemati, F., Soma, E., Appel, M., Ferté, J., Bernard, S., Puisieux, F., Couvreur, P. (1997) Reversion of multidrug resistance with polyalkylcyanoacrylate nanoparticles: mechanism of action, Br. J. Cancer, 76, 198–205
- Cooper, A. W., Harris, P. J., Kumar, G. K., Tebby, J. C. (1989) Hydrolysis of alkylcyanoacrylate and ethoxycarbonylpropenoylphosphonate polymers, J. Polym. Sci. Part A: Polym. Chem. 27, 1967–1974.
- Coover, H. W., Dreifus, D. W., O'Connor, J. T. (1990) Cyanoacrylate adhesives, in: Handbook of Adhesives, Third Edition ( I. Skeist, Ed.), New York: Van Nostrand Reinhold, 463–477.
- Costa, G., Cronin, J. P., Pepper, D. C., Loonan, C. (1983) Termination and transfer by acids in the pyridine-initiated polymerization of butyl cyanoacrylate, Eur. Polym. J. 19, 939–945.
- Couvreur, P., Kante, B., Roland, M., Guiot, P., Bauduin, P., Speiser, P. (1979) Polycyanoacrylate nanocapsules as potential lysosomotropic carriers: preparation, morphological and sorptive properties, J. Pharm. Pharmacol. 31, 331–332.
- Couvreur, P., Kante, B., Roland, M. (1980) Les vecteurs lysosomotropes, J. Pharm. Belg. 35, 51–60.
- Couvreur, P., Kante, B., Grislain, L., Roland, M., Speiser, P. (1982) Toxicity of polyalkycyanoacrylate nanoparticles. II. Doxorubicin-loaded nanoparticles, J. Pharm. Sci. 71, 790–792.
- Couvreur, C., Grislain, L., Lenaerts, V., Brasseur, F., Guiot, P., Biornacki, A. (1986) Biodegradable polymeric nanoparticles as drug carrier for antitumor agents, in: Polymeric Nanoparticles and Microspheres ( P. Guiot, P. Couvreur, Eds.), Boca Raton: CRC Press, 27–93.
- Couvreur, P., Vrancks, H., Brasseur, F., Roland, M. (1989) Toxicité des nanoparticles à base de polycyanoacrylates d'alkyle, S.T.P. Pharma Sci. 5, 31–37.
- Couvreur, P., Barratt, G., Fattal, E., Legrand, P., Vauthier, C. (2002) Nanocapsule technology: a review. Crit. Rev. Drug Deliv. Systems, (accepted for publication).
- Cronin, J. P., Pepper, D. C. (1988) Zwitterionic polymerization of butyl cyanoacrylate by triphenylphosphine and pyridine, Makromol.Chem. 189, 85–102.
- Cuvier, C., Roblot-Treupel, L., Chevillard, S., Millot, J. M., Manfait, M., Bastein, G., Couvreur, P., Poupon, M. F. (1992) Doxorubicin-loaded nanoparticles bypass tumor multidrug resistance, Biochem. Pharmacol. 44, 509–517.
- Daeman, T., Regts, J., Meesters, M., Ten Kate, M. T., Bakker-Woudenberg, I. A. J. M., Scherphof, G. (1997) Toxicity of doxorubicin entrapped within long-circulating liposomes, J. Controlled Rel. 44, 1–9.
- Damgé, C., Michel, C., Aprahamian, M., Couvreur, P. (1988) New approach for oral administration of insulin with polyalkylcyanoacrylate nanocapsules as drug carrier, Diabetes 37, 246–251.
- Damgé, C., Michel, C., Aprahamian, M., Couvreur, P., Devissaguet, J. P. (1990) Nanocapsules as carriers for oral peptide delivery, J. Controlled Rel. 13, 233–239.
- Damgé, C., Vonderscher, J., Marbach, P., Pinget, M. (1997) Poly(alkylcyanoacrylate) nanocapsules as a delivery system in the rat for octreotide, a long-acting somatostatin analogue, J. Pharm. Pharmacol. 49, 949–954.
- Desai, S. D., Blanchard, J. (2000) Pluronic F127-based ocular delivery systems containing biodegradable polyisobutylcyanoacrylate nanocapsules of pilocarpine, J. Delivery Targeting Therap. Agents 7, 201–207.
- Diepold, R., Kreuter, J., Guggenbuhl, P., Robinson, J. R. (1989) Distribution of poly-hexyl-2-cyano-[3-14C]acrylate nanoparticles in healthy and chronically inflamed rabbit eyes, Int. J. Pharm. 54, 149–153.
- Dikov, V., Kotzev, D., Kabaivanov, V. (1988) Polymerization of ethyl 2-cyanoacrylate in the presence of poly(butadiene-co-acrylonitrile), Br. Polym. J. 20, 9–12.
- Donnelly, E. F., Pepper, D. C. (1981) Solubilities, viscosities and unperturbed dimensions of poly(ethyl cyanoacrylate)s and poly(butyl cyanoacrylate)s, Makromol. Chem. Rap. Comm. 2, 439–442.
- Donnelly, E. F., Johnston, D. S., Pepper, D. C. (1977) Ionic and zwitterionic polymerization of n-alkyl 2-cyanoacrylates, Polymer Lett. Ed. 15, 399–405.
- Douglas, S. J., Illum, L., Davis, S. S. (1985) Particle size and size distribution of poly(butyl 2-cyanoacrylate) nanoparticles. II. Influence of stabilizers, J. Colloid Interface Sci. 103, 154–163.
- Douglas, S. J., Illum, L., Davis, S. S. (1986a) Poly(butyl-2-cyanoacrylate) nanoparticles with differing surface charges, J. Controlled Rel. 3, 15–23.
- Douglas, S. J., Davis, S. S., Illum, L. (1986b) Biodistribution of poly(butyl 2-cyanoacrylate) nanoparticles in rabbits, Int. J. Pharm. 34, 145–152.
- Duchene, D., Wouessidjewe, D., Ponchel, G. (1999) Cyclodextrins and carrier systems, J. Controlled Rel. 62, 263–268.
- El-Samaligy, M. S., Rojanasakul, Y., Charlton, J. F., Weinstein, G. W., Lim, J. K. (1996) Ocular disposition of nanoencapsulated acyclovir and ganciclovir via intravitreal injection in rabbit's eye, Drug Delivery 3, 93–97.
- Eromosele, I. C. (1991) Effect of acetic acid on the polymerization of butylcyanoacrylate by tetrabutylammonium acetate in tetrahydrofuran, J. Macromol. Sci. Chem. A28, 347–358.
- Eromosele, I. C., Pepper, D. C. (1989a) Anionic polymerization of butyl cyanoacrylate by tetrabutylammonium salts, 1. Initiation processes, Makromol. Chem. 190, 3085–3094.
- Eromosele, I. C., Pepper, D. C. (1989b) Anionic polymerization of butyl cyanoacrylate by tetrabutylammonium salts, 2. Propagation rate constants, Makromol. Chem. 190, 3095–3103.
- Eromosele, I. C., Pepper, D. C., Ryan, B. (1989) Water effects on the zwitterionic polymerization of cyanoacrylates, Makromol. Chem. 190, 1613–1622.
- Fattal, E., Vauthier, C. (2002) Nanoparticles as drug delivery systems, in: Encyclopedia of Pharmaceutical Technology ( J. Swarbrick, J. C. Boylan, Eds.), New York: Marcel Dekker, 1874–1892.
- Fattal, E., Youssef, M., Couvreur, P., Andremont, A. (1989) Treatment of experimental salmonellosis in mice with ampicillin-bound nanoparticles, Antimicrob. Agents Chemother. 33, 1540–1543.
- Fattal, E., Peracchia, M. T., Couvreur, P. (1997) Poly(alkylcyanoacrylates), in: Handbook of Biodegradable Polymers ( A. J. Dombs, J. Kost, D. M. Wisenman, Eds.), Amsterdam: Harwood Academic Publishers, Chapter 10, 183–202.
- Fattal, E., Vauthier, C., Aynié, I., Nakada, Y., Lambert, G., Malvy, C., Couvreur, P. (1998) Biodegradable polyalkycyanoacrylate nanoparticles for the delivery of oligonucleotides, J. Controlled Rel. 53, 137–143.
- Fernàndez-Urrusuno, R., Fattal, E., Porquet, D., Feger, J., Couvreur, P. (1995) Evaluation of liver toxicological effects induced by polyalkylcyanoacrylate nanoparticles, Toxicol. Appl. Pharmacol. 130, 272–279.
-
Fernàndez-Urrusuno, R.,
Fattal, E.,
Rodrigues, J. M., Jr.,
Féger, J.,
Bedossa, P.,
Couvreur, P.
(1996)
Effect of polymeric nanoparticle administration on the clearance activity of the mononuclear phagocyte system in mice,
J. Biomed. Mater. Res. 31,
401–408.
10.1002/(SICI)1097-4636(199607)31:3<401::AID-JBM15>3.0.CO;2-L CAS PubMed Web of Science® Google Scholar
- Fernàndez-Urrusuno, R., Fattal, E., Féger, J., Couvreur, P., Thérond, P. (1997) Evaluation of hepatic antioxidant systems after intravenous administration of polymeric nanoparticles, Biomaterials, 18, 511–517.
- Forestier, F., Gerrier, P., Chaumard, C., Quéro, A. M., Couvreur, P., Labarre, C. (1992) Effect of nanoparticle-bound ampicillin on the survival of Listeria monocytogenes in mouse peritoneal macrophages, J. Antimicrob. Chemother. 30, 173–179.
- Fouarge, M., Dewulf, M., Couvreur, P., Roland, M., Vrancks, H. (1989) Development of dehydroemetine nanoparticles for the treatment of visceral leishmaniasis, J. Microencapsulation 6, 29–34.
- Fresta, M., Puglisi, G., Giommona, G., Cavallaro, G., Micali, N., Furneri, P. M. (1995) Pefloxacin mesilate- and ofloxacin-loaded polyethylcyanoacrylate nanoparticles: characterization of the colloidal drug carrier formulation, J. Pharm. Sci. 84, 895–901.
- Fresta, M., Cavallaro, G., Giammona, G., Wehrli, E., Puglisi, G. (1996) Preparation and characterization of polyethyl-2-cyanoacrylate nanocapsules containing antiepileptic drugs, Biomaterials 17, 751–758.
- Fresta, M., Fontana, G., Bucolo, C., Cavallaro, G., Giammona, G., Puglisi, G. (2001) Ocular tolerability and in vivo bioavailability of poly(ethylene glycol) (PEG)-coated polyethyl-2-cyanoacrylate nanospheres-encapsulated acyclovir, J. Pharm. Sci. 90, 288–297.
- Gallardo, M. M., Roblot-Treupel, L., Mahuteau, J., Genin, I., Couvreur, P., Plat, M., Puisieux, F. (1989) Proceedings, 5th International Congress Pharm. Technol., Chatenay-Malabry, France: Assoc. Pharm. Galenique Ind., Volume 4, 46–47.
- Gallardo, M. M., Couarraze, G., Denizot, B., Treupel, L., Couvreur, P., Puisieux, F. (1993) Preparation and purification of isohexylcyanoacrylate nanocapsules, Int. J. Pharm. 100, 55–64.
- Gasco, M., Trotta, M. (1986) Nanoparticles from microemulsions, Int. J. Pharm. 29, 267–268.
- Gaspar, R., Opperdoes, F. R., Preat, V., Roland, M. (1992a) Drug targeting with polyalkylcyanoacrylate nanoparticles – in vitro activity of primaquine-loaded nanoparticles against intracellular Leishmania donovani, Ann. Trop. Med. Parasitol. 86, 41–49.
- Gaspar, R., Preat, V., Opperdoes, F. R., Roland, M. (1992b) Macrophage activation by polymeric nanoparticles of poly(alkylcyanoacrylates): activity against Leishmania donovani associated with hydrogen peroxide production, Pharm. Res. 9, 782–787.
- Gautier, J. C., Grangier, J. L., Barbier, A., Dupont, P., Dussosoy, D., Pastor, G., Couvreur, P. (1992) Biodegradable nanoparticles for subcutaneous administration of growth hormone releasing factor (hgrf), J. Controlled Rel. 3, 205–210.
- Ghanem, G. E., Joubran, C., Arnould, R., Lejeune, F., Fruhling, J. (1993) Labelled polycyanoacrylate nanoparticles for human in vivo use, Appl. Radiat. Isot. 44, 1219–1224.
- Gibaud, S., Andreux, J. P., Weingarten, C., Renard, M., Couvreur, P. (1994) Increased bone marrow toxicity of doxorubicin bound to nanoparticles, Eur. J. Cancer 30A, 820–826.
- Gibaud, S., Rousseau, C., Weingarten, C., Favier, R., Douay, L., Andreux, J. P., Couvreur, P. (1998) Polyalkylcyanoacrylate nanoparticles as carriers for granulocyte-colony stimulating factor (g-csf), J. Controlled. Rel. 52, 131–139.
- Giddings, J. C. (1993) Field-flow fractionation: analysis of macromolecular, colloidal and particular materials, Science, 260, 1456–1465.
- Grangier, J. L., Puygrenier, M., Gautier, J. C., Couvreur, P. (1991) Nanoparticles as carriers for growth hormone releasing factor, J. Controlled Rel. 15, 3–13.
- Grislain, L., Couvreur, P., Lenaerts, V., Roland, M. (1983) Pharmacokinetics and biodistribution of a biodegradable drug-carrier, Int. J. Pharm. 15, 335–345.
- Guize, V., Drouin, J. Y., Benoit, J., Mahuteau, J., Dumont, P., Couvreur, P. (1990) Vidarabine-loaded nanoparticles: a physicochemical study, Pharm. Res. 7, 736–741.
- Henderson, A. M., Stephenson, M. (1992) 3-methoxybutylcyanoacrylate: evaluation of biocompatibility and bioresorption, Biomaterials 13, 1077–1084.
- Huve, P., Verrecchia, T., Bazile, D., Vauthier, C., Couvreur, P. (1994) Simultaneous use of size exclusion chromatography and photon correlation spectroscopy for poly(lactic acid) nanoparticle characterization, Chromatographia 675, 129–139.
- Ibrahim, A., Couvreur, P., Roland, M., Speiser, P. (1983) New magnetic drug carrier, J. Pharm. Pharmacol. 35, 59–61.
- Illum, L., Davis, S. S., Muller, R. H., Mak, E., West, P. (1987) The organ distribution and circulation of intravenously injected colloidal carriers sterically stabilized with a block copolymer – poloxamin 908, Life Sci. 40, 356–374.
- Irache, J., Durrer, C., Ponchel, G., Duchene, D. (1993) Determination of nanoparticle concentration in latexes by turbidimetry, Int. J. Pharm. 90, R9–R12.
- Jaffre, H., Wade, C. W. R., Hegyeli, A. F., Rice, R., Hodge, J. (1986) Synthesis and bioevaluation of alkyl-2-cyanoacryloyl glycolate as potential soft tissue adhesives, J. Biomed. Mater. Res. 20, 205–212.
- Jeon, S. I., Lee, J. H., Andrade, J. D., De Gennes, P. G. (1991) Protein-surface interactions in the presence of polyethylene oxide, J. Colloid Interface Sci. 142, 149–158.
- Kante, B., Couvreur, P., Dubois-Krack, G., De Meester, C., Guiot, P., Roland, M., Mercier, M., Speiser, P. (1982) Toxicity of polyalkylcyanoacrylate nanoparticles I: Free nanoparticles, J. Pharm. Sci., 71, 786–790.
- Kattan, J., Droz, J. P., Couvreur, P., Marino, J. P., Boutan-Laroze, A., Rougier, P., Brault, P., Vranckx, H., Grognet, J. M., Morge, X., Sancho-Garnier, H. (1992) Phase I clinical trial and pharmacokinetic evaluation of doxorubicin carried by polyisohexylcyanoacrylate nanoparticles, Invest. New Drugs 10, 191–199.
- Kreuter, J. (1983) Physico-chemical characterization of polyacrylic nanoparticles, Int. J. Pharm. 14, 43–58.
- Kreuter, J. (1994) Nanoparticles, in: Colloidal Drug Delivery Systems ( J. Kreuter, Ed.), New York: Marcel Dekker, 219–342.
- Kulkarni, R. K., Porter, H. J., Leonard, F. (1973) Glass transition temperature of poly(alkylcyanoacrylates), J. Appl. Polym. Sci. 17, 3509–3514.
- Labib, A., Lenaerts, V., Chouinard, F., Leroux, J. C., Ouellet, R., Van Lier, J. E. (1991) Biodegradable nanospheres containing phthalocyanines and naphthalocyanines for targeted photodynamic tumor therapy, Pharm. Res. 8, 1027–1031.
- Lambert, G., Fattal, E., Brehier, A., Feger, J., Couvreur, P. (1998) Effect of polyisobutylcyanoacrylate nanoparticles and lipofectin loaded with oligonucleotides on cell viability and PKC alpha neosynthesis in HepG2 cells, Biochimie 80, 969–976.
- Lambert, G., Fattal, E., Pinto-Alphandary, H., Gulik, A., Couvreur, P. (2000) Polyisobutylcyanoacrylate nanocapsules containing an aqueous core as a novel colloidal carrier for the delivery of oligonucleotides, Pharm. Res. 17, 707–714.
- Lambert, G., Bertrand, J. R., Fattal, E., Subra, F., Pinto-Alphandary, H., Malvy, C., Auclair, C., Couvreur, P. (2001a) EWS Fli-1 antisense nanocapsules inhibits Ewing sarcoma-related tumor in mice, Biochem. Biophys. Res. Commun. 279, 401–406.
- Lambert, G., Fattal, E., Couvreur, P. (2001b) Nanoparticulate systems for the delivery of antisense oligonucleotides, Int. J. Pharm. 47, 99–112.
- Langer, K., Seegmüller, E., Zimmer, A., Kreuter, J. (1994) Characterization of polybutylcyanoacrylate nanoparticles: Quantification of PBCA polymer and dextran, Int. J. Pharm. 110, 21–27.
- Lenaerts, V., Raymond, P., Juhasz, J., Simard, M. A., Jolicoeur, C. (1989) New method for the preparation of cyanoacrylic nanoparticles with improved colloidal properties, J. Pharm. Sci. 78, 1051–1052.
- Leonard, F., Kulkarni, R. K., Brandes, G., Nelson, J., Cameron, J. J. (1966) Synthesis and degradation of poly(alkyl α-cyanoacrylates), J. Appl. Polym. Sci. 10, 259–272.
- Lescure, F., Zimmer, C., Roy, D., Couvreur, P. (1992) Optimization of polycyanoacrylate nanoparticle preparation: Influence of sulfur dioxide and pH on nanoparticle characteristics, J. Colloid Interface Sci. 154, 77–86.
- Ley, D., Couvreur, P., Lenaerts, V., Roland, M, Speiser, P. (1984) Etude du mécanisme de dégradation des nanoparticules de polycyanoacrylate d'alkyle, Labo Pharma-Probl. Tech. 32, 100–104.
- Li, Y. P., Pei, Y. Y., Zhou, Z. H., Zhang, X. Y., Gu, Z. H., Ding, J., Zhou, J. J., Gao, X. J., Zhu, J. H. (2001a) Stealth polycyanoacrylate nanoparticles as tumor necrosis factor-α carriers: pharmacokinetics and anti-tumor effects, Biol. Pharm. Bull. 24, 662–665.
- Li, Y. P., Pei, Y. Y., Zhou, Z. H., Zhang, X. Y., Gu, Z. H., Ding, J., Zhou, J. J., Gao, X. J. (2001b) PEGylated polycyanoacrylate nanoparticles as tumor necrosis factor-α carrier, J. Controlled Rel. 71, 287–296.
- Lowe, P. J., Temple, C. S. (1994) Calcitonin and insulin in isobutylcyanoacrylate nanocapsules: protection against proteases and effect on intestinal absorption in rats, J. Pharm. Pharmacol. 46, 547–552.
- Marchal-Heussler, L., Fessi, H., Devissaguet, J. P., Hoffman, M., Maincent, P. (1992) Colloidal drug delivery systems for the eye. A comparison of the efficacy of three different polymers: polyisobutylcyanoacrylate, polylactic-co-glycolic acid, poly-epsilon-caprolactone, S.T.P. Pharma Sci. 2, 98–104.
- Montanaro, L., Arciola, C. R., Cenni, E., Ciapetti, G., Savioli, F., Filippini, F., Barsanti, L. A. (2001) Cytotoxicity, blood compatibility and antimicrobial activity of two cyanoacrylate glues for surgical use, Biomaterials 22, 59–66.
- Monza da Silveira, A., Ponchel, G., Puisieux, F., Duchène, D. (1998) Combined poly(isobutylcyanoacrylate) and cyclodextrins nanoparticles for enhancing the encapsulation of lipophilic drugs, Pharm. Res. 15, 1051–1055.
- Müller, R. H., Lherm, C., Herbort, J., Couvreur, P. (1990) In vitro model for the degradation of alkylcyanoacrylate nanoparticles, Biomaterials 11, 590–595.
- Nakada, Y., Fattal, E., Foulquier, M., Couvreur, P. (1996) Pharmacokinetics and biodistribution of oligonucleotide adsorbed onto poly(alkylcyanoacrylate) nanoparticles after intravenous administration to mice, Pharm. Res. 13, 38–43.
- Nehan, N., Birkinshaw, C., Clarke, C. (2001) Poly n-butyl cyanoacrylate nanoparticles: a mechanistic study of polymerization and particle formation, Biomaterials 22, 1335–1344.
- Nemati, F., Dubernet, C., Colin de Verdière, A., Poupon, M. F., Treupel-Acar, L., Puisieux, F., Couvreur, P. (1994) Some parameters influencing cytotoxicity of free doxorubicin-loaded nanoparticles in sensitive and multidrug resistant leukemic murine cells: incubation time, number of nanoparticles per cell, Int. J. Pharm. 102, 55–62.
- Olivier, J. C., Taverna, M., Vauthier, C., Couvreur, P., Baylocq-Ferrier, D. (1994) Capillary electrophoresis monitoring of the competitive adsorption of albumin onto the orosomucoid-coated polyisobutylcyanoacrylate nanoparticles, Electrophoresis 15, 234–239.
- Olivier, J. C., Vauthier, C., Taverna, M., Puisieux, F., Ferrier, D., Couvreur, P. (1996) Stability of orosomucoid-coated poly(isobutylcyanoacrylate) nanoparticles in the presence of serum, J. Controlled Rel. 40, 157–168.
- Oowaki, H., Matsuda, S., Sakai, N., Ohta, T., Iwata, H., Sadato, A., Taki, W., Hashimoto, N., Ikada, Y. (2000) Non-adhesive cyanoacrylate as an embolic material for endovascular neurosurgery, Biomaterials 21, 1039–1046.
- Otsu, T., Yamada, B., Kusayama, S., Nagao, S. (1979) Radical copolymerization of ethyl α-cyanoacrylate in the presence of effective inhibitors against anionic polymerization, Kobunshi Ronbunshu 36, 797–802.
- Page-Clisson, M. E., Pinto-Alphandary, H., Chachaty, E., Couvreur, P., Andremont, A. (1998) Drug targeting of polyalkylcyanoacrylate nanoparticles is not efficient against persistent Salmonella, Pharm. Res. 15, 544–549.
- Passirani, C., Barratt, G., Devissaguet, J. P., Labarre, D. (1998) Interactions of nanoparticles bearing heparin or dextran covalently bound to poly(methylmethacrylate) with the complement system, Life Sci. 62, 775–785.
- Pepper, D. C. (1978) Anionic and zwitterionic polymerization of α-cyanoacrylates, J. Polym. Sci.: Polym. Symp. 62, 65–77.
- Peracchia, M. T., Desmaële, D., Couvreur, P., D'Angelo, J. (1997a) Synthesis of a novel poly(MePEG cyanoacrylate-co-alkylcyanoacrylate) amphiphilic copolymer for nanoparticle technology, Macromolecules 30, 846–851.
-
Peracchia, M. T.,
Vauthier, C.,
Puisieux, F.,
Couvreur, P.
(1997b)
Development of sterically stabilized poly(isobutyl 2-cyanoacrylate) nanoparticles by chemical coupling of poly(ethylene glycol),
J. Biomed. Mater. Res. 34,
317–326.
10.1002/(SICI)1097-4636(19970305)34:3<317::AID-JBM6>3.0.CO;2-N CAS PubMed Web of Science® Google Scholar
- Peracchia, M. T., Vauthier, C., Popa, M. I., Puisieux, F., Couvreur, P. (1997c) Investigation of the formation of sterically stabilized poly(ethylene glycol/isobutylcyanoacrylate) nanoparticles by chemical grafting of polyethylene glycol during the polymerization of isobutyl cyanoacrylate, S.T.P. Pharma Sci. 7, 513–520.
- Peracchia, M. T., Vauthier, C., Passirani, C., Couvreur, P., Labarre, D. (1997d) Complement consumption by poly(ethylene glycol) in different conformations chemically coupled to poly(isobutyl 2-cyanoacrylate) nanoparticles, Life Sci. 61, 749–761.
- Peracchia, M. T., Vauthier, C., Desmaële, D., Gulik, A., Dedieu, J. C., Demoy, M., D'Angelo, J., Couvreur, P. (1998a) Pegylated nanoparticles from a novel methoxypolyethylene glycol cyanoacrylate-hexadecyl cyanoacrylate amphiphilic copolymer, Pharm. Res. 15, 548–554.
- Peracchia, M. T., Desmaële, D., Vauthier, C., Labarre, D., Fattal, E., D'Angelo, J., Couvreur, P. (1998b) Development of novel technologies for the synthesis of biodegradable pegylated nanoparticles, in: Targeting of Drugs 6: Strategies for Stealth Therapeutic Systems ( G. Gregoriadis, B McCormack, Eds.), New York: Plenum Press, 225–239.
- Peracchia, M. T., Harnisch, S., Pinto-Alphandary, H., Gulik, A., Dedieu, J. C., Desmaële, D., D'Angelo, J., Muller, R. H., Couvreur, P. (1999a) Visualization of in vitro protein-rejecting properties of PEGylated Stealth® polycyanoacrylate nanoparticles, Biomaterials 20, 1269–1275.
- Peracchia, M. T., Fattal, E., Desmaële, D., Besnard, M., Noël, J. P., Gomis, J. M., Appel, M., D'Angelo, J., Couvreur, P. (1999b) Stealth® PEGylated polycyanoacrylate nanoparticles for intravenous administration and splenic targeting, J. Controlled Rel. 60, 121–128.
- Pinto-Alphandary, H., Balland, O., Laurent, M., Andremont, A., Puisieux, F., Couvreur, P. (1994) Intracellular visualization of ampicillin-loaded nanoparticles in peritoneal macrophages infected in vitro with Salmonella typhimurium, Pharm. Res. 11, 38–46.
- Pinto-Alphandary, H., Aboubakar, M., Jaillard, D., Couvreur, P., Vauthier, C. Visualization of insulin-loaded nanocapsules: in vitro characterization and in vivo study after oral administration to rats. (submitted for publication)
- Pirker, S., Kruse, J., Noe, C., Langer, K., Zimmer, A., Kreuter, J. (1996) Characterization of polybutylcyanoacrylate nanoparticles. Part II: determination of polymer content by NMR-analysis, Int. J. Pharm 128, 189–195.
- Puglisi, G., Fresta, M., Giammona, G., Venture, C. A. (1995) Influence of the preparation conditions in poly(ethylcyanoacrylate) nanocapsules formation, Int. J. Pharm. 125, 283–287.
- Rollot, J. M., Couvreur, P., Roblot-Treupel, L., Puisieux, F. (1986) Physicochemical and morphological characterization of polyisobutyl cyanoacrylate nanocapsules, J. Pharm. Sci., 75, 361–364.
-
Rowell, R. L.
(1990)
Characterization of polymer colloids, in: An Introduction to Polymer Colloids ( F. Candau, R. H. Ottewill, Eds.), Dordrecht, The Netherlands: Kluwer Academic Publishers,
187–208.
10.1007/978-94-009-0521-4_7 Google Scholar
- Rupp, R. A., Hellwig, U., Schellhorn, U., Kohlbrecher, J., Wiedenmann, A., Woods, J. (1997) Study of holographic gratings in poly(methyl-2-cyanoacrylate) by neutron diffraction, Polymer 38, 2299–2305.
- Ryan, B., McCann, G. (1996) Novel sub-ceiling temperature rapid depolymerization-repolymerization reactions of cyanoacrylate polymers, Macromol. Rapid Commun. 17, 217–227.
- Scherer, D., Robinson, J. R., Kreuter, J. (1994) Influence of enzymes on the stability of polybutylcyanoacrylate nanoparticles, Int. J. Pharm. 101, 165–168.
- Schwab, G., Chavany, C., Duroux, I., Goubin, G., Lebeau, J., Helene, C., Saison-Behmoaras, T. (1994) Antisense oligonucleotides adsorbed to polyalkylcyanoacrylate nanoparticles specifically inhibit mutated Ha-ras-mediated cell proliferation and tumorigenicity in nude mice, Proc. Natl. Acad. Sci. USA 91, 10460–10464.
- Seijo, B., Fattal, E., Roblot-Treupel, L., Couvreur, P. (1990) Design of nanoparticles of less than 50 nm diameter: preparation, characterization and drug loading, Int. J. Pharm. 62, 1–7.
- Simeonova, M., Chorbadjiev, K., Antchva, M. (1998) Study of the effect of polybutylcyanoacrylate nanoparticles and their metabolites on primary immune response in mice to sheep red blood cells, Biomaterials 19, 2187–2193.
- Skeist, I., Miron, J. (1977) Adhesive composition, in: Encyclopedia of Polymer Science and Engineering ( N. Bikales, Ed.), New York: Wiley Interscience Inc., Suppl. Volume 2, 1–19.
- Soma, C. E., Dubernet, C., Barratt, G., Nemati, F., Appel, M., Benita, S., Couvreur, P. (1999) Ability of doxorubicin-loaded nanoparticles to overcome multidrug resistance of tumor cells after their capture by macrophages, Pharm. Res. 16, 1710–1716.
- Stein, M., Hamacher, E. (1992) Degradation of polybutyl-2-cyanoacrylate microparticles, Int. J. Pharm. 80, R11–R13.
- Stella, B., Arpicco, S., Peracchia, M. T., Desmaële, D., Hoebeke, J., Renoir, M., D'Angelo, J., Cattel, L., Couvreur, P. (2000) Design of folic acid-conjugated nanoparticles for drug targeting, J. Pharm. Sci. 89, 1452–1464.
- Storm, G., Steerenberg, P. A., Emmen, F., van Borssum Waalkes, M., Crommelin, D. J. A. (1988) Release of doxorubicin from peritoneal macrophages exposed in vivo to doxorubicin-containing liposomes, Biochim. Biophys. Acta 965, 136– 145.
- Tan, J. S., Butterfield, D. E., Voycheck, C. L., Caldwell, K. D., Li, J. T. (1993) Surface modification of nanoparticles by PEO/PPO block copolymers to minimize interactions with blood components and prolong blood circulation in rats, Biomaterials 14, 823–833.
- Treupel, L., Poupon, M. F., Couvreur, P., Puisieux, F. (1991) Vectorisation de la doxorubicine dans des nanosphères et réversion de la résistance pléiotropique des cellules tumorales, Comptes Rendus de l'Académie de Médecine Séries III 313, 171–174
- Tseng, Y. C., Hyon, S. H., Ikada, Y. (1990) Modification of the synthesis and investigation of properties for 2-cyanoacrylates, Biomaterials 11, 73–79.
- Urlaub, E., Popp, J., Roman, V. E., Kiefer, W., Lankers, M., Rössling, G. (1998) Raman spectroscopy monitoring of the polymerization of cyanoacrylate, Chem. Phys. Lett. 298, 177–182.
-
Vansnick, L.,
Couvreur, P.,
Christiaens-Ley, D.,
Roland, M.
(1985)
Molecular weights of free and drug-loaded nanoparticles,
Pharm. Res. 1,
36–41.
10.1023/A:1016366022712 Google Scholar
- Vauthier, C., Schmidt, C., Couvreur, P. (1999) Measurement of the density of polymeric nanoparticulate drug carriers made of poly(alkylcyanoacrylate) and poly(lactic acid) derivatives, J. Nanoparticle Res. 1, 411–418.
- Verdun, C., Couvreur, P., Vranckx, H., Lenaerts, V., Roland, M. (1986) Development of a nanoparticle controlled release formulation for human use, J. Controlled Rel. 3, 205–210.
- Verdun, C., Brasseur, F., Vranckx, H., Couvreur, P., Roland, M. (1990) Tissue distribution of doxorubicin associated with polyisohexyl-cyanoacrylate nanoparticles, Cancer Chemother. Pharmacol. 26, 13–18.
- Vezin, W. R., Florence, A. T. (1980) In vitro heretogenous degradation of poly(n-alkyl α-cyanoacrylates), J. Biomed. Mater. Res. 14, 93–106.
- Vittaz, M., Bazile, D., Spenlehauer, G., Verrecchia, T., Veillard, M., Puisieux, F., Couvreur, P. (1996) Effect of PEO surface density on long circulating PLA-PEO nanoparticles which are very low complement activators, Biomaterials 17, 1575–1581.
- Vranckx, H., Demoustier, M., Deleers, M. (1996) A new nanocapsule formulation with hydrophilic core: application to the oral administration of salmon calcitonin in rats, Eur. J. Pharm. Biopharm. 42, 345–347.
- Watnasirichaikul, S., Davies, N. M., Rades, R., Tucker, I. G. (2000) Preparation of biodegradable insulin nanocapsules from biocompatible microemulsions, Pharm. Res. 17, 684–689.
- Wohlgemuth, M., Mächtle, W., Mayer, C. (2000) Improved preparation and physical studies of polybutylcyanoacrylate nanocapsules, J. Microencapsulation 17, 437–448.
- Yamada, B., Yoshioka, M., Otsu, T. (1983) Determination of absolute rate constants for radical polymerization and copolymerization of ethyl α-cyanoacrylate in the presence of effective inhibitors against anionic polymerization, Makromol. Chem. 184, 1025–1033.
- Yang, S. C., Ge, H. X., Hu, Y., Jiang, X. Q., Yang, C. Z. (2000) Formation of positively charged poly(butyl cyanoacrylate) nanoparticles stabilized by chitosan, Colloid Polym. Sci. 278, 285–292.
- Youssef, M., Fattal, E., Alonso, M. J., Roblot-Treupel, L., Sauzière, C., Omnes, A., Couvreur, P., Andremont, A. (1988) Effectiveness of nanoparticle-bound ampicillin in the treatment of Listeria monocytogenes infection in athymic nude mice, Antimicrob. Agents Chemother. 32, 1204–1207.
- Zimmer, A., Antisense oligonucleotide delivery with polyhexylcyanoacrylate nanoparticles as carriers, Methods: A Companion to Methods in Enzymology 18, 286–295.
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