Poly(alkycyanoacrylate) nanoparticles for enhanced delivery of therapeutics - Is there real potential?

Expert Opinion on Drug Delivery

Volumn 6, Issue 4, 2009, Pages 371-387

  Graf, Anja ^a   McDowell, Arlene ^a   Rades, Thomas ^a  

^a UNIVERSITY OF OTAGO   (New Zealand)

Author keywords

Alkylcyanoacrylate; Microemulsions; Nanoparticles; Oral delivery; Protein delivery

Indexed keywords

ACICLOVIR; AVAROL; BOVINE SERUM ALBUMIN; CALCITONIN; DARODIPINE; DOXORUBICIN; GANCICLOVIR; GONADORELIN; HEPARIN; HUMAN INSULIN; INDOMETACIN; INSULIN; INSULIN LISPRO; IODINATED POPPYSEED OIL; LEUCINE ENKEPHALIN[2 DEXTRO ALANINE 6 ARGININE]; LOPERAMIDE; METHOTREXATE; NANOPARTICLE; NEUTRAL INSULIN; OLIGODEOXYNUCLEOTIDE; PILOCARPINE; POLY(ALKYLCYANOACRYLATE); POLY(BUTYLCYANOACRYLATE); POLY(ETHYLCYANOACRYLATE); POLY(ISOBUTYLCYANOACRYLATE); POLY(ISOHEXYLCYANOACRYLATE); POLYMER; PROBENECID; RECOMBINANT GRANULOCYTE COLONY STIMULATING FACTOR; SAQUINAVIR; UNCLASSIFIED DRUG; UNINDEXED DRUG; CYANOACRYLATE DERIVATIVE; DRUG CARRIER; PEPTIDE; PROTEIN;

BIOCOMPATIBILITY; BIODEGRADABILITY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DEGRADATION; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG PENETRATION; DRUG RELEASE; DRUG SOLUBILITY; DRUG SYNTHESIS; ENCAPSULATION; HUMAN IMMUNODEFICIENCY VIRUS 2; IN VITRO STUDY; IN VIVO CULTURE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MICROEMULSION; MOLECULAR WEIGHT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PHARMACODYNAMICS; POLYMERIZATION; PROTEIN TRANSPORT; REVIEW; ANIMAL; CHEMISTRY; EMULSION; HUMAN; METHODOLOGY;

ANIMALS; CHEMISTRY, PHARMACEUTICAL; CYANOACRYLATES; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; EMULSIONS; HUMANS; NANOPARTICLES; PEPTIDES; POLYMERS; PROTEINS;

EID: 67649134795     PISSN: 17425247     EISSN: None     Source Type: Journal    
DOI: 10.1517/17425240902870413     Document Type: Review

References (126)

1. Vauthier C, Dubernet C, Fattal E, et al. Poly(alkylcyanoacrylates) as biodegradable materials for biomedical applications. Adv Drug Deliv Rev 2003;55(4):519-548 •• This review provides a comprehensive overview of the various applications of poly(alkylcyanoacrylates). (Pubitemid 36423302)
2. Couvreur P, Kante B, Roland M, et al. Polycyanoacrylate nanocapsules as potential lysosomotropic carriers - preparation, morphological and sorptive properties. J Pharm Pharmacol 1979;31(5):331-332 (Pubitemid 9207599)
3. Panyam J, Labhasetwar V. Biodegradable nanoparticles for drug and gene delivery to cells and tissue. Adv Drug Deliv Rev 2003;55(3):329-347 (Pubitemid 36297053)
4. Morishita M, Peppas NA. Is the oral route possible for peptide and protein drug delivery? Drug Discov Today 2006;11(19-20):905-910 • This article provides an excellent summary of the current possibilities in oral peptide and protein delivery.
5. Allemann E, Gurny R, Doelker E. Drug-loaded nanoparticles - preparation methods and drug targeting Issues. Eur J Pharm Biopharm 1993;39(5):173-191 (Pubitemid 23361352)
6. Moghimi SM, Hunter AC, Murray JC. Long-circulating and target-specific nanoparticles: theory to practice. Pharmacol Rev 2001;53(2):283-318
7. BioAlliancePharma. 16/07/2008 BioAlliance Pharma suspends the Phase II/III trial of doxorubicin Transdrug® in primary liver cancer, following advice from the Drug Safety Monitoring Board and the Steering Committee. [Internet publication] 2008; Available from: http://www.bioalliancepharma.com/ [Cited October 2008]
8. Krauel K, Pitaksuteepong T, Davies NM, Rades T. Entrapment of bioactive molecules in poly (alkylcyanoacrylate) nanoparticles. Am J Drug Deliv 2004;2(4):251-259 • This review is a valuable discussion on encapsulation versus sorption and influencing factors. (Pubitemid 40045490)
9. Al Khouri Fallouh N, Roblot-Treupel L, Fessi H, et al. Development of a new process for the manufacture of polyisobutylcyanoacrylate nanocapsules. Int J Pharm 1986;28(2-3):125-132 • This article provides the first description of interfacial polymerisation of PACA using an o/w template. (Pubitemid 16187088)
10. Weiss CK, Ziener U, Landfester K. A route to nonfunctionalized and functionalized poly(n-butylcyanoacrylate) nanoparticles: preparation in miniemulsion. Macromolecules 2007;40(4):928-938 (Pubitemid 46383742)
11. Gasco MR, Trotta M. Nanoparticles from microemulsions. Int J Pharm 1986;29(2-3):267-268 • This article provides the first description of interfacial polymerisation of PACA using microemulsions. (Pubitemid 16102019)
12. Couvreur P. Polyalkylcyanoacrylates as colloidal drug carriers. Crit Rev Ther Drug Carrier Syst 1988;5(1):1-20 (Pubitemid 18159949)
13. Fitch RM, Tsai C-H. Polymer colloids: particle formation in nonmicellar systems. J Polymer Sci B Polym Lett 1970;8(10):703-710
14. Behan N, Birkinshaw C, Clarke N. Poly n-butyl cyanoacrylate nanoparticles: a mechanistic study of polymerisation and particle formation. Biomaterials 2001;22(11):1335-1344 • This article provides a very good explanation of the mechanism of PACA nanoparticle formation. (Pubitemid 32409955)
15. Reddy LH, Murthy RR. Influence of polymerization technique and experimental variables on the particle properties and release kinetics of methotrexate from poly(butylcyanoacrylate) nanoparticles. Acta Pharmaceutica 2004;54(2):103-118 (Pubitemid 38954725)
16. Grangier JL, Puygrenier M, Gautier JC, Couvreur P. Nanoparticles as carriers for growth hormone releasing factor. J Control Release 1991;15(1):3-13
17. Leonard F, Kulkarni RK, Brandes G, et al. Synthesis and degradation of poly (alkyl α-cyanoacrylates). J Appl Polym Sci 1966;10(2):259-272
18. Gibaud S, Rousseau C, Weingarten C, et al. Polyalkylcyanoacrylate nanoparticles as carriers for granulocyte-colony stimulating factor (G-CSF). J Control Release 1998;52(1-2):131-139 (Pubitemid 28123180)
19. Hillery AM, Toth I, Florence AT. Co-polymerised peptide particles II: oral uptake of a novel co-polymeric nanoparticulate delivery system for peptides. J Control Release 1996;42(1):65-73 (Pubitemid 26297877)
20. Hillery AM, Toth I, Shaw AJ, Florence AT. Co-polymerised peptide particles (CPP) I: synthesis, characterisation and in vitro studies on a novel oral nanoparticulate delivery system. J Control Release 1996;41(3):271-281
21. Liang M, Davies NM, Toth I. Increasing entrapment of peptides within poly(alkyl cyanoacrylate) nanoparticles prepared from water-in-oil microemulsions by copolymerization. Int J Pharm 2008;362(1-2):141-146
22. Aboubakar M, Puisieux F, Couvreur P, et al. Study of the mechanism of insulin encapsulation in poly(isobutylcyanoacrylate) nanocapsules obtained by interfacial polymerization. J Biomed Mater Res 1999;47(4):568-576 (Pubitemid 29468562)
23. Kafka A, Kleffmann T, Rades T, McDowell A. The use of MALDI-TOF mass spectrometry to identify co-polymerization in PACA nanoparticles 35th Annual Meeting and Exposition of the Controlled Release Society. New York, New York: Controlled Release Society 2008
24. El-Samaligy MS, Rohdewald P, Mahmoud HA. Polyalkyl cyanoacrylate nanocapsules. J Pharm Pharmacol 1986;38(3):216-218 • This article provides the first description of interfacial polymerisation of PACA using a w/o template. (Pubitemid 16162510)
25. Soppimath KS, Aminabhavi TM, Kulkarni AR, Rudzinski WE. Biodegradable polymeric nanoparticles as drug delivery devices. J Control Release 2001;70(1-2):1-20 (Pubitemid 32144788)
26. Vranckx H, Demoustier M, Deleers M. A new nanocapsule formulation with hydrophilic core: application to the oral administration of salmon calcitonin in rats. Eur J Pharm Biopharm 1996;42(5):345-347 (Pubitemid 26384371)
27. Watnasirichaikul S, Davies NM, Rades T, Tucker IG. Preparation of biodegradable insulin nanocapsules from biocompatible microemulsions. Pharm Res 2000;17(6):684-689 • This article provides the first description of PACA nanoparticles prepared from a w/o microemulsion for oral peptide delivery. (Pubitemid 30670633)
28. Krauel K, Davies NM, Hook S, Rades T. Using different structure types of microemulsions for the preparation of poly(alkylcyanoacrylate) nanoparticles by interfacial polymerization. J Control Release 2005;106(1-2):76-87 • This is the first study done on the use of microemulsions with different structure-types for the preparation of PACA nanoparticles. (Pubitemid 41140083)
29. Holtzscherer C, Durand JP, Candau F. Polymerization of acrylamide in nonionic microemulsions - characterization of the microlatices and polymers formed. Colloid Polym Sci 1987;265(12):1067-1074
30. Krauel K, Graf A, Hook SM, et al. Preparation of poly (alkylcyanoacrylate) nanoparticles by polymerization of water-free microemulsions. J Microencapsul 2006;23(5):499-512 (Pubitemid 44446592)
31. Damgé C, Aprahamian M, Balboni G, et al. Polyalkylcyanoacrylate nanocapsules increase the intestinal absorption of a lipophilic drug. Int J Pharm 1987;36(2-3):121-125 (Pubitemid 17070781)
32. Ritschel WA. Microemulsions for improved peptide absorption from the gastrointestinal-tract. Methods Find Exp Clin Pharmacol 1991;13(3):205-220
33. Watnasirichaikul S, Rades T, Tucker IG, Davies NM. In vitro release and oral bioactivity of insulin in diabetic rats using nanocapsules dispersed in biocompatible microemulsion. J Pharm Pharmacol 2002;54(4):473-480
34. Kawakami K, Yoshikawa T, Hayashi T, et al. Microemulsion formulation for enhanced absorption of poorly soluble drugs - II. In vivo study. J Control Release 2002;81(1-2):75-82 (Pubitemid 34454851)
35. Graf A, Jack KS, Whittaker AK, et al. Protein delivery using nanoparticles based on microemulsions with different structure-types. Eur J Pharm Sci 2008;33(4-5):434-444
36. Graf A, Rades T, Hook SM. Oral insulin delivery using nanoparticles based on microemulsions with different structure-types: optimisation and in vivo evaluation. Eur J Pharm Sci 2009;37(1):53-61 • This is one of the first studies to use PACA nanoparticles based on structurally different microemulsions for oral peptide delivery describing possibilities and limitations.
37. Pitaksuteepong T, Davies NM, Tucker IG, Rades T. Factors influencing the entrapment of hydrophilic compounds in nanocapsules prepared by interfacial polymerisation of water-in-oil microemulsions. Eur J Pharm Biopharm 2002;53(3):335-342 (Pubitemid 34303296)
38. Lambert G, Fattal E, Pinto-Alphandary H, et al. Polyisobutylcyanoacrylate nanocapsules containing an aqueous core as a novel colloidal carrier for the delivery of oligonucleotides. Pharm Res 2000;17(6):707-714 (Pubitemid 30670637)
39. Monza da Silveira A, Ponchel G, Puisieux F, Duchene D, et al. Combined poly(isobutylcyanoacrylate) and cyclodextrins nanoparticles for enhancing the encapsulation of lipophilic drugs. Pharm Res 1998;15(7):1051
40. Duchêne D, Ponchel G, Wouessidjewe D. Cyclodextrins in targeting: application to nanoparticles. Adv Drug Deliv Rev 1999;36(1):29-40
41. Graf A, Ablinger E, Peters S, et al. Microemulsions containing lecithin and sugar-based surfactants: nanoparticle templates for delivery of proteins and peptides. Int J Pharm 2008;350(1-2):351-360
42. Damgé C, Vonderscher J, Marbach P, Pinget M. Poly(alkyl cyanoacrylate) nanocapsules as a delivery system in the rat for octreotide, a long-acting somatostatin analogue. J Pharm Pharmacol 1997;49(10):949-954
43. Hillaireau H, Le Doan T, Chacun H, et al. Encapsulation of mono- and oligo-nucleotides into aqueous-core nanocapsules in presence of various water-soluble polymers. Int J Pharm 2007;331(2):148-152 (Pubitemid 46216668)
44. Damgé C, Michel C, Aprahamian M, Couvreur P. New approach for oral administration of insulin with polyalkylcyanoacrylate nanocapsules as drug carrier. Diabetes 1988;37(2):246-251 (Pubitemid 18066612)
45. Lowe PJ, Temple CS. Calcitonin and insulin in isobutylcyanoacrylate nanocapsules - protection against proteases and effect on intestinal absorption in rats. J Pharm Pharmacol 1994;46(7):547-552 (Pubitemid 24213278)
46. Arias JL, Gallardo V, Ruiz MA, Delgado AV. Ftorafur loading and controlled release from poly(ethyl-2-cyanoacrylate) and poly(butylcyanoacrylate) nanospheres. Int J Pharm 2007;337(1-2):282-290 (Pubitemid 46756034)
47. Cournarie F, Cheron M, Besnard M, Vauthier C. Evidence for restrictive parameters in formulation of insulin-loaded nanocapsules. Eur J Pharm Biopharm 2004;57(2):171-179 •• This is an excellent publication highlighting the various factors that affect the entrapment of insulin in PACA nanoparticles. (Pubitemid 38283692)
48. Müller RH, Lherm C, Herbort J, et al. Alkylcyanoacrylate drug carriers: I. Physicochemical characterization of nanoparticles with different alkyl chain-length. Int J Pharm 1992;84(1):1-11
49. Cournarie F, Auchere D, Chevenne D, et al. Absorption and efficiency of insulin after oral administration of insulin-loaded nanocapsules in diabetic rats. Int J Pharm 2002;242(1-2):325-328 (Pubitemid 34899481)
50. Aboubakar M, Puisieux F, Couvreur P, Vauthier C. Physico-chemical characterization of insulin-loaded poly(isobutylcyanoacrylate) nanocapsules obtained by interfacial polymerization. Int J Pharm 1999;183(1):63-66 (Pubitemid 29248830)
51. Pepper DC. Kinetics and mechanisms of zwitterionic polymerizations of alkyl cyanoacrylates. Polym J 1980;12(9):629-637 (Pubitemid 11461567)
52. Page-Clisson M-E, Gibaud S, Pinto-Alphandary H, et al. Polyisobutylcyanoacrylate nanoparticles as drug carriers: influence of sulfur dioxide on the physico-chemical characteristics of ciprofloxacin- and doxorubicin-loaded nanoparticles. Int J Pharm 1998;166(1):117-120 (Pubitemid 28239745)
53. Lescure F, Zimmer C, Roy D, Couvreur P. Optimization of polyalkylcyanoacrylate nanoparticle preparation: influence of sulfur dioxide and pH on nanoparticle characteristics. J Colloid Interface Sci 1992;154(1):77-86
54. Michel C, Aprahamian M, Defontaine L, et al. The effect of site of administration in the gastrointestinal tract on the absorption of insulin from nanocapsules in diabetic rats. J Pharm Pharmacol 1991;43(1):1-5
55. Radwan MA. Enhancement of absorption of insulin-loaded polyisobutylcyanoacrylate nanospheres by sodium cholate after oral and subcutaneous administration in diabetic rats. Drug Dev Ind Pharm 2001;27(9):981-989 (Pubitemid 33101459)
56. Roques M, Damgé C, Michel C, et al. Encapsulation of insulin for oral administration preserves interaction of the hormone with its receptor in vitro. Diabetes 1992;41(4):451-456
57. Sullivan CO, Birkinshaw C. In vitro degradation of insulin-loaded poly (n-butylcyanoacrylate) nanoparticles. Biomaterials 2004;25(18):4375-4382
58. Damgé C, Vranckx H, Balschmidt P, Couvreur P. Poly(alkyl cyanoacrylate) nanospheres for oral administration of insulin. J Pharm Sci 1997;86(12):1403-1409
59. Behan N, Birkinshaw C. Preparation of poly(butyl cyanoacrylate) nanoparticles by aqueous dispersion polymerisation in the presence of insulin. Macromol Rapid Commun 2001;22(1):41-43 (Pubitemid 33225335)
60. Vauthier C, Labarre D, Ponchel G. Design aspects of poly(alkylcyanoacrylate) nanoparticles for drug delivery. J Drug Target 2007;15(10):641-663 •• This is an excellent review on the state-of-the-art of PACA nanoparticles. (Pubitemid 350201318)
61. Watnasirichaikul S, Rades T, Tucker IG, Davies NM. Effects of formulation variables on characteristics of poly (ethylcyanoacrylate) nanocapsules prepared from w/o microemulsions. Int J Pharm 2002;235(1-2):237-246 (Pubitemid 34185454)
62. Wohlgemuth M, Mayer C. Pulsed field gradient NMR on polybutylcyanoacrylate nanocapsules. J Colloid Interface Sci 2003;260(2):324-331 (Pubitemid 36398626)
63. Aboubakar M, Couvreur P, Pinto-Alphandary H, et al. Insulin-loaded nanocapsules for oral administration: in vitro and in vivo investigation. Drug Dev Res 2000;49(2):109-117 (Pubitemid 30479912)
64. Puglisi G, Fresta M, Giammona G, Ventura CA. Influence of the preparation conditions on poly(Ethylcyanoacrylate) nanocapsule formation. Int J Pharm 1995;125(2):283-287
65. Florence AT. Issues in oral nanoparticle drug carrier uptake and targeting. J Drug Target 2004;12(2):65-70 (Pubitemid 38786914)
66. Damgé C, Aprahamian M, Humbert W, Pinget M. Ileal uptake of polyalkylcyanoacrylate nanocapsules in the rat. J Pharm Pharmacol 2000;52(9):1049-1056 (Pubitemid 30742015)
67. Aprahamian M, Michel C, Humbert W, et al. Transmucosal passage of polyalkylcyanoacrylate nanocapsules as a new drug carrier in the small intestine. Biol Cell 1987;61(1-2):69-76 (Pubitemid 18046633)
68. Damgé C, Michel C, Aprahamian M, et al. Nanocapsules as carriers for oral peptide delivery. J Control Release 1990;13(2-3):233-239 (Pubitemid 20313521)
69. Florence AT, Hillery AM, Hussain N, Jani PU. Nanoparticles as carriers for oral peptide absorption: studies on particle uptake and fate. J Control Release 1995;36:39-46
70. Foster KA, Yazdanian M, Audus KL. Microparticulate uptake mechanisms of in-vitro cell culture models of the respiratory epithelium. J Pharm Pharmacol 2001;53(1):57-66 (Pubitemid 32123700)
71. Desai MP, Labhasetwar V, Amidon GL, Levy RJ. Gastrointestinal uptake of biodegradable microparticles: effect of particle size. Pharm Res 1996;13(12):1838-1845 (Pubitemid 27034116)
72. des Rieux A, Fievez V, Garinot M, et al. Nanoparticles as potential oral delivery systems of proteins and vaccines: a mechanistic approach. J Control Release 2006;116(1):1-27
73. Yoo HS, Park TG. Biodegradable nanoparticles containing protein-fatty acid complexes for oral delivery of salmon calcitonin. J Pharm Sci 2004;93(2):488-495 (Pubitemid 38174268)
74. Ponchel G, Irache JM. Specific and non-specific bioadhesive particulate systems for oral delivery to the gastrointestinal tract. Adv Drug Deliv Rev 1998;34(2-3):191-219 (Pubitemid 28535112)
75. Peracchia MT, Fattal E, Desmaele D, et al. Stealth(R) PEGylated polycyanoacrylate nanoparticles for intravenous administration and splenic targeting. J Control Release 1999;60(1):121-128 (Pubitemid 29255834)
76. Chauvierre C, Labarre D, Couvreur P, Vauthier C. Novel polysaccharide-decorated poly (isobutyl cyanoacrylate) nanoparticles. Pharm Res 2003;20(11):1786-1793 (Pubitemid 37449452)
77. Lemarchand C, Gref R, Couvreur P. Polysaccharide-decorated nanoparticles. Eur J Pharm Biopharm 2004;58(2):327-341 (Pubitemid 39037239)
78. Stella B, Arpicco S, Peracchia MT, et al. Design of folic acid-conjugated nanoparticles for drug targeting. J Pharm Sci 2000;89(11):1452-1464 (Pubitemid 30805251)
79. Calvo P, Gouritin B, Brigger I, et al. PEGylated polycyanoacrylate nanoparticles as vector for drug delivery in prion diseases. J Neurosci Methods 2001;111(2):151-155 (Pubitemid 32930050)
80. Couvreur P, Lenaerts V, Kante B, et al. Oral and parenteral administration of insulin associated to hydrolysable nanoparticles. Acta Pharmaceutica Technologica 1980;26:220-222
81. Mesiha MS, Sidhom MB, Fasipe B. Oral and subcutaneous absorption of insulin poly(isobutylcyanoacrylate) nanoparticles. Int J Pharm 2005;288(2):289-293 (Pubitemid 40038582)
82. Couvreur P, Vauthier C. Nanotechnology: intelligent design to treat complex disease. Pharm Res 2006;23(7):1417-1450
83. Brannon-Peppas L, Blanchette JO. Nanoparticle and targeted systems for cancer therapy. Adv Drug Deliv Rev 2004;56(11):1649-1659
84. Koo Y-EL, Reddy GR, Bhojani M, et al. Brain cancer diagnosis and therapy with nanoplatforms. Adv Drug Deliv Rev 2006;58(14):1556-1577 (Pubitemid 44820505)
85. deVerdiere AC, Dubernet C, Nemati F, et al. Reversion of multidrug resistance with polyalkylcyanoacrylate nanoparticles: towards a mechanism of action. Br J Cancer 1997;76(2):198-205
86. Brigger I, Morizet J, Laudani L, et al. Negative preclinical results with stealth nanospheres-encapsulated Doxorubicin in an orthotopic murine brain tumor model. J Control Release 2004;100:29-40 (Pubitemid 39445983)
87. Byrne JD, Betancourt T, Brannon-Peppas L. Active targeting schemes for nanoparticle systems in cancer therapeutics. Adv Drug Deliv Rev 2008;60(15):1615-1626
88. Zhang L, Gu FX, Chan JM, et al. Nanoparticles in medicine: therapeutic applications and developments. Clin Pharmacol Ther 2007;83(5):761-769
89. Rathbone MJ, Martinez MN. Modified release drug delivery in veterinary medicine. Drug Discovery Today 2002;7(15):823-829 • This article presents key concepts that must be considered in the design of controlled release dosage forms for animals and describes the first commercially available microparticulate formulation for use in animals. (Pubitemid 34876961)
90. Brayden DJ. Novel drug delivery strategies in veterinary medicine. Irish Vet J 2003;56(6):310-316 (Pubitemid 36706947)
91. Winzenburg G, Schmidt C, Fuchs S, Kissel T. Biodegradable polymers and their potential use in parenteral veterinary drug delivery systems. Adv Drug Deliv Reviews 2004;56(10):1453-1466 •• This review is an excellent and comprehensive discussion on the topic. (Pubitemid 38748826)
92. Medlicott NJ, Waldron NA, Foster TP. Sustained release veterinary parenteral products. Adv Drug Deliv Rev 2004;56(10):1345-1365 (Pubitemid 38748820)
93. McDowell A, McLeod BJ, Rades T, Tucker IG. Application of pharmaceutical drug delivery for biological control of the common brushtail possum in New Zealand: a review. Wildlife Res 2006;33(8):679-689 (Pubitemid 46011105)
94. McDowell A, McLeod BJ. Physiology and pharmacology of the brushtail possum gastrointestinal tract: Relationship to the human gastrointestinal tract. Adv Drug Deliv Rev 2007;59(11):1121-1132 (Pubitemid 47615202)
95. McDowell A, McLeod B, Rades T, Tucker IG. Pharmacokinetics of insulin nanoparticles in a marsupial - the brushtail possum. 33th Annual Meeting and Exposition of the Controlled Release Society. Vienna, Austria: Controlled Release Society 2006
96. Yang L, Chu JS, Fix JA. Colon-specific drug delivery: new approaches and in vitro/in vivo evaluation. Int J Pharm 2002;235(1-2):1-15 (Pubitemid 34185432)
97. Kante B, Couvreur P, Dubois-Krack G, et al. Toxicity of polyalkylcyanoacrylate nanoparticles I: Free nanoparticles. J PharmSci 1982;71(7):786-790
98. Wade CWR, Leonard F. Degradation of poly(methyl 2-cyanoacrylates). J Biomed Mater Res 1972;6(3):215-220
99. Lenaerts V, Couvreur P, Christiaens-Leyh D, et al. Degradation of poly (isobutyl cyanoacrylate) nanoparticles. Biomaterials 1984;5(2):65-68 (Pubitemid 14169302)
100. Mundargi RC, Babu VR, Rangaswamy V, et al. Nano/micro technologies for delivering macromolecular therapeutics using poly(d,l-lactide-co-glycolide) and its derivatives. J Control Release 2008;125(3):193-209
101. Damgé C, Maincent P, Ubrich N. Oral delivery of insulin associated to polymeric nanoparticles in diabetic rats. J Control Release 2007;117(2):163-170 (Pubitemid 46161872)
102. El-Samaligy MS, Rojanasakul Y, Charlton JF, et al. Ocular disposition of nanoencapsulated acyclovir and ganciclovir via intravitreal injection in rabbit's eye. Drug Deliv J Deliv Target Ther Agents 1996;3(2):93-97 (Pubitemid 26281549)
103. Radwan MA, Aboul-Enein HY. The effect of oral absorption enhancers on the in vivo performance of insulin-loaded poly(ethylcyanoacrylate) nanospheres in diabetic rats. J Microencapsul 2002;19(2):225-235 (Pubitemid 34100615)
104. Beck PH, Kreuter J, Muller WEG, Schatton W. Improved peroral delivery of avarol with polybutylcyanoacrylate nanoparticles. Eur J Pharm Biopharm 1994;40(3):134-137 (Pubitemid 24217258)
105. O'Hagan DT, Palin KJ, Davis SS. Poly (butyl-2-cyanoacrylate) particles as adjuvants for oral immunisation. Vaccine 1989;7:213-216
106. Zhang Q, Shen Z, Nagai T. Prolonged hypoglycemic effect of insulin-loaded polybutylcyanoacrylate nanoparticles after pulmonary administration to normal rats. Int J Pharm 2001;218(1-2):75-80 (Pubitemid 32406158)
107. Hillery AM, Toth I, Florence AT. Biological activity of luteinizing hormone releasing hormone after oral dosing with a nanoparticulate delivery system: co-polymerised peptide particles. Pharm Sci 1996;2:281-283 (Pubitemid 28121825)
108. Stieneker F, Kersten G, van Bloois L, et al. Comparison of 24 different adjuvants for inactivated HIV-2 split whole virus as antigen in mice. Induction of titres of binding antibodies and toxicity of the formulations. Vaccine 1995;13(1):45-53
109. Hubert B, Atkinson J, Guerret M, et al. The preparation and acute antihypertensive effects of a nanocapsular form of darodipine, a dihydropyridine calcium entry blocker. Pharm Res 1991;8(6):734-738
110. Ammoury N, Fessi H, Devissaguet JP, et al. Jejunal absorption, pharmacological activity, and pharmacokinetic evaluation of indomethacin-loaded poly(d,l-lactide) and poly(isobutyl-cyanoacrylate) nanocapsules in rats. Pharm Res 1991;8(1):101-105
111. Saï P, Damgé C, Rivereau AS, et al. Prophylactic oral administration of metabolically active insulin entrapped in isobutylcyanoacrylate nanocapsules reduces the incidence of diabetes in non-obese diabetic mice. J Autoimmun 1996;9(6):713-721 (Pubitemid 27047020)
112. Lambert G, Bertrand JR, Fattal E, et al. EWS Fli-1 antisense nanocapsules inhibits ewing sarcoma related tumor in mice. Biochem Biophys Res Commun 2000;279:401-406 (Pubitemid 32016729)
113. Desai SD, Blanchard J. Pluronic® F127-based ocular delivery system containing biodegradable polyisobutylcyanoacrylate nanocapsules of pilocarpine. Drug Deliv 2000;7(4):201-207 (Pubitemid 32057551)
114. Zimmer A. Antisense oligonucleotide delivery with polyhexylcyanoacrylate nanoparticles as carriers. Companion Methods Enzymol 1999;18:286-295 (Pubitemid 29443614)
115. Fresta M, Cavallaro G, Giammona G, et al. Preparation and characterization of polyethyl-2-cyanoacrylate nanocapsules containing antiepileptic drugs. Biomaterials 1996;17(8):751-758 (Pubitemid 26108342)
116. Boudad H, Legrand P, Lebas G, et al. Combined hydroxypropyl-[beta]- cyclodextrin and poly(alkylcyanoacrylate) nanoparticles intended for oral administration of saquinavir. Int J Pharm 2001;218(1-2):113-124 (Pubitemid 32406162)
117. Fresta M, Fontana G, Bucolo C, et al. Ocular tolerability and in vivo bioavailability of poly(ethylene glycol) (PEG)-coated polyethyl-2-cyanoacrylate nanosphere-encapsulated acyclovir. J Pharm Sci 2001;90(3):288-297 (Pubitemid 32209890)
118. Das D, Lin S. Double-coated poly (butylcynanoacrylate) nanoparticulate delivery systems for brain targeting of dalargin via oral administration. J Pharm Sci 2005;94(6):1343-1353 (Pubitemid 40904197)
119. Li Y-P, Pei Y-Y, Zhou Z-H, et al. PEGylated polycyanoacrylate nanoparticles as tumor necrosis factor-[alpha] carriers. J Control Release 2001;71(3):287-296 (Pubitemid 32276048)
120. Li Y-P, Pei Y-Y, Zhou Z-H, et al. Stealth polycyanoacrylate nanoparticles as tumor necrosis factor-alpha; carriers: pharmacokinetics and anti-tumor effects. Biol Pharm Bulletin 2001;24(6):662-665 (Pubitemid 32586657)
121. Kreuter J, Alyautdin RN, Kharkevich DA, Ivanov AA. Passage of peptides through the blood-brain barrier with colloidal polymer particles (nanoparticles). Brain Res 1995;674:171-174
122. Gulyaev AE, Gelperina SE, Skidan AS, et al. Significant transport of doxorubicin into the brain with polysorbate 80-coated nanoparticles. Pharm Res 1999;16:1564-1569 (Pubitemid 29510553)
123. Gelperina SE, Khalansky AS, Skidan IN, et al. Toxicological studies of doxorubicin bound to polysorbate 80-coated poly(butyl cyanoacrylate) nanoparticles in healthy rats and rats with intracranial glioblastoma. Toxicol Lett 2002;126(2):131-141 (Pubitemid 34075270)
124. Alyautdin RN, Petrov VE, Langer K, et al. Delivery of loperamide across the blood-brain barrier with polysorbate 80-coated polybutylcyanoacrylate nanoparticles. Pharm Res 1997;14:325-328 (Pubitemid 27160944)
125. Friese A, Seiller E, Quack G, et al. Increase of the anticonvulsive activity of a novel NMDA receptor antagonist using poly(butylcyanoacrylate) nanoparticles as parenteral controlled release system. Eur J Pharm Biopharm 2000;49:103-109 (Pubitemid 30126057)
126. Wilson B, Samanta MK, Santhi K, et al. Targeted delivery of tacrine into the brain with polysorbate 80-coated poly(n-butylcyanoacrylate) nanoparticles. Eur J Pharm Biopharm 2008;70:75-84