Oral administration of peptides and proteins: nanoparticles and cyclodextrins as biocompatible delivery systems

Bibliography

• 1  Allémann E, Leroux J-C, Gurny R: Polymeric nano- and microparticles for the oral delivery of peptides and peptidomimetics. Adv. Drug Deliv. Rev.34(1–2),171–189 (1998).Crossref, Medline, CAS, Google Scholar
• 2  Aungst BJ, Saitoh H, Burcham DL, Huang S-M, Mousa SA, Hussain MA: Enhancement of the intestinal absorption of peptides and nonpeptides. J. Control. Release41(1–2),19–31 (1996).Crossref, CAS, Google Scholar
• 3  Florence AT, Hillery AM, Hussain N, Jani PU: Nanoparticles as carriers for oral peptide absorption: studies on particle uptake and fate. J. Control. Release36(1–2),39–46 (1995).Crossref, CAS, Google Scholar
• 4  Haeberlin B, Gengenbacher T, Meinzer A, Fricker G: Cyclodextrins – useful excipients for oral peptide administration? Int. J. Pharm.137(1),103–110 (1996).Crossref, CAS, Google Scholar
• 5  Jung T, Kamm W, Breitenbach A, Kaiserling E, Xiao JX, Kissel T: Biodegradable nanoparticles for oral delivery of peptides: is there a role for polymers to affect mucosal uptake? Eur. J. Pharm. Biopharm.50(1),147–160 (2000).Crossref, Medline, CAS, Google Scholar
• 6  Prego C, Torres D, Fernandez-Megia E, Novoa-Carballal R, Quinoa E, Alonso MJ: Chitosan-PEG nanocapsules as new carriers for oral peptide delivery: effect of chitosan pegylation degree. J. Control. Release111(3),299–308 (2006).Crossref, Medline, CAS, Google Scholar
• 7  Sakuma S, Hayashi M, Akashi M: Design of nanoparticles composed of graft copolymers for oral peptide delivery. Adv. Drug Deliv. Rev.47(1),21–37 (2001).Crossref, Medline, CAS, Google Scholar
• 8  Salamat-Miller N, Johnston TP: Current strategies used to enhance the paracellular transport of therapeutic polypeptides across the intestinal epithelium. Int. J. Pharm.294(1–2),201–216 (2005).Crossref, Medline, CAS, Google Scholar
• 9  Sarciaux JM, Acar L, Sado PA: Using microemulsion formulations for oral drug delivery of therapeutic peptides. Int. J. Pharm.120(2),127–136 (1995).Crossref, CAS, Google Scholar
• 10  Still JG: Development of oral insulin: progress and current status. Diabetes Metab. Res. Rev.18(S1),S29–S37 (2002).Crossref, Medline, CAS, Google Scholar
• 11  Nakamura K, Murray RJ, Joseph JI, Peppas NA, Morishita M, Lowman AM: Oral insulin delivery using P(MAA-g-EG) hydrogels: effects of network morphology on insulin delivery characteristics. J. Control. Release95(3),589–599 (2004).Crossref, Medline, CAS, Google Scholar
• 12  TenHoor CN, Dressman JB: Oral absorption of peptides and proteins. Stp Pharma. Sci.2(4),301–312 (1992).CAS, Google Scholar
• 13  Cheng J, Teply BA, Jeong SY et al.: Magnetically responsive polymeric microparticles for oral delivery of protein drugs. Pharm. Res.23(3),557–564 (2006).Crossref, Medline, CAS, Google Scholar
• 14  Ho RH, Kim RB: Transporters and drug therapy: implications for drug disposition and disease. Clin. Pharmacol. Ther.78(3),260–277 (2005).Crossref, Medline, CAS, Google Scholar
• 15  Pinto Reis C, Neufeld RJ, Ribeiro AJ, Veiga F: Nanoencapsulation II. Biomedical applications and current status of peptide and protein nanoparticulate delivery systems. Nanomedicine2(2),53–65 (2006).Crossref, Medline, Google Scholar
• 16  Pauletti GM, Gangwar S, Knipp GT et al.: Structural requirements for intestinal absorption of peptide drugs. J. Control. Release41(1–2),3–17 (1996).Crossref, CAS, Google Scholar
• 17  Uekama K, Hirayama F, Irie T: Cyclodextrin drug carrier systems. Chem. Rev.98(5),2045–2076 (1998).Crossref, Medline, CAS, Google Scholar
• 18  Bilati U, Allemann E, Doelker E: Strategic approaches for overcoming peptide and protein instability within biodegradable nano- and microparticles. Eur. J. Pharm. Biopharm.59(3),375–388 (2005).Crossref, Medline, CAS, Google Scholar
• 19  Wang W: Protein aggregation and its inhibition in biopharmaceutics. Int. J. Pharm.289(1–2),1–30 (2005).Crossref, Medline, CAS, Google Scholar
• 20  Tavornvipas S, Tajiri S, Hirayama F, Arima H, Uekama K: Effects of hydrophilic cyclodextrins on aggregation of recombinant human growth hormone. Pharm. Res.21(12),2369–2376 (2004).Crossref, Medline, CAS, Google Scholar
• 21  Langguth P, Bohner V, Heizmann J et al.: The challenge of proteolytic enzymes in intestinal peptide delivery. J. Control. Release46(1–2),39–57 (1997).Crossref, CAS, Google Scholar
• 22  Fjellestad-Paulsen A, Soderberg-Ahlm C, Lundin S: Metabolism of vasopressin, oxytocin, and their analogues in the human gastrointestinal tract. Peptides16(6),1141–1147 (1995).Crossref, Medline, CAS, Google Scholar
• 23  Lundin S, Pantzar N, Broeders A, Ohlin M, Westrom BR: Differences in transport rate of oxytocin and vasopressin analogues across proximal and distal isolated segments of the small intestine of the rat. Pharm. Res.8(10),1274–1280 (1991).Crossref, Medline, CAS, Google Scholar
• 24  Lang VB, Langguth P, Ottiger C et al.: Structure-permeation relations of met-enkephalin peptide analogues on absorption and secretion mechanisms in Caco-2 monolayers. J. Pharm. Sci.86(7),846–853 (1997).Crossref, Medline, CAS, Google Scholar
• 25  Mizuma T, Koyanagi A, Awazu S: Intestinal transport and metabolism of glucose-conjugated kyotorphin and cyclic kyotorphin: metabolic degradation is crucial to intestinal absorption of peptide drugs. Biochim. Biophys. Actav.1475(1),90–98 (2000).Crossref, Medline, CAS, Google Scholar
• 26  Bernkop-Schnurch A: The use of inhibitory agents to overcome the enzymatic barrier to perorally administered therapeutic peptides and proteins. J. Control. Release52(1–2),1–16 (1998).Crossref, Medline, CAS, Google Scholar
• 27  Fix JA: Strategies for delivery of peptides utilizing absorption-enhancing agents. J. Pharm. Sci.85(12),1282–1285 (1996).Crossref, Medline, CAS, Google Scholar
• 28  Leibach FH, Ganapathy V: Peptide transporters in the intestine and the kidney. Annu. Rev. Nutr.16(1),99–119 (1996).Crossref, Medline, CAS, Google Scholar
• 29  Sundaram U, Wisel S, Coon S: Mechanism of inhibition of proton: dipeptide co-transport during chronic enteritis in the mammalian small intestine. Biochim. Biophys. Acta1714(2),134–140 (2005).Crossref, Medline, CAS, Google Scholar
• 30  Quintanar-Guerrero D, Allémann E, Fessi H, Doelker E: Applications of the ion-pair concept to hydrophilic substances with special emphasis on peptides. Pharm. Res.14(2),119–127 (1997).Crossref, Medline, CAS, Google Scholar
• 31  Xin Hua Z: Overcoming enzymatic and absorption barriers to non-parenterally administered protein and peptide drugs. J. Control. Release29(3),239–252 (1994).Crossref, Google Scholar
• 32  Salama NN, Eddington ND, Fasano A: Tight junction modulation and its relationship to drug delivery. Adv. Drug Deliv. Rev.58(1),15–28 (2006).Crossref, Medline, CAS, Google Scholar
• 33  Sharma P, Varma MVS, Chawla HPS, Panchagnula R: Absorption enhancement, mechanistic and toxicity studies of medium chain fatty acids, cyclodextrins and bile salts as peroral absorption enhancers. Farmaco60(11–12),884–893 (2005).Crossref, Medline, CAS, Google Scholar
• 34  Foger F, Schmitz T, Bernkop-Schnurch A: In vivo evaluation of an oral delivery system for P-gp substrates based on thiolated chitosan. Biomaterials27(23),4250–4255 (2006).Crossref, Medline, Google Scholar
• 35  Ambudkar SV, Kim I-W, Sauna ZE: The power of the pump: mechanisms of action of P-glycoprotein (ABCB1). Eur. J. Pharm. Biopharm.27(5),392–400 (2006).CAS, Google Scholar
• 36  Kim RB: Drugs as P-glycoprotein substrates, inhibitors, and inducers. Drug Metab. Rev.34(1–2),47–54 (2002).Crossref, Medline, CAS, Google Scholar
• 37  Ejendal KFK, Hrycyna CA: Differential sensitivities of the human ATP-binding cassette transporters ABCG2 and P-glycoprotein to cyclosporin A. Mol. Pharmacol.67(3),902–911 (2005).Crossref, Medline, CAS, Google Scholar
• 38  Yunomae K, Arima H, Hirayama F, Uekama K: Involvement of cholesterol in the inhibitory effect of dimethyl-β-cyclodextrin on P-glycoprotein and MRP2 function in Caco-2 cells. FEBS Lett.536(1–3),225–231 (2003).Crossref, Medline, CAS, Google Scholar
• 39  Oda M, Saitoh H, Kobayashi M, Aungst BJ: β-cyclodextrin as a suitable solubilizing agent for in situ absorption study of poorly water-soluble drugs. Int. J. Pharm.280(1–2),95–102 (2004).Crossref, Medline, CAS, Google Scholar
• 40  Kreuter J: Nanoparticle-based drug delivery systems. J. Control. Release16(1–2),169–176 (1991).Crossref, CAS, Google Scholar
• 41  Pinto Reis C, Neufeld RJ, Ribeiro AJ, Veiga F: Nanoencapsulation I. Methods for preparation of drug-loaded polymeric nanoparticles. Nanomedicine2(1),8–21 (2006).Crossref, Medline, Google Scholar
• 42  Allémann E, Gurny R, Doelker E: Drug-loaded nanoparticles – preparation methods and drug targeting issues. Eur. J. Pharm. Biopharm.39(5),173–191 (1993).CAS, Google Scholar
• 43  Panyam J, Labhasetwar V: Biodegradable nanoparticles for drug and gene delivery to cells and tissue. Adv. Drug Deliv. Rev.55(3),329–347 (2003).Crossref, Medline, CAS, Google Scholar
• 44  Magenheim B, Benita S: Nanoparticle characterization: a comprehensive physicochemical approach. Stp Pharma Sci.1(4),221–241 (1991).CAS, Google Scholar
• 45  Soppimath KS, Aminabhavi TM, Kulkarni AR, Rudzinski WE: Biodegradable polymeric nanoparticles as drug delivery devices. J. Control. Release70(1–2),1–20 (2001).Crossref, Medline, CAS, Google Scholar
• 46  Vauthier C, Dubernet C, Fattal E, Pinto-Αndary H, Couvreur P: Poly(alkylcyanoacrylates) as biodegradable materials for biomedical applications. Adv. Drug Deliv. Rev.55(4),519–548 (2003).Crossref, Medline, CAS, Google Scholar
• 47  Aguiar MMG, Rodrigues JM, Silva Cunha A: Encapsulation of insulin–cyclodextrin complex in PLGA microspheres: a new approach for prolonged pulmonary insulin delivery. J. Microencapsul.21(5),553–564 (2004).Crossref, Medline, CAS, Google Scholar
• 48  Beletsi A, Panagi Z, Avgoustakis K: Biodistribution properties of nanoparticles based on mixtures of PLGA with PLGA–PEG diblock copolymers. Int. J. Pharm.298(1),233–241 (2005).Crossref, Medline, CAS, Google Scholar
• 49  Duan Y, Sun X, Gong T, Wang Q, Zhang Z: Preparation of DHAQ-loaded mPEG–PLGA–mPEG nanoparticles and evaluation of drug release behaviors in vitro/in vivo. J. Mater. Sci. Mater. Med.17(6),509–516 (2006).Crossref, Medline, CAS, Google Scholar
• 50  Kang F, Jiang G, Hinderliter A, DeLuca PP, Singh J: Lysozyme stability in primary emulsion for PLGA microsphere preparation: effect of recovery methods and stabilizing excipients. Pharm. Res.19(5),629–633 (2002).Crossref, Medline, CAS, Google Scholar
• 51  Koushik K, Dhanda D, Cheruvu N, Kompella U: Pulmonary delivery of deslorelin: large-porous PLGA particles and HPβCD complexes. Pharm. Res.21(7),1119–1126 (2004).Crossref, Medline, CAS, Google Scholar
• 52  Li Y-P, Pei Y-Y, Zhang X-Y et al.: PEGylated PLGA nanoparticles as protein carriers: synthesis, preparation and biodistribution in rats. J. Control. Release71(2),203–211 (2001).Crossref, Medline, CAS, Google Scholar
• 53  Quaglia F, De Rosa G, Granata E, Ungaro F, Fattal E, Immacolata La Rotonda M: Feeding liquid, non-ionic surfactant and cyclodextrin affect the properties of insulin-loaded poly(lactide-co-glycolide) microspheres prepared by spray-drying. J. Control. Release86(2–3),267–278 (2003).Crossref, Medline, CAS, Google Scholar
• 54  Shakweh M, Besnard M, Nicolas V, Fattal E: Poly (lactide-co-glycolide) particles of different physicochemical properties and their uptake by peyer's patches in mice. Eur. J. Pharm. Biopharm.61(1–2),1–13 (2005).Crossref, Medline, CAS, Google Scholar
• 55  Teixeira M, Alonso MJ, Pinto MMM, Barbosa CM: Development and characterization of PLGA nanospheres and nanocapsules containing xanthone and 3-methoxyxanthone. Eur. J. Pharm. Biopharm.59(3),491–500 (2005).Crossref, Medline, CAS, Google Scholar
• 56  Zhang Z, Feng S-S: The drug encapsulation efficiency, in vitro drug release, cellular uptake and cytotoxicity of paclitaxel-loaded poly(lactide)-tocopheryl polyethylene glycol succinate nanoparticles. Biomaterials27(21),4025–4033 (2006).Crossref, Medline, CAS, Google Scholar
• 57  Nguyen CA, Allemann E, Schwach G, Doelker E, Gurny R: Cell interaction studies of PLA-MePEG nanoparticles. Int. J. Pharm.254(1),69–72 (2003).Crossref, Medline, CAS, Google Scholar
• 58  Yi Y, Kim JH, Kang H-W, Oh HS, Kim SW, Seo MH: A polymeric nanoparticle consisting of mPEG-PLA-Toco and PLMA-COONa as a drug carrier: improvements in cellular uptake and biodistribution. Pharm. Res.22(2),200–208 (2005).Crossref, Medline, CAS, Google Scholar
• 59  Gao H, Yang YW, Fan YG, Ma JB: Conjugates of poly(dl-lactic acid) with ethylenediamino or diethylenetriamino bridged bis(β-cyclodextrin)s and their nanoparticles as protein delivery systems. J. Control. Release (2007) (In Press).Google Scholar
• 60  Sakuma S, Sudo R, Suzuki N et al.: Behavior of mucoadhesive nanoparticles having hydrophilic polymeric chains in the intestine. J. Control. Release81(3),281–290 (2002).Crossref, Medline, CAS, Google Scholar
• 61  Norris DA, Puri N, Sinko PJ: The effect of physical barriers and properties on the oral absorption of particulates. Adv. Drug Deliv. Rev.34(2–3),135–154 (1998).Crossref, Medline, CAS, Google Scholar
• 62  O’Hagan DT: Intestinal translocation of particulates – implications for drug and antigen delivery. Adv. Drug Deliv. Rev.5(3),265–285 (1990).Crossref, Google Scholar
• 63  Jani PU, Florence AT, McCarthy DE: Further histological evidence of the gastrointestinal absorption of polystyrene nanospheres in the rat. Int. J. Pharm.84(3),245–252 (1992).Crossref, CAS, Google Scholar
• 64  Ermak TH, Giannasca PJ: Microparticle targeting to M cells. Adv. Drug Deliv. Rev.34(2–3),261–283 (1998).Crossref, Medline, CAS, Google Scholar
• 65  Gilligan CA, Li Wan Po A: Oral vaccines: design and delivery. Int. J. Pharm.75(1),1–24 (1991).Crossref, CAS, Google Scholar
• 66  Jani PU, McCarthy DE, Florence AT: Nanosphere and microsphere uptake via Peyer's patches: observation of the rate of uptake in the rat after a single oral dose. Int. J. Pharm.86(2–3),239–246 (1992).Crossref, CAS, Google Scholar
• 67  Eldridge JH, Hammond CJ, Meulbroek JA, Staas JK, Gilley RM, Tice TR: Controlled vaccine release in the gut-associated lymphoid tissues. I. Orally administered biodegradable microspheres target the peyer's patches. J. Control. Release11(1–3),205–214 (1990).Crossref, CAS, Google Scholar
• 68  Owens DE III, Peppas NA: Opsonization, biodistribution, and pharmacokinetics of polymeric nanoparticles. Int. J. Pharm.307(1),93–102 (2006).Crossref, Medline, CAS, Google Scholar
• 69  Peracchia MT, Fattal E, Desmaele D et al.: Stealth PEGylated polycyanoacrylate nanoparticles for intravenous administration and splenic targeting. J. Control. Release60(1),121–128 (1999).Crossref, Medline, CAS, Google Scholar
• 70  Lemarchand C, Gref R, Couvreur P: Polysaccharide-decorated nanoparticles. Eur. J. Pharm. Biopharm.58(2),327–341 (2004).Crossref, Medline, CAS, Google Scholar
• 71  Del Valle EMM: Cyclodextrins and their uses: a review. Process Biochem.39(9),1033–1046 (2004).Crossref, CAS, Google Scholar
• 72  Szejtli J: Cyclodextrins properties and applications. Drug Invest.2(S4),11–21 (1990).Crossref, Google Scholar
• 73  Thorsteinn L, Brewster ME: Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J. Pharm. Sci.85(10),1017–1025 (1996).Crossref, Medline, Google Scholar
• 74  Stella VJ, Rajewski RA: Cyclodextrins: their future in drug formulation and delivery. Pharm. Res.14(5),556–567 (1997).Crossref, Medline, CAS, Google Scholar
• 75  Challa R, Ahuja A, Ali J, Khar RK: Cyclodextrins in drug delivery: an updated review. AAPS PharmSciTech.6(2),E329–E357 (2005).Crossref, Medline, Google Scholar
• 76  Li J, Xiao H, Li J, Zhong Y: Drug carrier systems based on water-soluble cationic β-cyclodextrin polymers. Int. J. Pharm.278(2),329–342 (2004).Crossref, Medline, CAS, Google Scholar
• 77  Irie T, Uekama K: Cyclodextrins in peptide and protein delivery. Adv. Drug Deliv. Rev.36(1),101–123 (1999).Crossref, Medline, CAS, Google Scholar
• 78  Nagase Y, Hirata M, Arima H et al.: Protective effect of sulfobutyl ether β-cyclodextrin on DY-9760e-induced hemolysis in vitro. J. Pharm. Sci.91(11),2382–2389 (2002).Crossref, Medline, CAS, Google Scholar
• 79  Hirayama F, Mieda S, Miyamoto Y, Arima H, Uekama K: Heptakis(2,6-di-O-methyl-3-O-acetyl)-β-cyclodextrin: a water-soluble cyclodextrin derivative with low hemolytic activity. J. Pharm. Sci.88(10),970–975 (1999).Crossref, Medline, CAS, Google Scholar
• 80  Arima H, Yunomae K, Morikawa T, Hirayama F, Uekama K: Contribution of cholesterol and phospholipids to inhibitory effect of dimethyl-β-cyclodextrin on efflux function of P-glycoprotein and multidrug resistance-associated protein 2 in vinblastine-resistant Caco-2 cell monolayers. Pharm. Res.21(4),625–634 (2004).Crossref, Medline, CAS, Google Scholar
• 81  Veiga F, Teixeira-Dias JJC, Kedzierewicz F, Sousa A, Maincent P: Inclusion complexation of tolbutamide with β-cyclodextrin and hydroxypropyl-β-cyclodextrin. Int. J. Pharm.129(1–2),63–71 (1996).Crossref, CAS, Google Scholar
• 82  Veiga F, Fernandes C, Teixeira F: Oral bioavailability and hypoglycaemic activity of tolbutamide/cyclodextrin inclusion complexes. Int. J. Pharm.202(1–2),165–171 (2000).Crossref, Medline, CAS, Google Scholar
• 83  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.19(2),225–235 (2002).Crossref, Medline, CAS, Google Scholar
• 84  Redenti E, Pietra C, Gerloczy A, Szente L: Cyclodextrins in oligonucleotide delivery. Adv. Drug Deliv. Rev.53(2),235–244 (2001).Crossref, Medline, CAS, Google Scholar
• 85  Hirayama F, Uekama K: Cyclodextrin-based controlled drug release system. Adv. Drug Deliv. Rev.36(1),125–141 (1999).Crossref, Medline, CAS, Google Scholar
• 86  Lin M, Jayawickrama DA, Rose RA, DelViscio JA, Larive CK: Nuclear magnetic resonance spectroscopic analysis of the selective complexation of the cis and trans isomers of phenylalanylproline by β-cyclodextrin. Anal. Chim. Acta.307(2–3),449–457 (1995).Crossref, CAS, Google Scholar
• 87  Aachmann FL, Otzen DE, Larsen KL, Wimmer R: Structural background of cyclodextrin-protein interactions. Protein Eng.16(12),905–912 (2003).Crossref, Medline, CAS, Google Scholar
• 88  Angelova A, Ringard-Lefebvre C, Baszkin A: Drug-cyclodextrin association constants determined by surface tension and surface pressure measurements: I. host–guest complexation of water soluble drugs by cyclodextrins: polymyxin B-β cyclodextrin system. J. Colloid Interface Sci.212(2),275–279 (1999).Crossref, Medline, CAS, Google Scholar
• 89  Camilleri P, Haskins NJ, Hewlett DR: β-Cyclodextrin interacts with the Alzheimer amyloid β-A4 peptide. FEBS Lett.341(2–3),256–258 (1994).Crossref, Medline, CAS, Google Scholar
• 90  Garcia-Fuentes M, Trapani A, Alonso MJ: Protection of the peptide glutathione by complex formation with α-cyclodextrin: NMR spectroscopic analysis and stability study. Eur. J. Pharm. Biopharm. (2007) (In Press).Google Scholar
• 91  Kamphorst AO, Mendes de Sa I, Faria AM, Sinisterra RD: Association complexes between ovalbumin and cyclodextrins have no effect on the immunological properties of ovalbumin. Eur. J. Pharm. Biopharm.57(2),199–205 (2004).Crossref, Medline, CAS, Google Scholar
• 92  Matilainen L, Jarvinen K, Toropainen T et al.: In vitro evaluation of the effect of cyclodextrin complexation on pulmonary deposition of a peptide, cyclosporin A. Int. J. Pharm.318(1–2),41–48 (2006).Crossref, Medline, CAS, Google Scholar
• 93  De Rosa G, Larobina D, La Rotonda MI, Musto P, Quaglia F, Ungaro F: How cyclodextrin incorporation affects the properties of protein-loaded PLGA-based microspheres: the case of insulin/hydroxypropyl-β-cyclodextrin system. J. Control. Release102(1),71–83 (2005).Crossref, Medline, CAS, Google Scholar
• 94  Junior JMR, de Melo Lima K, de Matos Jensen CE, de Aguiar MMG, da Silva Cunha Junior A: The effect of cyclodextrins on the in vitro and in vivo properties of insulin-loaded poly (d,l-lactic-co-glycolic acid) microspheres. Artif. Organs27(5),492–497 (2003).Crossref, Medline, Google Scholar
• 95  Castellanos IJ, Flores G, Griebenow K: Effect of cyclodextrins on a-chymotrypsin stability and loading in PLGA microspheres upon S/O/W encapsulation. J. Pharm. Sci.95(4),849–858 (2006).Crossref, Medline, CAS, Google Scholar
• 96  Sigurjonsdottir JF, Loftsson T, Masson M: Influence of cyclodextrins on the stability of the peptide salmon calcitonin in aqueous solution. Int. J. Pharm.186(2),205–213 (1999).Crossref, Medline, CAS, Google Scholar
• 97  Kang F, Singh J: Conformational stability of a model protein (bovine serum albumin) during primary emulsification process of PLGA microspheres synthesis. Int. J. Pharm.260(1),149–156 (2003).Crossref, Medline, CAS, Google Scholar
• 98  Jones IIG, Zhou X, Lu L: Inclusion by β-cyclodextrin of a pyrene-labeled dipeptide photoprobe. Tetrahedron Lett.43(34),6079–6082 (2002).Crossref, CAS, Google Scholar
• 99  Nakate T, Yoshida H, Ohike A, Tokunaga Y, Ibuki R, Kawashima Y: Improvement of pulmonary absorption of cyclopeptide FK224 in rats by co-formulating with β-cyclodextrin. Eur. J. Pharm. Biopharm.55(2),147–154 (2003).Crossref, Medline, CAS, Google Scholar
• 100  Yue IC, Poff J, Cortes ME et al.: A novel polymeric chlorhexidine delivery device for the treatment of periodontal disease. Biomaterials25(17),3743–3750 (2004).Crossref, Medline, CAS, Google Scholar
• 101  Duchene D, Ponchel G, Wouessidjewe D: Cyclodextrins in targeting: application to nanoparticles. Adv. Drug Deliv. Rev.36(1),29–40 (1999).Crossref, Medline, CAS, Google Scholar
• 102  da Silveira AM, Ponchel G, Puisieux F, Duchêne D: Combined Poly(isobutylcyanoacrylate) and cyclodextrins nanoparticles for enhancing the encapsulation of lipophilic drugs. Pharm. Res.15(7),1051–1055 (1998).Crossref, Medline, CAS, Google Scholar
• 103  Maestrelli F, Garcia-Fuentes M, Mura P, Alonso MJ: A new drug nanocarrier consisting of chitosan and hydoxypropylcyclodextrin. Eur. J. Pharm. Biopharm. (2007) (In Press).Google Scholar
• 104  Vandervoort J, Ludwig A: Preparation and evaluation of drug-loaded gelatin nanoparticles for topical ophthalmic use. Eur. J. Pharm. Biopharm.57(2),251–261 (2004).Crossref, Medline, CAS, Google Scholar
• 105  Boudad H, Legrand P, Lebas G, Cheron M, Duchene D, Ponchel G: Combined hydroxypropyl-β-cyclodextrin and poly(alkylcyanoacrylate) nanoparticles intended for oral administration of saquinavir. Int. J. Pharm.218(1–2),113–124 (2001).Crossref, Medline, CAS, Google Scholar
• 106  Cavalli R, Peira E, Caputo O, Gasco MR: Solid lipid nanoparticles as carriers of hydrocortisone and progesterone complexes with β-cyclodextrins. Int. J. Pharm.182(1),59–69 (1999).Crossref, Medline, CAS, Google Scholar
• 107  Utsuki T, Brem H, Pitha J et al.: Potentiation of anticancer effects of microencapsulated carboplatin by hydroxypropyl α-cyclodextrin. J. Control. Release40(3),251–260 (1996).Crossref, CAS, Google Scholar
• 108  Gao H, Wang YN, Fan YG, Ma JB: Synthesis of a biodegradable tadpole-shaped polymer via the coupling reaction of polylactide onto mono(6-(2-aminoethyl)amino-6-deoxy)-β-cyclodextrin and its properties as the new carrier of protein delivery system. J. Control. Release107(1),158–173 (2005).Crossref, Medline, CAS, Google Scholar
• 109  Duchene D, Wouessidjewe D, Ponchel G: Cyclodextrins and carrier systems. J. Control. Release62(1–2),263–268 (1999).Crossref, Medline, CAS, Google Scholar
• 110  Jerry N, Anitha Y, Sharma CP, Poulose S: In vivo absorption studies of insulin from an oral delivery system. Drug Deliv.8(1),19–23 (2001).Crossref, Medline, CAS, Google Scholar
• 111  Bibby DC, Davies NM, Tucker IG: Mechanisms by which cyclodextrins modify drug release from polymeric drug delivery systems. Int. J. Pharm.197(1–2),1–11 (2000).Crossref, Medline, CAS, Google Scholar
• 112  Memisoglu E, Bochot A, Sen M, Charon D, Duchêne D, Hincal AA: Amphiphilic β-cyclodextrins modified on the primary face: synthesis, characterization, and evaluation of their potential as novel excipients in the preparation of nanocapsules. J. Pharm. Sci.91(5),1214–1224 (2002).Crossref, Medline, CAS, Google Scholar
• 113  Sallas F, Niikura K, Nishimura S-I: A practical synthesis of amphiphilic cyclodextrins fully substituted with sugar residues on the primary face. Chem. Commun.5,596–597 (2004).Crossref, Medline, Google Scholar
• 114  Peroche S, Degobert G, Putaux J-L, Blanchin M-G, Fessi H, Parrot-Lopez H: Synthesis and characterisation of novel nanospheres made from amphiphilic perfluoroalkylthio-β-cyclodextrins. Eur. J. Pharm. Biopharm.60(1),123–131 (2005).Crossref, Medline, CAS, Google Scholar
• 115  Liu Y, Yan-Li Zhao and Zhang H-Y: Recognition-induced supramolecular porous nanosphere formation from cyclodextrin conjugated by cholic acid langmuir. Langmuir22(7),3434–3438 (2006).Crossref, Medline, CAS, Google Scholar
• 116  Javierre I, Nedyalkov M, Petkova V et al.: Direct investigation of the vectorization properties of amphiphilic cyclodextrins in phospholipid films. J. Colloid Interface Sci.254(1),120–128 (2002).Crossref, Medline, CAS, Google Scholar
• 117  Lahiani-Skiba M, Bounoure F, Shawky-Tous S, Arnaud P, Skiba M: Optimization of entrapment of metronidazole in amphiphilic β-cyclodextrin nanospheres. J. Pharm. Biomed. Anal.41(3),1017–1021 (2006).Crossref, Medline, CAS, Google Scholar
• 118  Choisnard L, Gèze A, Putaux J-L, Wong Y-S, Wouessidjewe D: Nanoparticles of – cyclodextrin esters obtained by self-assembling of biotransesterified – cyclodextrins. Biomacromolecules7(2),515–520 (2006).Crossref, Medline, CAS, Google Scholar
• 119  Choisnard L, Gèze A, Bigan M, Putaux J-L, Wouessidjewe D: Efficient size control of amphiphilic cyclodextrin nanoparticles through a statistical mixture design methodology. J. Pharm. Sci.8(3),593–600 (2005).CAS, Google Scholar
• 120  Geze A, Aous S, Baussanne I, Putaux J, Defaye J, Wouessidjewe D: Influence of chemical structure of amphiphilic β-cyclodextrins on their ability to form stable nanoparticles. Int. J. Pharm.242(1–2),301–305 (2002).Crossref, Medline, CAS, Google Scholar
• 121  Gulik A, Delacroix H, Wouessidjewe D, Skiba M: Structural properties of several amphiphile cyclodextrins and some related nanospheres. An X-ray scattering and freeze-fracture electron microscopy study. Langmuir14(5),1050–1057 (1998).Crossref, CAS, Google Scholar
• 122  Memisoglu-Bilensoy E, Dogan AL, Hincal AA: Cytotoxic evaluation of injectable cyclodextrin nanoparticles. J. Pharm. Pharmacol.58(5),585–598 (2006).Crossref, Medline, CAS, Google Scholar
• 123  Memisoglu-Bilensoy E, Hincal AA: Sterile, injectable cyclodextrin nanoparticles: effects of γ irradiation and autoclaving. Int. J. Pharm.311(1–2),203–208 (2006).Crossref, Medline, CAS, Google Scholar
• 124  Memisoglu-Bilensoy E, Vural I, Bochot A, Renoir JM, Duchene D, Hincal AA: Tamoxifen citrate loaded amphiphilic β-cyclodextrin nanoparticles: in vitro characterization and cytotoxicity. J. Control. Release104(3),489–496 (2005).Crossref, Medline, CAS, Google Scholar
• 125  Sortino S, Mazzaglia A, Monsu Scolaro L, Marino Merlo F, Valveri V, Sciortino MT: Nanoparticles of cationic amphiphilic cyclodextrins entangling anionic porphyrins as carrier-sensitizer system in photodynamic cancer therapy. Biomaterials27(23),4256–4265 (2006).Crossref, Medline, CAS, Google Scholar
• 126  Skiba M, Duchene D, Puisieux F, Wouessidjewe D: Development of a new colloidal drug carrier from chemically-modified cyclodextrins: nanospheres and influence of physicochemical and technological factors on particle size. Int. J. Pharm.129(1–2),113–121 (1996).Crossref, CAS, Google Scholar
• 127  Skiba M, Morvan C, Duchene D, Puisieux F, Wouessidjewe D: Evaluation of gastrointestinal behaviour in the rat of amphiphilic β-cyclodextrin nanocapsules, loaded with indomethacin. Int. J. Pharm.126(1–2),275–279 (1995).Crossref, CAS, Google Scholar
• 128  Falvey P, Woo C, Raphael L et al.: Bilayer vesicles of amphiphilic cyclodextrins: host membranes that recognize guest molecules. Chem. Eur. J.11(4),1171–1180 (2005).Crossref, Medline, CAS, Google Scholar
• 129  Mazzaglia A, Angelini N, Darcy R et al.: Novel heterotopic colloids of anionic porphyrins entangled in cationic amphiphilic cyclodextrins: spectroscopic investigation and intracellular delivery. Chem. Eur. J.9(23),5762–5769 (2003).Crossref, Medline, CAS, Google Scholar
• 130  Memisoglu E, Bochot A, Sen M, Duchene D, Hincal AA: Non-surfactant nanospheres of progesterone inclusion complexes with amphiphilic b-cyclodextrins. Int. J. Pharm.251(1–2),143–153 (2003).Crossref, Medline, CAS, Google Scholar
• 131  Veiga MD, Ahsan F: Influence of surfactants (present in the dissolution media) on the release behaviour of tolbutamide from its inclusion complex with β-cyclodextrin. Eur. J. Pharm. Biopharm.9(3),291–299 (2000).CAS, Google Scholar
• 132  Memisoglu E, Bochot A, Özalp M, Sen M, duchene D, Hincal AA: Direct formation of nanospheres from amphiphilic β-cyclodextrin inclusion complexes. Pharm. Res.20(1),117–125 (2003).Crossref, Medline, CAS, Google Scholar
• 133  Trapani G, Lopedota A, Boghetich G et al.: Encapsulation and release of the hypnotic agent zolpidem from biodegradable polymer microparticles containing hydroxypropyl-β-cyclodextrin. Int. J. Pharm.268(1–2),47–57 (2003).Crossref, Medline, CAS, Google Scholar