Advanced search
Publication Cover
Therapeutic Delivery Volume 3, 2012 - Issue 1
Submit an article Journal homepage
114
Views
0
CrossRef citations to date
0
Altmetric
Review

Molecular Buckets: Cyclodextrins for Oral Cancer Therapy

Patricia Callejaa Department of Pharmacy & Pharmaceutical Technology University of Navarra31080PamplonaSpain
,
Judit Huartea Department of Pharmacy & Pharmaceutical Technology University of Navarra31080PamplonaSpain
,
Maite Agüerosa Department of Pharmacy & Pharmaceutical Technology University of Navarra31080PamplonaSpain
,
Luisa Ruiz-Gatóna Department of Pharmacy & Pharmaceutical Technology University of Navarra31080PamplonaSpain
,
Socorro Espuelasa Department of Pharmacy & Pharmaceutical Technology University of Navarra31080PamplonaSpain
&
Juan M Iracheb [email protected]
Pages 43-57 | Published online: 19 Dec 2011

References

  • Halfdanarson TR , JatoiA. Oral cancer chemotherapy: the critical interplay between patient education and patient safety. Curr. Oncol. Rep.12(4), 247–252 (2010).
  • Weingart SN , BrownE, BachPBet al. NCCN Task Force report: oral chemotherapy. J. Natl Compr. Canc. Netw. 3, S1–S14 (2008).
  • Payne SA . A study of quality of life in cancer patients receiving palliative chemotherapy. Soc. Sci. Med.35(12), 1505–1509 (1992).
  • Liu G , FranssenE, FitchMI, WarnerE. Patient preferences for oral versus intravenous palliative chemotherapy. J. Clin. Oncol.15(1), 110–115 (1997).
  • Pasquier E , KavallarisM, AndreN. Metronomic chemotherapy: new rationale for new directions. Nat. Rev. Clin. Oncol.7(8), 455–465 (2010).
  • Irshad S . MN. Considerations when choosing oral chemotherapy: identifying and responding to patient need. Eur. J. Cancer Care19(Suppl. 1), 5–11 (2010).
  • Terwogt JM , SchellensJH, HuininkWW, BeijnenJH. Clinical pharmacology of anticancer agents in relation to formulations and administration routes. Cancer Treat. Rev.25(2), 83–101 (1999).
  • Kuppens IE , BreedveldP, BeijnenJH, SchellensJH. Modulation of oral drug bioavailability: from preclinical mechanism to therapeutic application. Cancer Invest.23(5), 443–464 (2005).
  • Washington N , WashingtonC, WilsonC. In: Physiological Pharmaceutics: Barriers to Drug Absorption. Taylor and Francis Group, London, UK (2011).
  • Zhang Y , BenetLZ. The gut as a barrier to drug absorption: combined role of cytochrome P450 3A and P-glycoprotein. Clin. Pharmacokinet.40(3), 159–168 (2001).
  • Thummel KE . Gut instincts: CYP3A4 and intestinal drug metabolism. J. Clin. Invest.117(11), 3173–3176 (2007).
  • Cai Z , WangY, ZhuLJ, LiuZQ. Nanocarriers: a general strategy for enhancement of oral bioavailability of poorly absorbed or pre-systemically metabolized drugs. Curr. Drug Metab.11(2), 197–207 (2010).
  • Roger E , LagarceF, GarcionE, BenoitJP. Biopharmaceutical parameters to consider in order to alter the fate of nanocarriers after oral delivery. Nanomedicine (Lond.)5(2), 287–306 (2010).
  • Bansal T , AkhtarN, JaggiM, KharRK, TalegaonkarS. Novel formulation approaches for optimising delivery of anticancer drugs based on Pgp modulation. Drug Discov. Today14(21–22), 1067–1074 (2009).
  • Villiers A . Sur la fermentation de la fécule par l‘action du ferment butyrique. Compt. Rend. Acad. Sci.112, 536–538 (1891).
  • Loftsson T , DucheneD. Cyclodextrins and their pharmaceutical applications. Int. J. Pharm.329(1–2), 1–11 (2007).
  • Szejtli J . Past, present, and future of cyclodextrin research. Pure Appl. Chem.76(10), 1825–1845 (2004).
  • Uekama K , OtagiriM. Cyclodextrins in drug carrier systems. Crit. Rev. Ther. Drug Carrier Syst.3(1), 1–40 (1987).
  • Albers E , MullerBW. Cyclodextrin derivatives in pharmaceutics. Crit. Rev. Ther. Drug Carrier Syst.12(4), 311–337 (1995).
  • Uekama K . Design and evaluation of cyclodextrin-based drug formulation. Chem. Pharm. Bull. (Tokyo)52(8), 900–915 (2004).
  • Szejtli J . Cyclodextrin Technology. Kluwer Academic Publisher, Dordrecht, The Netherlands (1988).
  • Loftsson T , BrewsterME. Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J. Pharm. Sci.85(10), 1017–1025 (1996).
  • Rajewski RA , StellaVJ. Pharmaceutical applications of cyclodextrins. 2. In vivo drug delivery. J. Pharm. Sci.85(11), 1142–1169 (1996).
  • Duchene D , WouessidjeweD. Industrial uses of cyclodextrins and their derivatives. J. Coord. Chem.27(1–3), 223–236 (1992).
  • Thompson DO . Cyclodextrins – enabling excipients: their present and future use in pharmaceuticals. Crit. Rev. Ther. Drug Carrier Syst.14(1), 1–104 (1997).
  • Frank DW , GrayJE, WeaverRN. Cyclodextrin nephrosis in the rat. Am. J. Pathol.83(2), 367–382 (1976).
  • Debouzy JC , FauvelleF, CrouzySet al. Mechanism of alpha-cyclodextrin induced hemolysis. 2. A study of the factors controlling the association with serine-, ethanolamine-, and choline-phospholipids. J. Pharm. Sci. 87(1), 59–66 (1998).
  • Irie T , UekamaK. Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation. J. Pharm. Sci.86(2), 147–162 (1997).
  • Singh M , SharmaR, BanerjeeUC. Biotechnological applications of cyclodextrins. Biotechnol. Adv.20(5–6), 341–359 (2002).
  • Carrier RL , MillerLA, AhmedI. The utility of cyclodextrins for enhancing oral bioavailability. J. Control. Release123(2), 78–99 (2007).
  • Hirayama F , UekamaK. Cyclodextrin-based controlled drug release system. Adv. Drug Deliv. Rev.36(1), 125–141 (1999).
  • Challa R , AhujaA, AliJ, KharRK. Cyclodextrins in drug delivery: an updated review. AAPS PharmSciTech.6(2), E329–E357 (2005).
  • Amidon GL , LennernasH, ShahVP, CrisonJR. A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm. Res.12(3), 413–420 (1995).
  • Yu LX , AmidonGL, PolliJEet al. Biopharmaceutics classification system: the scientific basis for biowaiver extensions. Pharm. Res. 19(7), 921–925 (2002).
  • Loftsson T , MassonM, BrewsterME. Self-association of cyclodextrins and cyclodextrin complexes. J. Pharm. Sci.93(5), 1091–1099 (2004).
  • Loftsson T , MagnusdottirA, MassonM, SigurjonsdottirJF. Self-association and cyclodextrin solubilization of drugs. J. Pharm. Sci.91(11), 2307–2316 (2002).
  • Pitha J , HoshinoT, TorreslabandeiraJ, IrieT. Preparation of drug–hydroxypropylcyclodextrin complexes by a method using ethanol or aqueous ammonium hydroxide as co-solubilizers. Int. J. Pharm.80(2–3), 253–258 (1992).
  • Loftsson T , MagnusdottirA, MassonM. Self association and cyclodextrin solubilization of NSAIDs. J. Incl. Phenom. Macro.44(1–4), 213–218 (2002).
  • Davis ME , BrewsterME. Cyclodextrin-based pharmaceutics: past, present and future. Nat. Rev. Drug Discov.3(12), 1023–1035 (2004).
  • Avdeef A , BendelsS, TsinmanO, TsinmanK, KansyM. Solubility-excipient classification gradient maps. Pharm. Res.24(3), 530–545 (2007).
  • Park JS , KimCK. Solubility enhancers for oral drug delivery: can chemical structure manipulation be avoided? Am. J. Drug Deliv.2(2), 113–130 (2004).
  • Loftsson T , JarhoP, MassonM, JarvinenT. Cyclodextrins in drug delivery. Expert Opin. Drug Deliv.2(2), 335–351 (2005).
  • Park K . Efficient oral delivery of paclitaxel using cyclodextrin complexes. J. Control. Release145(1), 1 (2010).
  • Cserhati T , ForgacsE, HolloJ. Interaction of taxol and other anticancer drugs with alpha-cyclodextrin. J. Pharm. Biomed. Anal.13(4–5), 533–541 (1995).
  • Badawy SIF , GhorabMM, AdeyeyeCM. Bioavailability of danazol-hydroxypropyl-beta-cylodextrin complex by different routes of administration. Int. J. Pharm.145(1–2), 137–143 (1996).
  • Madan J , DhimanN, ParmarVKet al. Inclusion complexes of noscapine in beta-cyclodextrin offer better solubility and improved pharmacokinetics. Cancer Chemoth. Pharmacol. 65(3), 537–548 (2010).
  • Yavuz B , BilensoyE, VuralI, SumnuM. Alternative oral exemestane formulation: improved dissolution and permeation. Int. J. Pharm.398(1–2), 137–145 (2010).
  • Yavuz B , SarisozenC, VuralI, BilensoyE, SumnuM. An alternative cyclodextrin based formulation for oral anticancer drug exemestane: in vitro and cell culture studies. J. Control. Release148(1), e83–84 (2010).
  • Kikuchi M , HirayamaF, UekamaK. Improvement of chemical instability of carmoful in beta-cyclodextrin solid complex by utilizing some organic acids. Chem. Pharm. Bull. (Tokyo)35(1), 315–319 (1987).
  • Piette M , EvrardB, FrankenneFet al. Pharmacokinetic study of a new synthetic MMP inhibitor (Ro 28–2653) after IV and oral administration of cyclodextrin solutions. Eur. J. Pharm. Sci. 28(3), 189–195 (2006).
  • Nakanishi K , NadaiT, MasadaM, MiyajimaK. Effect of cyclodextrins on biological membrane. II. Mechanism of enhancement on the intestinal absorption of non-absorbable drug by cyclodextrins. Chem. Pharm. Bull. (Tokyo)40(5), 1252–1256 (1992).
  • Gottesman MM , PastanI. Biochemistry of multidrug resistance mediated by the multidrug transporter. Annu. Rev. Biochem.62, 385–427 (1993).
  • Fenyvesi F , FenyvesiE, SzenteLet al. Pgp inhibition by membrane cholesterol modulation. Eur. J. Pharm. Sci. 34(4–5), 236–242 (2008).
  • Ishikawa M , YoshiiH, FurutaT. Interaction of modified cyclodextrins with cytochrome P-450. Biosci. Biotechnol. Biochem.69(1), 246–248 (2005).
  • Garrigues A , EscargueilAE, OrlowskiS. The multidrug transporter, P-glycoprotein, actively mediates cholesterol redistribution in the cell membrane. Proc. Natl Acad. Sci. USA99(16), 10347–10352 (2002).
  • Arima H , YunomaeK, HirayamaF, UekamaK. Contribution of Pgp to the enhancing effects of dimethyl-beta-cyclodextrin on oral bioavailability of tacrolimus. J. Pharmacol. Exp. Ther.297(2), 547–555 (2001).
  • Pathak SM , MusmadeP, DengleSet al. Enhanced oral absorption of saquinavir with methyl-beta-cyclodextrin-preparation and in vitro and in vivo evaluation. Eur. J. Pharm. Sci. 41(3–4), 440–451 (2010).
  • Fenyvesi F , KissT, FenyvesiEet al. Randomly methylated beta-cyclodextrin derivatives enhance taxol permeability through human intestinal epithelial Caco-2 cell monolayer. J. Pharm. Sci. 100(11), 4734–4744 (2011).
  • Munoz M , DeschenauxR, ColemanAW. Observation of microscopic patterning at the air water interface by mixtures of amphiphilic cyclodextrins: a compression isotherm and Brewster angle microscopy study. J. Phys. Org. Chem.12(5), 364–369 (1999).
  • Bilensoy E , DoganL, SenM, HincalA. Complexation behavior of antiestrogen drug tamoxifen citrate with natural and modified beta-cyclodextrins. J. Incl. Phenom. Macro.57(1–4), 651–655 (2007).
  • Duchene D , PonchelG, WouessidjeweD. Cyclodextrins in targeting. Application to nanoparticles. Adv. Drug Deliv. Rev.36(1), 29–40 (1999).
  • Duchene D , WouessidjeweD, PonchelG. Cyclodextrins and carrier systems. J. Control. Release62(1–2), 263–268 (1999).
  • Memisoglu-Bilensoy E , VuralL, BochotAet al. Tarnoxifen citrate loaded amphiphilic beta-cyclodextrin nanoparticles: in vitro characterization and cytotoxicity. J. Control. Release 104(3), 489–496 (2005).
  • Cryan SA , HolohanA, DonohueR, DarcyR, O‘DriscollCM. Cell transfection with polycationic cyclodextrin vectors. Eur. J. Pharm. Sci.21(5), 625–633 (2004).
  • Bilensoy E , HincalAA. Recent advances and future directions in amphiphilic cyclodextrin nanoparticles. Expert Opin. Drug Deliv.6(11), 1161–1173 (2009).
  • Lemos-Senna E , WouessidjeweD, LesieurS, PuisieuxF, CourrazeG, DucheneD. Evaluation of the hydrophobic drug loading characteristics in nanoprecipitated amphiphilic cyclodextrin nanospheres. Pharm. Dev. Technol.3(1), 85–94 (1998).
  • Wouessidjewe D , SkibaM, LeroyLechatFet al. A new concept in drug delivery based on ‘skirt-shaped cyclodextrin aggregates‘ – present state and future prospects. Stp. Pharma. Sci. 6(1), 21–28 (1996).
  • Lemos-Senna E , WouessidjeweD, LesieurS, DucheneD. Preparation of amphiphilic cyclodextrin nanospheres using the emulsification solvent evaporation method. Influence of the surfactant on preparation and hydrophobic drug loading. Int. J. Pharm.170(1), 119–128 (1998).
  • Lemos-Senna E , WouessidjeweD, DucheneD, LesieurS. Amphiphilic cyclodextrin nanospheres: particle solubilization and reconstitution by the action of a non-ionic detergent. Colloid. Surface. B10(5), 291–301 (1998).
  • Memisoglu E , BochotA, OzalpMet al. Direct formation of nanospheres from amphiphilic beta-cyclodextrin inclusion complexes. Pharm. Res. 20(1), 117–125 (2003).
  • Memisoglu E , BochotA, SenM, DucheneD, HincalAA. Non-surfactant nanospheres of progesterone inclusion complexes with amphiphilic beta-cyclodextrins. Int. J. Pharm.251(1–2), 143–153 (2003).
  • Vural I , Memisoglu-BilensoyE, RenoirJMet al. Transcription efficiency of tamoxifen citrate-loaded beta-cyclodextrin nanoparticles. J. Drug Deliv. Sci. Technol. 15(5), 339–342 (2005).
  • Bilensoy E , GurkaynakO, ErtanM, SenM, HincalAA. Development of nonsurfactant cyclodextrin nanoparticles loaded with anticancer drug paclitaxel. J. Pharm. Sci.97(4), 1519–1529 (2008).
  • Bilensoy E , GurkaynakO, DoganAL, HincalAA. Safety and efficacy of amphiphilic beta-cyclodextrin nanoparticles for paclitaxel delivery. Int. J. Pharm.347(1–2), 163–170 (2008).
  • Cirpanli Y , BilensoyE, DoganAL, CalisS. Comparative evaluation of polymeric and amphiphilic cyclodextrin nanoparticles for effective camptothecin delivery. Eur. J. Pharm. Biopharm.73(1), 82–89 (2009).
  • Cirpanli Y , AllardE, PassiraniCet al. Antitumoral activity of camptothecin-loaded nanoparticles in 9L rat glioma model. Int. J. Pharm. 403(1–2), 201–206 (2011).
  • Quaglia F , OstacoloL, MazzagliaAet al. The intracellular effects of non-ionic amphiphilic cyclodextrin nanoparticles in the delivery of anticancer drugs. Biomaterials 30(3), 374–382 (2009).
  • Sortino S , MazzagliaA, ScolaroLMet al. Nanoparticles of cationic amphiphilic cyclodextrins entangling anionic porphyrins as carrier-sensitizer system in photodynamic cancer therapy. Biomaterials 27(23), 4256–4265 (2006).
  • Tsuruo T , IidaH, TsukagoshiS, SakuraiY. Overcoming of vincristine resistance in p388 leukemia in vivo and in vitro through enhanced cyto-toxicity of vincristine and vinblastine by verapamil. Cancer Res.41(5), 1967–1972 (1981).
  • van Asperen J , van Tellingen O, van der Valk MA, Rozenhart M, Beijnen JH. Enhanced oral absorption and decreased elimination of paclitaxel in mice cotreated with cyclosporin A. Clin. Cancer Res.4(10), 2293–2297 (1998).
  • Bardelmeijer HA , BeijnenJH, BrouwerKRet al. Increased oral bioavailability of paclitaxel by GF120918 in mice through selective modulation of P-glycoprotein. Clin. Cancer Res. 6(11), 4416–4421 (2000).
  • Dong YC , FengSS. Poly(D,L-lactide-co-glycolide)/montmorillonite nanoparticles for oral delivery of anticancer drugs. Biomaterials26(30), 6068–6076 (2005).
  • Woo JS , LeeCH, ShimCK, HwangSJ. Enhanced oral bioavailability of paclitaxel by coadministration of the Pgp inhibitor KR30031. Pharm. Res.20(1), 24–30 (2003).
  • Ponchel G , IracheJM. Specific and non-specific bioadhesive particulate systems for oral delivery to the gastrointestinal tract. Adv. Drug Deliver. Rev.34(2–3), 191–219 (1998).
  • Woodley J . Bioadhesion – new possibilities for drug administration? Clin. Pharmacokinet.40(2), 77–84 (2001).
  • Bernkop-Schnürch A . Mucoadhesive systems in oral drug delivery. Drug Discov. Today Technol.2(1), 83–87 (2005).
  • Florence AT , HilleryAM, HussainN, JaniPU. Factors affecting the oral uptake and translocation of polystyrene nanoparticles – histological and analytical evidence. J. Drug Target.3(1), 65–70 (1995).
  • Bertholon I , PonchelG, LabarreD, CouvreurP, VauthierC. Bioadhesive properties of poly(alkylcyanoacrylate) nanoparticles coated with polysaccharide. J. Nanosci. Nanotechnol.6(9–10), 3102–3109 (2006).
  • Chen J , YangWL, LiGet al. Transfection of mEpo gene to intestinal epithelium in vivo mediated by oral delivery of chitosan-DNA nanoparticles. World J. Gastroentero. 10(1), 112–116 (2004).
  • Feng SS , MeiL, AnithaP, GanCW, ZhouWY. Poly(lactide)-vitamin E derivative/montmorillonite nanoparticle formulations for the oral delivery of Docetaxel. Biomaterials30(19), 3297–3306 (2009).
  • Arangoa MA , CampaneroMA, RenedoMJ, PonchelG, IracheJM. Gliadin nanoparticles as carriers for the oral administration of lipophilic drugs. Relationships between bioadhesion and pharmacokinetics. Pharm. Res.18(11), 1521–1527 (2001).
  • Arbos P , CampaneroMA, ArangoaMA, IracheJM. Nanoparticles with specific bioadhesive properties to circumvent the pre-systemic degradation of fluorinated pyrimidines. J. Control. Release96(1), 55–65 (2004).
  • Arbos P , CampaneroMA, ArnangoaMA, RenedoMJ, IracheJM. Influence of the surface characteristics of PVM/MA nanoparticles on their bioadhesive properties. J. Control. Release89(1), 19–30 (2003).
  • Lamprecht A , SchaferU, LehrCM. Size-dependent bioadhesion of micro- and nanoparticulate carriers to the inflamed colonic mucosa. Pharm. Res.18(6), 788–793 (2001).
  • Montisci MJ , DembriA, GiovannuciGet al. Gastrointestinal transit and mucoadhesion of colloidal suspensions of Lycopersicon esculentum L. and Lotus tetragonolobus lectin-PLA microsphere conjugates in rats. Pharm. Res. 18(6), 829–837 (2001).
  • Arbos P , ArangoaMA, CampaneroMA, IracheJM. Quantification of the bioadhesive properties of protein-coated PVM/MA nanoparticles. Int. J. Pharm.242(1–2), 129–136 (2002).
  • Salman HH , GamazoC, CampaneroMA, IracheJM. Bioadhesive mannosylated nanoparticles for oral drug delivery. J. Nanosci. Nanotechnol.6(9–10), 3203–3209 (2006).
  • Salman HH , GamazoC, AguerosM, IracheJM. Bioadhesive capacity and immunoadjuvant properties of thiamine-coated nanoparticles. Vaccine25(48), 8123–8132 (2007).
  • Llabot JM , SalmanH, MillottiGet al. Bioadhesive properties of poly(anhydride) nanoparticles coated with different molecular weights chitosan. J. Microencapsul. 28(5), 455–463 (2011).
  • Agueros M , AresesP, CampaneroMAet al. Bioadhesive properties and biodistribution of cyclodextrin-poly(anhydride) nanoparticles. Eur. J. Pharm. Sci. 37(3–4), 231–240 (2009).
  • Areses P , AgüerosMT, QuincocesGet al. Molecular imaging techniques to study the biodistribution of orally administered 99mTc-labelled naive and ligand-tagged nanoparticles. Mol. Imaging Biol. 13(6), 1215–1223 (2011).
  • Agueros M , ZabaletaV, EspuelasS, CampaneroMA, IracheJM. Increased oral bioavailability of paclitaxel by its encapsulation through complex formation with cyclodextrins in poly(anhydride) nanoparticles. J. Control. Release145(1), 2–8 (2010).
  • Sparano JA , WangML, MartinoSet al. Weekly paclitaxel in the adjuvant treatment of breast cancer. New Engl. J. Med. 358(16), 1663–1671 (2008).
  • Montana M , DucrosC, VerhaeghePet al. Albumin-bound paclitaxel: the benefit of this new formulation in the treatment of various cancers. J. Chemother. 23(2), 59–66 (2011).
  • Sandler A , GrayR, PerryMCet al. Paclitaxel-carboplatin alone or with bevacizumab for non-small-cell lung cancer. New Engl. J. Med. 355(24), 2542–2550 (2006).
  • Zhan M , TaoWY, PanSH, SunXY, JiangHC. Low-dose metronomic chemotherapy of paclitaxel synergizes with cetuximab to suppress human colon cancer xenografts. Anticancer Drug.20(5), 355–363 (2009).
  • Dhanikula AB , PanchagnulaR. Localized paclitaxel delivery. Int. J. Pharm.183(2), 85–100 (1999).
  • da Silveira AM , PonchelG, PuisieuxF, DucheneD. Combined poly(isobutylcyanoacrylate) and cyclodextrins nanoparticles for enhancing the encapsulation of lipophilic drugs. Pharm. Res.15(7), 1051–1055 (1998).
  • Agueros M , Ruiz-GatonL, VauthierCet al. Combined hydroxypropyl-beta-cyclodextrin and poly(anhydride) nanoparticles improve the oral permeability of paclitaxel. Eur. J. Pharm. Sci. 38(4), 405–413 (2009).
  • Calvo J , LavanderaJ, AgüerosM, IracheJ. Cyclodextrin/poly(anhydride) nanoparticles as drug carriers for the oral delivery of atovaquone. Biomed. Microdevices13(6), 1015–1025 (2011).
  • Mooguee M , OmidiY, DavaranS. Synthesis and in vitro release of adriamycin from star-shaped poly(lactide-co-glycolide) nano- and microparticles. J. Pharm. Sci.99(8), 3389–3397 (2010).
  • Wang TW , ZhangCL, LiangXJ, LiangW, WuY. Hydroxypropyl-beta-cyclodextrin copolymers and their nanoparticles as doxorubicin delivery system. J. Pharm. Sci.100(3), 1067–1079 (2011).
  • McCormack B , GregoriadisG. Entrapment of cyclodextrin-drug complexes into liposomes: potential advantages in drug delivery. J. Drug Target.2(5), 449–454 (1994).
  • Wang X , DengL, CaiLet al. Preparation, characterization, pharmacokinetics, and bioactivity of honokiol-in-hydroxypropyl-β-cyclodextrin in liposome. J. Pharm. Sci. 100(8), 3357–3364 (2011).
  • Arima H , YunomaeK, MorikawaT, HirayamaF, UekamaK. Contribution of cholesterol and phospholipids to inhibitory effect of dimethyl-beta-cyclodextrin on efflux function of Pgp and multidrug resistance-associated protein 2 in vinblastine-resistant Caco-2 cell monolayers. Pharm. Res.21(4), 625–634 (2004).
  • Uekama K . Pharmaceutical application of cyclodextrins as multi-functional drug carriers. Yakugaku Zasshi124(12), 909–935 (2004).
  • Bellanger N , PerlyB. NMR investigations of the conformation of new cyclodextrin-based amphiphilic transporters for hydrophobic drugs - molecular lollipops. J. Mol. Struct.273, 215–226 (1992).
  • Dodziuk H , ChmurskiK, JurczakJet al. A dynamic NMR study of self-inclusion of a pendant group in amphiphilic 6-thiophenyl-6-deoxycyclodextrins. J. Mol. Struct. 519, 33–36 (2000).
  • Kawabata Y , MatsumotoM, TanakaMet al. Formation and deposition of monolayers of amphiphilic beta-cyclodextrin derivatives. Chem. Lett. 11, 1933–1934 (1986).
  • Liu FY , KildsigDO, MitraAK. Complexation of 6-acyl-O-beta-cyclodextrin derivatives with steroids – effects of chain-length and substitution degree. Drug Dev. Ind. Pharm.18(15), 1599–1612 (1992).
  • Zhang P , LingCC, ColemanAW, ParrotlopezH, GalonsH. Formation of amphiphilic cyclodextrins via hydrophobic esterification at the secondary hydroxyl face. Tetrahedron Lett.32(24), 2769–2770 (1991).
  • Zhang P , ParrotlopezH, TchoreloffPet al. Self-organizing systems based on amphiphilic cyclodextrin diesters. J. Phys. Org. Chem. 5(8), 518–528 (1992).
  • Lesieur S , CharonD, LesieurPet al. Phase behavior of fully hydrated DMPC-amphiphilic cyclodextrin systems. Chem. Phys. Lipids 106(2), 127–144 (2000).
  • Canceill J , JullienL, LacombeL, LehnJM. Channel-type molecular-structures. 2. synthesis of bouquet-shaped molecules based on a beta-cyclodextrin core. Helv. Chim. Acta75(3), 791–812 (1992).
  • Wenz G . Synthesis and characterization of some lipophilic per(2,6-di-O-alkyl)cyclomalto-oligosaccharides. Carbohyd. Res.214(2), 257–265 (1991).
  • Auzely-Velty R , Djedaini-PilardF, DesertS, PerlyB, ZembT. Micellization of hydrophobically modified cyclodextrins. 1. Micellar structure. Langmuir16(8), 3727–3734 (2000).
  • Mazzaglia A , AngeliniN, DarcyRet 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).
  • Matsumoto M , MatsuzawaY, NoguchiS, SakaiH, AbeM. Structure of hybrid Langmuir-Blodgett films of amphiphilic cyclodextrin and water-soluble azobenzene. Mol. Cryst. Liq. Cryst.425, 475–482 (2004).
  • Dubes A , BouchuD, LamartineR, Parrot-LopezH. An efficient regio-specific synthetic route to multiply substituted acyl-sulphated beta-cyclodextrins. Tetrahedron Lett.42(52), 9147–9151 (2001).
  • Granger CE , FelixCP, Parrot-LopezHP, LangloisBR. Fluorine containing beta-cyclodextrin: a new class of amphiphilic carriers. Tetrahedron Lett.41(48), 9257–9260 (2000).
  • Peroche S , DegobertG, PutauxJLet al. Synthesis and characterisation of novel nanospheres made from amphiphilic perfluoroalkylthio-beta-cyclodextrins. Eur. J. Pharm. Biopharm. 60(1), 123–131 (2005).
  • Skiba M , Skiba-LahianiM, ArnaudP. Design of nanocapsules based on novel fluorophilic cyclodextrin derivatives and their potential role in oxygen delivery. J. Incl. Phenom. Macro.44(1–4), 151–154 (2002).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.