Potential use of the complex of doxorubicin with folate-conjugated methyl-β-cyclodextrin for tumor-selective cancer chemotherapy

References

• Wong HL, Bendayan R, Rauth AM, et al. Chemotherapy with anticancer drugs encapsulated in solid lipid nanoparticles. Adv Drug Deliv Rev 2007;59:491–504
   PubMed Web of Science ®Google Scholar
• Chen H, Ahn R, Van den Bossche J, et al. Folate-mediated intracellular drug delivery increases the anticancer efficacy of nanoparticulate formulation of arsenic trioxide. Mol Cancer Ther 2009;8:1955–63
   PubMed Web of Science ®Google Scholar
• Gabizon A, Tzemach D, Gorin J, et al. Improved therapeutic activity of folate-targeted liposomal doxorubicin in folate receptor-expressing tumor models. Cancer Chemother Pharmacol 2010;66:43–52
   PubMed Web of Science ®Google Scholar
• Lu Y, Low PS. Folate-mediated delivery of macromolecular anticancer therapeutic agents. Adv Drug Deliv Rev 2002;54:675–93
   PubMed Web of Science ®Google Scholar
• Mi Y, Liu Y, Feng SS. Formulation of docetaxel by folic acid-conjugated d-α-tocopheryl polyethylene glycol succinate 2000 (Vitamin E TPGS(2k)) micelles for targeted and synergistic chemotherapy. Biomaterials 2011;32:4058–66
   PubMed Web of Science ®Google Scholar
• Nukolova NV, Oberoi HS, Cohen SM, et al. Folate-decorated nanogels for targeted therapy of ovarian cancer. Biomaterials 2011;32:5417–26
   PubMed Web of Science ®Google Scholar
• Roche AC, Fajac I, Grosse S, et al. Glycofection: facilitated gene transfer by cationic glycopolymers. Cell Mol Life Sci 2003;60:288–97
   PubMed Web of Science ®Google Scholar
• Kobayashi T, Ishida T, Okada Y, et al. Effect of transferrin receptor-targeted liposomal doxorubicin in P-glycoprotein-mediated drug resistant tumor cells. Int J Pharm 2007;329:94–102
   PubMed Web of Science ®Google Scholar
• Harata M, Soda Y, Tani K, et al. CD19-targeting liposomes containing imatinib efficiently kill Philadelphia chromosome-positive acute lymphoblastic leukemia cells. Blood 2004;104:1442–9
   PubMed Web of Science ®Google Scholar
• Kim IY, Kang YS, Lee DS, et al. Antitumor activity of EGFR targeted pH-sensitive immunoliposomes encapsulating gemcitabine in A549 xenograft nude mice. J Control Release 2009;140:55–60
   PubMed Web of Science ®Google Scholar
• Mamot C, Drummond DC, Greiser U, et al. Epidermal growth factor receptor (EGFR)-targeted immunoliposomes mediate specific and efficient drug delivery to EGFR- and EGFRvIII-overexpressing tumor cells. Cancer Res 2003;63:3154–61
   PubMed Web of Science ®Google Scholar
• Schiffelers RM, Koning GA, ten Hagen TL, et al. Anti-tumor efficacy of tumor vasculature-targeted liposomal doxorubicin. J Control Release 2003;91:115–22
   PubMed Web of Science ®Google Scholar
• Low PS, Kularatne SA. Folate-targeted therapeutic and imaging agents for cancer. Curr Opin Chem Biol 2009;13:256–62
   PubMed Web of Science ®Google Scholar
• Antony AC. The biological chemistry of folate receptors. Blood 1992;79:2807–20
   PubMed Web of Science ®Google Scholar
• Limmon GV, Arredouani M, McCann KL, et al. Scavenger receptor class-A is a novel cell surface receptor for double-stranded RNA. FASEB J 2008;22:159–67
   PubMed Web of Science ®Google Scholar
• Uekama K, Hirayama F, Irie T. Cyclodextrin drug carrier systems. Chem Rev 1998;98:2045–76
   PubMed Web of Science ®Google Scholar
• Uekama K, Otagiri M. Cyclodextrins in drug carrier systems. Crit Rev Ther Drug Carrier Syst 1987;3:1–40
   PubMed Web of Science ®Google Scholar
• Caliceti P, Salmaso S, Semenzato A, et al. Synthesis and physicochemical characterization of folate-cyclodextrin bioconjugate for active drug delivery. Bioconjug Chem 2003;14:899–908
   PubMed Web of Science ®Google Scholar
• Salmaso S, Semenzato A, Caliceti P, et al. Specific antitumor targetable β-cyclodextrin-poly(ethylene glycol)-folic acid drug delivery bioconjugate. Bioconjug Chem 2004;15:997–1004
   PubMed Web of Science ®Google Scholar
• Zhang H, Cai Z, Sun Y, et al. Folate-conjugated β-cyclodextrin from click chemistry strategy and for tumor-targeted drug delivery. J Biomed Mater Res A 2012;100:2441–9
   PubMed Web of Science ®Google Scholar
• Stella VJ, He Q. Cyclodextrins. Toxicol Pathol 2008;36:30–42
   PubMed Web of Science ®Google Scholar
• Stella VJ, Rao VM, Zannou EA, Zia VV. Mechanisms of drug release from cyclodextrin complexes. Adv Drug Deliv Rev 1999;36:3–16
   PubMed Web of Science ®Google Scholar
• Okamatsu A, Motoyama K, Onodera R, et al. Folate-appended β-Cyclodextrin as a promising tumor targeting carrier for antitumor drugs in vitro and in vivo. Bioconjug Chem 2013;24:724–33
   PubMed Web of Science ®Google Scholar
• Motoyama K, Arima H, Toyodome H, et al. Effect of 2,6-di-O-methyl-α-cyclodextrin on hemolysis and morphological change in rabbit's red blood cells. Eur J Pharm Sci 2006;29:111–19
   PubMed Web of Science ®Google Scholar
• Motoyama K, Toyodome H, Onodera R, et al. Involvement of lipid rafts of rabbit red blood cells in morphological changes induced by methylated β-cyclodextrins. Biol Pharm Bull 2009;32:700–5
   PubMed Web of Science ®Google Scholar
• Ohtani Y, Irie T, Uekama K, et al. Differential effects of α-, β- and γ-cyclodextrins on human erythrocytes. Eur J Biochem 1989;186:17–22
   PubMedGoogle Scholar
• Galbiati F, Razani B, Lisanti MP. Emerging themes in lipid rafts and caveolae. Cell 2001;106:403–11
   PubMed Web of Science ®Google Scholar
• Park EK, Park MJ, Lee SH, et al. Cholesterol depletion induces anoikis-like apoptosis via FAK down-regulation and caveolae internalization. J Pathol 2009;218:337–49
   PubMed Web of Science ®Google Scholar
• Grosse PY, Bressolle F, Pinguet F. Antiproliferative effect of methyl-β-cyclodextrin in vitro and in human tumour xenografted athymic nude mice. Br J Cancer 1998;78:1165–9
   PubMed Web of Science ®Google Scholar
• Onodera R, Motoyama K, Arima H. Design and evaluation of folate-appended methyl-β-cyclodextrin as a new antitumor agent. J Incl Phenom Macrocycl Chem 2011;70:321–6
   Web of Science ®Google Scholar
• Onodera R, Motoyama K, Okamatsu A, et al. Potential use of folate-appended methyl-β-cyclodextrin as an anticancer agent. Sci Rep 2013;3:1104 (1--9). doi: 10.1038/srep01104
   PubMed Web of Science ®Google Scholar
• Hamasaki K, Kogure K, Ohwada K. A biological method for the quantitative measurement of tetrodotoxin (TTX): tissue culture bioassay in combination with a water-soluble tetrazolium salt. Toxicon 1996;34:490–5
   PubMed Web of Science ®Google Scholar
• Arima H, Chihara Y, Arizono M, et al. Enhancement of gene transfer activity mediated by mannosylated dendrimer/α-cyclodextrin conjugate (generation 3, G3). J Control Release 2006;116:64–74
   PubMed Web of Science ®Google Scholar
• Wada K, Arima H, Tsutsumi T, et al. Improvement of gene delivery mediated by mannosylated dendrimer/α-cyclodextrin conjugates. J Control Release 2005;104:397–413
   PubMed Web of Science ®Google Scholar
• Bakkour Y, Vermeersch G, Morcellet M, et al. Formation of cyclodextrin inclusion complexes with doxycyclin-hyclate: NMR investigation of their characterisation and stability. J Incl Phenom Macrocycl Chem 2006;54:109–14
   Web of Science ®Google Scholar
• 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 2003;536:225–31
   PubMed Web of Science ®Google Scholar
• Oda Y, Kobayashi N, Yamanoi T, et al. Beta-cyclodextrin conjugates with glucose moieties designed as drug carriers: their syntheses, evaluations using concanavalin A and doxorubicin, and structural analyses by NMR spectroscopy. Med Chem 2008;4:244–55
   PubMed Web of Science ®Google Scholar
• Wen JQ, Cui W. Studies on the composition and stability constant of inclusion complexes of β-cyclodextrin with fluorouracil and ftorafur by NMR. Yao Xue Xue Bao 1990;25:345–8
   PubMedGoogle Scholar
• Upadhyay AK, Singh S, Chhipa RR, et al. Methyl-β-cyclodextrin enhances the susceptibility of human breast cancer cells to carboplatin and 5-fluorouracil: involvement of Akt, NF-κB and Bcl-2. Toxicol Appl Pharmacol 2006;216:177–85
   PubMed Web of Science ®Google Scholar
• Soliman HA, Olesen H. Folic acid binding by human plasma albumin. Scand J Clin Lab Invest 1976;36:299–304
   PubMed Web of Science ®Google Scholar
• Zhang S, Liu X, Bawa-Khalfe T, et al. Identification of the molecular basis of doxorubicin-induced cardiotoxicity. Nat Med 2012;18:1639–42
   PubMed Web of Science ®Google Scholar