Design and evaluation of folate-appended methyl-β-cyclodextrin as a new antitumor agent

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 70, Issue 3-4, 2011, Pages 321-326

  Onodera, Risako ^a   Motoyama, Keiichi ^a   Arima, Hidetoshi ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

Antitumor drug; Folic acid; Methyl cyclodextrin; Tumor targeting

Indexed keywords

EID: 80051794359     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-010-9843-z     Document Type: Conference Paper

References (27)

1. ME O'Brien N Wigler M Inbar R Rosso E Grischke A Santoro R Catane DG Kieback P Tomczak SP Ackland F Orlandi L Mellars L Alland C Tendler 2004 Reduced cardiotoxicity and comparable efficacy in a phase III trial of pegylated liposomal doxorubicin HCl (CAELYX/Doxil) versus conventional doxorubicin for first-line treatment of metastatic breast cancer Ann. Oncol. 15 440 449 10.1093/annonc/mdh097 (Pubitemid 38444547)
2. M Harata Y Soda K Tani J Ooi T Takizawa M Chen Y Bai K Izawa S Kobayashi A Tomonari F Nagamura S Takahashi K Uchimaru T Iseki T Tsuji TA Takahashi K Sugita S Nakazawa A Tojo K Maruyama S Asano 2004 CD19-targeting liposomes containing imatinib efficiently kill Philadelphia chromosome-positive acute lymphoblastic leukemia cells Blood 104 1442 1449 10.1182/blood-2004-02-0588 1:CAS:528:DC%2BD2cXnt1ersrc%3D (Pubitemid 39166523)
3. AC Roche I Fajac S Grosse N Frison C Rondanino R Mayer M Monsigny 2003 Glycofection: facilitated gene transfer by cationic glycopolymers Cell. Mol. Life Sci. 60 288 297 10.1007/s000180300024 1:CAS:528:DC%2BD3sXns1Wksrc%3D (Pubitemid 36343909)
4. H Chen R Ahn J Van den Bossche DH Thompson TV O'Halloran 2009 Folate-mediated intracellular drug delivery increases the anticancer efficacy of nanoparticulate formulation of arsenic trioxide Mol. Cancer. Ther. 8 1955 1963 10.1158/1535-7163.MCT-09-0045 1:CAS:528:DC%2BD1MXosVymsbg%3D
5. Y Lu PS Low 2002 Folate-mediated delivery of macromolecular anticancer therapeutic agents Adv. Drug. Deliv. Rev. 54 675 693 10.1016/S0169-409X(02) 00042-X 1:CAS:528:DC%2BD38XmsVeqtrk%3D (Pubitemid 35247522)
6. H Hatakeyama H Akita K Maruyama T Suhara H Harashima 2004 Factors governing the in vivo tissue uptake of transferrin-coupled polyethylene glycol liposomes in vivo Int. J. Pharm. 281 25 33 10.1016/j.ijpharm.2004.05.025 1:CAS:528:DC%2BD2cXmtFCmurk%3D (Pubitemid 39024260)
7. Y Miyajima H Nakamura Y Kuwata JD Lee S Masunaga K Ono K Maruyama 2006 Transferrin-loaded nido-carborane liposomes: tumor-targeting boron delivery system for neutron capture therapy Bioconjug. Chem. 17 1314 1320 10.1021/bc060064k 1:CAS:528:DC%2BD28XnvVKhsL0%3D (Pubitemid 44455341)
8. IY Kim YS Kang DS Lee HJ Park EK Choi YK Oh HJ Son JS Kim 2009 Antitumor activity of EGFR targeted pH-sensitive immunoliposomes encapsulating gemcitabine in A549 xenograft nude mice J. Control. Release 140 55 60 10.1016/j.jconrel. 2009.07.005 1:CAS:528:DC%2BD1MXht1OiurfP
9. RM Schiffelers GA Koning TL ten Hagen MH Fens AJ Schraa AP Janssen RJ Kok G Molema G Storm 2003 Anti-tumor efficacy of tumor vasculature-targeted liposomal doxorubicin. J. Control Release 91 115 122 10.1016/S0168-3659(03) 00240-2 1:CAS:528:DC%2BD3sXmsVSkurw%3D (Pubitemid 37288882)
10. CP Leamon PS Low 2001 Folate-mediated targeting: from diagnostics to drug and gene delivery. Drug Discov Today 6 44 51 1:CAS:528:DC%2BD3MXntlOrsg%3D%3D (Pubitemid 32156966)
11. N Parker MJ Turk E Westrick JD Lewis PS Low CP Leamon 2005 Folate receptor expression in carcinomas and normal tissues determined by a quantitative radioligand binding assay Anal. Biochem. 338 284 293 10.1016/j.ab.2004.12.026 1:CAS:528:DC%2BD2MXitVaqur0%3D (Pubitemid 40312593)
12. L Szente J Szejtli 1999 Highly soluble cyclodextrin derivatives: chemistry, properties, and trends in development Adv. Drug Deliv. Rev. 36 17 28 10.1016/S0169-409X(98)00092-1 1:CAS:528:DyaK1MXksFegtw%3D%3D (Pubitemid 29074474)
13. K Uekama M Otagiri 1987 Cyclodextrins in drug carrier systems Crit. Rev. Ther. Drug Carrier Syst. 3 1 40 1:CAS:528:DyaL2sXptVSisA%3D%3D (Pubitemid 17231927)
14. K Motoyama H Arima H Toyodome T Irie F Hirayama K Uekama 2006 Effect of 2, 6-di-O-methyl-α-cyclodextrin on hemolysis and morphological change in rabbit's red blood cells Eur. J. Pharm. Sci. 29 111 119 10.1016/j.ejps.2006.06. 002 1:CAS:528:DC%2BD28XpsVWlsbc%3D (Pubitemid 44332884)
15. K Motoyama H Toyodome R Onodera T Irie F Hirayama K Uekama H Arima 2009 Involvement of lipid rafts of rabbit red blood cells in morphological changes induced by methylated β-cyclodextrins Biol. Pharm. Bull. 32 700 705 10.1248/bpb.32.700 1:CAS:528:DC%2BD1MXmsVSksb8%3D
16. Y Ohtani T Irie K Uekama K Fukunaga J Pitha 1989 Differential effects of α-, β- and γ-cyclodextrins on human erythrocytes Eur. J. Biochem. 186 17 22 10.1111/j.1432-1033.1989.tb15171.x 1:CAS:528: DyaK3cXntlaltA%3D%3D (Pubitemid 20015121)
17. F Galbiati B Razani MP Lisanti 2001 Emerging themes in lipid rafts and caveolae Cell 106 403 411 10.1016/S0092-8674(01)00472-X 1:CAS:528: DC%2BD3MXmsFOitb8%3D (Pubitemid 32786984)
18. K Simons R Ehehalt 2002 Cholesterol, lipid rafts, and disease J. Clin. Invest. 110 597 603 1:CAS:528:DC%2BD38Xmslyisbc%3D (Pubitemid 34988781)
19. RG Anderson K Jacobson 2002 A role for lipid shells in targeting proteins to caveolae, rafts, and other lipid domains Science 296 1821 1825 10.1126/science.1068886 1:CAS:528:DC%2BD38Xktl2rt78%3D (Pubitemid 34596260)
20. K Motoyama K Kameyama R Onodera N Araki F Hirayama K Uekama H Arima 2009 Involvement of PI3K-Akt-Bad pathway in apoptosis induced by 2, 6-di-O-methyl-β-cyclodextrin, not 2, 6-di-O-methyl-α-cyclodextrin, through cholesterol depletion from lipid rafts on plasma membranes in cells Eur. J. Pharm. Sci. 38 249 261 10.1016/j.ejps.2009.07.010 1:CAS:528: DC%2BD1MXhtFGqtL%2FP
21. PY Grosse F Bressolle F Pinguet 1998 Antiproliferative effect of methyl-β-cyclodextrin in vitro and in human tumour xenografted athymic nude mice Br. J. Cancer 78 1165 1169 10.1038/bjc.1998.648 1:CAS:528: DyaK1cXntlSqs7c%3D (Pubitemid 28479145)
22. H Arima Y Chihara M Arizono S Yamashita K Wada F Hirayama K Uekama 2006 Enhancement of gene transfer activity mediated by mannosylated dendrimer/α-cyclodextrin conjugate (generation 3, G3) J. Control. Release 116 64 74 10.1016/j.jconrel.2006.08.026 1:CAS:528:DC%2BD28Xht1emsrfE (Pubitemid 44792299)
23. K Wada H Arima T Tsutsumi Y Chihara K Hattori F Hirayama K Uekama 2005 Improvement of gene delivery mediated by mannosylated dendrimer/α- cyclodextrin conjugates J. Control. Release 104 397 413 10.1016/j.jconrel.2005. 02.016 1:CAS:528:DC%2BD2MXkt1agsrk%3D (Pubitemid 40724937)
24. K Hamasaki K Kogure K Ohwada 1996 A biological method for the quantitative measurement of tetrodotoxin (TTX): tissue culture bioassay in combination with a water-soluble tetrazolium salt Toxicon. 34 490 495 10.1016/0041-0101(95)00151-4 1:CAS:528:DyaK28XjtFCltLg%3D (Pubitemid 26130128)
25. N Ono H Arima F Hirayama K Uekama 2001 A moderate interaction of maltosyl-α-cyclodextrin with Caco-2 cells in comparison with the parent cyclodextrin Biol. Pharm. Bull. 24 395 402 10.1248/bpb.24.395 1:CAS:528:DC%2BD3MXisFalsb4%3D (Pubitemid 32377608)
26. K Takahashi K Hattori F Toda 1984 Monotosylated α- and β-cyclodextrins prepared in an alkaline aqueous solution Tetrahedron Lett. 25 3331 3334 10.1016/S0040-4039(01)81377-0 1:CAS:528:DyaL2cXmtFWmu78%3D
27. T Murakami K Harata S Morimoto 1988 Synthesis and chiral recognition property of 3-acetylamino-3-deoxy-β-cyclodextrin Chem. Lett. 17 553 556 10.1246/cl.1988.553