Confocal laser scanning microscopy (CLSM) based evidence for cell permeation by mono-4-(N-6-deoxy-6-amino-β-cyclodextrin)-7-nitrobenzofuran (NBD-β-CyD)

International Journal of Pharmaceutics

Volumn 403, Issue 1-2, 2011, Pages 15-22

  Wei, Hai ^a   Zheng, Weizhong ^a,b   Diakur, James ^a,c   Wiebe, Leonard I ^a,d  

^a SHANGHAI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

^b Labs Mart Inc   (Canada)

^c Canam Bioresearch Inc   (Canada)

^d CROSS CANCER INSTITUTE   (Canada)

Author keywords

Cyclodextrin; 4 Chloro 7 nitrobenz 2 oxa 1,3 diazole (NBD); Confocal laser scanning microscopy (CLSM); Intracellular uptake in vitro; NBD adamantine; NBD glucose

Indexed keywords

AMANTADINE; BETA CYCLODEXTRIN DERIVATIVE; GLUCOSE; MONO 4 (N 6 DEOXY 6 AMINO BETA CYCLODEXTRIN) 7 NITROBENZOFURAN; PLASMA PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; CELL MEMBRANE PERMEABILITY; CELL STRAIN HEPG2; CELLULAR DISTRIBUTION; CONFOCAL LASER MICROSCOPY; CYTOPLASM; DRUG ACCUMULATION; DRUG STRUCTURE; DRUG TRANSPORT; DRUG UPTAKE; ENDOCYTOSIS; FLUORESCENCE ANALYSIS; HUMAN; HUMAN CELL; MITOCHONDRION; PRIORITY JOURNAL; PROTEIN BLOOD LEVEL; TEMPERATURE DEPENDENCE;

AMANTADINE; BENZOFURANS; BETA-CYCLODEXTRINS; BIOLOGICAL TRANSPORT; BLOOD PROTEINS; CELL CULTURE TECHNIQUES; CELL LINE, TUMOR; CELL MEMBRANE; CELL MEMBRANE PERMEABILITY; CYCLODEXTRINS; DRUG CARRIERS; DRUG STABILITY; ENDOCYTOSIS; FLUORESCENT DYES; GLUCOSE; HUMANS; KINETICS; MICROSCOPY, CONFOCAL; MOLECULAR STRUCTURE; SPECTROMETRY, FLUORESCENCE; SUBCELLULAR FRACTIONS; TEMPERATURE;

EID: 78650176966     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2010.09.032     Document Type: Article

References (47)

1. G.H. Anderson, F.M. Robbins, F.J. Domingues, R.G. Moores, and C.L. Long The utilization of scharfinger dextrins by the rat Toxicol. Appl. Pharmacol. 5 1963 257
2. V.M. Atger, M. Moya, G.W. Stoudt, W.V. Rodrigueza, M.C. Phillips, and G.H. Rothblat Cyclodextrins as catalysts for the removal of cholesterol from macrophage foam cells J. Clin. Invest. 99 1997 773 780
3. V. Borroni, C.J. Baier, T. Lang, I. Bonini, M.M. White, I. Garbus, and F.J. Barrantes Cholesterol depletion activates rapid internalization of submicron-sized acetylcholine receptor domains at the cell membrane Mol. Membr. Biol. 24 2007 1 15
4. B. Brady, N. Lynam, T. O'Sullivan, C. Ahern, and R. Darcy 6-O-p-Toluenesulfonyl-β-cyclodextrin Org. Syntheses 77 2000 220
5. A. de Raadt, and A.E. Stuetz A simple convergent synthesis of the mannosidase inhibitor 1-deoxymannonojirimycin from sucrose Tetrahedron Lett. 33 1992 189 192
6. M.R. Eftink, M.L. Andy, K. Bystrom, H.D. Perlmutter, and D.S. Kristol Cyclodextrin inclusion complexes: studies of the variation in the size of acyclic guests J. Am. Chem. Soc. 111 1989 6765 6772
7. R. Feederle, M. Pajatsch, E. Kremmer, and A. Bock Metabolism of cyclodextrins by Klebsiella oxytoca M5a1: purification and characterization of a cytoplasmically located cyclodextrinase Arch. Microbiol. 165 1996 206 212
8. G. Fiedler, M. Pajatsch, and A. Bock Genetics of novel starch utilisation pathway present in Klebsiella oxytoca J. Mol. Biol. 256 1996 279 291
9. B. Flourie, C. Molis, L. Achour, H. Dupas, C. Hatat, and J.C. Rambaud Fate of β-cyclodextrin in the human intestine J. Nutr. 123 1993 676 680
10. 14C-β-cyclodextrin in rat Drug Res. 35 1985 1042 1047
11. P.B. Ghosh, and M.W. Whitehouse 7-Chloro-4-nitrobenzo-2-oxa-1,3-diazole: a new fluorogenic reagent for amino acids and other amines Biochem. J. 108 1968 155 156
12. M. Grouselle, O. Tueux, P. Dabadie, D. Georgescaud, and J.P. Mazat Effect of local anaesthetics on mitochondrial membrane potential in living cells Biochem. J. 271 1990 269 272
13. P. Guldberg, P.T. Straten, A. Brick, V. Ahrenkiel, A.F. Kirkin, and J. Zeuthen Disruption of the MMAC1/PTEN gene by deletion or mutation is a frequent event in malignant melanoma Cancer Res. 57 1997 3660 3663
14. K. Hamasaki, H. Ikeda, A. Nakamura, A. Ueno, F. Toda, I. Suzuki, and T. Osa Fluorescent sensors of molecular recognition. Modified cyclodextrins capable of exhibiting guest-responsive twisted intramolecular charge transfer fluorescence J. Am. Chem. Soc. 115 1993 5035 5040
15. S. Hanessian Sugar lactams. 111. Synthesis of five- six-, and seven-membered analogs J. Org. Chem. 34 1969 675 681
16. E. Hardegger, G. Zanetti, K. Steiner, and P.H. von krist 6-Desoxy-6-amino-β-glucosehydrochlorid und konstitution einiger zwischenprodukte Helv. Chim. Acta 26 1963 282 287
17. Y. Higashi, S. Nakamura, H. Matsumura, and Y. Fujii Simultaneous liquid chromatographic assay of amantadine and its four related compounds in phosphate-buffered saline using 4-fluoro-7-nitro-2,1,3-benzoxadiazole as a fluorescent derivatization reagent Biomed. Chromatogr. 2006 423 428
18. T. Higuchi, and K.A. Connors C.N. Reilly, Advances in Analytical Chemistry Instrumentation vol. 4 1965 Wiley-Interscience New York 117 212
19. F. Hirayama, M. Yamamoto, and K. Uekama Acid-catalyzed hydrolysis of maltosyl-beta-cyclodextrin J. Pharm. Sci. 81 1992 913 916
20. L. Hovgaard, and H. Bronsted Drug delivery studies in Caco-2 monolayers. IV. Absorption enhancer effects of cyclodextrins Pharm. Res. 12 1995 1328 1332
21. H. Ikeda, T. Murayama, and A. Ueno Bile acids-selective chemosensors based on NBD-amine-modified cyclodextrins J. Inclusion Phenom. Macrocyclic Chem. 56 2006 101 105
22. T. Irie, and K. Uekama Pharmaceutical application of cyclodextrin. III. Toxicological issues and safety evaluation J. Pharm. Sci. 86 1997 147 162
23. L.V. Johnson, M.L. Walsh, and L.B. Chen Localization of mitochondria in living cells with rhodamine 123 Proc. Natl. Acad. Sci. 77 1980 990 994
24. E.P.C. Kilsdonk, P.G. Yancey, G.W. Stoudt, F.W. Bangerter, W.J. Johnson, M.C. Phillips, and G.H. Rothblat Cellular cholesterol efflux mediated by cyclodextrins J. Biol. Chem. 270 1995 17250 17256
25. B.B. Knowles, C.C. Howe, and D.P. Aden Human hepatocellular carcinoma cell lines secrete the major plasma proteins and hepatitis B surface antigen Science 209 1980 497 499
26. Y. Kubota, M. Fukuda, M. Muroguchi, and K. Koizumi Absorption, distribution and excretion of β-cyclodextrin and glucosyl-β- cyclodextrin in rats Biol. Pharm. Bull. 19 1996 1068 1072
27. D. Lambert, C.A. O'Neill, and P.J. Padfield Methyl-beta-cyclodextrin increases permeability of Caco-2 cell monolayers by displacing specific claudins from cholesterol rich domains associated with tight junctions Cell. Physiol. Biochem. 20 1980 495 506
28. D. Lambert, C.A. O'Neill, and P.J. Padfield Depletion of Caco-2 cell cholesterol disrupts barrier function by altering the detergent solubility and distribution of specific tight-junction proteins Biochem. J. 387 Pt 2 2005 553 560
29. - in cultured human endothelial cells Scand. J. Clin. Lab. Invest. 48 1988 565 571
30. E. Marttin, C.J. Verhoef, C. Cullander, S.G. Romeijn, J.F. Nagelkerke, and F.W. Merkus Confocal laser scanning microscopic visualization of the transport of dextrans after nasal administration to rats: effects of absorption enhancers Pharm. Res. 4 1997 631 637
31. E. Marttin, J.C. Verhoef, F. Spies, J. Van der Meulan, J.F. Nagelkerke, H.K. Koerten, and F.W. Merkus The effect of methylated beta-cyclodextrins on the tight junctions of the rat nasal respiratory epithelium: electron microscopic and confocal laser scanning microscopic visualization studies J. Control. Rel. 57 1999 205 213
32. M. Masson, T. Loftsson, G. Masson, and E. Stefansson Cyclodextrins as permeation enhancers: some theoretical evaluations and in vitro testing J. Control. Rel. 59 1999 107 118
33. L. Matilainen, T. Toropainen, H. Vihola, J. Hirvonen, T. Järvinen, P. Jarho, and K. Järvinen In vitro toxicity and permeation of cyclodextrins in Calu-3 cells J. Control. Rel. 126 2008 10 16
34. K. Matsubara, K. Abe, T. Irie, and K. Uekama Improvement of nasal bioavailability of luteinizing hormone-releasing hormone agonist, buserelin, by cyclodextrin derivatives in rats J. Pharm. Sci. 84 1995 1295 1300
35. G.G. Miller, K. Brown, A.M. Ballangrud, O. Barajas, Z. Xiao, J. Tulip, W.J. Lown, J.M. Leithoff, J.M. Allalunis-Turner, R.D. Mehta, and R.B. Moore Preclinical assessment of hypocrellin B and hypocrellin B derivatives as sensitizers for photodynamic therapy of cancer: progress update Photochem. Photobiol. 65 1997 714 722
36. I. Miyazawa, H. Ueda, H. Nagase, T. Endo, S. Kobayashi, and T. Nagai Physicochemical properties and inclusion complex formation of delta-cyclodextrin Eur. J. Pharm. Sci. 3 1995 153 162
37. E.B. Neufeld, A.M. Cooney, J. Pitha, E.A. Dawidowicz, N.K. Dwyer, P.G. Pentchev, and E.J. Blanchette-Mackie Intracellular trafficking of cholesterol monitored with a cyclodextrin J. Biol. Chem. 271 1996 21604 21613
38. R.E. Ostlund, R. Seemayer Jr., S. Gupta, R. Kimmel, E.L. Ostlund, and W.R. Sherman A stereospecific myo-inositol/d-chiro-inositol transporter in HepG2 liver cells J. Biol. Chem. 271 1996 10073 10078
39. M. Pajatsch, M. Gerhart, R. Peist, R. Horlacher, W. Boos, and A. Bock The periplasmic cyclodextrin binding protein CymE from Klebsiella oxytoca and its role in maltodextrin and cyclodextrin transport J. Bacteriol. 180 1998 2630 2635
40. R.C. Petter, J.S. Salek, C.T. Sikorski, G. Kumaravel, and F.T. Lin Cooperative binding by aggregated mono-6-(alkylamino)-β-cyclodextrins J. Am. Chem. Soc. 112 1990 3860 3868
41. S.K. Rodal, G. Skretting, O. Garred, F. Vilhardt, B. van Deurs, and K. Sandvig Extraction of cholesterol with methyl-beta-cyclodextrin perturbs formation of clathrin-coated endocytic vesicles Mol. Biol. Cell. 10 1999 961 974
42. D.A. Skoog, F.J. Holler, and T.A. Nieman Principles of Instrumental Analysis fifth ed. 1998 Harcourt Brace & Company Press Orlando, FL
43. L. Speizer, R. Haugland, and H. Kutchai Asymmetric transport of a fluorescent glucose analogue by human erythrocytes Biochim. Biophys. Acta 815 1985 75 84 (Pubitemid 15071517)
44. 14C-labelled β-cyclodextrin in rats Arzneim - Forsch Drug Res. 30 1980 808 810
45. J. Szejtli J.E.D. Davies, Cyclodextrin Technology 1988 Kluwer Academic Press Dordrecht, The Netherlands
46. K. Tekeo, H. Mitoh, and K. Uemura Selective chemical modification of cyclomalto-oligosaccharides via tert-butyldimethylsilylation Carbohydr. Res. 187 1989 203 221
47. X.-H. Yang, S. Singh, P. Kumar, J. Diakur, and L.I. Wiebe β-Cyclodextrin complexes of hydrolyzable adamantanoyl-IUdR prodrugs-radioiodination and biodistribution in mice bearing implanted KBALB tumor Curr. Radiopharmaceut. 2 2009 137 142