Cyclodextrins and Cellular Interactions

Cyclodextrins in Pharmaceutics, Cosmetics, and Biomedicine: Current and Future Industrial Applications

Volumn , Issue , 2011, Pages 287-295

  Dreyfuss, Justin M ^a   Oppenheimer, Steven B ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

CDs, interfering with adhesive interactions during developmental processes; Cyclodextrins (CDs) and cellular interactions; Membrane cholesterol levels, effects on organelle activities movement of molecules within cell

Indexed keywords

EID: 84886452394     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470926819.ch15     Document Type: Chapter

References (87)

1. Ambrose, Z., Compton, L., Piatak, M., Lu, D., Alvord, G.W., Lubomirski, M.S., Hildreth, J.E.K., Lifson, J.D., Miller, C.J., KewalRamani, V.N. (2008). Incomplete protection against simian immunodeficiency virus vaginal transmission in rhesus macaques by a topical antiviral agent revealed by repeat challenges. J. Virol., 82, 6591-6599.
2. Andre, S., Kaltner, H., Furuike, T., Nishimura, S., Gabius, H. (2004). Persubstituted cyclodextrin-based glycoclusters as inhibitors of protein-carbohydrate recognition using purified plant and mammalian lectins and wild-type and lectin-genetransfected tumor cells as targets. Bioconjugate Chem., 15, 87-98.
3. Baorto, D.M., Gao, Z., Malaviya, R., Dustin, M.L., van der Merwea, A., Lublin, D.M., Abraham, S.N. (1997). Survival of FimH-expressing enterobacteria in macrophages relies on glycolipid traffic. Nature, 389, 636-639.
4. Barman, S., Nayak, D.P. (2007). Lipid raft disruption by cholesterol depletion enhances influenza Avirus budding from MDCK cells. J. Virol., 81, 12169-12178.
5. Bhattacharya, B., Roy, P. (2008). Bluetongue virus outer capsid protein VP5 interacts with membrane lipid rafts via a SNARE domain. J. Virol., 82, 10600-10612.
6. Brewer, C.F., Miceli, M.C., Baum, L.G. (2002). Clusters, bundles, arrays and lattices: novel mechanisms for lectinsaccharide-mediated cellular interactions. Curr. Opin. Struct. Biol., 12, 616-623.
7. Campbell, S., Gaus, K., Bittman, R., Jessup, W., Crowe, S., Mak, J. (2004). The raft-promoting property of virion-associated cholesterol, but not the presence of virion-associated Brij 98 rafts, is a determinant of human immunodeficiency virus type 1 infectivity. J. Virol., 78, 10556-10565.
8. Chassin, C., Bens, M., de Barry, J., Courjaret, R., Bossu, J.L., Cluzeaud, F., Mkaddem, S.B., Gibert, M., Poulain, B., Popoff, M.R., Vandewalle, A. (2007). Pore-forming epsilon toxin causes membrane permeabilization and rapid ATP depletionmediated cell death in renal collecting duct cells. Am. J. Physiol. Renal Physiol., 293, 927-937.
9. Chen, X., Resg, M. (2002). Cholesterol depletion from the plasma membrane triggers ligand independent activation of the EGF receptor. J. Biol. Chem., 277, 49631-49637.
10. Doncel, G.F. (2006). Exploiting common target in human fertilization and HIV infection: development of novel contraceptive microbicides. Hum. Reprod. Update, 12, 103-117.
11. Dreja, K., Voldstedkund, M., Vinten, J., Tranum-Jensen, J., Hellstrand, P., Sward, K. (2002). Cholesterol depletion disrupts caveolae and differentially impairs agonist-induced arterial contraction. Arterioscler. Thromb. Vasc. Biol., 22, 1267-1275.
12. Duan, M.S., Zhao, N., Ossurardotti, I.B., Thorsteinsson, T., Loftsson, T. (2005). Cyclodextrin solubilization of the antibacterial agents triclosan and triclocarbon: formation of aggregates and higher-order complexes. Int. J. Pharm., 297, 213-222.
13. Funk, A., Mhamdi, M., Hohenberg, H., Heeren, J., Reimer, R., Lambert, C., Prange, R., Sirma, H. (2008). Duck hepatitis B virus required cholesterol for endosomal escape during virus entry. J. Virol., 82, 10532-10542.
14. Garcia-Lopez, J.J., Hernandez-Mateo, F., Isac-Garcia, J., Kim, J. M., Roy, R., Santoyo-Gonzalez, F., Vargas-Berenguel, A. (1999). Synthesis of per-glycosylated b-cyclodextrins having enhanced lectin binding affinity. J. Org. Chem., 64, 522-531.
15. Giesemann, T., Jank, T., Gerhard, R., Maier, E., Just, I., Benz, R., Aktories, K. (2006). Cholesterol-dependent pore formation of Clostridium difficile toxin A. J. Biol. Chem., 281, 10808-10815.
16. Gosens, R., Stelmack, G., Dueck, G., McNeil, K.D., Yamasaki, A., Gerthoffer, W.T., Unruh, H., Gounni, A.S., Zaagsma, J., Halayko, A.J. (2006). Role of caveolin-1 in p42/p44 MAP kinase activation and proliferation of human airway smooth muscle. Am. J. Physiol. Lung Cell Mol. Physiol., 291, L523-L534.
17. Graham, D.R.M., Chertova, E., Hilburn, J.M., Arthur, L.O., Hildreth, J.E.K. (2003). Cholesterol depletion of human immunodeficiency virus type 1 and simian immunodeficiency virus with b-cyclodextrin inactivates and permeabilizes the virions: evidence for virion-associated lipid rafts. J. Virol., 77, 8237-8248.
18. Grimm, M.O.W., Grimm, H.S., Tomic, I., Beyreuther, K., Hartmann, T., Bergmann, C. (2008). Independent inhibition of Alzheimer disease b-and c-secretase cleavage by lowered cholesterol levels. J. Biol. Chem., 283, 11302-11311.
19. Ha, H., Kwak, H.B., Lee, S.K., Na, D.S., Rudd, C.E., Lee, Z.H., Kim, H. (2003). Membrane rafts play a crucial role in receptor activator of nuclear factor kB (RANK) signaling and osteoclast function. J. Biol. Chem., 273, 18573-18580.
20. Hess, S.T., Kumar, M., Verma, A., Farrington, J., Kenworthy, A., Zimmerberg, J. (2005). Quantitative electron microscopy and fluorescence spectroscopy of the membrane distribution of influenza hemagglutinin. J. Cell Biol., 169, 965-976.
21. Huang, Q., Shen, H., Shui, G., Wenk, M., Ong, C. (2006). Emodin inhibits tumor cell adhesion through disruption of the membrane lipid raft-associated integrin signaling pathway. Cancer Re., 66, 5807-5815.
22. John, B., Herrin, B., Raman, C., Wang, Y., Bobbitt, K., Brody, B., Justement, L.B. (2003). The B cell coreceptor CD22 associates with AP50, a clathrin-coated pit adapter protein, via tyrosine-dependent interaction. J. Immunol., 170, 3534-3543.
23. Kanee, A. http://www.mawhiba.org.sa/NR/rdonlyres/2923D2E4-2B92-4632-BF5C-5284E93E33D8/0/Abdullah-KaneeRSI2007.pdf.
24. Kansau, I., Berger, C., Hospital, M., Amsellem, R., Nicolas, V., Servin, A., Bernet-Camard, M. (2004). Zipper-like internalization of Dr-positive Escherichia coli by epithelial cells is preceded by an adhesin-induced mobilization of Raf-associated molecules in the initial step of adhesion. Infect. Immun., 72, 3733-3742.
25. Keller, P., Simons, K. (1998). Cholesterol is required for surface transport of influenza virus hemagglutinin. J. Cell Biol., 140, 1357-1367.
26. Kilsdonk, E.P.C., Yancey, P.G., Stoudt, G.W., Bangerter, F.W., Johnson, W.J., Phillips, M.C., Rothblat, G.H. (1995). Cellular cholesterol efflux mediated by cyclodextrins. J. Biol. Chem., 270, 17250-17256.
27. Kovbasnjuk, O., Edidin, M., Donowitz, M. (2001). Role of lipid rafts in shiga toxin 1 interaction with the apical surface of Caco-2 cells. J. Cell Sci., 114, 4025-4031.
28. Laliberte, J.P., McGinnes, L.W., Peeples, M.E., Morrison, T.G. (2006). Integrity of membrane lipid rafts is necessary for the ordered assembly and release of infectious Newcastle disease virus particles. J. Virol., 80, 10652-10662.
29. Laliberte, J.P., McGinnes, L.W., Morrison, T.G. (2007). Incorporation of functional HN-F glycoprotein-containing complexes into Newcastle disease virus is dependent on cholesterol and membrane lipid raft integrity. J. Virol., 81, 10636-10648.
30. Larbi, A., Douziech, N., Khalil, A., Dupuis, G., Gherairï, S., Guérard, K.P., Fülüp, T. Jr. (2004). Effects of methyl-betacyclodextrin on T lymphocytes lipid rafts with aging. Exp. Gerontol. 39, 551-558.
31. Leshchyns'ka, I., Sytnky, V., Morrow, J.S., Schachnew, M. (2003). Neural cell adhesion molecule (NCAM) association with PKC-b2 via b-I spectrin is implicated in NCAM-mediated neurite outgrowth. J. Cell Biol., 161, 625-639.
32. Leyt, J., Melamed-Book, N., Vaerman, J., Cohen, S.,Weiss, A. M., Aroeti, B. (2007). Cholesterol-sensitive modulation of transcytosis. Mol. Biol. Cell, 18, 2057-2071.
33. Linder, A.E., Leite, R., Lauria, K., Mills, T.M., Webb, R.C. (2005). Penile erection requires association of soluble guanylyl cyclase with endothelial caveolin-1 in rat corpus cavernosum. Am. J. Physiol. Integr. Compar. Physiol., 290, 1302-1308.
34. Liu, S.M., Cogny, A., Kockx, M., Deat, R.T., Gaus, K., Jessup, W., Kritharides, L. (2003). Cyclodextrins differentially mobilize free and esterified cholesterol from primary human foam cell macrophages. J. Lipid Res., 44, 1156-1166.
35. Locke, D., Koreen, I.V., Liu, J.Y., Harris, A. (2004). Reversible pore block of connexin channels by cyclodextrins. J. Biol. Chem., 279, 22883-22892.
36. Loftsson, T., Leeves, N., Bjornsdóttir, B., Duffy, L.,Másson, M. (1999). Effect of cyclodextrins and polymers on triclosan availability and substantivity in toothpastes in vivo. J. Pharm. Sci., 88, 1254-1258.
37. Maguy, A., Hebert, T.E., Nattel, S. (2005). Involvement of lipid rafts and caveolae in cardiac ion channel function. Cardiovasc. Res., 69, 798-807.
38. Martin Del Valle, E.M. (2003). Cyclodextrins and their uses: a review. Process Biochem., 39, 1033-1046.
39. Mermelstein, C.S., Portilho, D.M., Medeiros, R.B., Matos, A. R., Einicker-Lama, M., Tortelote, G.G.,Vieyra, A., Costa, M.L. (2005). Cholesterol depletion by methyl-b-cyclodextrin enhances myoblast fusion and induces the formation of myotubes with disorganized nuclei. Cell Tissue Res., 319, 289-297.
40. Morris, D.P., Lei, B., Wu, Y., Michelotti, G.A., Schwinn, D. (2007). The a1a-adrenergic receptor occupies membrane rafts with its G protein effectors but internalizes via clathrin-coated pits. J. Biol. Chem., 283, 2973-2985.
41. Muller, K., Muller, P., Pincemy, G., Kurtz, A., Labbe, C. (2008). Characterization of sperm plasma membrane properties after cholesterol modification: consequences for cryopreservation of rainbow trout spermatozoa. Biol. Reprod., 78, 390-399.
42. Murphy, A.J., Woollard, K.J., Hoang, A., Mukhamedova, N., Stirzaker, R.A., McCormick, S.P.A., Remaley, A.T., Sviridov, D., Chin-Dustin, J. (2008). High density lipoprotein reduces the human monocyte inflammatory response. Arterioscler. Thromb. Vasc. Biol., 28, 2071-2077.
43. Nagahama, M., Hayashi, S., Morimitsu, S., Sakurai, J. (2003). Biological activities and pore-formation of Clostridium perfringens b-toxin in HL 60 cells. J. Biol. Chem., 278, 36934-36941.
44. Nagahama, M., Yamaguchi, A., Hagiyama, T., Ohkubo, N., Kobayashi, K., Sakurai, J. (2004). Binding and internalization of Clostridium perfringens iota-toxin in lipid rafts. Infect. Immun., 72, 3267-3275.
45. Nam, J.H., Lee, H.S., Nguren, Y.H., Kang, T.M., Lee, S.W., Kim, H.Y., Kim, S.J., Earm, Y.E., Kim, S.J. (2007). Mechanosensitive activation of K{thorn} channel via phospholipase C-induced depletion of phosphatidylinositol 4,5-bisphosphate in B lymphocytes. J. Physiol., 582 (3), 977-990.
46. Nyasae, L.K., Hubbarb, A.L., Tuma, P.L. (2003). Transcytotic efflux from early endosomes is dependent on cholesterol and glycosphingolipids in polarized hepatic cells. Mol. Biol. Cell, 14, 2689-2705.
47. Oda, M., Matsuno, T., Shiihara, R., Ochi, S., Yamauchi, R., Imagawa, H., Nagahama, M., Nishizawa, M., Sakurai, J. (2008). The relationship between the metabolism of sphingomyelin species and hemolysis of sheep erythrocytes by Clostridium perfringens a-toxin. J. Lipid Res., 49, 1039-1047.
48. O'Donnell, V., LaRocco, M., Baxt, B. (2008). Heparan sulfate binding foot-and-mouth disease virus enters cells via caleolamediated endocytosis. J. Virol., 82, 9075-9085.
49. Ohara-Imaizumi, M., Nishiwaki, C., Kikuta, T., Kumakura, K., Nakamichi, Y., Nagamatsu, S. (2004). Site of docking and fusion of insulin secretory granules in live MIN6 b cells analyzed by TAT-conjugated anti-syntaxin 1 antibody and total internal reflection fluorescence microscopy. J. Biol. Chem., 279, 8403-8408.
50. Ottico, E., Prinetti, A., Prioni, S., Giannotta, C., Basso, L., Chigorno, V., Sonnino, S. (2003). Dynamics of membrane lipid domains in neuronal cells differentiated in culture. J. Lipid Res., 44, 2142-2151.
51. Popik, W., Alce, T.M., Au, W. (2002). Human immunodeficiency virus type 1 uses lipid raft-colocalized CD4 and chemokine receptors for productive entry into CD4{thorn} T cells. J. Virol., 76, 4709-4722.
52. Pouvreau, S., Berthier, C., Blaineau, S., Amsellem, J., Coronado, R., Strube, C. (2004). Membrane cholesterol modulates dihydropyridine receptor function in mice fetal skeletal muscle cells. J. Physiol., 552 (2), 365-381.
53. Prior, I.A. Muncke, C., Parton, R.G., Hancock, J.F. (2003). Direct visualization of Ras proteins in spatially distinct cell surface microdomains. J. Cell Biol., 160, 165-170.
54. Riff, J.D., Callahan, J.W., Sherman, P.M. (2005). Cholesterolenriched membrane microdomains are required for inducing host cell cytoskeleton rearrangements in response to attachingeffacing Escherichia coli. Infect. Immun., 73, 7113-7125.
55. Ringerike, T., Blystad, F.D., Levy, F.O., Madshus, I.H., Stang, E. (2002). Cholesterol is important in control of EGF receptor kinase activity but EGF receptors are not concentrated in caveolae. J. Cell Sci., 115, 1331-1340.
56. Russo, L.M., McKee, M., Brown, D. (2006) Methyl-b-cyclodextrin induces vasopressin-independent apical accumulation of aquaporin-2 in the isolated, perfused rat kidney. Am. J. Physiol. Renal Physiol., 291, F246-F253.
57. Sadler, S.E., Jacobs, N.D. (2004). Stimulation of Xenopus laevis oocyte maturation by methyl-b-cyclodextrin. Biol. Reprod., 70, 1685-1692.
58. Sajadi, S., Rojas, P., Oppenheimer, S.B. (2007). Cyclodextrin, a probe for studying adhesive interactions. Acta Histochem., 109, 338-342.
59. Sampson, L.J., Hayabuchi, Y., Standen, N.B., Dart, C. (2004). Caveolae localize protein kinase A signaling to arterial ATPsensitive potassium channels. Circ. Res., 95, 1012-1018.
60. Sandgren, S., Wittrup, A., Cheng, F., Jonsson, M., Eklund, E., Busch, S., Beltig, M. (2004). The human antimicrobial peptide LL-37 transfers extracellular DNA plasmid to the nuclear compartment of mammalian cells via lipid rafts and proteoglycan-dependent endocytosis. J. Biol. Chem., 279, 17951-17956.
61. Schols, D., De Clercq, E., Witvrouw, M., Nakashima, H., Snoeck, R., Pauwels, R., Van Schepdael, A., Claes, P. (1991). Sulphated cyclodextrins are potent anti-HIV agents acting synergistically with 2,3-dideoxynucleoside analogues. Antiviral Chem. Chemother., 2, 45-53.
62. Seveau, S., Bierne, H., Giroux, S., Prevost, M., Cossart, P. (2004). Role of lipid rafts in E-cadherin-and HGF-R/Metmediated entry of Listeria monocytogenes into host cell. J. Cell Biol., 166, 743-753.
63. Shrimpton, C.N., Borthakur, G., Larrucea, S., Cruz, M.A., Dong, J., Lopez, J. (2002). Localization of the adhesion receptor glycoprotein Ib-IX-V complex to lipid rafts is required for platelet adhesion and activation. J. Exp. Med. 196, 1057-1066.
64. Shmygol, A., Noble, K., Wray, S. (2007). Depletion of membrane cholesterol eliminates the Ca2{thorn}-activated component of outward potassium current and decreases membrane capacitance in rat uterine myocytes. J. Physiol., 581 (2), 445-456.
65. Smith, S.M.L., Lei, Y., Liu, J., Cahill, M.E., Hagen, G.M., Barisas, B.G., Roess, D.A. (2006). Luteinizing hormone receptors translocate to plasma membrane microdomains after binding of human chorionic gonadotropin. Endocrinology, 147, 1789-1795.
66. Steck, T.L.,Ye, J., Lange,Y. (2002). Probing red cell membrane cholesterol movement with cyclodextrin. Biophys. J., 83, 2118-2125.
67. Stuven, E., Porat, A., Shimron, F., Fass, E., Kaloyanova, D., Brugger, B.,Wieland, F.T., Elazar, Z., Helms, J.B. (2003). Intra-Golgi protein transport depends on a cholesterol balance in the lipid membrane. J. Biol. Chem., 278, 53112-53122.
68. Szoke, T., Kayser, K., Baumhakel, J., Trojan, I., Furak, J., Tiszlavicz, L., Horvath, A., Szluha, K., Gabius, H., Andre, S. (2005). Prognostic significance of endogenous adhesion/growth-regulatory lectins in lung cancer. Oncology, 69, 167-174.
69. Takeo, T., Hoshii, T., Kondo, Y., Toyodome, H., Arima, H., Yamamura, K., Irie, T., Nakagata, N. (2008). Methyl-b-cyclodextrin improves fertilizing ability of C57BL/6 mouse sperm after freezing and thawing by facilitating cholesterol efflux from the cells. Biol. Reprod., 78, 546-551.
70. Tamilselvam, B., Daefler, S. (2008). Francisella targets cholesterol-rich host cell membrane domains for entry into macrophages. J. Immunol., 180, 8262-8271.
71. Thorp, E.B., Gallagher, T.M. (2004). Requirements for CEACAMs and cholesterol during murine coronavirus cell entry. J. Virol., 78, 2682-2692.
72. Triantafilou, M., Miyake, K., Golenbock, D.T., Triantafilou, K. (2002). Mediators of innate immune recognition of bacteria concentrate in lipid rafts and facilitate lipopolysaccharideinduced cell activation. J. Cell Sci., 115, 2603-2611.
73. Tsujikawa, H., Song, Y.,Watanabe, M., Masumiya, H., Gupte, S., Ochi, R., Okada, T. (2007). Cholesterol depletion modulates basal L-type Ca2{thorn} current and abolishes its b-adrenergic enhancement in ventricular myocytes. Am. J. Physiol. Heart Circ. Physiol., 294, H285-H292.
74. Vassilieva, E.V., Gerner-Smidt, K., Ivanov, A.I., Nusrat, A. (2008). Lipid rafts mediate internalization of b1-integrin in migrating intestinal epithelial cells. Am. J. Physiol. Gastrointest. Liver Physiol., 295, G965-G976.
75. Vikman, J., Jimenez-Feltstrom, J., Nyman, P., Thelin, J., Eliasson, L. (2009). Insulin secretion is highly sensitive to desorption of plasma membrane cholesterol. FASEB J., 23, 58-67.
76. Watabe, M., Aoyama, K., Nakaki, T. (2008).Adominant role of GTRAP3-18 in neuronal glutathione synthesis. J. Neurosci., 28, 9404-9413.
77. Weiner, D.B.,Williams,W.V.,Weisz, P.B., Greene, M.I. (1992). Synthetic cyclodextrin derivatives inhibit HIV infection in vitro. Pathobiology, 60, 206-212.
78. Wolf, A.A., Fukinaga, Y., Lencer, W.I. (2002). Uncoupling of the cholera toxin GM1 ganglioside-receptor complex from endocytosis, retrograde Golgi trafficking, and downstream signal transduction by depletion of membrane cholesterol. J. Biol. Chem., 277, 16249-16256.
79. Xia, F., Leung, Y.M., Gaisano, G., Gao, X., Chen, Y., Manning, J.E., Fox, M., Bhattacharjee, A., Wheeler, M.B., Gaisano, H.Y., Tsushima, R.G. (2007). Targeting of voltage-gated K{thorn} and Ca2{thorn} channels and soluble N-ethylmaleimide-sensitive factor attachment protein receptor proteins to cholesterol-rich lipid rafts in pancreatic a-cells: effects on glucagon stimulus-secretion coupling. Endocrinology, 148, 2157-2167.
80. Xu, Y., Takeda, S., Nakata, T., Noda, Y., Tanaka, T., Hirokawa, N. (2002). Role of KIFC3 motor protein in Golgi positioning and integration. J. Cell Biol., 158, 293-303.
81. Xu, W., Yoon, S., Huang, P., Wang, Y., Chen, C., Chong, P.L., Liu-Chen, L. (2006). Localization of the k opioid receptor in lipid rafts. J. Pharmacol. Exp. Ther., 317, 1295-1306.
82. Yamamoto, Na., Yamamoto, No. Petroll, M.W., Cavanagh, H. D., Jester, J.V. (2005). Internalization of Pseudomonas aeruginosa is mediated by lipid rafts in contact lens-wearing rabbit and cultured human corneal epithelial cells. Invest. Ophthalmol. Vis. Sci., 46, 1348-1355.
83. Young, J., Tang, Z., Yu, Q., Yu, D., Wu, Y. (2008). Selective killing of HIV-I-positive macrophages and T cells by the Revdependent lentivirus carrying anthrolysin O from Bacillus anthracis. Retrovirology, 5, doi: 10.1186/1742-4690-5-36.
84. Yu, L., Cao, G., Repa, J., Stangl, H. (2004). Sterol regulation of scavenger receptor class B type I in macrophages. J. Lipid Res., 45, 889-899.
85. Zacco, A., Togo, J., Spence, K., Ellis, A., Lloyd, A., Furlong, S., Piser, T. (2003). 3-Hydroxy-3-methylglutaryl coenzyme a reductase inhibitors protect cortical neurons from excitotoxicity. J. Neurosci., 23, 11104-11111.
86. Zamir, O., Charlton, M. (2006). Cholesterol and synaptic transmitter release at crayfish neuromuscular junction. J. Physiol., 571 (1), 83-99.
87. Zhuang, M., Oltean, D., Gomez, I., Pullikuth, A.K., Soberon, M., Bravo, A., Gill, S.S. (2002). Heliothis virescens and Manduca sexta lipid rafts are involved in Cry 1A toxin binding to the midgut epithelium and subsequent pore formation. J. Biol. Chem., 277, 13863-13872.