Structural effects of oligosaccharide-branched cyclodextrins on the dual recognition toward lectin and drug

Journal of Inclusion Phenomena

Volumn 44, Issue 1-4, 2002, Pages 39-47

  Abe, Hideyoshi ^a   Kenmoku, Akira ^a   Yamaguch, Noriyuki ^a   Hattori, Kenjiro ^a  

^a TOKYO POLYTECHNIC UNIVERSITY   (Japan)

Author keywords

cyclodextrin; AFM; Association constant; Doxorubicin; Galactose; Oligosaccharide; PNA lectin; SPR

Indexed keywords

CYCLODEXTRIN; GALACTOSE; LECTIN; OLIGOSACCHARIDE;

ANIMAL CELL; ATOMIC FORCE MICROSCOPY; CARBOHYDRATE ANALYSIS; CONFERENCE PAPER; DRUG DELIVERY SYSTEM; LIVER CELL; MOLECULAR INTERACTION; NONHUMAN; QUANTITATIVE ANALYSIS; RAT;

EID: 0347026185     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1023008210637     Document Type: Conference Paper

References (79)

1. (a) W.M. Watkins and A. Gottschalk, eds.: Glycoproteins, Elsevier, Amsterdam, pp. 830-891.
2. (b) J.P. Drgid, D.C. Old, and E.H. Beochly, eds.: Bacterial Adherence, Chapman and Hall, London, pp. 185-217 (1980).
3. (c) N. Sharon and H. Lis: Lectins, Chapman and Hall, New York (1989).
4. (d) A. Varki, , R. Cummings, J.H. Esko, H. Freeze, G. Hart, and J. Marth, eds., Essentials Glycobiology, Cold Spring Harbor Laboratory Press, Cold Spring Harbor (1999).
5. (a) Y.C. Lee and R.T. Lee,: Acc. Chem. Res. 28, 321-327 (1995).
6. (b) Y.C. Lee, R.C. Lee, K. Rice, Y. Ichikawa, and T.-C. Wong: Pure Appl. Chem. 63, 499-506 (1991).
7. (c) A. Kichler and F. Schuber: Glycoconjugate J. 12, 275-281 (1995).
8. (a) K. Akiyoshi, H. Takanabe, T. Sato, H. Kondo, and J. Sunamoto: Chem. Lett. 473 (1990).
9. (b) S. Tuchiya, Y. Ramaki, T. Hara, K. Hosoi, and A. Okada: Biopharm. Drug. Dispos. 7, 549-558 (1986).
10. (c) H. Ishikawa, T. Hara, Y. Aramaki, S. Tuchiya, and K. Hosoi: Pham. Res. 7, 542-546 (1990).
11. (a) D. Zanini and R. Roy: J. Am. Chem. Soc. 119, 2088 (1997).
12. (b) D. Zanini and R. Roy: J. Org. Chem. 63, 3486 (1998).
13. (c) P.R. Ashton, S.E. Boyd, C.L. Brown, S.A. Nepagodiev, E.W. Meijier, H.W.I. Peerlings, and J.F. Stoddart: Chem. Eur. J. 3, 974 (1997).
14. (d) P.R. Ashton, E.F. Hounsell, N. Jayaraman, T.M. Nielsen, N. Spencer, J.F. Stoddart, and M. Young: J. Org. Chem. 63, 3429-2473 (1998).
15. (e) K. Aoi, K. Itoh, and M. Okada: Macromolecules 28, 5391 (1995).
16. (f) T.K. Lindhorst and C. Kieburg: Angew. Chem., Int. Ed. Engl. 35, 1953 (1996).
17. (g) F.W. Zeng and S.C. Zimmerman: Chem. Rev. 97, 1681 (1997).
18. (h) P.R. Ashton, S.E. Boyd, C.L. Brown, and J.F. Stoddart: Angew. Chem., Int. Ed. Engl. 36, 732 (1997).
19. (a) S.J. Meunier and R. Roy: Tetrahedron Lett. 37, 5469-5472 (1996).
20. (b) A. Marra, M.C. Scherrmann, A. Dondoni, A. Casnati, P. Minari, and R. Ungaro: Angew. Chem., Int. Ed. Engl. 33, 2479-2481 (1994).
21. (c) A. Marra, A. Dondoni, and F.J. Sannone: Org. Chem. 61, 5155-5158 (1996).
22. (d) A. Dondoni, A. Marra, M.C. Scherrmann, A. Casnati, F. Sannone, and R. Ungaro: Chem. Eur. J. 3, 1774-1782 (1997).
23. (e) A. Dondoni, M. Kleban, and A. Marra: Tetrahedron Lett. 38, 7801-7804 (1997).
24. (f) K. Ariga, K. Isoyama, O. Hayashida, Y. Aoyama, and Y. Okahata: Chem. Lett. 1007-1008 (1998).
25. (g) T. Fujimoto, C. Shimizu, O. Hayashida, and Y. Aoyama: J. Am. Chem. Soc. 119, 6676-6677 (1997).
26. (h) O. Hayashida, C. Shimizu, T. Fujimoto, and Y. Aoyama: Chem. Lett. 1998, 13-14.
27. (i) T. Fujimoto, C. Shimizu, O. Hayashida, and Y. Aoyama: J. Am. Chem. Soc. 120, 601-602 (1998).
28. (j) T. Fujimoto, C. Shimizu, O. Hayashida, and Y. Aoyama: J. Am. Chem. Soc. 119, 6676-6677 (1997).
29. (k) O. Hayashida, M. Kato, K. Ariga, and Y. Aoyama: J. Am. Chem. Soc. 121, 11597-11598 (1999),
30. (a) D.A. Fulton and J.F. Stoddart: Org. Lett. 2, 1113-1116 (2000).
31. (b) J.J. García-López, F. Hernández-Mateo, J. Isac-García, J.M. Kim, R. Roy, F. Sautoyo-González, and A.J. Vargas-Berenguel: Org. Chem. 64, 522-531 (1999).
32. (c) H. Parrot-Lopez, H. Galons, A.W. Coleman, J. Mahuteau, and M. Miocque, Tetrahedron Lett. 33, 209-212 (1992).
33. (d) F. Attioui, A. Al-Omar, E. Leary, H. Parrot-Lopez, C. Auge, A.W. Coleman, C. Finance, and R. Bonaly: J. Chem. Soc., Chem. Commun. 1019-1020 (1995).
34. (e) J.M. García Fernández, C.O. Mellet, S. Maciejewski, and J. Defaye: J. Chem. Soc. Chem. Commun. 2741-2742 (1996).
35. (f) H. Parrot-Lopez, E. Leray, and A.W. Coleman: Supramol. Chem. 3, 37-42 (1993).
36. (g) H.H. Baer, Y. Shen, F. Santoyo-Gonzáles, A. Vargas-Berenguel, and J. Isac-García: Carbohydr. Res. 235, 129-139 (1992).
37. (h) K. Koizumi, S. Kitahata, and H. Hashimoto: Method in Enzymology 247(B), 64-87 (1994).
38. (i) V. Lainé, A. Coste-Sarguet, A. Gadelle, J. Defaye, B. Pealy, and F. Djedaïni-Pilard: J. Chem. Soc., Perkin Trans. 2, 1479-1487 (1995).
39. (j) C.O. Mellet, J.M. Benito, J.M. García-Fernándes, H. Law, K. Chmurski, J. Defaye, M.L. O'Sullivan, and H.N. Caro: Chem. Eur. J. 4, 2523-2531 (1998).
40. (k) J.J. García-López, F. Hernández-Mateo, J. Isac-García, J.M. Kim, R. Roy, F. Santoyo-González, and A. Vargas-Berenguel: J. Org. Chem. 64, 522-531 (1999).
41. (l) J.J. García-López, F. Santoyo-González, A. Vargas-Berenguel, and J.J. Giménez-Martínez: Chem. Eur. J. 5, 1775-1784 (1999).
42. (m) T. Furuike and S. Aiba: Chem. Lett. 69-70 (1999).
43. (n) L. DeRobertis, C. Lancelon-Pin, H. Drigues, F. Attioui, R. Bonaly, and A. Marsura: Bioorg. Med. Chem. Lett. 4, 1127-1130 (1994).
44. (o) T. Shinoda, S. Katatani, A. Maeda, Y. Konno, H. Hashimoto. K. Hara, K. Fujimoto, and T. Sonobe: Drug Develop. Ind. Pharm. 25, 1185-1192 (1999).
45. (p) T. Shinoda, A. Maeda, S. Kagatani, Y. Konno, T. Sonobe, M. Fukui, H. Hashimoto, K. Hara, and K. Fujita: Int. J. Pharm. 167, 147-154 (1998).
46. (q) C.O. Mellet, J. Defaye, and J.M.G. Fernandez: Biolog. J. Armenia 53, 70-81 (2001).
47. (r) I. Baussanne, J.M. Benito, C.O. Mellet, J.M.G. Fernandez, H. Law, and J. Defaye: Chem. Comm. 1489-1490 (2000).
48. (a) N. Yasuda, N. Aoki, H. Abe, and K. Hattori: Chem. Lett. 706-707 (2000).
49. (b) N. Aoki, N. Yasuda, H. Abe, and K. Hattori: Bull. Chem. Soc. Japan, submitted.
50. (c) H. Imata, K. Kubota, K. Hattori, M. Aoyagi, and C. Jindoh: Polym. J. 29, 563-567 (1997).
51. (d) H. Imata, K. Kubota, K. Hattori, M. Aoyagi, and C. Jindoh: Bio. Med. Chem. Lett. 7, 109-112 (1997).
52. (e) K. Hattori, H. Imata, K. Kubota, K. Matsuda, M. Aoyagi, K. Yamamoto, C. Jindoh, T. Yamanoi, and T. Inazu: Incl. Phenom. Mol. Recogn. 25, 69-72 (1996).
53. (f) K. Hattori, K. Takahashi, and T. Koshikawa: in T. Osa (ed.), Proceedings of the 7th International Cyclodextrins Symposium, Bussiness Center for Academic Societies, Tokyo, pp. 90-93 (1994).
54. (g) K. Matsuda, T. Inazu, K. Haneda, M. Mizuno, T. Yamanoi, K. Hattori, K. Yamamoto, and H. Kumagai, Bio. Med. Chem. Lett. 7, 2353-2356 (1997).
55. (h) K. Hattori: Biol. J. Armenia 53, 82-94 (2001).
56. (a) J. Szejtli: Cyclodextrin Technology, Kluwer Academic Publishers, Netherlands (1988).
57. (b) G. Wenz: Angew. Chem., Int. Ed. Engl. 33, 803-822 (1994).
58. (c) A.R. Khan, P. Forgo, K.J. Stine, and V.T. D'Souza: Chem. Rev. 98, 1977-1996 (1998).
59. (d) K.H. Fröming and J. Szejtli: Cyclodextrin in Pharmacy, Kluwer Academic Publishers, Netherlands (1992).
60. (e) K. Uekama, F. Hirayama, T. Irie, and D. Duchene, eds.: New Trends in Cyclodextrins and Derivatives, Editions de Sante, Paris, pp. 409-446 (1991).
61. (f) K. Uekama, F. Hirayama, and T. Irie: Chemical Reviews 98, 2045-2076 (1998).
62. (g) K. Uekama and T. Irie: Comprehensive Supramolecular Chemistry 13, Elsevier Science Ltd., Oxford, pp. 451-481 (1996).
63. (h) T. Nagai and H. Ueda: Comprehensive Supramolecular Chemistry, Vol. 13, Elsevier Science Ltd., Oxford, pp. 441-450 (1996).
64. P.O. Seglen: Methods Cell Biol. 13, 29-83 (1976).
65. (a) S.C. Shuster, R.V. Swanson, L.A. Alex, R.B. Bourret, and M.I. Simon: Nature 365, 343-347 (1993).
66. (b) P.R. Edward, A. Gill, D.V. Pollard-Knight, M. Hoare, P.E. Buckle, P.A. Lowe, and R.J. Leatherbarrow: Anal. Biochem. 231, 210 (1995).
67. (c) R.J. Davis, P.R. Edward, H.J. Watts, C.R. Lowe, P.E. Buckle, D. Yeund, T.M. Kinning, and D.V. Pollard-Knight: Techniques in Protein Chemistry V, Academic Press, San Diego, pp. 285-292 (1994).
68. (d) Private communication from Affinity Sensors.
69. (a) Y. Shinohara, F. Kim, M. Shimizu, M. Goto, M. Tosu, and Y. Hasegawa, Eur .J. Biochem. 221, 189-194 (1994).
70. (b) I. Okazaki, Y. Hasegawa, Y. Shinohara, T. Kamasaki, and R. Bhikhabhai: J. Mol. Recogn. 8, 95-99 (1995).
71. (c) A.M. Hutchinson: Anal. Biochem. 220, 303-307 (1994).
72. (d) D.A. Mann, M. Kanai, D.J. Maly, and L.L. Kiessling: J. Am. Chem. Soc. 120, 10575-10582 (1998).
73. (a) G. Puu, E. Artursson, I. Gustafson, M. Lundström, and J. Jass: Biosensors Bioelectronics 15, 31-41 (2000).
74. (b) I.M. Fisher and T. Tjärnhage: Biosensors Bioelectronics 15, 463-471 (2000).
75. (a) G. Ashwell and J. Harford: Ann. Rev. Biochem. 51, 531-554 (1982).
76. (b) K.G. Rice, O.A. Weisz, T. Barthel. Y.C. Lee, R.R. Townsend, and A.L. Hubbard: J. Biol. Chem. 264, 18429-18434 (1989).
77. (c) M. McPaul and P. Berg: Proc. Natl. Acad. Sci. USA 83, 8863-8867 (1986).
78. (a) R. Ravishankar, M. Ravindran, K. Suguna, A. Surolia, and M. Vijayan: Current Sci. 72, 855-861 (1997).
79. (b) R. Banerjee, K. Das, R. Ravishankar, K. Suguna, A. Surolia, and M. Vijayan: J. Mol. Biol. 259, 281-296 (1996).