Glycosyldisulfides from dynamic combinatorial libraries as O-glycoside mimetics for plant and endogenous lectins: Their reactivities in solid-phase and cell assays and conformational analysis by molecular dynamics simulations

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 18, 2006, Pages 6314-6326

  André, Sabine ^a   Pei, Zhichao ^b   Siebert, Hans Christian ^a   Ramström, Olof ^b   Gabius, Hans Joachim ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

Agglutinin; Combinatorial chemistry; Drug design; Dynamic chemistry; Galectin; Glycosyldisulfide; Neoglycoprotein

Indexed keywords

CARBOHYDRATE DERIVATIVE; GALACTOSIDE; GALECTIN 3; LIGAND; PLANT LECTIN;

ARTICLE; BINDING ASSAY; CELL ASSAY; COMBINATORIAL CHEMISTRY; COMBINATORIAL LIBRARY; COMPARATIVE STUDY; CONTROLLED STUDY; CROSS LINKING; DISULFIDE BOND; DRUG ACTIVITY; DRUG DETERMINATION; DRUG POTENCY; DRUG PROTEIN BINDING; HUMAN; HUMAN CELL; LECTIN BINDING; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; SOLID PHASE SYNTHESIS; STRUCTURE ACTIVITY RELATION;

BINDING SITES; CARBOHYDRATE CONFORMATION; CELL LINE; CELLS, CULTURED; COMBINATORIAL CHEMISTRY TECHNIQUES; COMPUTER SIMULATION; DISULFIDES; GLYCOCONJUGATES; GLYCOSIDES; HUMANS; LECTINS; MOLECULAR MIMICRY; STRUCTURE-ACTIVITY RELATIONSHIP; SURFACE PROPERTIES;

EID: 33747134305     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.05.045     Document Type: Article

References (128)

1. Gabius H.-J. Angew. Chem., Int. Ed. Engl. 27 (1988) 1267-1276
2. Angew. Chem. 100 (1988) 1321-1330
3. Lee Y.C., and Lee R.T. J. Biomed. Sci. 3 (1996) 221-237
4. Simon P.M. Drug Discovery Today 1 (1996) 522-528
5. Reuter G., and Gabius H.-J. Cell. Mol. Life Sci. 55 (1999) 368-422
6. Yamazaki N., Kojima S., Bovin N.V., André S., Gabius S., and Gabius H.-J. Adv. Drug Deliv. Rev. 43 (2000) 225-244
7. Gabius H.-J., Siebert H.-C., André S., Jiménez-Barbero J., and Rüdiger H. ChemBioChem 5 (2004) 740-764
8. Shriver Z., Raguram S., and Sasisekharan R. Nat. Rev. Drug Discov. 3 (2004) 863-873
9. Gabius H.-J. Eur. J. Biochem. 243 (1997) 543-576
10. Kaltner H., and Stierstorfer B. Acta Anat. 161 (1998) 162-179
11. Haltiwanger R.S., and Lowe J.B. Annu. Rev. Biochem. 73 (2004) 491-537
12. Olofsson S., and Bergström T. Ann. Med. 37 (2005) 154-172
13. Gabius H.-J. Crit. Rev. Immunol. 26 (2006) 43-79
14. Villalobo A., Nogales-Gonzales A., and Gabius H.-J. Trends Glycosci. Glycotechnol. 18 (2006) 1-37
15. Schmidt R.R. Strategies for the chemical synthesis of glycoconjugates. In: Gabius H.-J., and Gabius S. (Eds). Glycosciences: Status and Perspectives (1997), Chapman & Hall, London 31-53
16. Seitz O. ChemBioChem 1 (2000) 214-246
17. Brocke C., and Kunz H. Bioorg. Med. Chem. 10 (2002) 3085-3112
18. Unverzagt C., André S., Seifert J., Kojima S., Fink C., Srikrishna G., Freeze H., Kayser K., and Gabius H.-J. J. Med. Chem. 45 (2002) 478-491
19. André S., Unverzagt C., Kojima S., Frank M., Seifert J., Fink C., Kayser K., von der Lieth C.-W., and Gabius H.-J. Eur. J. Biochem. 271 (2004) 118-134
20. Holemann A., and Seeberger P.H. Curr. Opin. Biotechnol. 15 (2004) 615-622
21. André S., Kojima S., Gundel G., Russwurm R., Schratt X., Unverzagt C., and Gabius H.-J. Biochim. Biophys. Acta. 1760 (2006) 768-782
22. Laine R.A. The information-storing potential of the sugar code. In: Gabius H.J., and Gabius S. (Eds). Glycosciences: Status and Perspectives (1997), Chapman & Hall, London 1-14
23. Gabius H.-J., André S., Kaltner H., and Siebert H.-C. Biochim. Biophys. Acta 1572 (2002) 165-177
24. Schweizer F., and Hindsgaul O. Curr. Opin. Chem. Biol. 3 (1999) 291-298
25. Rüdiger H., Siebert H.-C., Solís D., Jiménez-Barbero J., Romero A., von der Lieth C.-W., Diaz-Mauriño T., and Gabius H.-J. Curr. Med. Chem. 7 (2000) 389-416
26. St. Hilaire P.M., and Meldal M. Angew. Chem., Int. Ed. 39 (2000) 1162-1179
27. Angew. Chem. 1112 (2000) 1210-1228
28. Barkley A., and Arya P. Chem. Eur. J. 7 (2001) 555-563
29. Nishimura S.-I. Curr. Opin. Chem. Biol. 5 (2001) 325-335
30. Ramström O., Bunyapaiboonsri T., Lohmann S., and Lehn J.-M. Biochim. Biophys. Acta 1572 (2002) 178-186
31. Wittmann V., and Seeberger S. Angew. Chem., Int. Ed. 43 (2004) 900-903
32. Angew. Chem. 2116 (2004) 2918-2921
33. Ramström O., and Lehn J.-M. Nat. Rev. Drug Discov. 1 (2002) 26-36
34. Sakai S., Shigemasa Y., and Sasaki T. Tetrahedron Lett. 38 (1997) 8145-8148
35. Sakai S., Shigemasa Y., and Sasaki T. Bull. Chem. Soc. Jpn. 72 (1999) 1313-1319
36. Ramström O., and Lehn J.-M. ChemBioChem 1 (2000) 41-47
37. Ramström O., Lohmann S., Bunyapaiboonsri T., and Lehn J.-M. Chem. Eur. J. 10 (2004) 1711-1715
38. de Waard A., Hickman S., and Kornfeld S. J. Biol. Chem. 251 (1976) 7581-7587
39. Leffler H., and Barondes S.H. J. Biol. Chem. 261 (1986) 10119-10126
40. Lee R.T., Ichikawa Y., Allen H.J., and Lee Y.C. J. Biol. Chem. 265 (1990) 7864-7871
41. Bharadwaj S., Kaltner H., Korchagina E.Y., Bovin N.V., Gabius H.-J., and Surolia A. Biochim. Biophys. Acta 1472 (1999) 191-196
42. Muñoz J.L., Garcia-Herrero A., Asensio J.L., Auzennaeau F.I., Cañada F.J., and Jiménez-Barbero J. J. Chem. Soc., Perkin Trans. 1 (2001) 867-872
43. Aguilera B., Jiménez-Barbero J., and Fernandez-Mayoralas A. Carbohydr. Res. 308 (1998) 19-27
44. Driguez H. ChemBioChem 2 (2001) 311-318
45. Pachamuthu K., and Schmidt R.R. Chem. Rev. 106 (2006) 160-187
46. Davis B.G., Ward S.J., and Rendle P.M. Chem. Commun. (2001) 189-190
47. Szilagyi L., Illyes T.-Z., and Herczegh P. Tetrahedron Lett. (2001) 3901-3903
48. Pei Z., Aastrup T., Anderson H., and Ramström O. Bioorg. Med. Chem. Lett. 15 (2005) 2707-2710
49. Hotchkiss T., Kramer H.B., Doores K.J., Gamblin D.P., Oldham N.J., and Davis B.G. Chem. Commun. (2005) 4264-4266
50. Pei, Z.; Larsson, R.; Aastrup, T.; Anderson, H.; Lehn, J.-M.; Ramström, O., Biosens. Bioelectron., in press.
51. Kayser K., Hoeft D., Hufnagl P., Caselitz J., Zick Y., André S., Kaltner H., and Gabius H.-J. Histol. Histopathol. 18 (2003) 771-779
52. Lahm H., André S., Hoeflich A., Kaltner H., Siebert H.-C., Sordat B., von der Lieth C.-W., Wolf E., and Gabius H.-J. Glycoconj. J. 20 (2004) 227-238
53. Sharma U.C., Pokharel S., Van Brakel T.J., Van Berlo J.H., Cleutjens J.P.M., Schroen B., André S., Crijns H.J.G.M., Gabius H.-J., Maessen J., and Pinto Y.M. Circulation 110 (2004) 3121-3128
54. Takenaka Y., Fukumori T., and Raz A. Glycoconj. J. 19 (2004) 543-549
55. Gabius H.-J. Anat. Histol. Embryol. 30 (2001) 3-31
56. Siebert H.-C., Jiménez-Barbero J., André S., Kaltner H., and Gabius H.-J. Methods Enzymol. 362 (2003) 417-434
57. Goldstein I.J., and Poretz R.D. In: Liener I.E., Sharon N., and Goldstein I.J. (Eds). The Lectins. Properties, Functions, and Applications in Biology and Medicine (1986), Academic Press, Orlando 33-247
58. Rüdiger H., and Gabius H.-J. Glycoconj. J. 18 (2001) 589-613
59. Sando S., Narita A., and Aoyama Y. Bioorg. Med. Chem. Lett. 14 (2004) 2835-2838
60. Lehrman M.A., Haltiwanger R.S., and Hill R.L. J. Biol. Chem. 261 (1986) 7426-7432
61. Dessen A., Gupta D., Sabesan S., Brewer C.F., and Sacchettini J.C. Biochemistry 34 (1995) 4933-4942
62. Audette G.F., Vandonselaar M., and Delbaere L.T. J. Mol. Biol. 304 (2000) 423-433
63. Niwa H., Tonevitsky A.G., Agapov I.I., Saward S., Pfuller U., and Palmer R.A. Eur. J. Biochem. 270 (2003) 2739-2749
64. Lee R.T., Gabius H.-J., and Lee Y.C. J. Biol. Chem. 267 (1992) 23722-23727
65. Lee R.T., Gabius H.-J., and Lee Y.C. Carbohydr. Res. 254 (1994) 269-276
66. Galanina O.E., Kaltner H., Khraltsova L.S., Bovin N.V., and Gabius H.-J. J. Mol. Recogn. 10 (1997) 139-147
67. Marker P.C., Stephan J.P., Lee J., Bald L., Mather J.P., and Cunha G.R. Dev. Biol. 233 (2001) 95-108
68. van den Berg T.K., Honing H., Franke N., van Remoortere A., Schiphorst W.E., Liu F.T., Deelder A.M., Cummings R.D., Hokke C.H., and van Die I. J. Immunol. 173 (2004) 1902-1907
69. Kopitz J., von Reitzenstein C., André S., Kaltner H., Uhl J., Ehemann V., Cantz M., and Gabius H.-J. J. Biol. Chem. 276 (2001) 35917-35923
70. Brewer C.F. Biochim. Biophys. Acta 1572 (2002) 255-262
71. André S., Kaltner H., Lensch M., Russwurm R., Siebert H.-C., Fallsehr C., Tajkhorshid E., Heck A.J.R., von Knebel Doeberitz M., Gabius H.-J., and Kopitz J. Int. J. Cancer 114 (2005) 46-57
72. Siebert, H.-C.; Rosen, J.; Seyrek, K.; Kaltner, H.; André, S.; Bovin, N. V.; Nyholm, P.-G.; Gabius, H.-J., Biochimie, in press.
73. Bock K., Duus J.O., and Refn S. Carbohydr. Res. 253 (1994) 51-67
74. Geyer A., Hummel G., Eisele T., Stefan R., and Schmidt R.R. Chem. Eur. J. 2 (1996) 981-988
75. Nilsson U., Johansson R., and Magnusson G. Chem. Eur. J. 2 (1996) 295-302
76. Garcia-Herrero A., Montero E., Muñoz J.L., Espinosa J.F., Vian A., Garcia J.L., Asensio J.L., Cañada F.J., and Jiménez-Barbero J. J. Am. Chem. Soc. 124 (2002) 4804-4810
77. Ramkumar R., Surolia A., and Podder S.K. Biochem. J. 308 (1995) 237-241
78. Bianchet M.A., Ahmed H., Vasta G.R., and Amzel L.M. Proteins 40 (2000) 378-388
79. Schwarz F.P., Ahmed H., Bianchet M.A., Amzel L.M., and Vasta G.R. Biochemistry 37 (1998) 5867-5877
80. Bachhawat-Sikder K., Thomas C.J., and Surolia A. FEBS Lett. 500 (2001) 75-79
81. Vasudevan S.V., and Balaji P.V. Biopolymers 63 (2002) 168-180
82. Gilleron M., Siebert H.-C., Kaltner H., von der Lieth C.-W., Kozar T., Halkes K.M., Korchagina E.Y., Bovin N.V., Gabius H.-J., and Vliegenthart J.F.G. Eur. J. Biochem. 252 (1998) 416-427
83. Alonso-Plaza J.M., Canales M.A., Jiménez M., Roldan J.L., Garcia-Herrero A., Iturrino L., Asensio J.L., Cañada F.J., Romero A., Siebert H.-C., André S., Solís D., Gabius H.-J., and Jiménez-Barbero J. Biochim. Biophys. Acta 1568 (2001) 225-236
84. Fernandez-Alonso M.C., Cañada F.J., Soli{dotless}́s D., Cheng X., Kumaran G., André S., Siebert H.-C., Mootoo D.R., Gabius H.-J., and Jiménez-Barbero J. Eur. J. Org. Chem. (2004) 1604-1613
85. Siebert H.-C., André S., Lu S.-Y., Frank M., Kaltner H., van Kuik J.A., Korchagina E.Y., Bovin N., Tajkhorshid E., Kaptein R., Vliegenthart J.F.G., van der Lieth C.-W., Jiménez-Barbero J., Kopitz J., and Gabius H.-J. Biochemistry 42 (2003) 14762-14773
86. Hiruma K., Kajimoto T., Weitz-Schmidt G., Ollmann I., and Wong C.-H. J. Am. Chem. Soc. 118 (1996) 9273-9278
87. Pei Z., Dong H., and Ramström O. J. Org. Chem. 70 (2005) 6952-6955
88. Wu A.M., Wu J.H., Tsai M.-S., Kaltner H., and Gabius H.-J. Biochem. J. 358 (2001) 529-538
89. Wu A.M., Wu J.H., Tsai M.-S., Liu J.-H., André S., Wasano K., Kaltner H., and Gabius H.-J. Biochem. J. 367 (2002) 653-664
90. Wu A.M., Wu J.H., Liu J.-H., Singh T., André S., Kaltner H., and Gabius H.-J. Biochimie 86 (2004) 317-326
91. Wu A.M., Singh T., Wu J.H., Lensch M., André S., and Gabius H.-J. Glycobiology 16 (2006) 524-537
92. Delacour D., Gouyer V., Zanetta J.P., Drobecq H., Leteurtre E., Grard G., Moreau-Hannedouche O., Maes E., Pons A., André S., Le Bivic A., Gabius H.-J., Manninen A., Simons K., and Huet G. J. Cell Biol. 169 (2005) 491-501
93. Sörme P., Qian Y., Nyholm P.-G., Leffler H., and Nilsson U.J. ChemBioChem 3 (2002) 183-189
94. Wada Y., Saito T., Matsuda N., Ohmoto H., Yoshino K., Ohashi M., Kondo H., Ishida H., Kiso M., and Hasegawa A. J. Med. Chem. 39 (1996) 2055-2059
95. Tsujishita H., Hiramatsu Y., Kondo N., Ohmoto H., Kondo H., Kiso M., and Hasegawa A. J. Med. Chem. 40 (1997) 362-369
96. Elad-Sfadia G., Haklai R., Ballan E., Gabius H.-J., and Kloog Y. J. Biol. Chem. 277 (2002) 37169-37175
97. Rotblat B., Niv H., André S., Kaltner H., Gabius H.-J., and Kloog Y. Cancer Res. 64 (2004) 3112-3118
98. Rorive S., Belot N., Decaestecker C., Lefranc F., Gordower L., Micik S., Maurage C.A., Kaltner H., Ruchoux M.M., Danguy A., Gabius H.-J., Salmon I., Kiss R., and Camby I. Glia 33 (2001) 241-255
99. Camby I., Belot N., Lefranc F., Sadeghi N., de Launoit Y., Kaltner H., Musette S., Darro F., Danguy A., Salmon I., Gabius H.-J., and Kiss R. J. Neuropathol. Exp. Neurol. 61 (2002) 585-596
100. Nagy N., Legendre H., Engels O., André S., Kaltner H., Wasano K., Zick Y., Pector J.-C., Decaestecker C., Gabius H.-J., Salmon I., and Kiss R. Cancer 97 (2003) 1849-1858
101. André S., Ortega P.J., Perez M.A., Roy R., and Gabius H.-J. Glycobiology 9 (1999) 1253-1261
102. André S., Frisch B., Kaltner H., Desouza D.L., Schuber F., and Gabius H.-J. Pharm. Res. 17 (2000) 985-990
103. André S., Pieters R.J., Vrasidas I., Kaltner H., Kuwabara I., Liu F.-T., Liskamp R.M.J., and Gabius H.-J. ChemBioChem 2 (2001) 822-830
104. André S., Liu B., Gabius H.-J., and Roy R. Org. Biomol. Chem. 1 (2003) 3909-3916
105. Ahmad N., Gabius H.-J., André S., Kaltner H., Sabesan S., Roy R., Liu B., Macaluso F., and Brewer C.F. J. Biol. Chem. 279 (2004) 10841-10847
106. Pravdic N., Franjicmihalic I., and Danilov B. Carbohydr. Res. 45 (1975) 302-306
107. Yang G.L., Franck R.W., Bittman R., Samadder P., and Arthur G. Org. Lett. 3 (2001) 197-200
108. Gamblin D.P., Garnier P., van Kasteren S., Oldham N.J., Fairbanks A.J., and Davis B.G. Angew. Chem., Int. Ed. 43 (2004) 828-833
109. Angew. Chem. 2116 (2004) 2846-2851
110. Savage P.B., and Gellman S.H. J. Am. Chem. Soc. 115 (1993) 10448-10449
111. Harrison A.W., Fisher J.F., Guido D.M., Couch S.J., Lawson J.A., Sutter D.M., Williams M.V., DeGraaf G.L., Rogers J.E., Pals D.T., and DuCharme D.W. Bioorg. Med. Chem. 2 (1994) 1339-1361
112. Rakotomanomana N., Lacombe J.M., and Pavia A.A. Carbohydr. Res. 197 (1990) 318-323
113. Macindoe W.M., van Oijen A.H., and Boons G.-J. Chem. Commun. (1998) 847-848
114. McBroom C.R., Samanen C.H., and Goldstein I.J. Methods Enzymol. 28 (1972) 212-219
115. Gabius H.-J., Engelhardt R., Rehm S., and Cramer F. J. Natl. Cancer Inst. 73 (1984) 1349-1357
116. Gabius H.-J. Anal. Biochem. 189 (1990) 91-94
117. Gabius H.-J., Wosgien B., Hendrys M., and Bardosi A. Histochemistry 95 (1991) 269-277
118. Purkrabkova T., Smetana Jr. K., Dvorankova B., Holikova Z., Bock C., Lensch M., André S., Pytlik R., Liu F.T., Klima J., Smetana K., Motlik J., and Gabius H.-J. Biol. Cell 95 (2003) 535-545
119. Jimenez M., Saiz J.L., André S., Gabius H.-J., and Solís D. Glycobiology 15 (2005) 1386-1395
120. Manning J.C., Seyrek K., Kaltner H., André S., Sinowatz F., and Gabius H.-J. Histol. Histopathol. 19 (2004) 1043-1060
121. André S., Unverzagt C., Kojima S., Dong X., Fink C., Kayser K., and Gabius H.-J. Bioconjug. Chem. 8 (1997) 845-855
122. André S., Kojima S., Prahl I., Lensch M., Unverzagt C., and Gabius H.-J. FEBS J. 272 (2005) 1986-1998
123. Gabius S., Joshi S.S., Gabius H.-J., and Sharp J.G. Anticancer Res. 11 (1991) 793-800
124. André S., Kaltner H., Furuike T., Nishimura S.-I., and Gabius H.-J. Bioconjug. Chem. 15 (2004) 87-98
125. André S., Kojima S., Yamazaki N., Fink C., Kaltner H., Kayser K., and Gabius H.-J. J. Cancer Res. Clin. Oncol. 125 (1999) 461-474
126. Sturm A., Lensch M., André S., Kaltner H., Wiedenmann B., Rosewicz S., Dignass A.U., and Gabius H.-J. J. Immunol. 173 (2004) 3825-3837
127. Siebert H.-C., Born K., André S., Frank M., Kaltner H., von der Lieth C.-W., Heck A.J.R., Jiménez-Barbero J., Kopitz J., and Gabius H.-J. Chem. Eur. J. 12 (2006) 388-402
128. Humphrey W., Dalke A., and Schulten K. J. Mol. Graph 14 (1996) 27-28 33-38