Trehalose glycolipids - Synthesis and biological activities

Carbohydrate Research

Volumn 356, Issue , 2012, Pages 25-36

  Khan, Ashna A ^a,b   Stocker, Bridget L ^b   Timmer, Mattie S M ^a  

^a VICTORIA UNIVERSITY OF WELLINGTON   (New Zealand)

^b MALAGHAN INSTITUTE OF MEDICAL RESEARCH   (New Zealand)

Author keywords

6,6 Diesters; Biological activity; Chemical synthesis; Sulfoglycolipids; Trehalose glycolipids

Indexed keywords

AMPHIPHILIC CHARACTER; BIOLOGICAL PROPERTIES; CHEMICAL SYNTHESIS; DIESTERS; GLYCOLIPIDS; NATURAL SOURCES; SULFOGLYCOLIPIDS;

FUNCTIONAL GROUPS; LIPIDS; STEREOCHEMISTRY;

BIOACTIVITY;

BCG VACCINE; CORD FACTOR; GLYCOLIPID; SULFATIDE; TREHALOSE; TREHALOSE DICORYNOMYCOLATES; TREHALOSE DIESTERS OF FATTY ACIDS; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; BIOLOGICAL ACTIVITY; CONFERENCE PAPER; DEACYLATION; HUMAN; IMMUNE SYSTEM; KLEBSIELLA PNEUMONIAE; LISTERIA MONOCYTOGENES; MYCOBACTERIUM TUBERCULOSIS; PHASE 1 CLINICAL TRIAL (TOPIC); PRIORITY JOURNAL; T LYMPHOCYTE ACTIVATION;

ANIMALS; BACTERIA; CAENORHABDITIS ELEGANS; CARBOHYDRATE CONFORMATION; CELL LINE, TUMOR; CELL SURVIVAL; CYTOKINES; ESTERS; GLYCOLIPIDS; HUMANS; MACROPHAGES; NEOPLASMS; NITRIC OXIDE; SURFACE-ACTIVE AGENTS; TREHALOSE;

EID: 84862315997     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2012.03.010     Document Type: Conference Paper

References (139)

1. D. Chatterjee Curr. Opin. Chem. Biol. 1 1997 579 588
2. J. Indrigo, R.L. Hunter Jr., and J.K. Actor Microbiology 149 2003 2049 2059
3. Rajni, Rao, N; Meena, L. S. Biotechnol. Res. Int. 2011, 7, Article ID 274693.
4. P.J. Brennan, and H. Nikaido Annu. Rev. Biochem. 64 1995 29 63
5. S. Penkov, F. Mende, V. Zagoriy, C. Erkut, R. Martin, U. Pässler, K. Schuhmann, D. Schwudke, M. Gruner, J. Mäntler, T. Reichert-Müller, A. Shevchenko, H.-J. Knölker, and T.V. Kurzchalia Angew. Chem., Int. Ed. 49 2010 9430 9435
6. G. Lemaire, J.-P. Tenu, and J.-F. Petit Med. Res. Rev. 6 1986 243 274
7. R. Ryll, Y. Kumazawa, and I. Yano Microbiol. Immunol. 45 2001 801 811
8. E. Lederer Chem. Phys. Lipids 16 1976 91 106
9. C. Asselineau, and J. Asselineau Prog. Chem. Fats Other Lipids 16 1978 59 99
10. H. Bloch J. Exp. Med. 91 1950 197 218
11. T. Ioneda, M. Lenz, and J. Pudles Biochem. Biophys. Res. Commun. 13 1963 110 114
12. P. Rapp, H. Bock, V. Wray, and F. Wagner J. Gen. Microbiol. 115 1979 491 503
13. C.L. Silva, J.L. Gesztesi, and T. Ioneda Chem. Phys. Lipids 24 1979 17 25
14. E. Vilkas, and A. Rojas Bull. Soc. Chim. Biol. 46 1964 689 701
15. S.W. Hunter, T. Fujiwara, R.C. Murphy, and P.J. Brennan J. Biol. Chem. 259 1984 9729 9734
16. S.W. Hunter, R.C. Murphy, K. Clay, M.B. Goren, and P.J. Brennan J. Biol. Chem. 258 1983 10481 10487
17. G. Middlebrook, C.M. Coleman, and W.B. Schaefer Proc. Natl. Acad. Sci. 45 1959 1801 1804
18. M.B. Goren, O. Brokl, P. Roller, H.M. Fales, and B.C. Das Biochemistry 15 1976 2728 2735
19. P. Domenech, M.B. Reed, C.S. Dowd, C. Manca, G. Kaplan, and C.E. Barry III J. Biol. Chem. 279 2004 21257 21265
20. M. Gilleron, S. Stenger, Z. Mazorra, F. Wittke, S. Mariotti, G. Böhmer, J. Prandi, L. Mori, G. Puzo, and G. De Libero J. Exp. Med. 199 2004 649 659
21. C.E. Barry III, R.E. Lee, K. Mdluli, A.E. Sampson, B.G. Schroeder, R.A. Slayden, and Y. Yuan Prog. Lipid Res. 37 1998 143 179
22. Y. Nishikawa, T. Katori, K. Kukita, and T. Ikekawa Nippon Kagaku Kaishi 10 1982 1661 1666
23. R. Toubiana, E. Ribi, C. McLaughlin, and S.M. Strain Cancer Immunol. Immunother. 2 1977 189 193
24. S. Kamiya Hirosaki Igaku 38 1986 712 719
25. E. Yarkoni, H.J. Rapp, J. Polonsky, and E. Lederer Int. J. Cancer 22 1978 564 569
26. K. Satoh Hirosaki Igaku 42 1991 455 464
27. M. Parant, F. Audibert, F. Parant, L. Chedid, E. Soler, J. Polonsky, and E. Lederer Infect. Immun. 20 1978 12 19
28. G.R. Olds, L. Chedid, E. Lederer, and A.A.F. Mahmoud J. Infect. Dis. 141 1980 473 478
29. E. Yarkoni, and A. Bekierkunst Infect. Immun. 14 1976 1125 1129
30. H. Schoenen, B. Bodendorfer, K. Hitchens, S. Manzanero, K. Werninghaus, F. Nimmerjahn, E.M. Agger, S. Stenger, P. Andersen, J. Ruland, G.D. Brown, C. Wells, and R. Lang J. Immunol. 184 2010 2756 2760
31. E. Ishikawa, T. Ishikawa, Y.S. Morita, K. Toyonaga, H. Yamada, O. Takeuchi, T. Kinoshita, S. Akira, Y. Yoshikai, and S. Yamasaki J. Exp. Med. 206 2009 2879 2888
32. R. Toubiana, and M.J. Toubiana Biochimie 55 1973 575 578
33. J. Polonsky, E. Soler, and J. Varenne Carbohydr. Res. 65 1978 295 300
34. J. Polonsky, G. Ferréol, R. Toubiana, and E. Lederer Bull. Soc. Chim. Fr. 1956 1471 1477
35. A. Liav, and M.B. Goren Chem. Phys. Lipids 27 1980 345 352
36. J.-F. Tocanne Carbohydr. Res. 44 1975 301 307
37. R. Toubiana, M.-J. Toubiana, B.C. Das, and A.C. Richardson Biochimie 55 1973 569 573
38. A.A. Khan, S.H. Chee, R.J. McLaughlin, J.L. Harper, F. Kamena, M.S.M. Timmer, and B.L. Stocker ChemBioChem 3 2011 2572 2576
39. E. Lederer Chem. Phys. Lipids 16 1976 91 106
40. S. Bottle, and I.D. Jenkins J. Chem. Soc., Chem. Commun. 1983 385
41. I.D. Jenkins, and M.B. Goren Chem. Phys. Lipids 41 1986 225 235
42. R. Toubiana, B.C. Das, J. Defaye, B. Mompon, and M.-J. Toubiana Carbohydr. Res. 44 1975 308 312
43. D. Johnson Carbohydr. Res. 237 1992 313 318
44. D.A. Johnson, and M.T. Livesay J. Carbohydr. Chem. 17 1998 969 974
45. A.K. Datta, K. Takayama, M.A. Nashed, and L. Anderson Carbohydr. Res. 218 1991 95 109
46. F.J. Plou, M.A. Cruces, M. Ferrer, G. Fuentes, E. Pastor, M. Bernabé, M. Christensen, F. Comelles, J.L. Parra, and A. Ballesteros J. Biotechnol. 96 2002 55 66
47. F.J. Plou, M.A. Cruces, E. Pastor, M. Ferrer, M. Bernabé, and A. Ballesteros Biotechnol. Lett. 21 1999 635 639
48. W. Tsuzuki, Y. Kitamura, T. Suzuki, and S. Kobayashi Biotechnol. Bioeng. 64 1999 267 271
49. M.W. Oosterom, F. Rantwijk, and R.A. Sheldon Biotechnol. Bioeng. 49 1996 328 333
50. O. Park, D. Kim, and J.S. Dordick Biotechnol. Bioeng. 70 2000 209 216
51. J. Chen, Y. Kimura, and S. Adachi J. Biosci. Bioeng. 100 2005 274 279
52. M. Kitagawa, P. Chalermisrachai, H. Fan, and Y. Tokiwa Macromol. Symp. 144 1999 247 256
53. T. Raku, M. Kitagawa, H. Shimakawa, and Y. Tokiwa J. Biotechnol. 100 2003 203 208
54. V.A. Sarpe, and S.S. Kulkarni J. Org. Chem. 76 2011 6866 6870
55. U. Pässler, M. Gruner, S. Penkov, T.V. Kurzchalia, and H.-J. Knölker Synlett 2011 2482 2486
56. F. Ishii, S. Takano, H. Kohya, and N. Ishida Gan To Kagaku Ryoho 11 1984 1629 1634
57. H. Kohya, F. Ishii, S. Takano, T. Katori, T. Ebina, and N. Ishida Gan To Kagaku Ryoho 13 1986 1897 1904
58. H. Kohya, F. Ishii, S. Takano, T. Katori, T. Ebina, and N. Ishida Jpn. J. Cancer Res. 77 1986 602 609
59. C.A. McLaughlin, E.E. Ribi, M.B. Goren, and R. Toubiana Natl. Inst. Allergy Infect. Dis. 4 1978 109 113
60. J. Davidsen, I. Rosenkrands, D. Christensen, A. Vangala, D. Kirby, Y. Perrie, E.M. Agger, and P. Andersen Biochim. Biophys. 1718 2005 22 31
61. L. Holten-Andersen, T.M. Doherty, K.S. Korsholm, and P. Andersen Infect. Immun. 72 2004 1608 1617
62. M. Henriksen-Lacey, A. Devitt, and Y. Perrie J. Controlled Release 154 2011 131 137
63. A. Laszlo, H.H. Baer, M.B. Goren, V. Handzel, and F. Papa Res. Microbiol. 145 1994 563 572
64. G. Puzo, G. Tissié, H. Aurelle, C. Lacave, and J.-C. Prome Eur. J. Biochem. 98 1979 99 105
65. M. Senn, T. Ioneda, J. Pudles, and E. Lederer Eur. J. Biochem. 1 1967 353 356
66. A.K. Datta, and K. Takayama Carbohydr. Res. 245 1993 151 158
67. A. Liav, and M.B. Goren Carbohydr. Res. 81 1980 C1 C3
68. A. Liav, B.C. Das, and M.B. Goren Carbohydr. Res. 94 1981 230 235
69. A. Liav, and M.B. Goren Carbohydr. Res. 125 1984 323 328
70. A. Liav, H.M. Flowers, and M.B. Goren Carbohydr. Res. 133 1984 53 58
71. A. Liav, and M.B. Goren Carbohydr. Res. 129 1984 121 129
72. A. Liav, and M.B. Goren Carbohydr. Res. 155 1986 229 235
73. J. Polonsky, and E. Lederer Bull. Soc. Chim. Fr. 1954 504 510
74. H.C. Huang, J.K. Rehmann, and G.R. Gray J. Org. Chem. 47 1982 4018 4023
75. Y. Kitano, Y. Kobayashi, and F. Sato J. Chem. Soc., Chem. Commun. 1985 498 499
76. M. Utaka, H. Higashi, and A. Takeda J. Chem. Soc., Chem. Commun. 1987 1368 1369
77. M. Nishizawa, R. Minagawa, D.M. Garcia, S. Hatakeyama, and H. Yamada Tetrahedron Lett. 35 1994 5891 5894
78. M. Nishizawa, D.M. Garcia, R. Minagawa, Y. Noguchi, H. Imagawa, H. Yamada, R. Watanabe, Y.C. Yoo, and I. Azuma Synlett 1996 452 454
79. M. Nishizawa, H. Yamamoto, H. Imagawa, V. Barbier-Chassefiére, E. Petit, I. Azuma, and D. Papy-Garcia J. Org. Chem. 72 2007 1627 1633
80. E. Yarkoni, H.J. Rapp, J. Polonsky, J. Varenne, and E. Lederer Infect. Immun. 26 1979 462 466
81. R. Ravindran, S. Bhowmick, A. Das, and N. Ali BMC Microbiol. 10 2010 181 191
82. A.-H. Hovav, Y. Fishman, and H. Bercovier Infect. Immun. 73 2005 250 257
83. M. Nishizawa, D.M. Garcia, R. Minagawa, Y. Noguchi, H. Imagawa, H. Yamada, R. Watanabe, Y.C. Yoo, and I. Azuma Synlett 1996 452 454
84. R. Watanabe, Y.C. Yoo, K. Hata, M. Mitobe, Y. Koike, M. Nishizawa, D.M. Garcia, Y. Nobuchi, H. Imagawa, H. Yamada, and I. Azuma Vaccine 17 1999 1484 1492
85. D.E. Minnikin, and N. Polgar Chem. Commun. 1966 648 649
86. D.E. Minnikin, and N. Polgar Tetrahedron Lett. 7 1966 2643 2647
87. M. Watanabe, Y. Aoyagi, M. Ridell, and D.E. Minnikin Microbiology 147 2001 1825 1837
88. M. Watanabe, Y. Aoyagi, H. Mitome, T. Fujita, H. Naoki, M. Ridell, and D.E. Minnikin Microbiology 148 2002 1881 1902
89. R.A. Al Dulayymi, M.S. Baird, and E. Roberts Chem. Commun. 2003 228 229
90. J.R. Al Dulayymi, M.S. Baird, and E. Roberts Tetrahedron 61 2005 11939 11951
91. J.R. Al Dulayymi, M.S. Baird, E. Roberts, and D.E. Minnikin Tetrahedron 62 2006 11867 11880
92. J.R. Al-Dulayymi, M.S. Baird, H. Mohammed, E. Roberts, and W. Clegg Tetrahedron 62 2006 4851 4862
93. J.R. Al Dulayymi, M.S. Baird, E. Roberts, M. Deysel, and J. Verschoor Tetrahedron 63 2007 2571 2592
94. G. Koza, C. Theunissen, J.R. Al Dulayymi, and M.S. Baird Tetrahedron 65 2009 10214 10229
95. D.Z. Al Kremawi, J.R. Al Dulayymi, and M.S. Baird Tetrahedron Lett. 51 2010 1698 1701
96. G. Toschi, and M.S. Baird Tetrahedron 62 2006 3221 3227
97. G. Koza, R. Rowles, C. Theunissen, J.R. Al-Dulayymi, and M.S. Baird Tetrahedron Lett. 50 2009 7259 7262
98. C. Driver, M.O. Balogun, G. Toschi, J.A. Verschoor, M.S. Baird, and L.A. Pilcher Tetrahedron Lett. 51 2010 1185 1186
99. J.R. Al Dulayymi, M.S. Baird, M. Maza-Iglesias, S.V. Beken, and J. Grooten Tetrahedron Lett. 50 2009 3702 3705
100. D. Seebach, and D. Wasmuth Helv. Chim. Acta 63 1980 197 200
101. G. Fráter, U. Muller, and W. Gunther Tetrahedron 40 1984 1269 1277
102. A.A. Khan, S.H. Chee, B.L. Stocker, and M.S.M. Timmer Eur. J. Org. Chem. 2012 995 1002
103. D. Grandjean, P. Pale, and J. Chuche Tetrahedron 47 1991 1215 1230
104. D. Nolibe, R. Masse, J.-P. Tenu, M. Lepoivre, and J.-F. Petit Cancer Immunol. Immunother. 23 1986 200 206
105. C.A. Mclaughlin, S.M. Strain, W.D. Bickel, M.B. Goren, I. Azuma, K. Milner, J.L. Cantrell, and E. Ribi Cancer Immunol. Immunother. 4 1978 61 68
106. E. Yarkoni, and A. Bekierkunst Infect. Immun. 14 1976 1125 1129
107. M. Parant, F. Parant, L. Chedid, J.C. Drapier, J.F. Petit, J. Wietzerbin, and E. Lederer J. Infect. Dis. 135 1977 771 777
108. H. Yamagami, T. Matsumoto, N. Fujiwara, T. Arakawa, K. Kaneda, I. Yano, and K. Kobayashi Infect. Immun. 69 2001 810 815
109. A. Bekierkunst J. Bacteriol. 96 1968 958 961
110. T.V. Guidry, R.L. Hunter Jr., and J.K. Actor Microbiology 153 2007 3360 3369
111. R.L. Hunter, M. Olsen, C. Jagannath, and J.K. Actor Am. J. Pathol. 168 2006 1249 1261
112. N. Saita, N. Fujiwara, I. Yano, K. Soejima, and K. Kobayashi Infect. Immun. 68 2000 5991 5997
113. J. Guiard, A. Collmann, M. Gilleron, L. Mori, G. De Libero, J. Prandi, and G. Puzo Angew. Chem., Int. Ed. 47 2008 9734 9738
114. J.M.H. Cheng, A.A. Khan, M.S.M. Timmer, and B.L. Stocker Int. J. Carbohydr. Chem. 2011 2011 13 Article ID 749591
115. E. Layre, D.C.-D. Paepe, G. Larrouy-Maumus, J. Vaubourgeix, S. Mundayoor, B. Lindner, G. Puzo, and M. Gilleron J. Lipid Res. 52 2011 1098 1110
116. H.H. Baer, and X. Wu Carbohydr. Res. 238 1993 215 230
117. L.F. Garcia-Alles, A. Collmann, C. Versluis, B. Lindner, J. Guiard, L. Maveyraud, E. Huc, J.S. Im, S. Sansano, T. Brando, S. Julien, J. Prandi, M. Gilleron, S.A. Porcelli, H. de la Salle, A.J.R. Heck, L. Mori, G. Puzo, L. Mourey, and G. De Libero Proc. Natl. Acad. Sci. 108 2011 17755 17760
118. J. Guiard, A. Collmann, L.F. Garcia-Alles, L. Mourey, T. Brando, L. Mori, M. Gilleron, J. Prandi, G. De Libero, and G. Puzo J. Immunol. 182 2009 7030 7037
119. R.J. Dubos, and G. Middlebrook Am. Rev. Tuberc. 58 1948 698 699
120. M.B. Goren, O. Brokl, B.C. Das, and E. Lederer Biochemistry 10 1971 72 81
121. J.D. Mougous, M.D. Leavell, R.H. Senaratne, C.D. Leigh, S.J. Williams, L.W. Riley, J.A. Leary, and C.R. Bertozzi Proc. Natl. Acad. Sci. 99 2002 17037 17042
122. T.D. Sirakova, A.K. Thirumala, V.S. Dubey, H. Sprecher, and P.E. Kolattukudy J. Biol. Chem. 276 2001 16833 16839
123. C. Rousseau, O.C. Turner, E. Rush, Y. Bordat, T.D. Sirakova, P.E. Kolattukudy, S. Ritter, I.M. Orme, B. Gicquel, and M. Jackson Infect. Immun. 71 2003 4684 4690
124. P. Domenech, M.B. Reed, C.S. Dowd, C. Manca, G. Kaplan, and C.E. Barry III J. Biol. Chem. 279 2004 21257 21265
125. S.E. Converse, J.D. Mougous, M.D. Leavell, J.A. Leary, C.R. Bertozzi, and J.S. Cox Proc. Natl. Acad. Sci. 100 2003 6121 6126
126. P. Kumar, M.W. Schelle, M. Jain, F.L. Lin, C.J. Petzold, M.D. Leavell, J.A. Leary, J.S. Cox, and C.R. Bertozzi Proc. Natl. Acad. Sci. 104 2007 11221 11226
127. J.C. Seeliger, C.M. Holsclaw, M.W. Schelle, Z. Botyanszki, S.A. Gilmore, S.E. Tully, M. Niederweis, B.F. Cravatt, J.A. Leary, and C.R. Bertozzi J. Biol. Chem. 2012 10.1074/jbc.M111315473
128. C.D. Leigh, and C.R. Bertozzi J. Org. Chem. 73 2008 1008 1017
129. E. Ade, G. Helmchen, and G. Heiligenmann Tetrahedron Lett. 21 1980 1137 1140
130. M.R. Pratt, C.D. Leigh, and C.R. Bertozzi Org. Lett. 5 2003 3185 3188
131. M.J. Hadd, and J. Gervay Carbohydr. Res. 320 1999 61 69
132. M.R. Pratt, C.D. Leigh, and C.R. Bertozzi Org. Lett. 5 2003 3185 3188
133. C.S. Barry, K.M. Backus, C.E. Barry III, and B.G. Davis J. Am. Chem. Soc. 133 2011 13232 13235
134. B. ter Horst, B.L. Feringa, and A.J. Minnaard Org. Lett. 9 2007 3013 3015
135. M.B. Goren, P.D. Hart, M.R. Young, and J.A. Armstrong Proc. Natl. Acad. Sci. 73 1976 2510 2514
136. M.J. Pabst, J.M. Gross, J.P. Brozna, and M.B. Goren J. Immunol. 140 1988 634 640
137. J.P. Brozna, M. Horan, J.M. Rademacher, K.M. Pabst, and M.J. Pabst Infect. Immun. 59 1991 2542 2548
138. L. Zhang, M.B. Goren, T.J. Holzer, and B.R. Andersen Infect. Immun. 56 1988 2876 2883
139. L. Zhang, D. English, and B.R. Andersen J. Immunol. 146 1991 2730 2736