Chemistry and biology of bile acids

Current Science

Volumn 87, Issue 12, 2004, Pages 1666-1683

  Mukhopadhyay, Samrat ^a,c   Maitra, Uday ^a,b  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

^c TATA INSTITUTE OF FUNDAMENTAL RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

VERTEBRATA;

EID: 22644439708     PISSN: 00113891     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (148)

1. Danielsson, H., In The Bile Acids: Chemistry, Physiology and Metabolism (eds Nair, P. P. and Kritchevsky, D.), Plenum Press, New York, 1973, vol. 2, pp. 1-32;
2. The Bile Acids: Chemistry, Physiology and Metabolism (eds Nair, P. P. and Kritchevsky, D.), Plenum Press, New York, 1971-73, vol. 1-3;
3. Hofmann, A. F., In Bile Acids and Hepatobiliary Disease (eds Northfield, T., Zentler-Munro, P. L. and Jazrawi, R. P.), Kluwer, Boston, 1999, pp. 303-332 and references therein;
4. Carey, M. C., In Phospholipids and Atherosclerosis (ed. Avogaro, P.), Raven Press, New York, 1983, pp. 33-63.
5. Hofmann, A. F., In The Liver: Biology and Pathology (eds Arias, I. M. et al.), Raven Press, New York, 1994, 3rd edn, p. 677;
6. Hofmann, A. F., News Physiol. Sci., 1999, 14, 24.
7. Nair, P. P. and Kritchevsky, D., In The Bile Acids: Chemistry, Physiology and Metabolism (eds Nair, P. P. and Kritchevsky, D.), Plenum Press, New York, 1971, vol. 1, pp. 1-9.
8. Thenard, L. J., Ann. Chim. (Paris), 1807, 64, 103;
9. Berzelius, J., Ann. Chim. (Paris), 1809, 71, 218;
10. Berzelius, J., Ann. Chim. (Paris), 1842, 43, 1;
11. Demarcay, H., Ann. Chim. (Paris), 1838, 27, 270.
12. Platner, E. A., Ann. Chim. (Paris), 1844, 51, 105;
13. Platner, E. A., J. Prakt. Chem. (I), 1846, 40, 129.
14. Strecker, A., Ann. Chim. (Paris), 1848, 67, 1;
15. Strecker, A., Ann. Chim. (Paris), 1849, 70, 149;
16. Mylius, F., Ber. Dtsch. Chem. Ges., 1886, 19, 374.
17. Wieland, H. and Sorage, H., Z. Physiol. Chem., 1916, 97, 1.
18. Wieland, H. and Weil, F. J., Z. Physiol. Chem., 1912, 80, 287;
19. Wieland, H. and Kapitel, W. Z., Physiol. Chem., 1933, 212, 269;
20. Windaus, A., Arch. Pharm., 1908, 246, 117;
21. Windaus, A. and Neukirchen, K., Ber. Dtsch. Chem. Ges., 1919, 52, 1918.
22. Hofmann, A. F., In Trends in Hepatology (eds Bianchi, L., Geork, W. and Popper, H.), MTP Press, Lancaster, 1985, pp. 3-27 and references therein.
23. Haslewood, G. A. D., Biol. Rev., 1964, 39, 537;
24. Haslewood, G. A. D., The Biological Importance of Bile Salts, North Holland Publishing Co, Amsterdam, 1978.
25. Russell, D. W., Annu. Rev. Biochem., 2003, 72, 137 and references therein.
26. SciFinder search using key words: 'chemical synthesis' + 'bile acid'. After submission of the manuscript, we came across the first total synthesis of chenodeoxycholic acid using an intramolecular cycloaddition reaction in a key step: Kametani, T., Suzuki, K. and Nemoto, H., J. Am. Chem. Soc., 1981, 103, 2890.
27. Chakravarti, D., Chakravarti, R. N. and Mitra, M. N., Nature, 1962, 193, 1071;
28. Mitra, M. N. and Elliott, W. H., J. Org. Chem., 1969, 34, 2170.
29. Kallner, A., Acta Chem. Scand., 1967, 21, 322;
30. Iida, T., Tamura, T., Matsumoto, T. and Chang, F. C., J. Lipid Res., 1985, 26, 874;
31. Iida, T., Momose, T., Nambara, T. and Chang, F. C., Chem. Pharm. Bull., 1986, 34, 1929;
32. Iida, T., Nishida, S., Chang, F. C., Niwa, T., Goto, J. and Nambara, T., Steroids, 1993, 58, 148.
33. Kakiyama, G. et al., J. Lipid Res., 2004, 45, 567;
34. Iida, T. et al., Chem. Pharm. Bull., 2002, 50, 1327;
35. Iida, T., Nambara, T. and Chang, F. C., S Falk Symp., 1995, 80, 8.
36. Iida, T., Yamaguchi, T., Nakamori, R., Hikisaka, M., Mano, N., Goto, J. and Nambara, T., J. Chem. Soc., Perkin Trans. 1, 2001, 2229.
37. Hagey, L. R., Schteingart, C. D., Ton-Nu, H-T. and Hofmann, A. F., J. Lipid. Res., 2002, 43, 685 and references therein.
38. Mukhopadhyay, S. and Maitra, U., Org. Lett., 2004, 6, 31.
39. Gallo-Torres, H. E., Lipids, 1970, 5, 379.
40. Wang, X., Wang, C. S., Tang, J., Dyda, F. and Zhang, X. C., Structure, 1997, 5, 1209.
41. Russell, D. W., Cell, 1997, 539, 1999;
42. Parks, D. J., Blanchard, S. G. and Bledsoe, R. K., Science, 1999, 284, 1365;
43. Makishima, M., Okamoto, A. Y. and Repa, J. J., Science, 1999, 284, 1362.
44. A useful site on bile acids: http://arbl.cvmbs.colostate.edu/hbooks/ pathphys/digestion/liver/
45. Nigro, N. D. and Campbell, R. L., In The Bile Acids: Chemistry, Physiology and Metabolism (eds Nair, P. P. and Kritchevsky, D.), Plenum Press, New York, 1976, vol. 3, pp. 155-168.
46. Cook, J. W., Kennaway, E. L. and Kennaway, N. M., Nature, 1940, 145, 627;
47. Hill, M. J., Drasar, B. S., Aries, V., Crowther, J. S., Hawksworth, G. and Williiams, R. E. O., Lancet, 1971, 1, 95.
48. Owen, R. W., J. Gastroenterol. Suppl., 1997, 222, 76;
49. Debruyne, P. R., Bruyneel, E. A., Li, X., Zimber, A., Gespach, C. and Marcel, M. M., Mutat. Res., 2001, 480-481, 359.
50. Small, D. M., Gastroenterology, 1966, 52, 607.
51. Bachrach, W. H. and Hofmann, A. F., Dig. Dis. Sci., 1982, 27, 737 and 833;
52. Hofmann, A. F., Ital. J. Gastroenterol., 1995, 27, 106.
53. Araki, Y.-I., Lee, A., Sugihara, G., Furuichi, M., Yamashita, S. and Ohseto, F., Colloids Surf. B, 1996, 8, 81;
54. Reid, D. G. et al., Chem. Phys. Lipids, 1991, 60, 143;
55. Fears, R., Brown, R., Ferres, H., Grenier, F. and Tyrrell, A. W., Biochem. Pharmacol., 1990, 40, 2029;
56. Anwer, M. S., O'maille, E. R. L., Hofmann, A. F., DiPietro, R. A. and Michelotti, E., Am. J. Physiol., 1985, 249, G479;
57. Borgstrom, B., Biochim. Biophys. Acta, 1977, 488, 381;
58. Firpi, A., Walker, J. T. and Lack, L., J. Lipid Res., 1975, 16, 379.
59. Fini, A., Fazio, A., Roda, A., Bellini, A. M., Mencini, E. and Guarneri, M., J. Pharm. Sci., 1992, 81, 726.
60. Bernheim, F. and Lack, L., J. Med. Chem., 1967, 10, 1096.
61. Berlati, F., Ceschel, G., Clerici, C., Pellicciari, R., Roda, A. and Ronchi, C., WO 9400126, 1994.
62. Marples, B. A. and Stretton, R. J., WO 9013298, 1990.
63. Kwan, K. H., Higuchi, W. I., Molokhia, A. M. and Hofmann, A. F., J. Pharm. Sci., 1977, 66, 1105.
64. Berlati, F., Ceschel, G., Roda, A., Roda, E. and Ronchi, C., WO 9400155, 1994.
65. Walker, S. et al., Proc. Natl. Acad. Sci. USA, 1996, 93, 1585;
66. Walker, S., Sofia, M. J. and Axelrod, H. R., Adv. Drug Delivery Rev., 1998, 30, 61.
67. Geall, A. J., Al-Hadithi, D. and Blagbrough, I. S., Bioconjugate Chem., 2002, 13, 481.
68. Tamminen, J. and Kolehmainen, E., Molecules, 2001, 6, 21;
69. Enhsen, A., Kramer, W. and Wess, G., Drug Discovery Today 1998, 3, 409.
70. Small, D. M., In The Bile Acids: Chemistry, Physiology and Metabolism (eds Nair, P. P. and Kritchevsky, D.), Plenum Press, New York, 1971, vol. 1, pp. 249-356;
71. Small, D. M., Adv. Chem. Ser., 1968, 84, 31;
72. Kratohvil, J. P., Adv. Colloid Interface Sci., 1986, 26, 131;
73. Mazer, N. A., Carey, M. C., Kwasnick, R. F. and Benedek, G. B., Biochemistry, 1979, 18, 3064;
74. Paul, R., Mathew, M. K., Narayanan, R. and Balaram, P., Chem. Phys. Lipid, 1979, 25, 345;
75. Carey, M. C., In Sterols and Bile Acids (eds Danielsson, H. and Sjövall, J.), Elsevier, 1985, pp. 354-425;
76. Esposito, G., Giglio, E., Pavel, N. V. and Zanobi, A., J. Phys. Chem., 1987, 91, 356;
77. Lopez, F., Samseth, J., Mortensen, K., Rosenqvist, E. and Rouch, J., Langmuir, 1996, 12, 6188;
78. Hjelm, R. P., Schteingert, C. D., Hofman, A. F. and Thiagrajan, P., J. Phys. Chem. B, 2000, 104, 197;
79. Coello, A., Meijide, F., Rodríguez Núñez, E. and Vázquez Tato, J., J. Pharm. Sci., 1996, 85, 9 and references therein.
80. Rich, A. and Blow, D. M., Nature, 1958, 182, 423;
81. Blow, D. M. and Rich, A., J. Am. Chem. Soc., 1960, 82, 3566;
82. Igimi, H. and Carey, M., J. Lipid. Res., 1980, 21, 72;
83. Terech, P., Smith, W. G. and Weiss, R. G., J. Chem. Soc. Faraday Trans., 1996, 92, 3157.
84. Phillies, G. D. J., J. Phys. Chem., 1981, 85, 3540;
85. Phillies, G. D. J., J. Colloid Interface Sci., 1982, 86, 226.
86. Mukhopadhyay, S., Ira, Krishnamoorthy, G. and Maitra, U., J. Phys. Chem. B, 2003, 107, 2189.
87. For a discussion on the models, see Maiti, N. C., Krishna, M. M. G., Britto, P. J. and Periasamy, N., J. Phys. Chem. B, 1997, 101, 11051 and references therein;
88. For time-resolved fluorescence anisotropy, see Lakowicz, J. R., In Principles of Fluorescence Spectroscopy, Plenum Press, New York, 1999.
89. Mukhopadhyay, S., Ph D thesis, Indian Institute of Science, Bangalore, India, 2004.
90. Chakrabarty, D., Hazra, P. and Sarkar, N., J. Phys. Chem. A, 2003, 107, 5887;
91. Chakrabarty, D., Hazra, P., Chakraborty, A. and Sarkar, N., J. Phys. Chem. B, 2003, 107, 13643.
92. Sen, S., Dutta, P., Mukherjee, S. and Bhattacharyya, K., J. Phys. Chem. B, 2002, 106, 7745.
93. Jimenez, R., Fleming, G. R., Kumar, P. V. and Maroncelli, M., Nature, 1994, 369, 471;
94. Nandi, N., Bhattacharyya, K. and Bagchi, B., Chem. Rev., 2000, 100, 2013;
95. Bhattacharyya, K., Acc. Chem. Res., 2003, 36, 95.
96. Koti, A. S. R., Krishna, M. M. G. and Periasamy, N., J. Phys. Chem. A, 2001, 105, 1767;
97. Ira, Koti, A. S. R., Krishnamoorthy, G. and Periasamy, N., J. Fluorescence, 2003, 13, 95;
98. Maciejewski, A., Kubicki, J. and Dobek, K., J. Phys. Chem. B, 2003, 107, 13986.
99. Sen, S., Dutta, P., Mukherjee, S. and Bhattacharyya, K., Phys. Chem. B, 2002, 106, 7745.
100. Carey, M. C. and Small, D. M., Am. J. Med., 1970, 49, 590.
101. Ueno, M., In Structure-Performance Relationships in Surfactants (eds Esumi, K. and Ueno, M.), Marcel and Dekker, New York, 1st edn, 1997, 147;
102. Wiedmann, T. S. and Kamel, L., J. Pharm. Sci., 2002, 91, 1743 and references therein.
103. Yuexian, L. and Dias, J. R., Chem. Rev., 1997, 97, 283;
104. Davis, A. P., Chem. Soc. Rev., 1993, 243.
105. Cobbledick, R. E. and Einstein, F. W. B., Acta Crystallogr., Sect. B, Struct. Crystallogr. Chem., 1980, 36, 287;
106. Miyata, M. and Sada, K., Comparative Supramolecular Chemistry (eds MacNicol, D. D., Toda, F. and Bishop, R.), Elsevier, Oxford. 1996, vol. 6, p. 147 and references therein.
107. McKenna, J., McKenna, J. M. and Thornthwaite, D. W., J. Chem. Soc., Chem. Commun., 1977, 809.
108. Hsieh, H.-P., Muller, J. G. and Burrows, C. S., J. Am. Chem. Soc., 1994, 116, 12077;
109. Kinneary, J. F., Roy, T. M., Albert, J. S., Yoon, H., Wagler, T. R., Shen, L. and Burrows, C. J., J. Inclusion Phenom. Mol. Recognit. Chem., 1989, 7, 155.
110. Aoyama, Y., Tanaka, Y. and Sugahara, S., J. Am. Chem. Soc., 1989, 111, 5397;
111. Tanaka, Y., Ubukata, Y. and Aoyama, Y., Chem. Lett., 1989, 1905;
112. Bonar-Law, R. P., Davis, A. P. and Murray, B. A., Angew. Chem., Int. Ed. Engl., 1990, 29, 1407;
113. Bhattarai, K. M., Bonar-Law, R. P., Davis, A. P. and Murray, B. A., J. Chem. Soc., Chem. Commun., 1992, 752.
114. Bhattarai, K. M., Davis, A. P., Perry, J. J. and Walter, C. J., J. Org. Chem., 1997, 62, 8463.
115. Davis, A. P., Perry, J. J. and Williams, R. P., J. Am. Chem. Soc., 1997, 119, 1793.
116. Davis, A. P., Menzer, S., Walsh, J. J. and Williams, D. J., Chem. Commun., 1996, 453.
117. Kohmoto, S., Fukui, D., Nagashima, T., Kishikawa, K., Yamamoto, M. and Yamada, K., Chem. Commun., 1996, 1869.
118. Bonar-Law, R. P. and Sanders, J. K. M., Tetrahedron Lett., 1992, 33, 2071.
119. Bonar-Law, R. P., Sanders, J. K. M., J. Am. Chem. Soc., 1995, 117, 259;
120. Bonar-Law, R. P. and Sanders, J. K. M., J. Chem. Soc., Chem. Commun., 1991, 574.
121. Bonar-Law, R. P., Mackay, L. G., Sanders, J. K. M., 1993, 456;
122. Mackay, L. G., Bonar-Law, R. P. and Sanders, J. K. M., J. Chem. Soc., Perkin Trans. 1, 1993, 1377.
123. Yoshino, N., Satake, A. and Kobuke, Y., Angew. Chem., Int. Ed. Engl., 2001, 40, 457.
124. Shawphun, S., Janout, V. and Regen, S. L., J. Am. Chem. Soc., 1999, 121, 5860;
125. Janout, V., Di Giorgio, C. and Regen, S. L., J. Am. Chem. Soc., 2000, 122, 2671;
126. Janout, V., Jing, B. and Regen, S. L., Bioconjugate Chem., 2002, 13, 351.
127. Maitra, U. and Balasubramanian, S., J. Chem. Soc., Perkin Trans. 1, 1995, 83.
128. Rao, P. and Maitra, U., Supramol. Chem., 1998, 9, 325.
129. Balasubramanian, R., Rao, P. and Maitra, U., Chem. Commun., 1999, 2353;
130. Balasubramanian, R., Rao, P. and Maitra, U., J. Org. Chem., 2001, 66, 3035.
131. Maitra, U., D'Souza, L. J. and Vijay Kumar, P., Supramol. Chem., 1998, 10, 97;
132. Maitra, U. and Bag, B. G., J. Org. Chem., 1994, 59, 6114.
133. Maitra, U. and D'Souza, L. J., J. Chem. Soc., Chem. Commun., 1994, 2793;
134. Maitra, U. and D'Souza, L. J., J. Org. Chem., 1996, 61, 9494.
135. Ropponen, J., Tamminen, J., Kolehmainen, E. and Rissanen, K., Synthesis, 2003, 2226.
136. Hishikawa, Y., Sada, K., Watanabe, R., Miyata, M. and Hanabusa, K., Chem. Lett., 1998, 795.
137. Maitra, U., Vijay Kumar, P., Chandra, N., D'Souza, L. J., Prasanna, M. D. and Raju, A. R., Chem. Commun., 1999, 595.
138. Willemen, H. M., Vermonden, T., Marcelis, A. T. M. and Sudhölter, E. J. R., Eur. J. Org. Chem., 2001, 2329.
139. Schryver, S. B., R. Soc. Proc. B, 1914, 87, 366;
140. Schryver, S. B., R. Soc. Proc. B, 1916, 89, 176;
141. Schryver, S. B., Roy. Soc. Proc. B, 1916, 89, 361;
142. Sobotka, H. and Czeczowiczka, N., J. Colloid Sci., 1958, 13, 188.
143. Bhattacharya, S., Maitra, U., Mukhopadhyay, S. and Srivastava, A., In Molecular Gels (eds Terech, P. and Wiess, R. G.), Kluwer, The Netherlands, 2004.
144. Maitra, U., Mukhopadhyay, S., Sarkar, A., Rao, P. and Indi, S. S., Angew. Chem., Int. Ed. Engl., 2001, 40, 2281;
145. Mukhopadhyay, S., Maitra, U., Ira Krishnamoorthy, G., Schmidt, J. and Talmon, Y., J. Am. Chem. Soc., 2004, 126, 15905.
146. Gundiah, G., Mukhopadhyay, S., Tumkurkar, U. G., Govindaraj, A., Maitra, U. and Rao, C. N. R., J. Mater. Chem., 2003, 13, 2118.
147. Sangeetha, N. M., Balasubramanian, R., Maitra, U., Ghosh, S. and Raju, A. R., Langmuir, 2002, 18, 7154; Unpublished results from our laboratory.
148. Maitra, U. and Babu, P., Steroids, 2003, 68, 459.