Intracellular thiol concentration modulating inflammatory response: Influence on the regulation of cell functions through cysteine prodrug approach

Current Medicinal Chemistry

Volumn 10, Issue 23, 2003, Pages 2599-2610

  Santangelo, Francesco ^a,b  

^a Zambon Group SpA   (Italy)

^b NONE   (Italy)

Author keywords

Acute phase proteins; Cysteine; Glutathione; Inflammation; N acetylcysteine; Oxidative stress; Thiol

Indexed keywords

ACETYLCYSTEINE; ACUTE PHASE PROTEIN; ALLOXAN; AMINE; ANTIOXIDANT; CARBOXYL GROUP; CERULETIDE; CONTRAST MEDIUM; CYCLOPHOSPHAMIDE; CYSTEAMINE DERIVATIVE; CYSTEINE; CYSTEINE DERIVATIVE; CYTOKINE; DOXORUBICIN; ESTER DERIVATIVE; GLUTATHIONE; GLUTATHIONE DERIVATIVE; I 152; IFOSFAMIDE; LIPOPOLYSACCHARIDE; MUCOLYTIC AGENT; PARACETAMOL; PLACEBO; PRODRUG; REACTIVE OXYGEN METABOLITE; SCAVENGER; SULFUR AMINO ACID; THIAZOLIDINE DERIVATIVE; THIOL; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIOXIDANT ACTIVITY; BIOCHEMISTRY; BIOSYNTHESIS; CELL CYCLE; CELL FUNCTION; CELL LEVEL; CELL PROTECTION; CHRONIC INFLAMMATION; CIRCULATION; CLINICAL TRIAL; CYTOKINE PRODUCTION; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG EFFICACY; DRUG STRUCTURE; GLUTATHIONE METABOLISM; HEMORRHAGIC CYSTITIS; HOMEOSTASIS; HUMAN; IMMUNOMODULATION; IMMUNOREACTIVITY; INFLAMMATION; KIDNEY INJURY; LIVER TOXICITY; LOW DRUG DOSE; NONHUMAN; OXIDATION; OXIDATION REDUCTION STATE; OXIDATIVE STRESS; PROTEIN MODIFICATION; REGULATORY MECHANISM; REVIEW; TISSUE INJURY;

ACETYLCYSTEINE; ACUTE-PHASE PROTEINS; ANIMALS; CELL CYCLE; CYSTEINE; CYTOKINES; GLUTATHIONE; HUMANS; INFLAMMATION; PRODRUGS; SULFHYDRYL COMPOUNDS; THIAZOLES;

EID: 0344393020     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867033456567     Document Type: Review

References (157)

1. Griffith, O.W.; Mulcahy, R.T. Adv. Enzymol. Relat. Areas Mol. Biol., 1999, 73, 209
2. Griffith, O.W. Free Radic. Biol. Med., 1999, 27, 922
3. Reid, M.; Jahoor, F. Curr. Opin. Clin. Nutr. Metab. Care, 2001, 4, 65.
4. Burgunder, J.; Lauterburg, B. Eur. J. Clin. Invest., 1987, 17, 408.
5. Griffith, O.W., Meister, A. Proc. Natl. Acad. Sci. USA, 1979, 76, 5606.
6. Blokhina, O.; Virolainen, E.; Fagerstedt, K.V. Ann. Bot. (Lond.) 2003, 91, 179
7. Droge, W. Physiol. Rev., 2002, 82, 47.
8. Meister, A.; Anderson, M.E. Ann. Rev. Biochem., 1983, 52, 711.
9. Doelman, C.J.; Bast, A. Free Radic. Biol. Med., 1990, 9, 381.
10. Meister, A. Methods Enzymol., 1995, 251, 3.
11. Deneke, S.M.; Fanburg, B.L. Am. J. Physiol., 1989, 257, L163.
12. Meister, A. Methods Enzymol., 1995, 251, 3.
13. Deas, O.; Dumont, C.; Molleraus, B.; Metivier, D.; Pasquier, C.; Bernard-Pomier, G.; Hirsch, F.; Charpentier, B.; Senik, A. Int. Immunol., 1997, 9, 117.
14. Kirscherf, R.; Fischbach, T.; Mihm, S.; Roth, S.; Hohenhaus-Sievert, E.; Weiss, C.; Edler, L.; Bartsch, P.; Droge, W. Faseb J., 1994, 8, 448.
15. Droge, W.; Breitkreutz, R. Proc. Nutr. Soc., 2000, 59, 595.
16. Hunter, E.A.; Grimble, R.F. J. Nutr., 1994, 124, 2319.
17. Zimmerman, R.J.; Marafino, Jr, B.J.; Chan, A.; Landre, P.; Winkelhake, J.L. J. Immunol., 1989, 142, 1405.
18. Peristeris, P.; Clark, B.; Gatti, S.; Faggioni, R.; Mantovani, A.; Mengozzi, M.; Orencole, S.F.; Sironi, M.; Ghezzi, P. Cell Immunol., 1992, 140, 390.
19. Hunter, E.A.; Grimble, R.F. Clin. Sci (Lond.), 1997, 92, 297.
20. Zafarullah, M.; Li, W.Q.; Sylvetser, J.; Ahmad, M. Cell Mol. Life Sci., 2003, 60, 6
21. Patch, E.R.; Timerman, A.P.; Lykens, M.G.; Merola, A.J. Chest, 1996, 100, 1397.
22. Forrester, T.E.; Badaloo, V.; Bennett, F.J.; Jackson, A.A. Eur. J. Clin. Nutr., 1990, 44, 847.
23. Altomare, E.; Vendemiale, G.; Albano, O. Life Sci., 1988, 43, 991.
24. Bernard, G.R.; Wheeler, A.P.; Arons, M.M.; Morris, P.E.; Paz, H.I.; Russell, J.A. Chest, 1997, 112, 164.
25. Harding, J.J. Biochem. J., 1970, 117, 957.
26. Ross, E.A.; Koo, L.C.; Moberly, J.B. Am. J. Kidney Dis., 1997, 30, 489.
27. Buhl, R.; Jaffe, H.A.; Holroyd, K.J.; Wells, F.B.; Mastrongeli, A.; Saltini, C.; Cantin, A.,M.; Crystal, R.G. Lancet, 1989, 2, 1294.
28. Jahoor, F.; Jackson, A.; Gazzard, B.; Philips, G.; Sharpstone, D.; Frazer, M.; Heird, W. Am. J. Physiol., 1999, 276, E205.
29. Lang, C.A.; Mills, B.J.; Mastropaolo, W.; Liu, M.C. J. Lab. Clin. Med., 2000, 135, 402.
30. Rahman, Q.; Abidi, P.; Afaq, F.; Schiffmann, D.; Mossman, B.T.; Kamp, D.W.; Athar, M. Crit. Rev. Toxicol., 1999, 29, 543.
31. Rahman, I.; MacNee, W. Eur. Respir. J., 2000, 16, 534.
32. Himmelfarb, J.; Stenvinkel, P.; Ikizler, T.A.; Hakim, R.M. Kidney Int., 2002, 62, 1524.
33. Foley, R.; Parfrey, P.S.; Sarnak, M.J. Am. J Kidney Dis., 1998, 32S, S112.
34. Ceballos-Picot, A.; Witko-Sarsat, V.; Merad-Boudia, M.; Nguyen, A.; Thévenin, M.; Jaudon, M.; Zingraff, J.; Verger, C.; Jungers, P.; Descamps-Latscha, B. Free Radic. Biol. Med., 1996, 21, 845.
35. Himmelfarb, J.; McMenamin, E.; McMonagle, E. Kidney Int., 2002, 61, 705.
36. Cho, E.S.; Sahyoun, N.; Stegin, L.D. J. Nutr., 1980, 111, 914.
37. Luo, J.L.; Hammarqvist, F.; Andersson, K.; Wernerman, J. Ann. Surg., 1996, 223, 420.
38. Hammarqvist, F.; Luo, J.; Cotgraeve, I.; Andersson, K.; Wernerman, J. Crit. Care Med, 1997, 25, 78.
39. Wernerman, J.; Hammarqvist, F. Curr. Opin. Clin. Nutr. Met. Care, 1999, 2, 487.
40. Lyons, J.; Rauh-Pfeiffer, A.; Ming-Yu, Y.; Lu, X.M.; Zurakowski, D.; Curley, M.; Collier, S.; Duggan, C.; Nurko, S.; Thompson, J.; Ajami, A.; Borgonha, S.; Young, V.R.; Castillo, L. Crit. Care Med., 2001, 29, 870.
41. Engelen, M.P.; Schols, A.M.; Does, J.D.; Deutz, N.E.; Wouters, E.F. Am. J. Respir. Crit. Care Med., 2000, 161, 98.
42. Cantin, A.M.; North, S.L.; Hubbard, R.C.; Crystal, R.G. J. Appl. Physiol., 1987, 63, 152.
43. Jenkinson, S.; Black, R.; Lawrence, R. J. Lab. Clin. Med., 1988, 112, 345.
44. Martensson, J.; Larsson, J.; Nordstrom, H. Eur. J. Clin. Invest., 1987, 17, 130.
45. Hack, V.; Breitkreutz, R.; Kinscherf, R.; Roher, H.; Bartsch, P.; Taut, F.; Benner, A.; Droge, W. Blood, 1998, 92, 59.
46. Droge, W.; Breitkreutz, R. Curr. Opin. Clin. Nutr. Met. Care, 19999, 2, 493.
47. Tager, M.; Dietzmann, J.; Thiel, U.; Neumann, K.; Ansorge, S. Free Radic. Res., 2001, 34, 137.
48. Tager, M.; Piecyk, A.; Kohnlein, T.; Thiel, U.; Ansorge, S.; Welte, T. Free Radic. Biol. Med., 2000, 29, 1160.
49. Cuthberson, D.P.Q. J. Med., 1932, 1, 233.
50. Grossman, C.M.; Sappington, T.S.; Burrow, B.A.; Lavietes, P.H.; Peters, T.P. J. Clin. Invest., 1945, 24, 523.
51. Geigin, R.D.; Klainer, A.S.; Beisel, W.R.; Hornick, R.B. N. Engl. J. Med., 1968, 278, 293.
52. Cuthberson, D.P; Tompsett, S.L. Br. J. Exp. Pathol., 1935, 1, 471.
53. Askanazi, J.; Carpentier, Y.A.; Michelsen, C.B.; Elwyn, D.H.; Furst, P.; kantrowitz, L.R.; Gump, F.E.; Kinney, J.M. Ann. Surg., 1980, 192, 78.
54. Obled, C.; Papet, I.; Breuillé, D. Curr. Opin. Clin. Nutr. Metab. Care, 2002, 5, 189.
55. Reeds, P.J; Furst, P. Curr. Opin. Clin. Nutr. Met. Care, 2001, 4, 35.
56. Reeds, P.J. J. Nutr., 2000, 130, 1835S-1840S.
57. Baumann, H.; Gauldie, J. Immunol. Today, 1994, 15, 74.
58. Gabay, C.; Kushner, I. N. Engl. J. Med., 1999, 340, 448.
59. Colley, C.M.; Fleck, A.; Goode, A.W.; Muller, B.R.; Myers, B.R. J. Clin. Pathol., 1983, 36, 203.
60. Watrelow, J.C. Proc. Nutr. Soc. India, 1991, 37, 59.
61. Breitkreutz, R.; Wagner, J.; Tokus, M.; Benner, A.; Rossol, S.; Pittack, N.; Stein, J.; Droge, W.; Holm, E. J. Mol. Med., 2001, 76, 671.
62. Baldertorp, L.; Martensson, J. Acta Med. Scand., 1980, 208, 293.
63. Fimistrom, O.; Lundquist, P.; Martensson, J.; Sorbo, B. Metabolism, 1983, 32, 732.
64. Larsson, J.; St Liljedahl, S.O.; Martensson, J.; Nordstrom, H.; Shildt, B.; Sorbo, B. J. Trauma, 1982, 22, 656.
65. Grimble, R.F. New Horizons, 1994, 2, 175.
66. Breitkreutz, R.; Holm, S.; Pittack, N.; Beichert, M.; Babylon A.; Yodoi, J.; Droge, W. AIDS Res. Human Retroviruses, 2000, 16, 203
67. Cuthbertson, D.P. Biochemical J., 1931, 25, 236.
68. Timbrell, J.; Sebra V.; Waterfield, C. Gen. Pharmacol., 1995, 26, 453.
69. Malmezat, T.; Breuillé, D.; Pouyet, C.; Mirand, P.; Obled, C. J. Nutr., 1998, 128, 97.
70. Breuillé, D.; Arnal, M.; Rambourdin, F.; Rosé, F.; Obled, C. Clin. Nutr., 1996, 15, 21 (Abs.).
71. Malmezat, T.; Breuillé, D.; Capitain, P.; Mirand, P.; Obled, C. J. Nutr., 2000, 130, 1239.
72. Hiramatsu, T.; Fukagawa, N.K.; Marchini, J.S. Am. J. Clin. Nutr., 1994, 60, 525.
73. Vina, J.; Gimenz, A.; Puertes, I.; Gasco, E.; Vina, J.R. Br. J. Nutr., 1992, 68, 421.
74. Vina, J.; Vento, M.; Garcia-Sala, F.; Purtes, I.; Gasco, E.; Sastre, J.; Asensi, M.; Pallardo, V. Am. J. Clin. Nutr., 1995, 61, 1067.
75. Martin, J.A.; Sastre, J.; Asuncion, J.G.; Pallardo, F.V.; Vina, J. JAMA, 2001, 285, 1444.
76. Malmezat, T.; Breuillé, D.; Pouyet, C.; Buffière, C.; Denis, P.; Mirand, P.P.; Obled, C. Am. J. Physiol. Endocrinol. Metab., 2000, 279, E1391.
77. De Bree, A.; Verschuren, W.M.M.; Kromhout, D.; Kluijtmans, L.A.J.; Blom, E.J. Pharm. Rev. 2002, 54, 599.
78. Wald, D.S.; Law, M.; Morris, J. K. BMJ 2002, 325, 1202
79. Grimble, R.F. Clin. Sci. (Lond), 1996, 91, 121.
80. Grimble, R.F. Nutr. Health, 1995, 10, 191.
81. Grimble, R.F.; Grimble, G.K. Nutrition, 1998, 14, 605.
82. Grimble, R.F. Nutr. Res., 1998, 18, 1297.
83. Grimble, R.F. Proc. Nutr. Soc., 2001, 60, 389
84. Taylor, C.G.; Nagy, L.E.; Bray, T.M. In Current Topics in Cellular Regulation; Academic Press Inc.: New York, 1996; Vol. 34, pp. 189-208.
85. Chawla, R.K.; Berry, C.J.; Kutner, M.H. Am. J. Ciln. Nutr., 1985, 42, 577.
86. Anderson, M.E.; Meister, A. In Methods in Enzymology; Jakoby, W.B.; Griffith, O.W., Ed.; Academic Press, Inc.: New York, 1987, Vol. 143, pp. 313-325.
87. Bonanomi, L.; Gazzaniga, A. Eur. J. Respir. Dis., 1980, Suppl. 111, 45.
88. Olsson, B.; Johansson, M.; Gabrielsson, J.; Bolme, P. Eur. J. Clin. Pharmacol., 1988, 34, 77.
89. Cotgreave, I.A.; Berggren, M.; Jones, T.W.; Dawson, J.; Moldeus, P. Biopharm. Drug Dispos., 1987, 8, 377.
90. Burgunder, J.M,; Varriale, A.; Lauterburg, B.H. Eur. J. Clin. Pharmacol., 1989, 36, 127.
91. Cotgreave, I.A.; Eklund, A.; Larsson, K.; Moldeus, P.W. Eur. J. Respir. Dis., 1987, 70, 73.
92. Yamauchi, A.; Ueda, N.; Hanafasura, S.; Yamashita, E.; Kihara, M.; Naito, S. J. Pharm. Pharmacol., 2002, 54, 205.
93. Uttamsingh, V.; Keller, D.A; Anders, M.W. Chem. Res. Toxicol., 1998, 11, 800.
94. Lauterburg, B.H, Corcoran, G.B.; Mitchell, J.R. J. Clin. Invest., 1983, 71, 980.
95. Aruoma, O.I.; Halliwell, B.; Hoey, B.M.; Butler, J. Free Radic. Biol. Med., 1989, 6, 593.
96. Cotgreave, I.A. In Antioxidant in Disease. Mechanism and Therapy, Advances in Pharmacology; Sies, H., Ed.; Academic Press Inc.: S. Diego, CA, 1997; Vol. 38, pp. 205-227.
97. Ventresca, G.P.; Cicchetti, V.; Ferrari, V. In Drugs in Bronchial Mucology; Braga and Allegra Ed.; Raven Press Ltd.: New York, 1989, pp.77-102.
98. Kim, H.; Seo, J.Y.; Roh, K.H.; Lim, J.W.; Kim, K.H. Free Radic. Biol. Med., 2000, 29, 674.
99. Blackwell, T.; Holden, E.; Christman B.; Christman, J. J. Immunol., 1996, 157, 1630.
100. Ho, E.; Chen, G.; Bray, T.M. FASEB J., 1999, 13, 1845.
101. Gukovsky, I.; Gukovskaya, A.; Blinman, T.; Zaninovic, V.; Pandol, S. Am. J. Physiol., 1998, 275, G1402-G1414.
102. Rangan, G.; Wang, Y.; Tay, Y.; Harris, D. Kidney Int., 1999, 56, 118-134.
103. Hayashi, K.; Takahata, H.; Kitagawa, N.; Kitange, G.; Kaminogo, M.; Shibata, S. Neurol. Res., 2001, 23, 731.
104. Khachigian, L.M.; Collins, T.; Fries, J.W.U. Am. J. Pathol. 1997, 151, 1225
105. Rota, C.; Bergamini, S.; Daneri, F.; Tomasi, A.; Virgili, F.; Iannone, A. Antioxid. Redox Signal 2002, 4, 221.
106. Millar, A.; Pavia, D.; Agnew, J.E.; Lopez-Vidriero, M.T.; Lauque, D.; Clarke, W. Br. J. Dis. Chest, 1985, 79, 262.
107. Webb, W.R. J. Thorac. Cardiovasc. Surg., 1962, 44, 330.
108. Multicenter Study Group Eur. J. Respir. Dis., 1980, 61, Suppl.111, 93.
109. Prescott, L.F.; Park, J.; Ballantyne, A.; Adriaenssens, P.; Proudfoot, A.T. Lancet, 1977, 2, 432.
110. Grandjean, E.M.; Berthet, P.H., Ruffmann, R.; Leuenberger, P.H. Pharmacol. Res., 2000, 42, 39.
111. Stey, C.; Steurer, J.; Bachmann, S.; Medici, T.C.; Tramer, M.R. Eur. Respir. J., 2000, 16, 253.
112. Roederer, M.; Staal, F.; Ela, S.W., Herzenberg, L.A. Pharmacology, 1993, 46, 121.
113. Meyskens, F.L. J. Cell. Biochem., 2000, 77 (34S), 115.
114. Ortolani, O.; Conti, A.; De Gaudio, A.R.; Moraldi, E.; Cantini, Q.; Novelli, G. Am. J. Respir. Crit. Care Med., 2000, 161, 1907.
115. Horowitz, J.D. Am. J. Med., 1991, 91, 113S.
116. Yarbro, J.W. Semin. Oncol., 1983, (Suppl. 1), 10, 1.
117. Morgan, L.R.; Holdiness, M.R.; Gillen, L.E. Semin. Oncol., 1983, 10, 56.
118. Sajkowska, A.; Wykretowicz, A.; Szczepanik, S.; Kempa, M.; Minczykowski, A.; Wysocki, H. Cardiology, 1999, 91, 60.
119. Pizzulli, L.; Hagendorff A.; Zirbes, M.; Jung, W.; Luderitz, B. Am. J. Cardiol., 1997, 79, 28.
120. Shyu, K.G.; Cheng, J.J.; Kuan, P. J. Am. Coll. Cardiol., 2002, 40, 1383.
121. Tepel, M.; van der Giet, M.; Scwarzfeld, C.; Lautfer, U.; Liermann, D.; Zidek, W. N. Eng. J. Med., 2000, 343, 180.
122. Oiry, J.; Mialocq, P.; Puy, J.Y.; Fretier, P.; Clayette, P.; Dormont, D.; Imbach, J.L. Bioorg. Med. Chem Lett., 2001, 11, 1189.
123. Grattagliano, I.; Vendemiale, G.; Deiss, V.B.; Junket, E.; Lauterburg, B.H. J. Pharmacol. Exp. Ther., 2000, 294, 155.
124. Kahns, A.H.; Bundgaard, H. Int. J. Pharm., 1990, 62, 193.
125. Shubert, M.P. J. Biol. Chem., 1936, 114, 341.
126. MacKenzie, C.G.; Harris, J. J. Biol. Chem. 1957, 227, 393.
127. Weber, H.U.; Fleming, J.F.; Miquel, J. Arch. Gerontol. Geriatr., 1982, 1, 299.
128. Nagasawa, H.T.; Goon, D.J.W.; Zera, R.T.; Yuzon, D.L. J. Med. Chem., 1982, 25, 489.
129. Nagasawa, H.T.; Goon, D.J.W.; Muldoon, W.P.; Zera, R.T. J. Med. Chem., 1984, 27, 591.
130. Boettcher, B.; Meister, A. In Methods in Enzymology; Jakoby, W.B.; Griffith O.W. Eds.; Academic Press Inc.: New York, 1985, Vol. 113, pp. 458-472.
131. Van der Werf, P.; Orlowski, M.; Meister, A. Proc. Natl. Acad. Sci. USA., 1971, 68, 2982.
132. Porta, P.; Aebi, S.; Summer, K., Lauterburg, B.H. J. Pharmacol. Exp. Ther., 1991, 257, 331.
133. Kalayian, R.C.; Skowron, G.; Emgushov, R.T.; Chance, M.; Spell, S.A.; Borum, P.R.; Webb, L.S.; Mayer, K.H.; Jackson, J.B., Yen-Lieberman, B. J. Acquir. Immune Defic. Syndr., 1994, 7, 369.
134. Vita, J.A.; Frei, B.; Holbrook, M.; Gokce, N.; Leaf, C.; Keaney, J.F. J. Clin. Invest., 1998, 101, 1408.
135. Roberts, J.C.; Nagasawa, H.T.; Zera, R.T.; Fricke, R.F.; Goon, D.J. J. Med. Chem., 1987, 30, 1891.
136. Roberts, J.C.; Francetic, D.J. Med Chem. Res., 1991, 1, 213.
137. Roberts, J.C.; Francetic, D.J.; Zera, R.T. Cancer Chemother. Pharmacol., 1991, 28, 166.
138. Roberts, J.C.; Phaneuf, H.L.; Szakacs, J.C.; Zera, R.T; Lamb, J.G.; Franklin, M.R. Chem. Res. Toxicol., 1998, 11, 1274.
139. Roberts, J.C.; Phaneuf, H.L.; Dominick, P.K.; Wilmore, B.H.; Cassidy, P.B. J. Label Comp. Radiopharmaceut., 1999, 42, 485.
140. Roberts, J.; Koch, K.E.; Detrick, S.R.; Wartes, R.L.; Lubec, G. Radiat. Res., 1995, 143, 203.
141. Yao, W.B.; Tomozawa, M.; Yukihiro, K.; Ubuka, T. Amino Acids, 1997, 12, 33.
142. Meister, A. Cancer Res., 1994, 54 (suppl), 1969S.
143. Witschi, A.; Reddy, S.; Stofer-Vogel, B.; Lauterburg, B.H. Eur. J. Clin. Pharmacol., 1992, 43, 667.
144. Aebi, S.; Assereto, R.; Lauterburg, L.H. Eur. J. Clin. Invest., 1991, 21, 103.
145. Anderson, M.E. Chem. Biol. Interact., 1998, 111/112, 1.
146. Anderson, M.E.; Luo, J.L. Semin. Liver Dis., 1998, 18, 415.
147. Anderson, M.E. Adv. Pharmacol., 1997, 38, 65.
148. Rizzoli, V.; Schiappelli, M.P.; Moretto, C.; Galzigna L. Eur. J. Lab. Med., 1995, 3, 11.
149. Takimoto-Kamimura, T.M.; Koyano, K.; Kitahara, S.; Fujii, K. Acta Cryst. C, 1990, C46, 2247.
150. Ohtsu, A.; Kitahara, S.; Fujii, K. Ophthalmic Res., 1991, 23, 51.
151. Kobayashi, H.; Kurokawa, T.; Kitahara, S.; Nonami, T.; Harada, A.; Nakao, A.; Sugiyama, S.; Ozawa, T.; Takagi, H. Transplantation, 1992, 54, 414.
152. Goto, H.; Tachi, K.; Arisawa, T.; Niwa, Y.; Hayakawa, T.; Sugiyama, S. Cancer Detect. Prev., 1998, 22, 153.
153. Nagasawa, H.T.; Cohen, J.F.; Holleschau, A.M.; Rathbun., W.B. J. Med. Chem., 1996, 39, 1676.
154. Andreadou, I.; Menge, W.M.; Commandeur, J.N.; Worthington, E.A.; Vermeulen, N.P. J. Med. Chem., 1996, 39, 2040.
155. Xie, Y.; Short, M.D.; Cassidy, P.B.; Roberts, J.C. Bioorg. Med. Chem. Lett., 2001, 11, 2911.
156. Ryzewski, J.; Gieldanowski, J.; Raberger, G.; Kossakowska, M. Arch. Immunol. Ther. Exp. (Warsz), 1979, 27, 733.
157. Kwapiszewski, W.; Sokolowska-Muszynska, M.; Iliaszenko, J.; Borkowski, L.; Witczak, M. Arch. Immunol. Ther. Experim., 1989, 37, 29.