Molecular-biological problems of drug design and mechanism of drug action: Metabolism of L-arginine (A review)

Pharmaceutical Chemistry Journal

Volumn 37, Issue 3, 2003, Pages 111-127

  Granik, V G ^a  

^a Organic Intermediates and Dyes Institute   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 CHLOROETHYL) 3 (4 METHYL)CYCLOHEXYL 1 NITROSUREA; 1 (2 CHLOROETHYL)NITROSUREA; ADENOSINE DERIVATIVE; AGMATINE; ARGININE; AZIRIDINOPUTRESCINE; CADAVERINE; CARMUSTINE; CHLORAMBUCIL; CISPLATIN; CLONIDINE; CYCLOHEXYLAMINE DERIVATIVE; DOXORUBICIN; EFLORNITHINE; FLUOROURACIL; LOMUSTINE; MOXONIDINE; N CHLOROSULFONYLDICYCLOHEXYLAMINE; N GAMMA AMINOPROPYLCADAVERINE; N(G) NITROARGININE METHYL ESTER; N1,N12 BIS(BETA CHLOROETHYL)SPERMINE; N1,N8 BIS(BETA CHLOROETHYL)SPERMIDINE; N4 METHYLSPERMIDINE; ORNITHINE DERIVATIVE; POLYAMINE; PUTRESCINE DERIVATIVE; SPERMIDINE DERIVATIVE; SPERMINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; UREA DERIVATIVE;

AMINO ACID ANALYSIS; ANTINEOPLASTIC ACTIVITY; BIOSYNTHESIS; CANCER CELL; CANCER CHEMOTHERAPY; CARCINOGENESIS; CATABOLISM; DRUG ACTIVITY; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG EFFECT; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; HUMAN; INHIBITION KINETICS; INTESTINE CELL; LIVER METABOLISM; MOLECULAR BIOLOGY; NONHUMAN; REGULATORY MECHANISM; REVIEW;

EID: 1642580727     PISSN: 0091150X     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1024578429137     Document Type: Review

References (118)

1. S. Moncada, R. M. S. Palmer, and E. A. Higgs, Pharmacol. Rev., 43, 109-141 (1991).
2. M. A. Marletta, J. Med. Chem., 37, 1899-1921 (1994).
3. O. W. Griffith and D. J. Stuehr, Annu. Rev. Physiol., 57, 707-736 (1995).
4. V. G. Granik, S. Yu. Ryabova, and N. B. Grigor'ev, Usp. Khim., 66(8), 792-807 (1997).
5. A. F. Vanin, Biokhimiya, 63(7), 924-938 (1998).
6. I. S. Severina, Biokhimiya, 63(7), 939-947 (1998).
7. E. B. Men'shikova, N. K. Zenkov, and V. P. Reutov, Biokhimiya, 65(4), 485-503 (2000).
8. Nitric Oxide. Basic Research and Clinical Application, R. J. Gryglewsky, and P. Minuz (eds.), IOS Press, Amsterdam, Berlin, Oxford, Tokyo, Washington, DC (2001).
9. D. Voet and J. G. Voet, Biochemistry, 2th Ed., John Wiley and Sons Inc., New York, Chichester, Brisbane, Toronto, Singapore (1995), p. 1290.
10. F. Murad, Neurotransmissions, X(2), 1-4 (1994).
11. H. Al-Sa'Doni and A. Ferro, Clin. Sci., 98, 507-520 (2000).
12. M. Feelish, J. Cardiovas. Pharm., 17(Suppl. 3), 25-33 (1991).
13. V. P. Reutov, E. G. Sorokina, V. E. Okhotin, and N. S. Kositsyn, Cyclic Transformations of Nitrogen Oxide in Mammals [in Russian], Nauka, Moscow (1998).
14. G. Wu and S. M. Morris, Biochem. J., 336, 1-17 (1998).
15. G. Wu, P. K. Devis, N. E. Flynn, et al., J. Nutr., 127, 2342-2349 (1997).
16. G. Wu, J. Nutr., 128, 1249-1252 (1998).
17. H. K. Berthold, R. J. Reeds, and P. D. Klein, Clin. Exp. Metab., 44, 466-479 (1995).
18. A. Leninger, Principles of Biochemistry, Worth, New York (1982).
19. V. G. Granik and N. B. Grigor'ev, Izv. Ross. Akad. Nauk, Ser. Khim., No. 8, 1268-1313 (2002).
20. V. G. Granik and N. B. Grigor'ev, Izv. Ross. Akad. Nauk, Ser. Khim., No. 11, 1819-1841 (2002).
21. P. G. Wang, M. Xian, X. Tang, et al., Chem. Rev., 102, 1091-1139 (2002).
22. S. M. Morris, D. K. Nakayama, A. K. Nussler, et al., The Biology of Nitric Oxide, Vol. 4, Enzymology, Biology and Immunology, S. Moncada, M. Feelish, R. Busse, E. A. Higgs (eds.), Portland Press, London (1994), pp. 301-303.
23. M. Hecker, W. C. Sessa, H. J. Harris, et al., Proc. Natl. Sci. USA, 87, 8612-8616 (1990).
24. S. M. Morris and T. R. Billiar, Am. J. Physiol., 266, E829-E839 (1994).
25. L. Xie and S. S. Gross, J. Biol. Chem., 272, 16624-16650 (1997).
26. G. Li, S. Regunathan, J. Barrow, et al., Science, 263, 966-969 (1994).
27. M. D. Mashkovskii, Drugs [in Russian], Torsing, Kharkov (1997).
28. M. D. Mashkovskii, Drugs of the XXI Century [in Russian], Novaya Volna, Moscow (1998).
29. J. Satriano, S. Matsufuji, Y. Marakami, et al., J. Biol. Chem., 273, 15313-15316 (1998).
30. R. C. Blantz, J. Satriano, F. Gabbai, and C. J. Kelly, Acta Physiol. Scand., 168, 21-27 (2000).
31. A. Galea, S. Regunathan, V. Eliopoulos, et al., Biochem. J., 316, 247-249 (1996).
32. M. J. Lortie, W. F. Novotny, and O. W. Peterson, J. Clin. Invest., 97, 413-420 (1996).
33. D. Schwartz, O. W. Peterson, M. Mendonca, et al., Am. J. Physiol., 272, F597-F601 (1997).
34. D. J. Stuer, Annu. Rev. Pharmacol. Toxicol., 37, 339-359 (1997).
35. G. M. Boga, R. Singh, S. Pervin, et al., Am. J. Physiol., 271, 1988-1998 (1996).
36. G. Wu and C. J. Meininger, Am. J. Physiol., 269, 1312-1318 (1995).
37. V. G. Granik, Drugs: Pharmacological, Biochemical, and Chemical Aspects, [in Russian], Vuz. Kniga, Moscow (2001).
38. M. A. Creager, S. M. Gallagher, X. J. Giverd, et al., J. Clin. Invest., 90, 1248-1255 (1992).
39. J. L. Dubois, R. Zelinsky, F. Roudot, et al., Am. J. Cardiol., 70, 1269-1276 (1992).
40. H. G. Williams-Ashman and Z. N. Canellakis, Perspect. Biol. Med., 22, 421-453 (1979).
41. A. E. Pegg and P. P. McCann, Am. J. Physiol., 243, 212-221 (1982).
42. C. W. Tabor and H. Tabor, Annu. Rev. Biochem., 53, 749-790 (1984).
43. A. E. Pegg, Biochem. J., 234, 249-262 (1986).
44. C. W. Porter and J. R. Sufrin, Anticancer. Res., 6, 525-542 (1986).
45. J. Janne, E. Hollta, A. Kallio, et al., Spec. Top. Endocrinol. Metab., 5, 227-293 (1983).
46. P. P. McCann and A. E. Pegg, A Sjoerdsma, Biological Significance and Basis for New Therapies, Orlando, FL: Academic Press (1987), pp. 1-371.
47. A. E. Pegg, Cancer Res., 48, 759-774 (1988).
48. A. E. Pegg, R. S. Wechter, R. S. Clark, et al., Biochemistry, 25, 379-384 (1986).
49. A Sjoerdsma and P. J. Schechter, Clin. Pharmacol. Ther., 35, 287-300 (1984).
50. A. E. Pegg, K.-C. Tang, and J. K. Coward, Biochemistry, 21, 5082-5086 (1982).
51. A. E. Pegg, D. B. Jones, and J. A. Secrist, Biochemistry, 21, 5097-5102 (1982).
52. L. Alhonen-Hongisto, P. Seppanen, and J. Janne, Biochem. J., 192, 941-945 (1982).
53. A. Kallio, J. Janne, Biochem. J., 212, 895-901 (1983).
54. A. Kallio, P. Nikula, and J. Janne, Biochem. J., 218, 641-644 (1984).
55. V. A. Levin, M. C. Chamberlain, M. D. Prados, et al., Cancer Treat. Rep., 71, 459-465 (1987).
56. R. Scleiffer, B. Duranton, F. Gosse, et al., Nitric Oxide: Biol., Chem., 4, 583-589 (2000).
57. N. Seiler, C. L. Atanasov, and F. Raul, Int. J. Oncol., 13, 993-1006 (1998).
58. F. Blachier, A. Mignon, and O. Soubrane, Nitric Oxide: Biol., Chem., 1, 268-272 (1997).
59. J. Satriano, S. Ishizuka, D. C. Archer, et al., Am. J. Physiol., 276, C 892-899 (1999).
60. A. Al'bert, Specific Toxicity [Russian Translation], Meditsina, Moscow (1989), Vois. 1 and 2.
61. G. I. Zhungietu and V. G. Granik, Basic Principles of Drug Design [in Russian], Moldova State University, Kishinev (2000).
62. V. G. Granik, Principles of Medicinal Chemistry [in Russian], Vuz. Kniga, Moscow (2001).
63. J. G. Cannon, Pharmacology for Chemists, Oxford University Press, N. Y., Oxford (1999).
64. S. W. Porter, R. J. Bergeron, and N. J. Stolowich, Cancer Res., 42, 4072-4078 (1982).
65. S. W. Porter, P. F. Cavanaugh, N. J. Stolowich, et al., Cancer Res., 45, 2050-2056 (1985).
66. W. D. W. Heston, C.-R. Yang, L. Pliner, et al., Cancer Res., 47, 3627-3631 (1987).
67. D. A. Wooley, A Study of Antimetabolites, New York (1952).
68. R. A. Cosero, R. J. Bergeron, and S. W. Porter, J. Cell. Physiol., 121, 476-482 (1984).
69. K. A. Govern, P. S. Clark, and A. E. Pegg, J. Cell Physiol., 127, 311-316 (1986).
70. S. W. Porter, B. Ganis, T. Vinson, et al., Cancer Res., 46, 6279-6285 (1986).
71. S. W. Porter, J. McManis, R. A. Casero, et al., Cancer Res., 47, 2821-2827 (1987).
72. B. G. Erwin and A. E. Pegg, Biochem. J., 238, 581-587 (1986).
73. R. Casero, B. Go, H. W. Theiss, et al., Cancer Res., 47, 3964-3967 (1987).
74. L. J. Marton, Pharmacol. Ther., 32, 183-190 (1987).
75. I. Sano, D. F. Deen, S. M. Oredsson, et al., Cancer Res., 44, 577-583 (1984).
76. L. J. Marton, V. A. Levin, S. J. Hervatin, et al., Cancer Res., 41, 4426-4433 (1981).
77. L. J. Marton, in: "Polyamine in Clinical Disorder" (D. F. Tierney, Moderator), West. J. Med., 142, 63-69 (1985).
78. J. Seidenfeld and R. K. A. Komar, Cancer Res., 45, 2132-2137 (1985).
79. A. V. Danilov, O. B. Romanova, I. K. Sorokina, et al., Vopr. Biol. Med. Farm. Khim., No. 2, 50-55 (2001).
80. J. M. Ducore and L. McNamara, Cancer Res., 46, 1068-1077 (1986).
81. M. A. Moore, H. Tsuda, T. Ogiso, et al., Cancer Lett., 25, 145-149 (1982).
82. T. Nakadate, E. Aizu, S. Yamamoto, et al., Jpn. J. Pharmacol., 37, 253-260 (1985).
83. R. A. Malt, A. N. Kingsnorth, G. M. Lamuraglia, et al., Adv. Enzym. Regul., 24, 93-97 (1985).
84. Y. Homma, S. Ozono, I. Numata, et al., Carcinogenesis (Lond.), 6, 159-166 (1985).
85. H. J. Thompson and A. M. Ronan, Carcinogenesis (Lond.), 7, 2003-2006 (1986).
86. N. D. Nigro, A. W. Bull, and M. E. Boyd, J. Natl. Cancer Inst., 77, 1309-1313 (1986).
87. G. D. Luk and S. B. Baylin, N. Engl. J. Med., 311, 80-87 (1984).
88. R. J. Moorehead, M. Hoper, and S. T. D. McKelvay, Br. J. Surg., 74, 364-368 (1987).
89. H. G. Williams-Ashman, J. Seidenfeld, and P. Galetti, Biochem. Pharmacol., 35, 1217-1224 (1982).
90. F. Schlenk, Adv. Enzymol., 54, 195-201 (1983).
91. H. Yamanaka, M. Kubota, D. A. Carson, Cancer Res., 47, 1771-1774 (1987).
92. P. S. Mamont, M.-C. Duchesne, J. Grove, et al., Exp. Cell. Res., 115, 387-392 (1978).
93. E. E. Medrano, O. R. Burrone, M. M. Ferrer, et al., FEBS Lett., 206, 106-108 (1986).
94. M. Carteni-Farina, G. Cacciapuoti, M. Porcelli, et al., Biochim. Biophys. Acta, 805, 158-167 (1984).
95. M. C. Pancaskie and D. D. Lakin, Biochem. Pharmacol., 36, 2063-2074 (1987).
96. T. M. Savarese, L. Y. Ghoda, and R. E. Park, In: Y.-C. Cheng, B. Goz, M. Mincoff (eds.), Development of Target Oriented Anticancer Drugs, Raven Press, New York (1983), pp. 129-142.
97. J. Loscalzo, Circulation, 101, 2126-2129 (2000).
98. N. Gocke, J. F. Keaney, B. Frei, et al., Circulation, 99, 3234-3239 (1999).
99. J. V. Mombouli, Drugs, 54(suppl. 5), 12-22 (1997).
100. M. A. Creager, S. M. Gallagher, X. J. Cirerd, et al., J. Clin. Invest., 90, 1248-1253 (1992).
101. J. L. Dubois-Rande, R. Zelinsky, F. Roudot, et al., Am. J. Cardiol., 70, 1269-1275 (1992).
102. M. T. Jay, S. Chirico, R. C. Siow, et al., Exp. Physiol., 82, 349-356 (1997).
103. K. Kikuta, T. Sawamura, S. Miwa, et al., Circ. Res., 83, 1088-1092 (1998).
104. H. Miuazaki, H. Matsuoka, J. P. Cooke, et al., Circulation, 99, 1141-1146 (1999).
105. D. Giuliano, R. Marfella, G. Verazzo, et al., J. Clin. Invest., 99, 433-438 (1997).
106. C. M. Giraldelo, A. Zappellini, N. N. Muscara, et al., Eur. J. Pharmacol., 257, 87-93 (1994).
107. J. P. F. Chin-Dusting, C. T. Alexander, R. J. Arnold, et al., J. Cardiovasc. Pharmacol., 28, 158-164 (1996).
108. A. Blum, L. Hathaway, L. Mincemoyer, et al., Circulation, 101, 2160-2166 (2000).
109. E. Stroes, J. Kastelein, F. Cosentino, et al., J. Clin. Invest., 99, 41-44 (1997).
110. G. M. Pieper, Hypertension, 31, 1047-1060 (1998).
111. V. Grill, O. Bjorkman, M. Gutniak, et al., Metabolism, 41, 28-34 (1992).
112. L. Hagenfeldt, G. Dahlquist, and B. Persson, Acta Pediatr. Scand., 794, 278-283 (1989).
113. T. C. Wascher, K. Posch, S. Wallner, et al., Biochem. Biophys. Res. Commun., 234, 35-38 (1997).
114. E. Brand and M. Sandberg, Organic Synth., Coll. Vol. II (1943), pp. 49-55.
115. K. Odo, J. Chem. Soc. Jpn., Pure Chem. Sect., 74, 774-778 (1953).
116. P. A. S. Smith, Organic Synth., Coll. Vol. IV (1963), pp. 819-824.
117. J. von Brown and W. Pinkernelle, Chem. Ber., 70, 1230-1237 (1937).
118. M. Israel, J. S. Rosenfield, and E. J. Modest, J. Med. Chem., 7(6), 710-718 (1964).