Isosteric analogues of nicotinamide adenine dinucleotide derived from furanfurin, thiophenfurin, and selenophenfurin as mammalian inosine monophosphate dehydrogenase (type I and II) inhibitors

Journal of Medicinal Chemistry

Volumn 41, Issue 10, 1998, Pages 1702-1707

  Franchetti, Palmarisa ^a   Cappellacci, Loredana ^a   Perlini, Paolo ^a   Jayaram, Hiremagalur N ^b   Butler, Adrian ^b   Schneider, Bryan P ^b   Collart, Frank R ^c   Huberman, Eliezer ^c   Grifantini, Mario ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

^b INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c ARGONNE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; INOSINATE DEHYDROGENASE; SELENAZOFURIN; SELENAZOLE 4 CARBOXAMIDE ADENINE DINUCLEOTIDE; SELENOPHENFURIN; THIOPHENFURIN; TIAZOFURIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ENZYME INHIBITORS; HUMANS; IMP DEHYDROGENASE; KINETICS; NAD; ORGANOSELENIUM COMPOUNDS; RECOMBINANT PROTEINS; RIBONUCLEOSIDES;

EID: 0032492952     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970772e     Document Type: Article

References (27)

1. Franchetti, P.; Cappellaci, L.; Grifantini, M.; Barzi, A.; Nocentini, G.; Yang, H.; O'Connor, A.; Jayaram, H. N.; Carrell, C.; Goldstein, B. M. Furanfurin and Thiophenfurin: Two Novel Tiazofurin Analogues. Synthesis, Structure, Antitumor Activity, and Interactions with Inosine Monophosphate Dehydrogenase. J. Med. Chent. 1995, 38, 3829-3837.
2. (a) Jaysram, H. N.; Smith, A. L.; Glazer, R. L; Johns, D. G.; Cooney, D. A. Studies on the mechanism of action of 2-β-Dribofuranosylthiazole-4-carboxamide (NSC-286193). II. Relationship Between Dose Level and Biochemical Effects in P388 Leukemia in vivo. Biochem. Pharmacol. 1982, 31, 3839-3845.
3. (b) Jayaram, H. N.; Ahluwalia, G. S.; Dion, R. L.; Gebeyehu, G.; Marquez, V. E.; Kelley, J. A.; Robins, R. K.; Cooney, D. A.; Johns, D. G. Conversion of 2-β-D-Ribofuranosylseienazole-4-carboxamide to an Analogue of NAD with Potent IMP Dehydrogenaseinhibitory Properties. Biochem. Pharmacol. 1983, 32, 2633-2636.
4. (c) Jayaram, H. N.; Dion, R. L.; Glazer, R. I.; Johns, D. G.; Robins, R. K.; Srivastava, P. C.; Cooney, D. A. Initial Studies on the Mechanism of Action of a New Oncolytic Thiazole Nucleoside, 2-β/3-D-Ribofuranosylthiazole-4-carboxamide. Biochem. Pharmacol. 1982, 31, 2371-2380.
5. (a) Cooney, D. A.; Jayaram, H. N.; Gebeyehu, G.; Betts, C. R.; Kelley, J. A.; Marquez, V. E.; Johns, D. G. The Conversion of 2-β-D-Ribofuranosylthiazole-4-carboxamide to an Analogue of NAD with Potent IMP-dehydrogenase-inhibitory Activity. Biochem. Pharmacol. 1982, 31, 2133-2136.
6. (b) Kuttan, R.; Robins, R. K.; Saunders, P. P. Inhibition of Inosinate Dehydrogenase Metabolites of 2-β-D-Ribofuranosylthiazole-4-carboxamide. Biochem. Biophys. Res. Commun. 1982, 107, 862-868.
7. (a) Srivastava, P. C.; Robins, R. K. Synthesis and Antitumor Activity of 2-β-D-Ribofuranosylselenazole-4-carboxamide and Related Derivatives. J. Med. Chem. 1983, 26, 445-448.
8. (b) Streeter, D.; Robins, R. K. Comparative in vitro Studies of Tiazofurin and a Selenazole Analogue. Biochem. Biophys. Res. Commun. 1983, 775, 544-550.
9. (c) Kirsi, J. J.; North, J.; McKernan, P. A.; Murray, B. K.; Canonico, P. G.; Muggins, J. W.; Srivastava, P. C.; Robins, R. K. Broad-spectrum Antiviral Activity of 2-β-D-Ribofuranosylselenazole-4-carboxamide, a New Antiviral Agent. Antimicrob. Agents Chemother. 1983, 24, 353-361.
10. (d) Goldstein, B. M.; Leary, J. F.; Parley, B. A.; Marquez, V. E.; Rowley, P. T. Induction of HL60 Cell Differentiation by Tiazofurin and Its Analogue; Characterization and Efficacy. Blood 1991, 78, 593-598.
11. Franchetti, P.; Cappellacci, L.; Abu Sheikha, G.; Jayaram, H. N.; Gurudutt, V. V.; Sint, T.; Schneider, B. P.; Jones, W. D.; Goldstein, B. M.; Perra, G.; De Montis, A.; Loi, A. G.; La Colla, P.; Grifantini, M. Synthesis, Structure, and Antiproliferative Activity of Selenophenfurin, an IMP Dehydrogenase Inhibitor Analogue of Selenazofurin. J. Med. Chem. 1997,40, 1731-1737.
12. Burling, F. T.; Goldstein, B. M. Computational Studies of Nonbonded Sulfur-Oxygen and Selenium-Oxygen Interactions in the Thiazole and Selenazole Nucleosides. J. Am. Chem. Soc. 1992, 774, 2313-2320 and references therein.
13. (a) Natsumeda, Y.; Ohno, S.; Kawasaki, H.; Konno, Y.; Weber, G.; Suzuki, K. Two Distinct cDNAs from Human IMP Dehydrogenase. J. Biol. Chem. 1990, 265, 5292-5295.
14. (b) Carr, S. F.; Papp, E.; Wu, J. C.; Natsumeda, Y. Characterization of Human Type I and Type II IMP Dehydrogenase. J. Biol. Chem. 1993, 268, 27286-27290.
15. (a) Konno, Y.; Natsumeda, Y.; Nagai, M.; Yamaji, Y.; Ohno, S.; Suzuki, K.; Weber, G. Expression of Human IMP Dehydrogenase Types I and II in Escherichia Coli and Distribution in Human Normal Lymphocytes and Leukemic Cell Lines. J. Biol. Chem. 1991, 266, 506-509.
16. (b) Nagai, M.; Natsumeda, Y.; Konno, Y.; Huffman, R.; Irino, S.; Weber, G. Selective Up-regulation of Type II Inosine S'-Monophosphate Dehydrogenase Messenger RNA Expression in Human Leukemias. Cancer Res. 1991, 51, 3886-3890.
17. (c) Nagai, M.; Natsumeda, Y.; Weber, G. Proliferationlinked Regulation of Type II IMP Dehydrogenase Gene in Human and Normal Lymphocytes and HL-60 Leukemic Cells. Cancer Res. 1992, 52, 258-261.
18. Yoshikawa, M.; Kato, T.; Takenishi, T. A Novel Method for Phosphorylation of Nucleosides to 5′-Nucleotides. Tetrahedron Lett. 1967, 50, 5065-5068.
19. (a) Cramer, F.; Neunhoeffer, H. Reaktionen von Adenosine-5′phosphorsaure-imidazolid-eine neue Synthese von Adenosindiphosphat und Flavin-adenin-dinucleotid. (Reaction of Adenosine 5′-phosphorimidazolide. New Synthesis of Adenosine Diphosphate and Flavin-adenin-dinucleotid.) Chem. Ber. 1962, 95, 1664-1669.
20. (b) Gebeyehu, G.; Marquez, V. E.; van Cott, A; Cooney, D. A.; Kelley, J. A.; Jayaram, H. N.; Ahluwalia, G. S.; Dion, R. L.; Wilson, Y. A.; Johns, D. G. Ribavirin, Tiazofurin, and Selenazofurin: Mononucleotides and Nicotinamide Adenine Dinucleotide Analogue. Synthesis, Structure, and Interactions with IMP Dehydrogenase. J. Med. Chem. 1985, 28, 99-105.
21. Magasanik, B.; Moyer, H. S.; Gehring, L. B. Enzymes Essential for the Biosynthesis of Nucleic Acid Guanine. I. Inosine-5′phosphate Dehydrogenase as Aerobacter Aerogenes. J. Biol. Chem. 1957, 226, 339-350.
22. Makara, G. M.; Keseru, G. M. On the Conformation of Tiazofurin Analogues. J. Med. Chem. 1997, 40, 4154-4159.
23. Goldstein, B. M.; Bell, J. E.; Marquez, V. E. Dehydrogenase Binding by Tiazofurin Anabolites. J. Med. Chem. 1990, 33, 1123-1127.
24. (a) Gharehbaghi, K.; Paull, K. D.; Kelly, J. A.; Barchi, J. J., Jr.; Marquez, V. E.; Cooney, D. A.; Monks, A.; Scudiero, D.; Krohn, K.; Jayaram, H. N. Cytotoxicity and Characterization of an Active Metabolite of Benzamide Riboside, a Novel Inhibitor of IMP Dehydrogenase. Int. J. Cancer 1994, 56, 892-899.
25. (b) Zatorski, A.; Watanabe, K. A.; Carr, S. F.; Goldstein, B. M.; Pankiewicz, K. W. Chemical Synthesis of Benzamide Adenine Dinucleotide: Inhibition of Inosine Monophosphate Dehydrogenase (Types I and II). J. Med. Chem. 1996, 39, 2422-2426.
26. Hager, P. W.; Collait, F. R.; Huberman, E.; Mitchell, B. S. Recombinant Human Inosine Monophosphate Dehydrogenase Type I and Type II Proteins. Purification and Characterization of Inhibitor Binding. Biochem. Pharmacol. 1995,49, 1323-1329.
27. Cleland, W. W. Statistical analysis of enzyme kinetics data. Methods Enzymol. 1979, 63, 103-138.