Stereoselective synthesis of sugar-modified enyne analogues of adenosine and uridine. Interaction with S-adenosyl-L-homocysteine hydrolase and antiviral and cytotoxic effects

Journal of Medicinal Chemistry

Volumn 47, Issue 21, 2004, Pages 5251-5257

  Wnuk, Stanislaw F ^a   Lewandowska, Elzbieta ^a,d   Sacasa, Pablo R ^a   Crain, Leigh N ^a   Zhang, Jinsong ^b   Borchardt, Ronald T ^b   De Clercq, Erik ^c  

^a FLORIDA INTERNATIONAL UNIVERSITY   (United States)

^b UNIVERSITY OF KANSAS   (United States)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^d POZNA UNIVERSITY OF LIFE SCIENCES   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

1 (5,6,7,8 TETRADEOXY 8 IODO BETA DEXTRO RIBO OCT 5 EN 7 YNOFURANOSYL)URACIL; 1 (5,6,7,8 TETRADEOXY BETA DEXTRO RIBO OCT 5 EN 7 YNOFURANOSYL)URACIL; 6' IODOHOMOVINYLNUCLEOSIDE DERIVATIVE; 9 (5,6,7,8 TETRADEOXY 8 IODO BETA DEXTRO RIBO OCT 5 EN 7 YNOFURANOSYL)ADENINE; 9 (5,6,7,8 TETRADEOXY BETA DEXTRO RIBO OCT 5 EN 7 YNOFURANOSYL)ADENINE; ADENOSINE DERIVATIVE; ADENOSYLHOMOCYSTEINASE; ETHYL 1 ADENIN 9 YL 1,5,6,7,8 PENTADEOXY BETA DEXTRO RIBO OCT 7 EN 5 YNOFURANURONATE; IODIDE ION; NICOTINAMIDE ADENINE DINUCLEOTIDE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOMEGALOVIRUS; CYTOTOXICITY; DEPROTECTION REACTION; DESILYLATION; DRUG ACTIVITY; DRUG BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INACTIVATION; ENZYME INHIBITION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; INCUBATION TIME; ISOMERIZATION; SONOGASHIRA REACTION; STEREOCHEMISTRY; VIRUS INHIBITION;

ADENOSINE; ADENOSYLHOMOCYSTEINASE; ALKYNES; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CELL LINE; HUMANS; PLACENTA; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; URIDINE;

EID: 4744363625     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040054+     Document Type: Article

References (41)

1. (a) Yuan, C.-S.; Liu, S.; Wnuk, S. F.; Robins, M. J.; Borchardt, R. T. Design and Synthesis of S-Adenosylhomocysteine Hydrolase Inhibitors as Broad-Spectrum Antiviral Agents. In Advances in Antiviral Drug Design; De Clercq, E., Ed.; JAI Press: Greenwich, 1996; Vol. 2, pp 41-88.
2. (b) Turner, M. A.; Yang, X.; Yin, D.; Kuczera, K.; Borchardt, R. T.; Howell, P. L. Structure and Function of S-Adenosylhomocysteine Hydrolase. Cell Biochem. Biophys. 2000, 33, 101-125.
3. (c) Wnuk, S. F. Targeting "Hydrolytic" Activity of the S-Adenosyl-L-homocysteine Hydrolase. Mini-Rev. Med. Chem. 2001, 1, 307-316.
4. (a) Chiang, P. K. Biological Effects of Inhibitors of S-Adenosyl-homocysteine Hydrolase, Pharmacol. Ther. 1998, 77, 115-134.
5. (b) Yuan, C.-S.; Saso, Y.; Lazarides, E.; Borchardt, R. T.; Robins, M. J. Recent Advances in S-Adenosyl-L-homocysteine Hydrolase Inhibitors and their Potential Clinical Applications. Exp. Opin. Ther. Patents 1999, 9, 1197-1206.
6. (a) Refsum, H.; Ueland, P. M.; Nygard, O.; Vollset, S. E. Homocysteine and Cardiovascular Disease. Annu. Rev. Med. 1998, 49, 31-62.
7. (b) Schneyder, G.; Roffi, M.; Pin, R.; Flammer, Y.; Lange, H.; Eberli, F. R.; Meier, B.; Turi, Z. G.; Hess, O. M. Decreased rate of coronary restenosis after lowering of plasma homocysteine levels. N. Engl. J. Med. 2001, 345, 1593-1600.
8. (a) McCarthy, J. R.; Jarvi, E. T.; Matthews, D. P.; Edwards, M. L.; Prakash, N. J.; Bowlin, T. L.; Mehdi, S.; Sunkara, P. S.; Bey, P. 4′, 5′-Unsaturated 5′-Fluoroadenosine Nucleosides: Potent Mechanism-Based Inhibitors of S-Adenosyl-L-homocysteine Hydrolase. J. Am. Chem. Soc. 1989, 111, 1127-1128.
9. (b) Yuan, C.-S.; Yeh, J.; Liu, S.; Borchardt, R. T. Mechanism of Inactivation of S-Adenosyl-L-homocysteine Hydrolase by Fluorine-containing Adenosine Analogues. J. Biol. Chem. 1003, 268, 17030-17037.
10. Wnuk, S. F.; Yuan, C.-S.; Borchardt, R. T.; Balzarini, J.; De Clercq, E.; Robins, M. J. Nucleic Acid Related Compounds. 84. Synthesis of 6′(E and Z)-Halohomovinyl Derivatives of Adenosine, Inactivation of S-Adenosyl-L- homocysteine Hydrolase, and Correlation of Anticancer and Antiviral Potencies with Enzyme Inhibition. J. Med. Chem. 1994, 37, 3579-3587.
11. (a) Wnuk, S. F.; Mao, Y.; Yuan, C.-S.; Borchardt, R. T.; Andrei, J.; Balzarini, J.; De Clercq, E.; Robins, M. J. Discovery of Type II (Covalent) Inactivation of S-Adenosyl-L-homocysteine Hydrolase. Synthesis and Evaluation of Dihalohomovinyl Nucleoside Analogues Derived from Adenosine. J. Med. Chem. 1998, 41, 3078-3083.
12. (b) Yuan, C.-S.; Wnuk, S. F.; Robins, M. J.; Borchardt, R. T. A Novel Mechanism-Based Inhibitor (6′-Bromo-5′,6′-didehydro-6′- deoxy-6′-fluorohomoadenosine) That Covalently Modifies Human Placental S-Adenosylhomocysteine Hydrolase. J. Biol. Chem. 1998, 273, 18191-18197.
13. (a) Parry, R. J.; Muscate, A.; Askonas, L. J. 9-(5′,6′- Dideoxy-β-D-ribo-hex-5′-ynofuranosyl)adenine, a Novel Irreversible Inhibitor of S-Adenosylhomocysteine Hydrolase. Biochemistry 1991, 30, 9988-9997.
14. (b) Matsuda, A.; Kosaki, H.; Yoshimura, Y.; Shuto, S.; Ashida, N.; Konno, K.; Shigeta, S. Nucleosides and Nucleotides. 142. An Alternative Synthesis of 9-(5,6-dideoxy-β-D-ribo-hex-5-ynofuranosyl)adenine and its Antiviral Activity. Bioorg. Med. Chem. Lett. 1995, 5, 1685-1688.
15. (a) Robins, M. J.; Wnuk, S. F.; Yang, X.; Yuan, C.-S.; Borchardt, R. T.; Balzarini, J.; De Clercq, E. Inactivation of S-Adenosyl-L-homocysteine Hydrolase and Antiviral Activity with 5′,5′,6′,6′-Tetradehydro- 6′-Deoxy-6′-Halohomoadenosine Analogues (4′-Haloacetylene Analogues Derived from Adenosine). J. Med. Chem. 1998, 41, 3857-3864.
16. (b) Yang, X.; Yin, D.; Wnuk, S. F.; Robins, M. J.; Borchardt, R. T. Mechanism of Inactivation of Human S-Adenosyl-L-homocysteine Hydrolase by 5′,5′,6′,6′-Tetrahydro-6′-Deoxy-6′- Halohomoadenosines. Biochemistry 2000, 39, 15234-15241.
17. (a) Turner, M. A.; Yuan, C.-S.; Borchardt, R. T.; Hershfield, M. S.; Smith, G. D.; Howell, P. L. Structure Determination of Selenomethionyl S-Adenosylhomocysteine Hydrolase using data at a single wavelength. Nat. Struct. Biol. 1998, 5, 369-376.
18. (b) Hu, Y.; Komoto, J.; Huang, Y.; Gomi, T.; Ogawa, H.; Takata, Y.; Fujioka, M.; Takusagawa, F. Crystal Structure of S-Adenosylhomocysteine Hydrolase from Rat Liver. Biochemistry 1999, 38, 8323-8333.
19. (a) Yin, D.; Yang, X.; Hu, Y.; Kuczera, K.; Schowen, R. L.; Borchardt, R. T.; Squier, T. C. Substrate Binding Stabilizes S-Adenosylhomocysteine Hydrolase in a Closed Conformation. Biochemistry 2000, 39, 9811-9819.
20. (b) Komoto, J.; Huang, Y.; Gomi, T.; Ogawa, H.; Takata, Y.; Fujioka, M.; Takusagawa, F. Effect of Site-directed Mutagenesis on Structure and Function of Recombinant Rat Liver S-Adenosylhomocysteine Hydrolase. J. Biol. Chem. 2000, 275, 32147-32156.
21. (c) Hu, Y.; Yang, X.; Yin, D.; Mahadevan, J.; Kuczera, K.; Schowen, R. L.; Borchardt, R. T. Computational Characterization of Substrate Binding and Catalysis in S-Adenosylhomocysteine Hydrolase. Biochemistry 2001, 40, 15143-15152.
22. (d) Elrod, P.; Zhang, J.; Yang, X.; Yin, D.; Hu, Y.; Borchardt, R. T.; Schowen, R. L. Contribution of Active Site Residues to the Partial and Overall Activities of Human S-Adenosylhomocysteine Hydrolase. Biochemistry 2002, 41, 8134-8142.
23. (e) Huang, Y.; Komoto, J.; Takata, Y.; Powell, D. R.; Gomi, T.; Ogawa, H.; Fujioka, M.; Takusagawa, F. Inhibition of S-Adenosylhomocysteine Hydrolase by Acyclic Sugar Adenosine Analogue D-Eritadenine. J. Biol. Chem. 2002, 277, 7474-7482.
24. (f) Yang, X.; Hu, Y.; Yin, D. H.; Turner, M. A.; Wang, M.; Borchardt, R. T.; Howell, P.; Kuczera, K.; Schowen, R. L. Catalytic strategy for S-Adenosylhomocysteine Hydrolase: Transition-State Stabilization and the Avoidance of Abortive Reactions. Biochemistry 2003, 42, 1900-1909.
25. (a) Muzard. M.; Guillerm, D.; Vandenplas, C.; Guillerm, G. 5′-Deoxy-5′-difluoromethylthioadenosine. A potent enzyme-activated acylating agent of S-adenosyl-L-homocysteine hydrolase. Bioorg. Med. Chem. Lett. 1997, 7, 1037-1040.
26. (b) Guillerm, G.; Guillerm, D.; Vandenplas-Witkowki, C.; Rogniaux, H.; Carte, N.; Leize, E.; Van Dorsselaer, A.; De Clercq, E.; Lambert, C. Synthesis, Mechanism of Action, and Antiviral Activity of a New Series of Covalent Mechanism-Based Inhibitors of S-adenosyl-L-Homocysteine Hydrolase. J. Med. Chem. 2001, 44, 2743-2752.
27. Jeong, L. S.; Yoo, S. J.; Lee, K. M.; Koo, M. J.; Choi, W. J.; Kim, H. O.; Moon, H. R.; Lee, M. Y.; Park, J. G.; Lee, S. K.; Chun, M. W. Design, Synthesis, and Biological Evaluation of Fluoroneplanocin A as the Novel Mechanism-Based Inhibitor of S-Adenosylhomocysteine Hydrolase. J. Med. Chem. 2003, 46, 201-203.
28. Wnuk, S. F.; Valdez, C. A.; Khan, J.; Moutinho, P.; Robins, M. J.; Yang, X.; Borchardt, R. T.; Balzarini, J.; De Clercq, E. Doubly Homologated Dihalovinyl and Acetylene Analogues of Adenosine. Synthesis, Interaction with S-Adenosyl-L-homocysteine Hydrolase, and Antiviral and Cytostatic Effects. J. Med. Chem. 2000, 43, 1180-1186.
29. Wnuk, S. F.; Ro, B.-O.; Valdez, C. A.; Lewandowska, E.; Valdez, N. X.; Sacasa, P. R.; Yin, D.; Zhang, J.; Borchardt, R. T.; De Clercq, E. Sugar-Modified Conjugated Diene Analogues of Adenosine and Uridine. Synthesis, Interaction with S-Adenosyl-L-homocysteine Hydrolase and Antiviral and Cytostatic Effects. J. Med. Chem. 2002, 45, 2651-2658.
30. (a) Diederich, F., Stang, P. J., Eds. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 1998.
31. (b) Miyaura, N., Ed. Topics in Current Chemistry: Cross-Coupling Reactions; Springer-Verlag: Berlin, 2002; Vol. 219.
32. Wnuk, S. F.; Robins, M. J. Nucleic Acid Related Compounds. 63. Syntheses of 5′-deoxy-5′-methyleneadenosine and related Wittig-extended nucleosides. Can. J. Chem. 1991, 69, 334-338.
33. (a) Wnuk, S. F.; Robins, M. J. Nucleic Acid Related Compounds. 67. Synthesis of 5′-amino and 5′-methylthio chain-extended nucleosides from uridine. Can. J. Chem. 1991, 69, 2104-2111.
34. (b) Wnuk, S. F.; Robins, M. J. Nucleic Acid Related Compounds. 78. Stereocontrolled syntheses of 6′(E and Z)-halovinyl analogues from uridine-derived vinylsulfones via vinyltin intermediates. Can. J. Chem. 1993, 71, 192-198.
35. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. A Convenient Synthesis of Acetylenes: Catalytic Substitutions of Acetylenic Hydrogen with Bromoalkenes, Iodoarenes, and Bromopyridines Tetrahedron Lett. 1975, 4467-4470.
36. (b) Sonogashira, K. Cross-coupling Reactions to sp Carbon Atoms. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds; Wiley-VCH: Weinheim, 1998; Chapter 5, pp 203-229.
37. Hofmeister, H.; Annen, K.; Laurent, H.; Wiechert, R. A novel Entry to 17α-Bromo- and 17α-Iodoethynyl Steroids. Angew. Chem., Int. Ed. Engl. 1984, 23, 727-729.
38. Kitz, R.; Wilson, I. B. Esters of Methanesulfonic Acid as Irreversible Inhibitors of Acetylcholinesterase. J. Biol. Chem. 1962, 237, 3245-3249.
39. (a) De Clercq, E.; Descamps, J.; Verhelst, G.; Walker, R. T.; Jones, A. S.; Torrence, P. F.; Shugar, D. Comparative Efficacy of Different Antiherpes Drugs against Different Strains of Herpes Simplex Virus. J. Infect. Dis. 1980, 141, 563-574.
40. (b) De Clercq, E. Antiviral and Antimetabolic Activities of Neplanocins. Antimicrob. Agents Chemother. 1985, 25, 309-321
41. (c) Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P.; Desmyter, J.; De Clercq, E. Rapid and Automated Tetrazolium-based Colorimetric Assays for the Detection of anti-HIV Compounds. J. Virol. Methods 1988, 20, 309-321