Diamine and Triamine Analogs and Derivatives as Inhibitors of Deoxyhypusine Synthase: Synthesis and Biological Activity

Journal of Medicinal Chemistry

Volumn 38, Issue 16, 1995, Pages 3053-3061

  Lee, Young Bok ^a   Park, Myung Hee ^a   Folk, J E ^a  

^a NATIONAL INSTITUTE OF DENTAL AND CRANIOFACIAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINO 7 ETHYLAMINOHEPTANE; 1 AMINO 7 GUANIDINOHEPTANE; AMINE; DEOXYHYPUSINE SYNTHASE; DEOXYHYPUSINE SYNTHASE INHIBITOR; DIAMINE; GUANIDINE DERIVATIVE; HYPUSINE; INITIATION FACTOR; PEPTIDE SYNTHASE; SPERMIDINE; TRIAMINE; TRITIUM; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CELL GROWTH; CHO CELL; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; GROWTH INHIBITION; NONHUMAN; PROTEIN SYNTHESIS; RAT; TESTIS;

AMINE OXIDOREDUCTASES; ANIMAL; BINDING, COMPETITIVE; CELL DIVISION; CHO CELLS; CRICETULUS; DIAMINES; HAMSTERS; HUMAN; LYSINE; MALE; PEPTIDE INITIATION FACTORS; POLYAMINES; RATS; SPERMIDINE; STRUCTURE-ACTIVITY RELATIONSHIP; TESTIS;

EID: 0029133121     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00016a008     Document Type: Article

References (37)

1. Park, M. H.; Wolff, E. C. Cell-Free Synthesis of Deoxyhypusine. J. Biol. Chem. 1988, 263, 15264-15269.
2. Wolff, E. C.; Park, M. H.; Folk, J. E. Cleavage of Spermidine as the First Step in Deoxyhypusine Synthesis. J. Biol. Chem. 1990, 265, 4793-4799.
3. Park, M. H.; Wolff, E. C.; Folk, J. E. Hypusine: Its Post- translational Formation in Eukaryotic Initiation Factor 5A and Its Potential Role in Cellular Regulation. Biofactors 1993, 4, 95104.
4. Park, M. H.; Wolff, E. C.; Folk, J. E. Is Hypusine Essential for Eukaryotic Cell Proliferation? Trends Biochem. Sci. 1993, 18, 475-479.
5. Kang, H. A.; Hershey, J. W. B. Effect of Initiation Factor elF- 5A Depletion on Protein Synthesis and Proliferation of Saccha romyces cerevisiae. J. Biol. Chem. 1994, 269, 3934-3940.
6. Park, M. H.; Wolff, E. C.; Lee, Y. B.; Folk, J. E. Antiproliferative Effects of Inhibitors of Deoxyhypusine Synthase. J. Biol. Chem. 1994, 269, 27827-27832.
7. Hanauske-Abel, H.; Park, M. H.; Hanauske, A. R.; Popowicz, A. M.; Lalande, M.; Folk, J. E. Inhibition of the G1-S Transition of the Cell Cycle by Inhibitors of Deoxyhypusine Hydroxylation. Biochim. Biophys. Acta. 1994, 1221, 115-124.
8. McCaffrey, T. A.; Pomerantz, K. B.; Sanborn, T. A.; Spokojny, A. M.; Du, B.; Park, M. H.; Folk, J. E.; Lamberg, A.; Kivirikko, K. I.; Falcone, D. J.; Mehta, S. B.; Hanauske-Abel, H. M. Specific Inhibition of eIF-5A and Collagen Hydroxylation by a Single Agent. Antiproliferative and Fibrosuppressive Effects on Smooth Muscle Cells from Human Coronary Arteries. J. Clin. Invest. 1995, 95, 446-455.
9. Ruhl, M.; Himmelspach, M.; Bahr, G. M.; Hammerschmid, F.; Jaksche, H.; Wolff, B.; Aschauer, H.; Farrington, G. K.; Probst, H.; Bevec, D.; Hauber, J. Eukaryotic Initiation Factor 5A is a Cellular Target of the Human Immunodeficiency Virus Type 1 Rev Activation Domain Mediating Trans-activation. J. Cell Biol. 1993, 123, 1309-1320.
10. Murphey, R. J.; Gerner, E. W. Hypusine Formation in Protein by a Two-Step Process in Cell Lysates. J. Biol. Chem. 1987, 262, 15033-15036.
11. Jakus, J.; Wolff, E. C.; Park, M. H.; Folk, J. E. Features of the Spermidine-Binding Site of Deoxyhypusine Synthase as Derived from Inhibitor Studies. J. Biol. Chem. 1993, 268, 13151-13159.
12. Kindler, K.; Melamed, G.; Matthies, D. Concerning the Conversion of Primary Amines into Secondary and Tertary Amines with Raney Nickel. Justus Liebigs Ann. Chem. 1961, 644, 23-30.
13. uC]Guanidino-9-azaheptadecane triacetate). J. Labelled Compd. Radiopharm. 1980, 17, 383-387.
14. Aspinall, S. R. A Synthesis of Tetrahydropyrimidines. J. Am. Chem. Soc. 1940, 62, 2160-2162.
15. Paz, M. A.; Henson, E.; Rombauer, R.; Abrash, L.; Blumenfeld, O. O.; Gallop, P. M. Amino Alcohols as Products of a Reductive Side Reaction of Denatured Collagen with Sodium Borohydride. Biochemistry 1970, 9, 2123-2127.
16. Wiley, P. F. Di-(y-aminopropyl) ether. J. Am. Chem. Soc. 1946, 68, 1867.
17. Edwards, M. L.; Prakash, N. J.; Stemerick, D. M.; Sunkara, S. P.; Bitonti, A. J.; Davis, G. F.; Dumont, J. A.; Bey, P. Polyamine Analogs with Antitumor Activity. J. Med. Chem. 1990, 33, 1369-1375.
18. Khomutov, A. R.; Khomutov, R. M. Synthesis of Aminooxy Analogs of Putrescine and Spermidine. Bioorg. Khim. 1989, 15, 698-703.
19. Boyer, J. H. Addition of Hydrazoic Acid to Conjugated Systems. J. Am. Chem. Soc. 1951, 73, 5248-5252.
20. Borch, R. F.; Bernstein, M. D.; Durst, H. D. The Cyanohydri- doborate Anion as a Selective Reducing Agent. J. Am. Chem. Soc. 1971, 93, 2897-2904.
21. Knouzi, N.; Vaultier, M.; Carrie, R. Reduction of Azides by Triphenylphosphine in the Presence of Water. Bull. Soc. Chim. Fr. 1985, 815-819.
22. Pinner, A. The Iminoesters and their Derivatives; Oppenheim: Berlin, 1892.
23. Easson, A. P. T.; Pyman, F. F. Amidines of Pharmacological Interest. J. Chem. Soc. (London) 1931, 2991-3001.
24. Kawai, S.; Hosono, T.; Shikinami, Y.; Yonechi, S. Investigation on Hypoglycemic Substances, 2 Isothiourea, Amidine and Urea Derivatives. Sci. Papers Inst. Phys. Chem. Res. Tokyo 1931, 16, 9-16.
25. Eitner, P.; Wetz, H. Concerning Nitrogenous Derivatives of the Higher Fatty Acids. Ber. Dtsch. Chem. Ges. 1893, 26, 2840-2847.
26. Grogan, C. H.; Rice, L. M.; Sullivan, M. X. Diisothiuronium Dihydrohalide Salts, J. Org. Chem. 1953, 18, 728-735.
27. Griffin, J. W.; Hey, D. H. Aminoalkanesulphonamides and Alkanedisulphonamides. J. Chem. Soc. 1952, 3334-3340.
28. Smith, T. A. Polyamine Oxidase (Oat Seedlings). Methods Ezymol. 1983, 94, 311-314.
29. Park, M. H.; Folk, J. E. Biosynthetic Labeling of Hypusine in Mammalian Cells. J. Biol. Chem. 1986, 261, 14108-14111.
30. Hudson, H. R.; Ojo, I. A. O.; Pianka, M. Guanidines with Antifungal (and Antibacterial) Activity-a Review. Internat Pest Control. 1986, 28, 148-155.
31. Clark, J.; Perrin, D. D. Prediction of the Strengths of Organic Bases. Q. Rev. Chem. Soc. 1964, 18, 295-320.
32. Hyvonen, T.; Alakuijala, L.; Andersson, L.; Khomutov, A. R.; Khomutov, R. M. 1-Aminooxy-3-aminopropane Reversibly Prevents the Proliferation of Cultured Baby Hamster Kidney Cells by Interfering with Polyamine Synthesis. J. Biol. Chem. 1988, 263, 11138-11144.
33. Eloranta, T. O.; Khomutov, A. R.; Khomutov, R. M.; Hyvonen, T. Aminooxy Analogs of Spermidine as Inhibitors of Spermine Synthase and Substrates of Hepatic Polyamine Acetylating Activity. J. Biochem. 1990, 108, 593-598.
34. John, R. A.; Charteris, A.; Fowler, L. J. The Reaction of Aminooxyacetate with Pyridoxal Phosphate-dependent Enzymes. Biochem J. 1978, 171, 771-779.
35. Park, M. H.; Cooper, H. L.; Folk, J. E. The Biosynthesis of Protein-bound Hypusine (AM4-amino-2-hydroxybutyl) lysine: Lysine as the Amino Acid Precursor and the Intermediate Role of Deoxyhypusine W′-(4-aminobutyl) lysine). J. Biol Chem, 1982, 257, 7217-7222.
36. Park, M. H.; Wolff, E. C.; Smit-McBride, Z.; Hershey, J. W. B.; Folk, J. E. Comparison of the Activities of Variant Forms of elF- 4D. J. Biol. Chem. 1991, 266, 7988-7994.
37. Smith, P. K.; Krohn, R. I.; Hermanson, G. T.; Mallia, A. K.; Gartner, F. H.; Provenzano, M. D.; Fujimoto, E. K.; Goeke, N. M.; Olson, B. J.; Klenk, D. C. Measurement of Protein using Bicinchoninic Acid. Anal. Biochem. 1985, 150, 76-85.