Biological activity of carbocyclic nucleosides

  • L. A. Agrofoglio
  • S. R. Challand

Abstract

The cellular processing and mechanism of action of carbocyclic nucleosides are in general similar to those of conventional nucleosides. They may undergo progressive phosphorylation to the corresponding mono- di- and triphosphates and any of these activated forms may interact with natural cellular processes. Sometimes the interaction is innocuous and has little or no effect upon cell viability but often significant inhibition of essential biochemical reactions occurs and in these cases measurable effects will be observable. One cellular class of enzymes to which carbocyclic nucleosides are not susceptible is the nucleoside phosphorylases, as a consequence of which they are extremely stable towards sugar—base cleavage.

Keywords

Thymidine Kinase Adenosine Deaminase Human Foreskin Fibroblast Pyrimidine Nucleoside Plaque Reduction Assay 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Borchardt, R., Keller, B., Patel-Thrombe, U. J. Biol. Chem. 1984, 259, 4353.Google Scholar
  2. 2.
    Barbosa, E., Moss, B. J. Biol. Chem. 1978, 253, 7698.Google Scholar
  3. 3.
    Bader, J. P., Brown, N. R., Chiang, P. K., Cantoni, G. L. Virology 1978, 89, 494.CrossRefGoogle Scholar
  4. 4.
    Hoffman, J. L. Arch. Biochem. Biophys. 1980, 205, 132.CrossRefGoogle Scholar
  5. 5.
    Heiland, S., Ueland, P. M. Can. Res. 1982, 42, 1130.Google Scholar
  6. 6.
    Hasobe, M., Mckee, J. G., Borcherding, D. R. et al. Mol. Pharmacol. 1988, 33, 713.Google Scholar
  7. 7.
    (a) Russ, P., Hegedus, L., Kelley, J. et al. Nucleosides Nucleotides 1992, 11, 351. (b) Marquez, V., Bodenteich, M. Nucleosides Nucleotides 1991, 10, 311. (c) Bodenteich, M., Marquez, V. Tetrahedron Lett. 1990, 31, 5977. (d) S. Kim, S., R. Fuller, R., V. Marquez, V. Nucleosides Nucleotides 1990, 9, 663. (e) Paisley, S., Wolfe, M., Borchardt, R. J. Med. Chem. 1989, 32, 1418. (f) Marquez, V., Lim, M., Treanor, S. et al. J. Med. Chem. 1988, 31, 1687. (g) Marquez, V., Tseng, C, Treanor, S., Driscoll, J. Nucleosides Nucleotides 1987, 6, 239. (h) De Clercq, E., Murase, J., Marquez, V. Biochem. Pharmacol. 1991,41, 1821.CrossRefGoogle Scholar
  8. 8.
    Copp, R. R., Marquez, V. E. J. Med. Chem. 1991, 34, 208.CrossRefGoogle Scholar
  9. 9.
    Agbaria, R., Ford, H., Kelley, J. A. et al. Anal. Biochem. 1993, 213, 90.CrossRefGoogle Scholar
  10. 10.
    Driscoll, J. S., Marquez, V. E. Stem Cells (Dayt) 1994, 12, 7.CrossRefGoogle Scholar
  11. 11.
    (a) Yaginuma, S., Muto, N., Tsujino, M. et al. J. Antibiotic. 1981, 34, 359. (b) Hayashi, M., Yaginuma, S., Yoshioka, H., Nakatsu, K. J. Antibiotic. 1981, 34, 675.CrossRefGoogle Scholar
  12. 12.
    De Clercq, E. J. Antimicrob. Agents Chemother. 1985, 28, 84.CrossRefGoogle Scholar
  13. 13.
    (a) Glazer, R. I., Knode, M. C. J. Biol. Chem. 1984, 259, 12964. (b) Inaba, M., Nagashima, S., Tsukagoshi, S., Sakurai, Y. Cancer Res. 1986, 46, 1063. (c) Hoshi, A., Yoshida, M., Ligo, M. et al. Pharmacobio-Dyn. 1986, 9, 202.Google Scholar
  14. 14.
    Obara, T., Shuto, S., Saito, Y. et al. J. Med. Chem. 1996, 39, 3847.CrossRefGoogle Scholar
  15. 15.
    (a) Shuto, S., Obara, T., Torija, M. et al. J. Med. Chem. 1992, 35, 324. (b) Shigeta, S., Mori, S., Baba, M. et al. Antimicrob. Agents Chemother. 1992, 36, 435. (c) Shuto, S., Obara, T., Kosugi, Y. et al. Biomed. Chem. Lett. 1994, 4, 605. (d) Shuto, S., Obara, T., Saito, Y. et al. J. Med. Chem. 1996, 39, 2392.CrossRefGoogle Scholar
  16. 16.
    (a) Borcherding, D. R., Narayanan, S., Hasobe, M. et al. J. Med. Chem. 1988, 31, 1729. (b) Tseng, C K. H., Marquez, V. E., Fuller, R. W. et al. J. Med. Chem. 1989, 32, 1442. (c) Hasobe, M., McKee, J. G., Borcherding, D. R., Borchardt, R. T. Antimicrob. Agents Chemother. 1987, 31, 1849.CrossRefGoogle Scholar
  17. 17.
    (a) Montgomery, J. A. Cancer Res. 1982, 42, 3911. (b) Montgomery, J. A. Med. Res. Rev. 1982, 2, 271.Google Scholar
  18. 18.
    (a) De Clercq, E. Biochem. Pharmacol. 1987, 36, 2567. (b) De Clercq, E. Nucleosides Nucleotides 1994, 13,1271.CrossRefGoogle Scholar
  19. 19.
    (a) Borchardt, R. T., Wu, Y. S. J. Med. Chem. 1974, 17, 862. (b) Borchardt, R. T., Huber, J. A., Wu, Y. S. J. Med. Chem. 1974, 17, 868. (c) Borchardt, R. T. Biochem. Pharmacol. 1975, 24, 1542. (d) Pugh, C S. G., Borchardt, R. T. Biochemistry 1982, 21, 1535. (e) Houston, D. M., Matuszewska, B., Borchardt, R. T. J. Med. Chem. 1985, 28, 478 and references cited in ref. (8). (f) Guranowski, A., Montgomery, J. A., Cantoni, G. L., Chiang, P. K. Biochemistry 1981, 20, 110.CrossRefGoogle Scholar
  20. 20.
    (a) Houston, D. M., Dolence, E. K., Keller, B. T. et al. J. Med. Chem. 1985, 28, 471. (b) Hoffmann, J. L. in Transmethylation, Usdin, E., Borchadrt, R. T., Creveling, C. R., eds, Elsevier/North Holland, New York, 1979, 181.CrossRefGoogle Scholar
  21. 21.
    Ault-Riche, D. B., Lee, Y., Yuan, C S. et al. Mol. Pharmacol. 1993, 43, 989.Google Scholar
  22. 22.
    Bartel, R. L., Borchardt, R. T. Mol. Pharmacol. 1984, 25, 418.Google Scholar
  23. 23.
    Dunham, E. W., Vince, R. J. Pharmacol. Exp. Ther. 1986, 238, 954.Google Scholar
  24. 24.
    Hasobe, M., Liang, H., Ault-Riche, D. B. et al. Antiviral Chem. Chemother. 1993, 4, 245.Google Scholar
  25. 25.
    Coulombe, R. T., Huie, J. M., R. P. Sharma, J. W. Huggins Drug Metab. Dispos. 1993, 21, 555.Google Scholar
  26. 26.
    Patil, S. D., Schneller, S. W., Hosoya, M. et al. J. Med. Chem. 1992, 35, 3372.CrossRefGoogle Scholar
  27. 27.
    Siddiqi, S. M., Chen, X., Schneller, S. W. J. Med. Chem. 1994, 37, 1382.CrossRefGoogle Scholar
  28. 28.
    Wnuk, S. F., Yuan, C.-S., Borchardt, R. T. et al. J. Med. Chem. 1997, 40, 1608.CrossRefGoogle Scholar
  29. 29.
    Shealy, Y. F., O’Dell, C. A., Shannon, W. M., Arnett, G. J. Med. Chem. 1984, 27, 1416.CrossRefGoogle Scholar
  30. 30.
    Secrist, J. A., Montgomery, J. A., Shealy, Y. F. et al. J. Med. Chem. 1987, 30, 746.CrossRefGoogle Scholar
  31. 31.
    Parker, W., Shaddix, S., Allan, P. et al. Mol. Pharmacol. 1991, 41, 245.Google Scholar
  32. 32.
    Price, P., Banerjee, R., Jeffrey, A., Acs, G. Hepatology 1992, 16, 8.CrossRefGoogle Scholar
  33. 33.
    (a) Mason, W. S., Cullen, J., Saputelli, J. et al. Hepatology 1994, 49, 398. (b) Fourel, I., Saputelli, J., Schaffer, P., Mason, W. S. J. Virol. 1994, 1059.CrossRefGoogle Scholar
  34. 34.
    Dong, Z., Zhu, B., Jeffrey, A. Exp. Parasitol 1992, 75, 257.CrossRefGoogle Scholar
  35. 35.
    Borthwick, A. D., Kirk, B. E., Biggadike, K. et al. J. Med. Chem. 1991, 34, 907.CrossRefGoogle Scholar
  36. 36.
    (a) Bisacchi, G. S., Chao, S. T., Bachard, C. et al. Bioorg. Med. Chem. Lett. 1997, 7, 127. (b) Slusarchyk, W. A., Field, A. K., Greytok, J. A. et al. Fifth International Conference on Antiviral Research, Vancouver, B.C., 1992 abstract no. 102; abstract published in Antiviral Res. 1992, Suppl. 1,17, 98.CrossRefGoogle Scholar
  37. 37.
    For similar example of carbocyclic adenosine analogue, see: Madhavan, G. V. B., McGee, D. P. C., Rydzewski, R. M. et al. J. Med. Chem. 1988, 31, 1798.CrossRefGoogle Scholar
  38. 38.
    De Rudder, J., Privat de Garilhe, M. Pathol. Bacteriol. 1966, 14, 369.Google Scholar
  39. 39.
    Cohen, S. S. Prog. Nucleic Acid Res. Mol Biol. 1966, 5, 1.Google Scholar
  40. 40.
    North, T. W., Cohen, S. S. Pharmacol Ther. 1979, 4, 81.CrossRefGoogle Scholar
  41. 41.
    Gentry, G. A., Aswell, J. F. Virology 1975, 65, 294.CrossRefGoogle Scholar
  42. 42.
    Machida, H., Sakada, S., Kuninaka, A., Yoshino, H. Antimicrob. Agents Chemother. 1981, 18, 47.CrossRefGoogle Scholar
  43. 43.
    Sakada, S., Shibuya, S., Machida, H. et al. Nucleic Acids Res. Symp. Ser. 1980, 8, s39.Google Scholar
  44. 44.
    De Clercq, E., Desgranges, C., Herdewijn, P. et al. J. Med. Chem. 1986, 29, 213.CrossRefGoogle Scholar
  45. 45.
    Vince, R., Daluge, S., Lee, H. et al. Science 1993, 221, 1405.CrossRefGoogle Scholar
  46. 46.
    Borthwick, A. D., Evans, D. N., Kirk, B. E. et al. J. Med. Chem. 1990, 33, 179.CrossRefGoogle Scholar
  47. 47.
    Lee, H., Vince, R. J. Pharm. Sci. 1980, 69, 1019.CrossRefGoogle Scholar
  48. 48.
    Shannon, W. M. in Antiviral Agents and Viral Diseases of Man, Galasso, G. J., ed., Raven Press, New York, 1984, chapter 3, p. 55.Google Scholar
  49. 49.
    Robins, R. K., Revenkar, G. R. in Antiviral Drug Development. A Multidisciplinary Approach, De Clercq, E., Walker, R. T., eds, Nato Advanced Study Institutes Series, Series A: Life Sciences, plenum Press, New York, 1987, 143, 11.Google Scholar
  50. 50.
    Baizarini, J., Bernaerts, R., Verbruggen, A., De Clercq, E. Mol. Pharmacol. 1989, 37, 402.Google Scholar
  51. 51.
    Balzarini, J., De Clercq, E., Baumgartner, H. et al. Mol. Pharmacol. 1989, 37, 395.Google Scholar
  52. 52.
    De Clercq, E., Desgranges, C, Herdewijn, P. et al. Proceedings of the Eighth International Symposium on Medicinal Chemistry, Nilsson, J. L. G., Dahlbom, R., eds, Swedish Pharmaceutical Press, Stockholm, 1985, 198.Google Scholar
  53. 53.
    Herdewijn, P., De Clercq, E., Balzarini, J., Vanderhaeghe, H. J. Med. Chem. 1985, 28, 550.CrossRefGoogle Scholar
  54. 54.
    Balzarini, J., De Clercq, E., Herdewijn, P., Robins, M. J. Mol. Pharmacol. 1985, 27, 578.Google Scholar
  55. 55.
    Shimada, N., Hasegawa, S., Harada, T. et al. J. Antibiot. 1986, 39, 1623.CrossRefGoogle Scholar
  56. 56.
    Norbeck, D. W., Kern, E., Hayashi, S. et al. J. Med. Chem. 1990, 33, 1285.CrossRefGoogle Scholar
  57. 57.
    (a) Hayashi, S., Norbeck, D. W., Rosenbrook, W. et al. Antimicrob. Agents Chemother. 1990, 34, 287. (b) Field, A. K., Tuomari, A. V., McGeever-Rubin, B. et al. Antiviral Res. 1990, 13, 41. (c) Maruyama, T., Sato, Y., Horii, T. et al. Chem. Pharm. Bull. 1990, 38, 2719.CrossRefGoogle Scholar
  58. 58.
    Hoshino, H., Shimizu, N., Shimada, N. et al. J. Antibiot. 1987, 40, 1077.CrossRefGoogle Scholar
  59. 59.
    (a) Shimada, S., Hasegawa, S., Saito, T. et al. J. Antibiot. 1987, 40, 1788. (b) Honjo, M., Maruyama, T., Sato, S., Horii, T. Chem. Pharm. Bull. 1989, 37, 1413. (c) Norbeck, D. W., Kern, E., Hayashi, S. et al. J. Med. Chem. 1990, 33, 1281. (e) Bisacchi, G., Braitman, A., Cianci, C W. et al. J. Med. Chem. 1991, 34, 1415. (f) Norbeck, D. W., Plattner, J., Rosen, T. J. et al. European Patent 0366059 A-2, May 2, 1990. (g) Kitagawa, M., Hasegawa, S., Saito, S. Tetrahedron Lett. 1991, 32, 3531.CrossRefGoogle Scholar
  60. 60.
    (a) Nishiyama, Y., Yamamoto, N., Takahash, K., Shimada, N. Antimicrob. Agents Chemother. 1988, 32, 1053. (b) Daikoku, T., Yamamoto, N., Saito, S. et al. Biochem. Biophys. Res. Commun. 1991, 176, 805.CrossRefGoogle Scholar
  61. 61.
    Sakuma, T., Saijo, M., Suzutani, T. et al. Antimicrob. Agents Chemother. 1991, 35, 1512.CrossRefGoogle Scholar
  62. 62.
    Nagahata, T., Kitagawa, M., Matsubara, K. Antimicrob. Agents Chemother. 1994, 38, 707.CrossRefGoogle Scholar
  63. 63.
    (a) Gharbaoui, T., Legraverend, M., Ludwig, O. et al. Tetrahedron 1995, 51, 1641.CrossRefGoogle Scholar
  64. 64.
    Jacobs, G. A., Tino, J. A., Zahler, R. Tetrahedron Lett. 1988, 30, 6955.CrossRefGoogle Scholar
  65. 65.
    Boumchita, H., Legraverend, M., Guilhem, J., Bisagni, E. Heterocycles 1991, 32, 867.CrossRefGoogle Scholar
  66. 66.
    Pecquet, P., Huet, F., Legraverend, M., Bisagni, E. Heterocycles 1992, 34, 739.CrossRefGoogle Scholar
  67. 67.
    Vite, G. D., Tino, J. A., Zahler, R. et al. Bioorg. Med. Chem. Lett. 1993, 3, 1211.CrossRefGoogle Scholar
  68. 68.
    Norbeck, D. W., Sham, H. L., Rosenbrook, W. et al. Nucleosides Nucleotides 1992, 11, 1383.CrossRefGoogle Scholar
  69. 69.
    Gharbaoui, T., Legraverend, M., Bisagni, E. Heterocycles 1992, 34, 739.CrossRefGoogle Scholar
  70. 70.
    (a) Thiers, B. H. Dermatol. Clin. 1990, 8, 583. (b) O’Brien, J. J., Campoli-Richards, D. M. Drugs 1989, 37, 233.Google Scholar
  71. 71.
    Nishiyama, Y., Yamamoto, N., Yamada, Y. et al. J. Antibiot. 1989, 42, 1854.CrossRefGoogle Scholar
  72. 72.
    Rao, S. N. J. Biomol. Struct. Dyn. 1992, 9, 719.CrossRefGoogle Scholar
  73. 73.
    Terry, B. J., Cianci, C W., Hagen, M. E. Mol. Pharmacol. 1991, 40, 591.Google Scholar
  74. 74.
    Shiota, H., Nitta, K., Naito, T. et al. Br. J. Ophthalmol. 1996, 80, 413.CrossRefGoogle Scholar
  75. 75.
    Slusarchyk, W. A., Bisacchi, G. S., Field, K. et al. J. Med. Chem. 1992, 35, 1799.CrossRefGoogle Scholar
  76. 76.
    (a) Nishizono, N., Koibe, N., Yamagata, Y. et al. Tetrahedron Lett. 1996, 37, 7569. (b) Kikuchi, Y., Nishiyama, S., Yamamura, S. et al. Bioorg. Med. Chem. Lett. 1996, 6, 1897. (c) Wu, J., Scneller, S. W., Seley, K. L. J. Med. Chem. 1997, 40, 1401. (d) Maruyama, T., Hanai, Y., Sato, Y. et al. Chem. Pharm. Bull. 1993, 41, 516. (e) Kikuchi, Y., Nishiyama, S., Yamamura, S. et al. Bioorg. Med. Chem. Lett. 1996, 6, 1897. (f) Maruyama, T., Fukuhara, M. Chem. Pharm. Bull. 1996, 44, 1407.CrossRefGoogle Scholar
  77. 77.
    (a) Marquez, V. E., Siddiqui, M. A., Ezzitouni, A. et al. J. Med. Chem. 1996, 39, 3739. (b) Rodriguez, J. B., Marquez, V. E., Nicklaus, M. C. et al. J. Med. Chem. 1994, 37, 3389.CrossRefGoogle Scholar
  78. 78.
    Altona, C., Sundaralingam, M. J. Am. Chem. Soc. 1972, 94, 8205.CrossRefGoogle Scholar
  79. 79.
    Siddiqui, M. A., Ford, H., Jr., George, C., Marquez, V. E. Nucleosides Nucleotides 1996, 15, 235.CrossRefGoogle Scholar
  80. 80.
    Shealy, Y. F., O’Dell, C. A., Shannon, W. M., Arnett, G. J. Med. Chem. 1983, 26, 156.CrossRefGoogle Scholar
  81. 81.
    Shealy, Y. F., O’Dell, C A., Arnett, G., Shannon, W. M. J. Med. Chem. 1986, 29, 79.CrossRefGoogle Scholar
  82. 82.
    (a) Vince, R., Hua, M., Brownell, J. et al. Biochem. Biophys. Res. Commun. 1988, 156, 1046. (b) Vince, R., Hua, M. J. Med. Chem. 1990, 33, 17. (c) Vince, R. Nucleic Acids Symp. Ser. 1991,25, 193.CrossRefGoogle Scholar
  83. 83.
    Coates, J., Ingall, H., Pearson, B. et al. Antiviral Res. 1991, 161.Google Scholar
  84. 84.
    Carter, S., Kessler, J., Rankin, C Antimicrob. Agents Chemother. 1990, 34, 1297.CrossRefGoogle Scholar
  85. 85.
    Bondoc, L., Shannon, W., Secrist, J. et al. Biochemistry 1990, 29, 9839.CrossRefGoogle Scholar
  86. 86.
    (a) Orr, D., Figueiredo, H., Mo, C.-L. et al. J. Biol. Chem. 1992, 267, 4177. (b) White, E. L., Parker, W. B., Ross, L. J., Shannon, W. M. Antiviral. Res. 1993, 22, 295.Google Scholar
  87. 87.
    (a) Patanella, J., Walsh, J. Drug Metab. Dispos. 1992, 20, 912. (b) Patanella, J. E., Walsh, J. S., Unger, S. E. et al. Drug. Metab. Dispos. 1990, 18, 1092. (c) Walsh, J. S., Patanella, J. E., Unger, S. E. et al. Drug. Metab. Dispos. 1990, 18, 1084.Google Scholar
  88. 88.
    (a) Parker, W., Shaddix, S., Bowdon, B. et al. Antimicrob. Agents Chemother. 1993, 37, 144. (c) Miller, W., Daluge, S., Garvey, E. et al. J. Biol. Chem. 1992, 267, 21220. (d) Parker, W., White, E., Shaddix, S. et al. J. Biol. Chem. 1991, 266, 1754. (e) Yeom, Y. H., Remmel, R. P., Huang, S. H. et al. Antimicrob. Agents Chemother. 1989, 33, 171. (f) Huang, S. H., Remmel, R. P., Zimmerman, C. L. Pharm. Res. 1991, 8, 739. (g) Soria, I., Zimmerman, C L. Pharm. Res. 1994, 11, 267. (h) Soria, I., Zimmerman, C. L. Drug. Metab. Dispos. 1993, 21, 724.CrossRefGoogle Scholar
  89. 89.
    Daluge, S. M., Good, S. S., Faletto, M. B. et al. Antimicrob. Agents Chemother.. 1997, 1082.Google Scholar
  90. 90.
    Faletto, M. B., Miller, W. H., Garvey, E. P. et al. Antimicrob. Agents Chemother. 1997, 41, 1099.Google Scholar
  91. 91.
    Tisdale, M., Alnadaf, T., Cousens, D. Antimicrob. Agents Chemother. 1997, 41, 1094.Google Scholar
  92. 92.
    Ho, H. T., Hitchcock, M. J. M. Antimicrob. Agents Chemother. 1989, 33, 884.CrossRefGoogle Scholar
  93. 93.
    Garvey, E., Krenitsky, T. A. Arch. Biochem. Biophys. 1992, 296, 161.CrossRefGoogle Scholar
  94. 94.
    Good, S. S., Daluge, S. M., Ching, S. V. et al. Antiviral Res. 1995, 26, A229.Google Scholar
  95. 95.
    McDowell, J., Symonds, W. T., Kumar, P. N. et al. in Abstracts of the 35th Interscience Conferences on Antimicrobial Agents and Chemotherapy, American Society for Microbiology, Washington DC, 1995, abstract no. 1109, p. 224.Google Scholar
  96. 96.
    Ching, S. V., Ayers, K. M., Dornsife, R. E. et al. in Abstract of the 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, American Society for Microbiology, Washington DC, 1994, abstract no. 188, p. 92.Google Scholar
  97. 97.
    Skolnik, P. R., Kosloff, B. R., Hirsch, M. S. J. Infect. Dis. 1988, 157, 508.CrossRefGoogle Scholar
  98. 98.
    Lusso, P., Ensoli, B., Markham, P. D. et al. Nature 1989, 337, 370.CrossRefGoogle Scholar
  99. 99.
    (a) Oxenrider, K., Bu, G., Sitz, T. FEBS Lett. 1993, 316, 273. (b) Zimmerman, C., Remmel R., Ibrahim, S. et al. Drug Metab. Dispos. 1992, 20, 47. (c) Smolenski, R., Montero, C, Duley, J., Simmonds, H. Biochem. Pharmacol. 1991, 42, 1767.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1998

Authors and Affiliations

  • L. A. Agrofoglio
    • 1
  • S. R. Challand
    • 2
  1. 1.Université d’OrléansOrléansFrance
  2. 2.BeckenhamUK

Personalised recommendations