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Synthetic Peptide Analogs of Somatostatin: Trends in the Synthesis of and Prospects in the Search for New Anticancer Drugs

  • MOLECULAR-BIOLOGICAL PROBLEMS OF DRUG DESIGN AND MECHANISM OF DRUG ACTION
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Pharmaceutical Chemistry Journal Aims and scope

The native hormone somatostatin plays an important role in vivo by acting on multiple targets via a family of five receptors to produce a broad spectrum of biological effects. Some peptide analogs of this enzyme are widely used in clinical practice. However, their clinical efficacy is limited because of some disadvantages. In this respect, the search for new drugs of this type is a critical task. In this review, we have summarized trends in the synthesis and biological effects of peptide somatostatin analogs since 1978 and future prospects for the development of these anticancer drugs.

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References

  1. W. Vale, P. Brazeau, G. Grant, et al., C. R. Hebd. Seances Acad. Sci., Ser. D, 275(25), 2913 – 2916 (1972).

    CAS  Google Scholar 

  2. P. Brazeau, W. Vale, R. Burgus, et al., Science, 179(4068), 77 – 79 (1973).

    Article  CAS  PubMed  Google Scholar 

  3. L. Pradayrol, H. Jornvall, V. Mutt, and A. Ribet, FEBS Lett., 109(1), 55 – 58 (1980).

    Article  CAS  PubMed  Google Scholar 

  4. S. Reichlin, N. Engl. J. Med., 309(25), 1556 – 1563 (1983).

    Article  CAS  PubMed  Google Scholar 

  5. T. L. Aleinikova, L. V. Avdeeva, and L. E. Andrianova, Biochemistry [in Russian], E. S. Severin (ed.), GEOTAR-Media, Moscow (2009), pp. 250 – 258.

    Google Scholar 

  6. I. I. Dedov, G. A. Mel'nichenko, and V. F. Fadeev, Endocrinology [in Russian], GEOTAR-Media, Moscow (2007), pp. 50 – 57.

    Google Scholar 

  7. L. Buscail, F. Vernejoul, P. Faure, et al., Ann. Endocrinol., 63(2), 13 – 18 (2002).

    Google Scholar 

  8. G. Olias, S. Viollet, H. Kusserow, et al., J. Neurochem., 89(5), 1057 – 1091 (2004).

    Article  CAS  PubMed  Google Scholar 

  9. M. Appetecchia and R. Baldelli, J. Exp. Clin. Cancer Res., 29:19, 1 – 12 (March, 2010).

  10. A. Nagy and A. V. Schally, Curr. Pharm. Des., 11(9), 1167 – 1180 (2005).

    Article  CAS  PubMed  Google Scholar 

  11. A. Kleemann, J. Engel, B. Kutscher, and D. Reichert, Pharmaceutical Substances: Syntheses, Patents, Applications, 5th Ed., Thieme, Germany (2009), pp. 994 – 996.

    Google Scholar 

  12. R. Barrie, E. A. Woltering, H. Hajarizadeh, et al., J. Surg. Res., 55(4), 446 – 450 (1993).

    Article  CAS  PubMed  Google Scholar 

  13. N. G. de la Torre, J. A. H. Wass, and H. E. Turner, Clin. Endocrinol. (Oxford, U. K.), 57(4), 425 – 441 (2002).

    Article  Google Scholar 

  14. R. L. Adams, I. P. Adams, S. W. Lindow, et al., Br. J. Cancer, 92(8), 1493 – 1498 (2005).

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  15. M. Kilian, J. I. Gregor, I. Heukamp, et al., Clin. Exp. Metastasis, 26(7), 719 – 727 (2009).

    Article  CAS  PubMed  Google Scholar 

  16. Y. C. Patel, Front. Neuroendocrinol., 20(3), 157 – 198 (1999).

    Article  CAS  PubMed  Google Scholar 

  17. W. Meyerhof, Rev. Physiol., Biochem. Pharmacol., 133, 55 – 108 (1998).

    CAS  Google Scholar 

  18. D. Rosskopf, M. Schurks, I. Manthey, et al., Am. J. Physiol.: Cell Physiol., 284(1), 179 – 190 (2003).

    Article  Google Scholar 

  19. J. P. Hannon, C. Nunn, B. Stolz, et al., J. Mol. Neurosci., 18(1 – 2), 15 – 27 (2002).

    Article  CAS  PubMed  Google Scholar 

  20. G. Weckbecker, I. Lewis, R. Albert, et al., Nat. Rev. Drug Discovery, 2(12), 999 – 1017, Supplementary information (2003).

  21. C. Bruns, I. Lewis, U. Briner, et al., Eur. J. Endocrinol., 146(5), 707 – 716 (2002).

    Article  CAS  PubMed  Google Scholar 

  22. J. C. Reubi, B. Waser, J. C. Schaer, and J. A. Laissue, Eur. J. Nucl. Med., 28(7), 836 – 846 (2001).

    Article  CAS  PubMed  Google Scholar 

  23. M. C. Champaneria, I. M. Modlin, I. Latich, et al., Molecular Targeting in Oncology, Humana Press, Totowa (2008), pp. 585 – 637.

    Book  Google Scholar 

  24. I. M. Chapman, A. Helfgott, and J. O. Willoughby, J. Endocrinol., 128(3), 369 – 374 (1991).

    Article  CAS  PubMed  Google Scholar 

  25. A. V. Schally, Cancer Res., 48(24), 6977 – 6985 (1988).

    CAS  PubMed  Google Scholar 

  26. W. Vale, J. Rivier, N. Ling, and M. Brown, Metab., Clin. Exp., 27(9), 1391 – 1401 (1978).

    Article  CAS  Google Scholar 

  27. D. F. Veber, R. M. Freidinger, D. S. Perlow, et al., Nature, 292(5818), 55 – 58 (1981).

    Article  CAS  PubMed  Google Scholar 

  28. A. G. Harris, Gut, 35(Suppl. 3), S1-S4 (1994).

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  29. J. Epelbaum, Prog. Neurobiol., 27(1), 63 – 100 (1986).

    Article  CAS  PubMed  Google Scholar 

  30. R. Z. Cai, B. Szoke, R. Lu, et al., Proc. Natl. Acad. Sci. USA, 83(6), 1896 – 1900 (1986).

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  31. R. Z. Cai, T. Karashima, J. Guoth, et al., Proc. Natl. Acad. Sci. USA, 84(6), 2502 – 2506 (1987).

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  32. I. Gottesman, J. Tobert, R. Vandlen, and J. Gerich, Life Sci., 38(24), 2211 – 2219 (1986).

    Article  CAS  PubMed  Google Scholar 

  33. G. Melen-Mucha and M. Pawlikowski, Somatostatin Analogs in Diagnostics and Therapy, Landes Bioscience, Austin (2007), pp. 91 – 100.

    Google Scholar 

  34. W. Bauer, U. Briner, W. Doepfner, et al., Life Sci., 31(11), 1133 – 1140 (1982).

    Article  CAS  PubMed  Google Scholar 

  35. A. J. Czernik and B. Petrack, J. Biol. Chem., 258(9), 5525 – 5530 (1983).

    CAS  PubMed  Google Scholar 

  36. D. F. Veber, R. Saperstein, R. F. Nutt, et al., Life Sci., 34(14), 1371 – 1378 (1984).

    Article  CAS  PubMed  Google Scholar 

  37. J. E. Taylor, A. E. Bogden, J. P. Moreau, and D. H. Coy, Biochem. Biophys. Res. Commun., 153(1), 81 – 86 (1988).

    Article  CAS  PubMed  Google Scholar 

  38. H. A. Schmid and A. P. Silva, J. Endocrinol. Invest., 28(11 Suppl. International), 28 – 35 (2005).

  39. P. M. Stewart, K. F. Kane, S. E. Stewart, et al., J. Clin. Endocrinol. Metab., 80(11), 3267 – 3272 (1995).

    CAS  PubMed  Google Scholar 

  40. E. Bajetta, G. Procopio, L. Catena, et al., Cancer, 107(10), 2474 – 2481 (2006).

    Article  CAS  PubMed  Google Scholar 

  41. H. Kessler, Angew. Chem., Int. Ed., 21(7), 512 – 523 (1982).

    Article  Google Scholar 

  42. C. Gilon, M. Huenges, B. Matha, et al., J. Med. Chem., 41(6), 919 – 929 (1998).

    Article  CAS  PubMed  Google Scholar 

  43. E. Falb, Y. Salitra, T. Yechezkel, et al., Biooorg. Med. Chem., 9(12), 3255 – 3264 (2001).

    Article  CAS  Google Scholar 

  44. M. Afargan, E. T. Janson, G. Geleman, et al., Endocrinology, 142(1), 477 – 486 (2001).

    Article  CAS  PubMed  Google Scholar 

  45. A. Carotenuto, D. D’Addona, E. Rivalta, et al., Lett. Org. Chem., 2(3), 274 – 279 (2005).

    Article  CAS  Google Scholar 

  46. D. D’Addona, A. Carotenuto, E. Novellino, et al., J. Med. Chem., 51(3), 512 – 520 (2008).

    Article  PubMed  Google Scholar 

  47. A. Di Cianni, A. Carotenuto, D. Brancaccio, et al., J. Med. Chem., 53(16), 6188 – 6197 (2010).

    Article  PubMed  Google Scholar 

  48. P. Martin-Gago, R. Ramon, E. Aragon, et al., Bioorg. Med. Chem. Lett., 24(1), 103 – 107 (2014).

    Article  CAS  PubMed  Google Scholar 

  49. G. Fridkin, T. Maina, B. A. Nock, et al., Bioorg. Med. Chem., 19(2), 798 – 806 (2011).

    Article  CAS  PubMed  Google Scholar 

  50. J. Chatterjee, C. Gilon, A. Hoffman, and H. Kessler, Acc. Chem. Res., 41(10), 1331 – 1342 (2008).

    Article  CAS  PubMed  Google Scholar 

  51. J. Chatterjee, B. Laufer, J. G. Beck, et al., ACS Med. Chem. Lett., 2(7), 509 – 514 (2011).

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  52. E. Biron, J. Chatterjee, O. Ovadia, et al., Angew. Chem., Int. Ed., 47(14), 2595 – 2599 (2008).

    Article  CAS  Google Scholar 

  53. W. G. Rajeswaran, S. J. Hocart, W. A. Murphy, et al., J. Med. Chem., 44(9), 1416 – 1421 (2001).

    Article  CAS  PubMed  Google Scholar 

  54. J. Erchegyi, R. Cescato, B.Waser, et al., J. Med. Chem., 54(17), 5981 – 5987 (2011).

    Article  CAS  PubMed  Google Scholar 

  55. J. Erchegyi, B. Penke, L. Simon, et al., J. Med. Chem., 46(26), 5587 – 5596 (2003).

    Article  CAS  PubMed  Google Scholar 

  56. J. C. Reubi, J. C. Schaer, S. Wenger, et al., Proc. Natl. Acad. Sci. USA, 97(25), 13973 – 13978 (2000).

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  57. J. Erchegyi, B. Waser, J. C. Schaer, et al., J. Med. Chem., 46(26), 5597 – 5605 (2003).

    Article  CAS  PubMed  Google Scholar 

  58. G. Liapakis, C. Hoeger, J. Rivier, and T. Reisine, J. Pharmacol. Exp. Ther., 276(3), 1089 – 1094 (1996).

    CAS  PubMed  Google Scholar 

  59. J. Erchegyi, R. Cescato, C. R. R. Grace, et al., J. Med. Chem., 52(9), 2733 – 2746 (2009).

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  60. R. Ramon, P. Martin-Gago, X. Verdaguer, et al., ChemBioChem, 12(4), 625 – 631 (2011).

    Article  CAS  PubMed  Google Scholar 

  61. S. Staykova, E. Naydenova, D. Wesselinova, et al., Protein Pept. Lett., 19(12), 1257 – 1262 (2012).

    Article  CAS  PubMed  Google Scholar 

  62. S. T. Staykova, B. D. Mihaylova, I. G. Goshev, et al., Bulg. Chem. Commun., 44(3), 233 – 237 (2012).

    CAS  Google Scholar 

  63. S. J. Hocart, R. Jain, W. A. Murphy, et al., J. Med. Chem., 42(11), 1863 – 1871 (1999).

    Article  CAS  PubMed  Google Scholar 

  64. T.-A. Tran, R.-H. Mattern, M. Afargan, et al., J. Med. Chem., 41(15), 2679 – 2685 (1998).

    Article  CAS  PubMed  Google Scholar 

  65. R. H. Mattern, S. B. Moore, T. A. Tran, et al., Tetrahedron, 56(50), 9819 – 9831 (2000).

    Article  CAS  Google Scholar 

  66. C. Caumes, T. Hjelmgaard, O. Roy, et al., MedChemComm, 3(12), 1531 – 1535 (2012).

    Article  CAS  Google Scholar 

  67. K. Gademann, T. Kimmerlin, D. Hoyer, and D. Seebach, J. Med. Chem., 44(15), 2460 – 2468 (2001).

    Article  CAS  PubMed  Google Scholar 

  68. K. Gademann and D. Seebach, Helv. Chim. Acta, 84(10), 2924 – 2937 (2001).

    Article  CAS  Google Scholar 

  69. A. Nagy, A. V. Schally, G. Halmos, et al., Proc. Natl. Acad. Sci. USA, 95(4), 1794 – 1799 (1998).

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  70. S. Radulovic, A. Nagy, B. Szoke, and A. V. Schally, Cancer Lett., 62(3), 263 – 271 (1992).

    Article  CAS  PubMed  Google Scholar 

  71. A. Saveanu, E. Lavaque, G. Gunz, et al., J. Clin. Endocrinol. Metab., 87(12), 5545 – 5552 (2002).

    Article  CAS  PubMed  Google Scholar 

  72. D. Ferone, A. Saveanu, M. D. Culler, et al., Eur. J. Endocrinol., 156, S23-S28 (2007).

    Article  CAS  PubMed  Google Scholar 

  73. G. Keri, J. Erchegyi, A. Horvath, et al., Proc. Natl. Acad. Sci. USA, 93(22), 12513 – 12518 (1996).

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  74. G. Keri, I. Mezo, Z. Vadasz, et al., Pept. Res., 6(5), 281 – 288 (1993).

    CAS  PubMed  Google Scholar 

  75. B. Szende and G. Keri, Anti-Cancer Drugs, 14(8), 585 – 588 (2003).

    Article  CAS  PubMed  Google Scholar 

  76. T. Vantus, G. Keri, Z. Krivickiene, et al., Cell. Signalling, 13(10), 717 – 725 (2001).

    Article  CAS  PubMed  Google Scholar 

  77. A. Miyazaki, Y. Tsuda, S. Fukushima, et al., J. Med. Chem., 51(16), 5121 – 5124 (2008).

    Article  CAS  PubMed  Google Scholar 

  78. I. Kuriyama, A. Miyazaki, Y. Tsuda, et al., Bioorg. Med. Chem., 21(2), 403 – 411 (2013).

    Article  CAS  PubMed  Google Scholar 

  79. I. Kuriyama, A. Miyazaki, Y. Tsuda, et al., Anticancer Res., 30(12), 4841 – 4850 (2010).

    CAS  PubMed  Google Scholar 

  80. L. I. Smirnova, S. V. Ustinkina, A. P. Smirnova, et al., RU Pat. No. 2,254,139, Jun. 20, 2005; Chem. Abstr., 143, 53473 (2005).

  81. I. Yu. Kubasova, L. M. Borisova, M. P. Kiseleva, et al., Ross. Bioterapevticheskii Zh., 5(3), 128 – 133 (2006).

    Google Scholar 

  82. Z. S. Shprakh, I. V. Yartseva, E. V. Ignat'eva, et al., Khim-farm. Zh., 48(3), 19 – 22 (2014); Pharm. Chem. J., 48(3), 159 – 162 (2014).

  83. A. N. Balaev, V. N. Osipov, V. E. Fedorov, et al., Ross. Bioterapevticheskii Zh., 11(4), 47 – 53 (2012).

    CAS  Google Scholar 

  84. A. N. Balaev, V. N. Osipov, V. E. Fedorov, et al., Ross. Bioterapevticheskii Zh., 12(3), 57 – 60 (2013).

    CAS  Google Scholar 

  85. E. I. Mikhaevich and M. A. Krasil'nikov, Byull. Eksp. Biol. Med., 154(11), 629 – 632 (2012).

    Google Scholar 

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Acknowledgments

The review was supported by the Russian Federation Ministry of Education and Science (under the auspices of Contract No. 14.576.21.0044).

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Authors and Affiliations

  1. Pharm-Sintez Company, Moscow, 115419, Russia, Vtoroi Roshchinskii Blvd., 8

    A. N. Balaev & V. N. Osipov

  2. FSUE State Scientific-Research Institute of Chemical Reagents and High Purity Chemical Substances, Moscow, 107076, Russia, Bogorodskii Val, 3

    D. S. Khachatryan

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  1. A. N. Balaev
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  2. V. N. Osipov
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  3. D. S. Khachatryan
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 49, No. 6, pp. 3 – 9, June, 2015.

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Balaev, A.N., Osipov, V.N. & Khachatryan, D.S. Synthetic Peptide Analogs of Somatostatin: Trends in the Synthesis of and Prospects in the Search for New Anticancer Drugs. Pharm Chem J 49, 345–351 (2015). https://doi.org/10.1007/s11094-015-1284-y

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  • DOI: https://doi.org/10.1007/s11094-015-1284-y

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