Aktywność biologiczna modyfikownych nukleozydów. Część 1

• Autorzy: Szlenkier M.

Warianty tytułu

EN

Biological activity of modified nucleosides. Part 1

• Języki publikacji: PL

Abstrakty

EN

Every year, hundreds of new nucleoside analogues are obtained in laboratories around the world. As early as in 1964, 3’-azidothymidine (AZT) was first synthesized, which turned out to be the main weapon in the fight against HIV viruses 20 years later. Part I of the review includes nucleosides possessing modifications in the base moiety or having other heterocyclic bases. Nucleosides modified in the sugar residue, because of a broad spectrum of examples, will be a subject of part II and III of the review. In the group of analogues modified in the base moiety the following derivatives among others are listed: 5-iodo-2’-deoxyuridine (IDU), E-5-(2- bromovinyl)-2’-deoxyuridine (BVDU), capecitabine – prodrug form of fluorouracil, 7-deazaadenosine, BCX4430 (immucillin-A) – 9-deazaadenosine derivative active against filoviruses such as Ebola virus (EBOV). In the group of nucleosides having a different heterocyclic base the following derivatives are listed: ribavirin (RBV) and its analogues – RBV triphosphate is an inhibitor of many viral enzymes involved in the replication cycle, mizoribine (MZB) – a naturally occurring nucleosidic immunosuppressor, 5-ethynyl-1-β-"-ribofuranosyl-imidazole-4-carboxamide (EICAR) which suppresses development of murine leukemia cell lines and has a broad spectrum of activity against RNA and DNA viruses. The C-nucleosides group includes e.g. oxazinomycin – a natural antibiotic with growth inhibitory properties against gram (+), gram (–) bacteria and sarcoma, and formycin A isolated from Streptomyces lavendulae, which has cytostatic and antiviral activity.

Słowa kluczowe

PL

nukleozydy modyfikowane; aktywność biologiczna; cele molekularne; mechanizm działania

EN

modified nucleosides; biological activity; molecular targets; mechanism of action

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2018
• Tom: [Z] 72, 3-4
• Strony: 109--126
• Opis fizyczny: Bibliogr. 52 poz., schem.

Twórcy

autor

Szlenkier M.

• Instytut Chemii Bioorganicznej Polskiej Akademii Nauk w Poznaniu, ul. Z. Noskowskiego 12/14, 61-704 Poznań

Bibliografia

• [1] J.P. Horwitz, J. Chua, M. Noel, J. Org. Chem., 1964, 29, 2076.
• [2] H. Mitsuya, K.J. Weinhold, P.A. Furman, M.H. St Clair, S.N. Lehrman, R.C. Gallo, D. Bolognesi, D.W. Barry, S. Broder, Proc. Natl. Acad. Sci. USA, 1985, 82, 7096.
• [3] E. De Clercq, J. Neyts, Handb. Exp. Pharmacol., 2009, 189, 53.
• [4] J. Boryski, Nowe tendencje w biologii molekularnej i inżynierii genetycznej oraz medycynie, J. Barciszewski, K. Łastowski, T. Twardowski (Red.), Sorus, Poznań 1996.
• [5] W.H. Prusoff, Biochim. Biophys. Acta, 1959, 32, 295.
• [6] H.C. Herrmann, Exp. Biol. Med., 1961, 107, 142.
• [7] J. Milecki, Na pograniczu chemii i biologii, tom III, J. Barciszewski, H. Koroniak (Red.), Wydawnictwo Naukowe UAM, Poznań 1999.
• [8] E. De Clercq, Biochem. Pharmacol., 2004, 68, 2301.
• [9] E. De Clercq, R.T. Walker, Antiviral Drug Development. A Multidisciplinary Approach, Plenum Press, New York 1988.
• [10] L. Geng, A.M. Huehls, J.M. Wagner, C.J. Huntoon, L.M. Karnitz, PLoS One, 2011, 6, 1.
• [11] C. McGuigan, C.J. Yarnold, G. Jones, S. Velazquez, H. Barucki, A. Brancale, G. Andrei, R. Snoeck, E. De Clercq, J. Balzarini, J. Med. Chem., 1999, 42, 4479.
• [12] C. McGuigan, R.N. Pathirana, R. Snoeck, G. Endrei, E. De Clercq, J. Med. Chem., 2004, 47, 1847.
• [13] C. Heidelberger, S.W. Anderson, Cancer Res., 1964, 24, 1979.
• [14] K.R. Wilhelmus, Cochrane Database Syst. Rev., 2010, 12, CD002898.
• [15] S. Altmann, C.R. Brandt, C.J. Murphy, R. Patnaikuni, T. Takla, J. Infect. Dis., 2011, 203, 683.
• [16] N. Suzuki, T. Emura, M. Fukushima, Int. J. Oncol., 2011, 39, 263.
• [17] N. Shimma, I. Umeda, M. Arasaki, C. Murasaki, K. Masubuchi, Y. Kohchi, M. Miwa, M. Ura, N. Sawada, H. Tahara, I. Kuruma, I. Horii, H. Ishitsuka, Bioorg. Med. Chem., 2000, 8, 1697.
• [18] F. Focher, C. Hildebrand, S. Freese, G. Ciarrocchi, T. Noonan, S. Sangalli, N. Brown, S. Spadari, G. Wright, J. Med. Chem., 1988, 31, 1496.
• [19] E. De Clercq, D.E. Bergstrom, A. Holý, J.A. Montgomery, Antiviral Res., 1984, 4, 119.
• [20] E. De Clercq, R. Bernaerts, D.E. Bergstrom, M.J. Robins, J.A. Montgomery, A. Holý, Antimicrob. Agents Chemother., 1986, 29, 3, 482.
• [21] R.J. Rousseau, L.B. Townsend, R.K. Robins, Biochemistry, 1966, 5, 756.
• [22] A. Hayden, P.W. Johnson, G. Packham, S.J. Crabb, Breast Cancer Res. Treat., 2011, 127, 109.
• [23] P. Franchetti, L. Cappellacci, S. Marchetti, L. Trincavelli, C. Martini, M.R. Mazzoni, A. Lucacchini, M. Grifantini, J. Med. Chem., 2002, 45, 1196.
• [24] G. Burnstock, G.E. Knight, Int. Rev. Cytol., 2004, 240, 301.
• [25] T.K. Warren, J. Wells, R.G. Panchal, K.S. Stuthman, N.L. Garza, S.A. Van Tongeren, L. Dong, C.J. Retterer, B.P. Eaton, G. Pegoraro, S. Honnold, S. Bantia, P. Kotian, X. Chen, B.R. Taubenheim, L.S. Welch, D.M. Minning, Y.S. Babu, W.P. Sheridan, S. Bavari, Nature, 2014, 508, 402.
• [26] T. Haneishi, T. Okazaki, T. Hata, C. Tamura, M. Nomura, A. Naito, I. Seki, M. Arai, J. Antibiot., 1971, 11, 797.
• [27] E. De Clercq, J. Med. Chem., 2016, 59, 2301.
• [28] A. Píscala, F. Šorm, Collect. Czech. Chem. Commun., 1964, 29, 2060.
• [29] D.J. Richel, L.P. Colly, E. Lurvink, R. Willemze, Br. J. Cancer, 1988, 58, 730.
• [30] E. Kaminskas, A.T. Farrell, Y.C. Wang, R. Sridhara, R. Pazdur, Oncologist, 2005, 10, 176.
• [31] C. Stresemann, F. Lyko, Int. J. Cancer, 2008, 123, 8.
• [32] H. Kantarjian, J.P. Issa, C.S. Rosenfeld, J.M. Bennett, A. Albitar, J. DiPersio, V. Klimek, J. Slack, C. de Castro, F. Ravandi, R. Helmer, L. Shen, S.D. Nimer, R. Leavitt, A. Raza, H. Saba, Cancer, 2006, 106, 1794.
• [33] M.J. Dapp, C.L. Clouser, S. Patterson, L.M. Mansky, J. Virol., 2009, 83, 11950.
• [34] P.T. Diamantopoulos, M. Michael, O. Benopoulou, E. Bazanis, G. Tzeletas, J. Meletis, G. Vayopoulos, N.-A. Viniou, Virol. J., 2012, 9, 1.
• [35] R.W. Sidwell, J.H. Huffman, G.P. Khare, L.B. Allen, J.T. Witkowski, R.K. Robins, Science, 1972, 177, 705.
• [36] J.D. Graci, C.E. Cameron, Rev. Med. Virol., 2006, 16, 37.
• [37] S. Crotty, D. Maag, J.J. Arnold, W. Zhong, J.Y.N. Lau, Z. Hong, R. Andino, C.E. Cameron, Nat. Med., 2000, 6, 1375.
• [38] A. Krajczyk, Nukleozydy 4,5-dipodstawione 1,2,3-triazolu i ich pochodne bicykliczne, Rozprawa doktorska, IChB PAN, Poznań 2015.
• [39] R. Zhu, M. Wang, Y. Xia, F. Qu, J. Neyts, L. Peng, Bioorg. Med. Chem. Lett., 2008, 18, 3321.
• [40] J. Wan, Y. Xia, Y. Liu, M. Wang, P. Rocchi, J. Yao, F. Qu, J. Neyts, J.L. Iovanna, L. Peng, J. Med. Chem., 2009, 52, 1144.
• [41] W.Y. Liu, H.Y. Li, B.X. Zhao, D.S. Shin, S. Lian, J.Y. Miao, Carbohyd. Res., 2009, 344, 1270.
• [42] H. Ishikawa, Curr. Med. Chem., 1999, 6, 575.
• [43] N. Minakawa, T. Takeda, T. Sasaki, A. Matsuda, T. Ueda, J. Med. Chem., 1991, 34, 778.
• [44] J. Zeidler, D. Baraniak, T. Ostrowski, Eur. J. Med. Chem., 2015, 97, 409.
• [45] P.C. Srivastava, M.V. Pickering, L.B. Allen, D.G. Streeter, M.T. Campbell, J.T. Witkowski, R.W. Sidwell, R.K. Robins, J. Med. Chem., 1977, 20, 256.
• [46] G. Tricot, H.N. Jayaram, G. Weber, R. Hoffman, Int. J. Cell Cloning, 1990, 8, 161.
• [47] P.C. Srivastava, R.K. Robins, J. Med. Chem., 1983, 26, 445.
• [48] H. Nishimura, M. Mayama, Y. Komatsu, H. Kato, N. Shimaoka, Y. Tanaka, J. Antibiot. (Tokoyo), 1964, 17, 148.
• [49] T. Böttcher, S.A. Sieber, J. Am. Chem. Soc., 2010, 132, 6964.
• [50] H.C. Kolb, M.G. Finn, K.B. Sharpless, Angew. Chem. Int. Ed., 2001, 40, 2004.
• [51] T. Ostrowski, P. Januszczyk, M. Cieslak, J. Kazmierczak-Baranska, B. Nawrot, E. Bartoszak-Adamska, J. Zeidler, Bioorg. Med. Chem., 2011, 19, 4386.
• [52] F. Amblard, J.H. Cho, R.F. Schinazi, Chem. Rev., 2009, 109, 4207.

Uwagi

Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2018).