Biokoniugaty antybiotykow jonoforowych : cele, strategie syntezy i właściwości

Antoszczak, M.; Kordylas, M.; Huczyński, A.

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Tytuł artykułu

Biokoniugaty antybiotykow jonoforowych : cele, strategie syntezy i właściwości

Autorzy

Antoszczak M. , Kordylas M. , Huczyński A.

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Warianty tytułu

Bioconjugates of ionophore antibiotics : goals, synthesis strategies and properties

Języki publikacji

Abstrakty

Polyether ionophore antibiotics (ionophores) represent a large group of naturally- occurring lipophilic compounds which are able to form complexes with the metal cations and transport them across the lipid membranes. This process disturbs the intercellular Na⁺/K⁺ concentration gradient and intracellular pH, and leads to the mitochondrial damages, cell swelling, vacuolization and finally to apoptosis process. For this reason, ionophores are commonly used in veterinary medicine as the non-hormonal growth-promoting as well as coccidiostatic agents. In this group particularly interesting are monensin and salinomycin (Fig. 1) because of their proved anti-tumour activity, including efficiency against multidrug- -resistant cancer cells and cancer stem cells of different origin. Improved synthetic derivatives of both polyether ionophores are thus of considerable current interest. Selective derivatization of these structures whose display multiple reactive functional groups and, in the case of salinomycin, a sensitive tricyclic spiroketal ring system is however non-trivial. Even so, semi-synthetic analogs reported to date includes i.a. selective derivatization of the carboxyl group, the three hydroxyl groups, the ketone group, the alkene, and epimerization of the characteristic tricyclic salinomycin unit (for more details see: M. Antoszczak, A. Huczyński, B. Brzezinski, Wiad. Chem., 2017, 71, 629). On the other hand, as part of the original program to develop innovatory anti- -cancer pro-drugs and prompted by the idea that cancer cells may be individually effectively killed by monensin and salinomycin, a very interesting direction of research is bioconjugation of these ionophores. In this context, our review article is focused on the possible role of hybrids of both ionophore antibiotics with other biologically active substances (natural amino acids, Cinchona alkaloids, flavonoids, nucleosides) in anti-bacterial and anti-cancer treatment, and gives an overview of their properties.

Słowa kluczowe

antybiotyki jonoforowe jonofory biokoniugacja hybrydy aktywność przeciwbakteryjna aktywność przeciwnowotworowa

ionophore antibiotics ionophores bioconjugation hybrids antibacterial activity anticancer activity

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2018

Tom

[Z] 72, 1-2

Strony

1--28

Opis fizyczny

Bibliogr. 72 poz., schem., tab.

Twórcy

autor

Antoszczak M.

michant@amu.edu.pl

Pracownia Chemii Bioorganicznej, Wydział Chemii, Uniwersytet im. Adama Mickiewicza, ul. Umultowska 89b, 61‒614 Poznań

autor

Kordylas M.

Pracownia Chemii Bioorganicznej, Wydział Chemii, Uniwersytet im. Adama Mickiewicza, ul. Umultowska 89b, 61‒614 Poznań

autor

Huczyński A.

Pracownia Chemii Bioorganicznej, Wydział Chemii, Uniwersytet im. Adama Mickiewicza, ul. Umultowska 89b, 61‒614 Poznań

Bibliografia

[1] World Health Organization – Cancer, [dostęp: 2018-01-31]. Dostępny w Internecie: http://www.who.int/cancer/en/
[2] V.T. DeVita Jr., E. Chu, Cancer Res., 2008, 68, 8643.
[3] B.A. Chabner, T.G. Roberts, Nat. Rev. Cancer, 2005, 5, 65.
[4] The Center for Disease Dynamics, Economics & Policy – raporty, [dostęp: 2018-01-31]. Dostępny w Internecie: http://www.cddep.org
[5] B. Das, G. Satyalakshmi, Mini-Rev. Org. Chem., 2012, 9, 169.
[6] G.M. Cragg, P.G. Grothaus, D.J. Newman, Chem. Rev., 2009, 109, 3012.
[7] D.J. Newman, G.M. Cragg, K.M. Snader, J. Nat. Prod., 2003, 66, 1022.
[8] A. Agtarap, J.W. Chamberlin, M. Pinkerton, L. Steinrauf, J. Am. Chem. Soc., 1967, 89, 5737.
[9] T. Fukuyama, K. Akasaka, D.S. Karanewsky, C.L.J. Wang, G. Schmid, Y. Kishi, J. Am. Chem. Soc., 1979, 101, 262.
[10] Y. Miyazaki, M. Shibuya, H. Sugawara, O. Kawaguchi, C. Hirsoe, J. Antibiot., 1974, 27, 814.
[11] Y. Kishi, S. Hatakeyama, M.D. Lewis, Total synthesis of polyether antibiotics narasin and salinomycin, [w:] Frontiers of Chemistry, [w:] Plenary and Keynote Lectures Presented at the 28th IUPAC Congress, K.J. Laidler (Red.), Oxford 1982, str. 287.
[12] P.J. Kocieński, R.C.D. Brown, A. Pommier, M. Procter, B. Schmidt, J. Chem. Soc., Perkin Trans., 1998, 1, 9.
[13] M.E. Yurkovich, P.A Tyrakis, H. Hong, Y. Sun, M. Samborskyy, K. Kamiya, P.F. Leadley, Chem. Bio. Chem., 2012, 13, 66.
[14] M. Suzuki, R. Ueoka, K. Takada, S. Okada, S. Ohtsuka, Y. Ise, S. Matsunag, J. Nat. Prod., 2012, 75, 1192.
[15] D.H Berg, R.L. Hamill, J. Antibiot, 1978, 31, 1.
[16] J. Rutkowski, B. Brzezinski, BioMed. Res. Int., 2013, 2013, 31
[17] M. Antoszczak, J. Rutkowski, A. Huczyński, Structure and biological activity of polyether ionophores and their semi-synthetic derivatives, [w:] Bioactive Natural Products. Chemistry and Biology, G. Brahmachari (Red.), 1st Edition, Wiley-VCH Verlag GmbH, Weinheim 2015, s. 107.
[18] Y.N. Antonenko, T.I. Rokitskaya, A. Huczyński, Biochim. Biophys. Acta Biomembr., 2015, 1848, 995.
[19] A. Huczyński, J. Janczak, D. Łowicki, B. Brzezinski, Biochim. Biophys. Acta Biomembr., 2012, 1818, 2108.
[20] A. Huczyński, Bioorg. Med. Chem. Lett., 2012, 22, 7002.
[21] S. Zhou, F. Wang, E.T. Wong, E. Fonkem, T.-C. Hsieh, J.M. Wu, E. Wu, Curr. Med. Chem., 2013, 20, 4095.
[22] D.A. Kevin II, D.A.F. Meujo, M.T. Hamann, Exp. Opin. Drug Disc., 2009, 4, 109.
[23] J.W. Westley, Adv. Appl. Microbiol., 1977, 22, 177.
[24] J. Guyot, G. Jeminet, M. Prudhomme, M. Sancelme, R. Meiniel, Lett. Appl. Microbiol., 1993, 16, 192.
[25] M. Mimouni, F.Z. Khardli, I. Warad, M. Ahmad, M.S. Mubarak, S. Sultana, T.B. Hadda, J. Mater. Environ. Sci., 2014, 5, 207.
[26] G.K. Podila, E. Rosen, M.J.D. San Fransisco, P.E. Kolattukudy, Phytopathology, 1995, 85, 238.
[27] D.C. Johnson, P.G. Spear, J. Virol., 1982, 43, 1102.
[28] R. Schlegel, M. Willingham, I. Pastan, Biochem. Biophys. Res. Commun., 1981, 102, 992.
[29] M. Marsh, J. Wellsteed, H. Kerm, Proc. Natl. Acad. Sci. U.S.A., 1982, 79, 5297.
[30] M. Nakamura, S. Kunimoto, Y. Takahashi, H. Naganawa, M. Sakaue, S. Inoue, T. Ohno, T. Takeuchi, Antimicrob. Agents Chemother., 1992, 36, 492.
[31] C. Gumila, M.L. Ancelin, G. Jeminet, A.M. Delort, G. Miquel, H.J. Vial, Antimicrob. Agents Chemother., 1996, 40, 602.
[32] J. Adovelande, J. Schrevel, Life Sci., 1996, 59, 309.
[33] C.M. Liu, T.E. Hermann, A. Downey, B.T. Prosser, E. Schildknecht, H.J. Palleroni, J.W. Westley, P.A. Miller, J. Antibiot, 1983, 36, 343.
[34] K. Ketola, P. Vainio, V. Fey, O. Kallioniemi, K. Iljin, Mol. Cancer Ther., 2010, 9, 3175.
[35] W.H. Park, E.S. Kim, B.K. Kim, Y.Y. Lee, Int. J. Oncol., 2003, 23, 197.
[36] W.H. Park, E.S. Kim, C.W. Jung, B.K. Kim, Y.Y. Lee, Int. J. Oncol., 2003, 22, 377.
[37] W.H. Park, J.G. Seol, E.S. Kim, W.K. Kang, Y.H. Im, C.W. Jung, B.K. Kim, Y.Y. Lee, Br. J. Haematol., 2002, 119, 400.
[38] M.J. Yoon, Y.J. Kang, I.Y. Kim, E.H. Kim, J.A. Lee, J.H. Lim, T.K. Kwon, K.S. Choi, Carcinogenesis, 2013, 34, 1918.
[39] M.S. Shaik, A. Chatterjee, M. Singh, J. Pharm. Pharmacol., 2004, 56, 899.
[40] M. Singh, A.J. Ferdous, N. Kanikkannan, G. Faulkner, Eur. J. Pharm. Biopharm., 2001, 52, 13.
[41] L.V. Nguyen, R. Vanner, P. Dirks, C.J. Eaves, Nat. Rev. Cancer, 2012, 12, 133.
[42] P.B. Gupta, T.T. Onder, G. Jiang, K. Tao, C. Kuperwasser, R.A. Weinberg, E.S. Lander, Cell, 2009, 138, 645.
[43] M. Antoszczak, A. Huczyński, Anticancer Agents Med. Chem., 2015, 15, 575.
[44] C. Naujokat, R. Steinhart, R. J. Biomed. Biotechnol., 2012, 2012, 950968.
[45] J.F. Lutz, Z. Zarafshani, Adv. Drug Deliv. Rev., 2008, 60, 958.
[46] G.R. Zimmermann, J. Lehra, C.T. Keith, Drug Discovery Today, 2007, 12, 34.
[47] J. Sakakibara, A. Nakamura, S.-I. Nagai, T. Ueda, T. Ishida, Chem. Pharm. Bull., 1988, 36, 4776.
[48] A. Nakamura, S.-I. Nagai, T. Ueda, N. Murakami, J. Sakakibara, H. Shibuya, I. Kitagawa, Chem. Pharm. Bull., 1991, 39, 1726.
[49] M. Antoszczak, M. Sobusiak, E. Maj, J. Wietrzyk, A. Huczyński, Bioorg. Med. Chem. Lett., 2015, 25, 3511.
[50] I. Skiera, M. Antoszczak, J. Trynda, J. Wietrzyk, P. Boratyński, K. Kacprzak, A. Huczyński, Chem. Biol. Drug Des., 2015, 86, 911.
[51] M. Antoszczak, G. Klejborowska, M. Kruszyk, E. Maj, J. Wietrzyk, A. Huczyński, Chem. Biol. Drug Des., 2015, 86, 1378.
[52] A. Huczyński, M. Antoszczak, N. Kleczewska, D. Baraniak, E. Maj, J. Stefańska, J. Wietrzyk, J. Janczak, L. Celewicz, Eur. J. Med. Chem., 2015, 93, 33.
[53] M. Antoszczak, E. Maj, N. Kleczewska, J. Wietrzyk, L. Celewicz, A. Huczyński, Med. Chem., 2017, 13, 127.
[54] B.S. Vig, K.M. Huttunen, K. Laine, J. Rautio, Adv. Drug Deliv. Rev., 2013, 65, 1370.
[55] Y. Zhou, C. Liang, F. Xue, W. Chen, X. Zhi, X. Feng, X. Bai, T. Liang, T Oncotarget, 2015, 6, 10350.
[56] W.G. Harker, D.L. Slade, W.S. Dalton, P.S. Meltzer, J.M. Trent, Cancer Res., 1989, 49, 4542.
[57] R.B. Badisa, S.F. Darling-Reed, P. Joseph, J.S. Cooperwood, L.M. Latinwo, C.B. Goldman, Anticancer Res., 2009, 29, 2993.
[58] O. Warburg, Science, 1956, 123, 309.
[59] K. Kacprzak, Chemistry and biology of Cinchona alkaloids, [w:] Handbook of Natural Products – Phytochemistry, Botany, Metabolism, K.G. Ramawat, J.M. Merillon (Red.), Heidelberg: Springer Berlin 2013, s. 605.
[60] E. Solary, L. Mannone, D. Moreau, D. Caillot, R.O. Casasnovas, H. Guy, M. Grandjean, J.E. Wolf, F. Andre, P. Fenaux, P. Canal, B. Chauffert, A. Wotawa, M. Bayssas, P. Genne, Leukemia, 2000, 14, 2085.
[61] D. Baraniak, K. Kacprzak, L. Celewicz, Bioorg. Med. Chem. Lett., 2011, 21, 723.
[62] D.Y. Lee, Y. Liu, J. Nat. Prod., 2003, 66, 1171.
[63] G. Serviddio, F. Bellanti, E. Stanca, P. Lunetti, M. Blonda, R. Tamborra, L. Siculella, G. Vendemiale, L. Capobianco, A.M. Giudetti, Free Radic. Biol. Med., 2014, 73, 117.
[64] R. Gazaak, D. Walterova, V. Křen, Curr. Med. Chem., 2007, 14, 315.
[65] A. Zarelli, V. Romanucci, C. Tuccillo, A. Federico, C. Loguercio, R. Gravante, G. Di Fabio, Bioorg. Med. Chem. Lett., 2014, 24, 5147.
[66] R. Gazak, K. Purchartova, P. Marhol, L. Živna, P. Sedmera, K. Valentova, N. Kato, H. Matsumura, K. Kaihatsu, V. Křen, Eur. J. Med. Chem., 2010, 45, 1059.
[67] M. Rooseboom, J.N. Commandeur, N.P. Vermeulen, Pharmacol. Rev., 2004, 56, 53.
[68] D.G. Power, N.E. Kemeny, Mol. Cancer Ther., 2009, 8, 1015.
[69] F. Wang, W. Dai, Y. Wang, M. Shen, K. Chen, P. Cheng, Y. Zhang, C. Wang, J. Li, Y. Zheng, J. Lu, J. Yang, R. Zhu, H. Zhang, Y. Zhou, L. Xu, C. Guo, PLoS One, 2014, 9, e97414.
[70] R. Yarchoan, H. Mitsuya, C.E. Myers, S.N. Broder, Eng. J. Med., 1989, 232, 726.
[71] C. Carbon, Clin. Microbiol. Infect., 2000, 6, 17.
[72] A.L. Simplicio, J.M. Clancy, J.F. Gilmer, Molecules, 2008, 13, 519.

Uwagi

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

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-03786c8c-dd66-4248-9de3-8356ef8cb11b