Artículos de revistas
Site-specific Modification Of The Anticancer And Antituberculosis Polyether Salinomycin By Biosynthetic Engineering
Registro en:
Chembiochem. Wiley-vch Verlag, v. 15, n. 14, p. 2081 - 2085, 2014.
14394227
10.1002/cbic.201402300
2-s2.0-84908176671
Autor
Luhavaya H.
Williams S.R.
Hong H.
De Oliveira L.G.
Leadlay P.F.
Institución
Resumen
Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) The complex bis-spiroacetal polyether ionophore salinomycin has been identified as a uniquely selective agent against cancer stem cells and is also strikingly effective in an animal model of latent tuberculosis. The basis for these important activities is unknown. We show here that deletion of the salE gene abolishes salinomycin production and yields two new analogues, in both of which the C18=C19 cis double bond is replaced by a hydroxy group stereospecifically located at C19, but which differ from each other in the configuration of the bis-spiroacetal. These results identify SalE as a novel dehydratase and demonstrate that biosynthetic engineering can be used to redirect the reaction cascade of oxidative cyclization to yield new salinomycin analogues for use in mechanism-of-action studies. 15 14 2081 2085 BBSRC; Biotechnology and Biological Sciences Research Council; Biotechnology and Biological Sciences Research Council; 2011/17510-6; FAPESP; Biotechnology and Biological Sciences Research Council Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Li, J., Cisar, J.S., Zhou, C.-Y., Vera, B., Williams, H., Rodriguez, A.D., Cravatt, B.F., Romo, D., (2013) Nat. Chem., 5, pp. 510-517 Weissman, K.J., Leadlay, P.F., (2005) Nat. Rev. Microbiol., 3, pp. 925-936 Hertweck, C., (2009) Angew. Chem. Int. Ed., 48, pp. 4688-4716 (2009) Angew. Chem., 121, pp. 4782-4811 Kendrew, S.G., Petkovic, H., Gaisser, S., Ready, S.J., Gregory, M.A., Coates, N.J., Nur-E-Alam, M., Wilkinson, B., (2013) Metab. Eng., 15, pp. 167-173 Moss, S.J., Stanley-Smith, A.E., Schell, U., Coates, N.J., Foster, T.A., Gaisser, S., Gregory, M.A., Wilkinson, B., (2013) MedChemComm, 4, pp. 324-331 Yurkovich, M.E., Tyrakis, P.A., Hong, H., Sun, Y., Samborskyy, M., Kamiya, K., Leadlay, P.F., (2012) ChemBioChem, 13, pp. 66-71 Jiang, C., Wang, H., Kang, Q., Liu, J., Bai, L., (2012) Appl. Environ. Microbiol., 78, pp. 994-1003 Gupta, P.B., Onder, T.T., Jiang, G., Tao, K., Kuperwasser, C., Weinberg, R.A., Lander, E.S., (2009) Cell, 138, pp. 645-659 Zobalova, R., Stantic, M., Stapelberg, M., Prokopova, K., Dong, L., Truksa, J., Neuzil, J., (2011) Cancer Stem Cells Theories and Practice, pp. 361-378. , (Ed.: S. Shostak), InTech, Rijeka Kopp, F., Hermawan, A., Oak, P.S., Herrmann, A., Wagner, E., Roidl, A., (2014) Mol. Cancer, 13, p. 16 Sala, C., Dhar, N., Hartkoorn, R.C., Zhang, M., Ha, Y.H., Schneider, P., Cole, S.T., (2010) Antimicrob. Agents Chemother., 54, pp. 4150-4158 Zhou, S., Wang, F., Wong, E.T., Fonkem, E., Hsieh, T.-C., Wu, J.M., Wu, E., (2013) Curr. Med. Chem., 20, pp. 4095-4101 Aho, J.E., Pihko, P.M., Rissa, T.K., (2005) Chem. Rev., 105, pp. 4406-4440 Antoszczak, M., Popiel, K., Stefańska, J., Wietrzyk, J., Maj, E., Janczak, J., Michalska, G., Huczyński, A., (2014) Eur. J. Med. Chem., 76, pp. 435-444 Borgström, B., Huang, X., Posta, M., Hegardt, C., Oredsson, S., Strand, D., (2013) Chem. Commun., 49, pp. 9944-9946 Leadlay, P.F., Staunton, J., Oliynyk, M., Bisang, C., Cortes, J., Frost, E., Hughes-Thomas, Z.A., Wilkinson, C.J., (2001) J. Ind. Microbiol. Biotechnol., 27, pp. 360-367 Gomez-Escribano, J.P., Bibb, M.J., (2011) J. Microb. Biotechnol., 4, pp. 207-215 Jones, A.C., Gust, B., Kulik, A., Heide, L., Buttner, M.J., Bibb, M.J., (2013) PLoS ONE, 8 Sun, P., Zhao, Q., Yu, F., Zhang, H., Wu, Z., Wang, Y., Wang, Y., Liu, W., (2013) J. Am. Chem. Soc., 135, pp. 1540-1548 Takahashi, S., Toyoda, A., Sekiyama, Y., Takagi, H., Nogawa, T., Uramoto, M., Suzuki, R., Osada, H., (2011) Nat. Chem. Biol., 7, pp. 461-468 Favre, S., Vogel, P., Gerber-Lemaire, S., (2008) Molecules, 13, pp. 2570-2600 Tosin, M., Demydchuk, Y., Parascandolo, J.S., Per, C.B., Leeper, F.J., Leadlay, P.F., (2011) Chem. Commun., 47, pp. 3460-3462 Tosin, M., Smith, L., Leadlay, P.F., (2011) Angew. Chem. Int. Ed., 50, pp. 11930-11933 (2011) Angew. Chem., 123, pp. 12136-12139 Pöplau, P., Frank, S., Morinaka, B.I., Piel, J., (2013) Angew. Chem. Int. Ed., 52, pp. 13215-13218 (2013) Angew. Chem., 125, pp. 13457-13460 Zhang, M.-Q., Gaisser, S., Nur-E-Alam, M., Sheehan, L.S., Vousden, W.A., Gaitatzis, N., Peck, G., Martin, C.J., (2008) J. Med. Chem., 51, pp. 5494-5497