Artículo

Maisuls, I.; Wolcan, E.; Piro, O.E.; Castellano, E.E.; Petroselli, G.; Erra-Balsells, R.; Cabrerizo, F.M.; Ruiz, G.T. "Synthesis, Structural Characterization and Biological Evaluation of Rhenium(I) Tricarbonyl Complexes with β-Carboline Ligands" (2017) ChemistrySelect. 2(27):8666-8672
Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Two β-carboline rhenium(I) complexes, fac-[Re(CO)3(dppz)(nHo)]O3SCF3 and fac-[Re(CO)3(nHo)2Cl] where dppz=dipyrido[3, 2-a:2′,3′-c] phenazine and nHo=9H-pyrido[3, 4-b]indole (norharmane), have been synthesized. These complexes were fully characterized by structural X-ray diffraction, 1H and 13C NMR, UV-vis absorption and FT-IR spectroscopy and mass spectrometry. Ground state geometry optimization was carried out in vacuo with the PBE0 hybrid functional using the LanL2DZ basis set. The characterization was complemented with TD-DFT calculations using several hybrid functionals. Cellular uptake and cytotoxic effect of both complexes against human lung carcinoma (A549) cells were evaluated. For comparative purpose, two related fac-[Re(CO)3(L)(nHo)]+ complexes (L=bpy and phen) were included in the biological studies. The anti-proliferative effect of the compounds was rationalized in terms of the different extension of the ligands π-system. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Registro:

Documento: Artículo
Título:Synthesis, Structural Characterization and Biological Evaluation of Rhenium(I) Tricarbonyl Complexes with β-Carboline Ligands
Autor:Maisuls, I.; Wolcan, E.; Piro, O.E.; Castellano, E.E.; Petroselli, G.; Erra-Balsells, R.; Cabrerizo, F.M.; Ruiz, G.T.
Filiación:INIFTA, UNLP (CCT La Plata-CONICET), Diag. 113 y 64, C.C. 16, Suc. 4, (B1906ZAA), La Plata, Argentina
IIB-INTECH – UNSAM-CONICET, I. Marino Km 8,2. CC 164, Chascomús, Buenos Aires, 7130, Argentina
Instituto IFLP (CCT La Plata-CONICET) y Depto. de Física, FCE-UNLP, C.C. 67, La Plata, 1900, Argentina
Instituto de Física de São Carlos, USP, C.P. 369, São Carlos, 13560, Brazil
CIHIDECAR-CONICET, Departamento de Química Orgánica, FCEyN, UBA, Pabellón II, 3er P., Ciudad Universitaria, Buenos Aires, 1428, Argentina
Palabras clave:Antitumor agent; Bioinorganic chemistry; Cytotoxicity; Rhenium tricarbonyl complexes; Structure elucidation
Año:2017
Volumen:2
Número:27
Página de inicio:8666
Página de fin:8672
DOI: http://dx.doi.org/10.1002/slct.201701961
Título revista:ChemistrySelect
Título revista abreviado:ChemistrySelect
ISSN:23656549
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_23656549_v2_n27_p8666_Maisuls

Referencias:

  • Viček, A., Jr., (2010) Top. Organomet. Chem., 29, pp. 73-114
  • Kumar, A., Sun, S.-S., Lees, A.J., (2010) Top. Organomet. Chem., 29, pp. 1-35
  • Balzani, V., Juris, A., Venturi, M., Campagna, S., Serroni, S., (1996) Chem. Rev., 96, pp. 759-834
  • Fox, M.A., Chanon, M., (1988) Photoinduced Electron Transfer
  • Grätzel, M., (1983) Energy Resources Through Photochemistry and Catalysis
  • Garcia, C.G., Jailson, F.L., Neyde, Y., Murakami, I., (2000) Coord. Chem. Rev., 196, pp. 219-247
  • Kuninobu, Y., Takai, K., (2011) Chem. Rev., 111, pp. 1938-1953
  • Kast, A., Dieckmann, S., Wähler, K., Völker, T., Kastl, L., Merkel, A.L., Vultur, A., Meggers, E., (2013) ChemMedChem., 8, pp. 924-927
  • Leonidova, A., Gasser, G., (2014) ACS Chem. Biol., 9 (10), pp. 2180-2193
  • Müller, C., Dumas, C., Hoffmann, U., Schubiger, P.A., Schibli, R., (2004) J. Organomet. Chem., 689, pp. 4712-4721
  • Hashimoto, K., Yoshihara, K., (2005) Top. Curr. Chem., 176, pp. 275-291
  • Schibli, R., Katti, K.V., Volkert, W.A., Barnes, C.L., (2001) Inorg. Chem., 40, pp. 2358-2362
  • Wei, L., Babich, J., Zubieta, J., (2005) Inorg. Chim. Acta, 358, pp. 3691-3700
  • Amoroso, A.J., Coogan, M.P., Dunne, J.E., Fernandez-Moreira, V., Hess, J.B., Hayes, A.J., Lloyd, D., Williams, C., (2007) Chem. Commun., 30, pp. 3066-3068
  • Thorp-Greenwood, F.L., Coogan, M.P., Mishra, L., Kumari, N., Rai, G., Saripella, S., (2012) New J. Chem., 36, pp. 1-180
  • Fernández-Moreira, V., Thorp-Greenwood, F.L., Amoroso, A.J., Cable, J., Court, J.B., Gray, V., Hayes, A.J., Coogan, M.P., (2010) Org. Biomol. Chem., 8, pp. 3888-3901
  • Balasingham, R.G., Thorp-Greenwood, F.L., Williams, C.F., Coogan, M.P., Pope, S.J.A., (2012) Inorg. Chem., 51, pp. 1419-1426
  • Fernandez-Moreira, V., Thorp-Greenwood, F.L., Coogan, M.P., (2009) Chem. Commun., 46, pp. 186-202
  • Kaplanis, M., Stamatakis, G., Papakonstantinou, V.D., Paravatou-Petsotas, M., Demopoulos, C.A., Mitsopoulou, C.A., (2014) J. Inorg. Biochem., 135, pp. 1-9
  • Uppal, B.S., Booth, R.K., Ali, N., Lockwood, C., Rice, C.R., Elliott, P.I.P., (2011) Dalton Trans., 40, p. 7610
  • Saavedra, H.H.M., Ragone, F., Ruiz, G.T., David-Gara, P.M., Wolcan, E., (2014) J. Phys. Chem. A., 118, pp. 9661-9674
  • Saavedra, H.H.M., Franca, C.A., Petroselli, G., Erra-Balsells, R., Ruiz, G.T., Wolcan, E., (2013) J. Organomet. Chem., 745, pp. 470-478
  • Ragone, F., Saavedra, H.H.M., David-Gara, P.M., Ruiz, G.T., Wolcan, E., (2013) J.Phys. Chem. A, 117, pp. 4428-4435
  • Ragone, F., Ruiz, G.T., Piro, O.E., Etcheverría, G.A., Cabrerizo, F.M., Petroselli, G., Erra-Balsells, R., Wolcan, E., (2012) Eur. J. Med. Chem., 30, pp. 4801-4810
  • Féliz, M.R., Rodriguez-Nieto, F., Ruiz, G.T., Wolcan, E., (1998) J. Photochem. Photobiol., A., 117, pp. 185-192
  • Torchia, G., Tocho, J., Piro, O.E., Juliarena, M.P., Ruiz, G.T., Wolcan, E., Féliz, M.R., (2002) Dalton Trans., pp. 2194-2202
  • Alomar, M.L., Rasse-Souriani, F.A.O., Gamuza, A., Cóceres, V.M., Cabrerizo, F.M., Angel, S.O., (2013) BMC Res. Notes, 6, pp. 1-6
  • Cao, R., Chen, H., Peng, W., Ma, Y., Hou, X., Guan, H., Liu, X., Xu, A., (2005) Eur. J. Med. Chem., 40, pp. 991-1001
  • Olmedo, M.G., Cerioni, L., González, M.M., Cabrerizo, F.M., Rapisarda, V.A., Volentini, S.I., (2017) Food Microbiol., 62, pp. 9-14
  • Olmedo, G.M., Cerioni, L., González, M.M., Cabrerizo, F.M., Volentini, S.I., Rapisarda, V.A., (2017) Front. Microbiol., 8, p. 347
  • Cao, R., Peng, W., Wang, Z., Xu, A., (2007) Curr. Med. Chem., 14, pp. 479-500
  • Gonzalez, M.M., Salum, M.L., Gholipour, Y., Cabrerizo, F.M., Erra-Balsells, R., (2009) Photochem. Photobiol. Sci., 8, pp. 1139-1149
  • Gonzalez, M.M., Arnbjerg, J., Denofrio, M.P., Erra-Balsells, R., Ogilby, P.R., Cabrerizo, F.M., (2009) J. Phys. Chem. A, 113, pp. 6648-6656
  • Cabrerizo, F.M., Arnbjerg, J., Denofrio, M.P., Erra-Balsells, R., Ogilby, P.R., (2010) ChemPhysChem., 11, pp. 796-798
  • Rasse-Souriani, F.A.O., Denofrio, M.P., Yañuk, J.G., Gonzalez, M.M., Wolcan, E., Seifermann, M., Erra-Balsells, R., Cabrerizo, F.M., (2016) Phys. Chem. Chem. Phys., 18, pp. 886-900
  • Vignoni, M., Erra-Balsells, R., Epe, B., Cabrerizo, F.M., (2014) J. Photochem. Photobiol., B., 132, pp. 66-71
  • Gonzalez, M.M., Vignoni, M., Pellon-Maison, M., Ales-Gandolfo, M.A., Gonzalez-Baró, M.R., Erra-Balsells, R., Epe, B., Cabrerizo, F.M., (2012) Org. Biomol. Chem., 10, pp. 1807-1819
  • Gonzalez, M.M., Rasse-Souriani, F.A.O., Franca, C.A., Diez, R.P., Gholipour, Y., Nonami, H., Erra-Balsells, R., Cabrerizo, F.M., (2012) Org. Biomol. Chem., 10, pp. 9359-9372
  • Guan, H., Liu, X., Peng, W., Cao, R., Ma, Y., Chen, H., Xu, A., (2006) Biochem. Biophys. Res. Commun., 342, pp. 894-901
  • Gonzalez, M.M., Pellon-Maison, M., Ales-Gandolfo, M.A., Gonzalez-Baró, M.R., Erra-Balsells, R., Cabrerizo, F.M., (2010) Org. Biomol. Chem., 8, pp. 2543-2552
  • Vignoni, M., Rasse-Souriani, F.A.O., Butzbach, K., Erra-Balsells, R., Epe, B., Cabrerizo, F.M., (2013) Org. Biomol. Chem., 11, pp. 5300-5309
  • Rasse-Souriani, F.A.O., Butzbach, K., Gonzalez, M.M., Cabrerizo, F.M., Epe, B., (2016) Photochem. Photobiol., 92, pp. 611-619
  • Maisuls, I., Wolcan, E., Piro, O.E., Etcheverría, G.A., Erra-Balsells, R., Petroselli, G., Cabrerizo, F.M., Ruiz, G.T., (2015) Dalton Trans., 44, pp. 17064-17074
  • Gearhart, D.A., Neafsey, E.J., Collins, M.A., (2002) Neurochem. Int., 40, pp. 611-620
  • Farrugia, L.J., (1997) J. Appl. Crystallogr., 30, p. 565
  • Fagioli, U.N., Garcia Einschlag, F.S., Cobos, C.J., Ruiz, G.T., Féliz, M.R., Wolcan, E., (2011) J. Phys. Chem. A., 115, pp. 10979-10987
  • Khan, R.A., Al-Farhan, K., de Almeida, A., Alsalme, A., Casini, A., Ghazzali, M., Reedijk, J., (2014) J.Inorg. Biochem., 140, pp. 1-5
  • Tarzi, O.I., Ponce, M.A., Cabrerizo, F.M., Bonesi, S.M., Erra-Balsells, R., (2005) ARKIVOC, 12, pp. 295-310
  • Vlček, A., Jr., Zális, S., (2007) Coord. Chem. Rev., 251, pp. 258-287
  • Zális, S., El-Nahhas, A., Blanco-Rodriguez, A.M., Van der Veen, R.M., Vlček, Jr., (2013) Inorg. Chem., 5210, pp. 5775-5785
  • Tan, C., Wu, S., Lai, S., Wang, M., Chen, Y., Zhou, L., Zhu, Y., Xu, A., (2011) Dalton Trans., 40, p. 8611
  • Chen, Y., Qin, M.-Y., Wang, L., Chao, H., Ji, L.-N., Xu, A., (2013) Eur. J. Med. Chem., 70, pp. 120-129
  • Schatzschneider, U., Niesel, J., Ott, I., Gust, R., Alborzinia, H., Wölfl, S., (2008) ChemMedChem., 3, pp. 1104-1109
  • Puckett, C.A., Barton, J.K., (2007) J. Am. Chem. Soc., 129, pp. 46-47
  • Ghezzi, A., Aceto, M., Cassino, C., Gabano, E., Osella, D., (2004) J. Inorg. Biochem., 98, pp. 73-78
  • Ruiz, G.T., Juliarena, M.P., Lezna, R.O., Wolcan, E., Feliz, M.R., Ferraudi, G., (2007) Dalton Trans., 20, pp. 2020-2029
  • Balasingham, R.G., Coogan, M.P., Thorp-Greenwood, F.L., (2011) Dalton Trans., 40, pp. 11663-11674
  • Photos, P.J., Bacakova, L., Discher, B., Bates, F.S., Discher, D.E., (2003) J. Controlled Release., 90, pp. 323-334
  • Tan, C., Lai, S., Wu, S., Hu, S., Zhou, L., Chen, Y., Wang, M., Xu, A., (2010) J. Med. Chem., 53, pp. 7613-7624

Citas:

---------- APA ----------
Maisuls, I., Wolcan, E., Piro, O.E., Castellano, E.E., Petroselli, G., Erra-Balsells, R., Cabrerizo, F.M.,..., Ruiz, G.T. (2017) . Synthesis, Structural Characterization and Biological Evaluation of Rhenium(I) Tricarbonyl Complexes with β-Carboline Ligands. ChemistrySelect, 2(27), 8666-8672.
http://dx.doi.org/10.1002/slct.201701961
---------- CHICAGO ----------
Maisuls, I., Wolcan, E., Piro, O.E., Castellano, E.E., Petroselli, G., Erra-Balsells, R., et al. "Synthesis, Structural Characterization and Biological Evaluation of Rhenium(I) Tricarbonyl Complexes with β-Carboline Ligands" . ChemistrySelect 2, no. 27 (2017) : 8666-8672.
http://dx.doi.org/10.1002/slct.201701961
---------- MLA ----------
Maisuls, I., Wolcan, E., Piro, O.E., Castellano, E.E., Petroselli, G., Erra-Balsells, R., et al. "Synthesis, Structural Characterization and Biological Evaluation of Rhenium(I) Tricarbonyl Complexes with β-Carboline Ligands" . ChemistrySelect, vol. 2, no. 27, 2017, pp. 8666-8672.
http://dx.doi.org/10.1002/slct.201701961
---------- VANCOUVER ----------
Maisuls, I., Wolcan, E., Piro, O.E., Castellano, E.E., Petroselli, G., Erra-Balsells, R., et al. Synthesis, Structural Characterization and Biological Evaluation of Rhenium(I) Tricarbonyl Complexes with β-Carboline Ligands. ChemistrySelect. 2017;2(27):8666-8672.
http://dx.doi.org/10.1002/slct.201701961