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Med. Chem."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"528","DOI":"10.1016\/S0020-1693(98)00114-5","author":"S\u00e1nchez-Delgado R. A.","year":"1998","journal-title":"Inorg. Chim. Acta."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"2319","DOI":"10.1016\/S0277-5387(00)00495-2","volume":"19","author":"Navarro M.","year":"2000","journal-title":"Polyhedron"},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1016\/S0010-8545(02)00177-7","volume":"236","author":"Tfouni E.","year":"2003","journal-title":"Coord. Chem. Rev."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1038\/sj.bjp.0707363","volume":"152","author":"Silva J. J. N.","year":"2007","journal-title":"Br. J. Pharmacol."},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"5177","DOI":"10.1128\/iai.62.11.5177-5182.1994","volume":"62","author":"Vespa G. N. R.","year":"1994","journal-title":"Infect. 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Chem."},{"key":"ref24\/cit24","doi-asserted-by":"crossref","first-page":"46","DOI":"10.1016\/S0022-0728(01)00557-5","volume":"511","author":"Bollo S.","year":"2001","journal-title":"J. Electroanal. Chem."},{"key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"419","DOI":"10.1016\/j.ccr.2004.09.016","volume":"249","author":"Toledo J. C.","year":"2005","journal-title":"Coord. Chem. Rev."},{"key":"ref26\/cit26","doi-asserted-by":"crossref","first-page":"5413","DOI":"10.1021\/ja00824a016","volume":"96","author":"Clarke M. J.","year":"1974","journal-title":"J. Am. Chem. Soc."},{"key":"ref27\/cit27","doi-asserted-by":"crossref","first-page":"571","DOI":"10.1021\/ic50181a011","volume":"17","author":"Franco D. W.","year":"1978","journal-title":"Inorg. Chem."},{"key":"ref28\/cit28","doi-asserted-by":"crossref","first-page":"1157","DOI":"10.1021\/ic50030a015","volume":"4","author":"Vogt L. H.","year":"1965","journal-title":"Inorg. Chem."},{"key":"ref29\/cit29","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1016\/0162-0134(91)84008-W","volume":"42","author":"Nothenberg M. S.","year":"1991","journal-title":"J. Inorg. Biochem."},{"key":"ref30\/cit30","doi-asserted-by":"crossref","first-page":"239","DOI":"10.1016\/j.ijpharm.2005.10.004","volume":"307","author":"Lamas M. C.","year":"2006","journal-title":"Int. J. Pharm."},{"key":"ref31\/cit31","unstructured":"Freshney, R.Culture of Animal Cells: A Manual of Basic Technique;Alan R. Liss, Inc.:New York, 1987, pp117."},{"key":"ref32\/cit32","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1016\/0022-1759(94)90236-4","volume":"171","author":"Lyons A. B.","year":"1994","journal-title":"J. Immunol. Methods"},{"key":"ref33\/cit33","doi-asserted-by":"crossref","first-page":"237","DOI":"10.1016\/S0378-4274(00)00226-5","volume":"116","author":"Melo P. S.","year":"2000","journal-title":"Toxicol. Lett."},{"key":"ref34\/cit34","doi-asserted-by":"crossref","first-page":"151","DOI":"10.1016\/0272-0590(85)90059-4","volume":"5","author":"Bruce R. D.","year":"1985","journal-title":"Fundam. Appl. Toxicol."},{"key":"ref35\/cit35","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1590\/S0074-02761987000200009","volume":"82","author":"Castro S. L.","year":"1986","journal-title":"Mem. Inst. Oswaldo Cruz"},{"key":"ref36\/cit36","author":"Silva J. J. N.","year":"2007","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref37\/cit37","doi-asserted-by":"crossref","first-page":"526","DOI":"10.1016\/j.ejmech.2005.12.006","volume":"41","author":"Silva R. S. F.","year":"2006","journal-title":"Eur. J. Med. Chem."},{"key":"ref38\/cit38","doi-asserted-by":"crossref","first-page":"150","DOI":"10.1128\/AAC.44.1.150-155.2000","volume":"44","author":"Molina J.","year":"2000","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref39\/cit39","doi-asserted-by":"crossref","first-page":"1359","DOI":"10.1128\/AAC.01170-06","volume":"51","author":"Ferraz M. L.","year":"2007","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref40\/cit40","doi-asserted-by":"crossref","first-page":"528","DOI":"10.1016\/S0020-1693(98)00114-5","volume":"275","author":"Sanchez-Delgado R.","year":"1998","journal-title":"Inorg. Chim. Acta"},{"key":"ref41\/cit41","doi-asserted-by":"crossref","first-page":"85","DOI":"10.1016\/S0020-1693(02)01277-X","volume":"344","author":"Otero L.","year":"2003","journal-title":"Inorg. Chim. Acta"},{"key":"ref42\/cit42","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1590\/S0074-02762004000200021","volume":"99","author":"Petray P. B.","year":"2004","journal-title":"Mem. Inst. Oswaldo Cruz"},{"key":"ref43\/cit43","doi-asserted-by":"crossref","first-page":"227","DOI":"10.1016\/0009-2797(95)03672-5","volume":"99","author":"Squella J. A.","year":"1996","journal-title":"Chem.\u2212Biol. Interact."},{"key":"ref44\/cit44","doi-asserted-by":"crossref","first-page":"343","DOI":"10.1016\/S0223-5234(00)00131-8","volume":"35","author":"Cerecetto H.","year":"2000","journal-title":"Eur. J. Med. Chem."},{"key":"ref45\/cit45","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1016\/j.bmc.2006.09.067","volume":"15","author":"Dias L. R. S.","year":"2007","journal-title":"Bioorg. Med. Chem."},{"key":"ref46\/cit46","doi-asserted-by":"crossref","first-page":"2768","DOI":"10.1016\/j.bmc.2007.01.009","volume":"15","author":"Porcal W.","year":"2007","journal-title":"Bioorg. Med. Chem."},{"key":"ref47\/cit47","doi-asserted-by":"crossref","first-page":"1109","DOI":"10.1161\/CIRCULATIONAHA.106.624296","volume":"115","author":"Marin-Neto J. A.","year":"2007","journal-title":"Circulation."},{"key":"ref48\/cit48","doi-asserted-by":"crossref","first-page":"1521","DOI":"10.1128\/AAC.49.4.1521-1528.2005","volume":"49","author":"Garcia S.","year":"2005","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref49\/cit49","volume-title":"Purification of Laboratory Chemicals","author":"Perrin D. D.","year":"1980"},{"key":"ref50\/cit50","volume-title":"The Manipulation of Air-Sensitive Compound","author":"Shriver D. F.","year":"1969"},{"key":"ref51\/cit51","doi-asserted-by":"crossref","first-page":"5068","DOI":"10.1021\/ja00484a026","volume":"100","author":"Clarke M. J.","year":"1978","journal-title":"J. Am. Chem. Soc."},{"key":"ref52\/cit52","doi-asserted-by":"crossref","first-page":"698","DOI":"10.1023\/A:1011910801212","volume":"15","author":"Galia E.","year":"1998","journal-title":"Pharm. Res."},{"key":"ref53\/cit53","doi-asserted-by":"crossref","first-page":"85","DOI":"10.1021\/mp034006h","volume":"1","author":"Kasim N. A.","year":"2004","journal-title":"Mol. Pharm."},{"key":"ref54\/cit54","unstructured":"Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A.Gaussian 03,revision C.02;Gaussian, Inc.:Wallingford, CT, 2004."},{"key":"ref55\/cit55","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","volume":"98","author":"Becke A. D.","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref56\/cit56","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","volume":"37","author":"Lee C.","year":"1988","journal-title":"Phys. Rev. B"},{"key":"ref57\/cit57","doi-asserted-by":"crossref","first-page":"10806","DOI":"10.1063\/1.480484","volume":"111","author":"Farkas O.","year":"1999","journal-title":"J. Chem. Phys."},{"key":"ref58\/cit58","doi-asserted-by":"crossref","first-page":"3098","DOI":"10.1103\/PhysRevA.38.3098","volume":"38","author":"Becke A. D.","year":"1988","journal-title":"Phys. Rev. A"},{"key":"ref59\/cit59","unstructured":"Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F.NBO 3.0;Theoretical Chemistry Institute:Madison, WI, 1998."},{"key":"ref60\/cit60","doi-asserted-by":"crossref","first-page":"3032","DOI":"10.1063\/1.474659","volume":"107","author":"Cances E.","year":"1997","journal-title":"J. Chem. Phys."},{"key":"ref61\/cit61","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1016\/0301-0104(81)85090-2","volume":"55","author":"Miertus S.","year":"1981","journal-title":"Chem. Phys."},{"key":"ref62\/cit62","volume-title":"Exploring Chemistry With Electronic Structure Methods","author":"Foresman J. 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