Antimony(V) and bismuth(V) complexes of lapachol: Synthesis, crystal structure and cytotoxic activity

Molecules

Volumn 16, Issue 12, 2011, Pages 10314-10323

  De Oliveira, Ludmila G ^a   Silva, Meiriane M ^a   De Paula, Flávia C S ^a   Pereira Maia, Elene C ^a   Donnici, Cláudio L ^a   De Simone, Carlos A ^b   Frézard, Frédéric ^a   Da Silva Júnior, Eufrânio N ^a   Demicheli, Cynthia ^a  

^a FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Antimony(V) complex; Bismuth(V) complex; Cancer; Cytotoxicity; Lapachol

Indexed keywords

ANTIMONY; BISMUTH; LAPACHOL; NAPHTHOQUINONE;

ARTICLE; CELL DEATH; CELL PROLIFERATION; CELL STRAIN K 562; CHEMISTRY; CONFORMATION; DRUG EFFECT; FEMALE; HUMAN; MIDDLE AGED; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTIMONY; BISMUTH; CELL DEATH; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; FEMALE; HUMANS; K562 CELLS; MAGNETIC RESONANCE SPECTROSCOPY; MIDDLE AGED; MOLECULAR CONFORMATION; NAPHTHOQUINONES;

EID: 84555189804     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules161210314     Document Type: Article

References (36)

1. Rao, K.V.; McBride, T.J.; Oleson, J.J. Recognition and evaluation of lapachol as an antitumor agent. Cancer Res. 1968, 28, 1952-1954.
2. Nagata, K.; Hirai, K.-I.; Koyama, J.; Wada, Y.; Tamura, T. Antimicrobial activity of novel furanonaphthoquinone analogs. Antimicrob. Agents Chemother. 1998, 42, 700-702. (Pubitemid 28114832)
3. de Andrade-Neto, V.F.; Goulart, M.O.F.; da Silva Filho, J.F.; da Silva, M.J.; Pinto, M.C.F.R.; Pinto, A.V.; Zalis, M.G.; Carvalho, L.H.; Krettli, A.U. Antimalarial activity of phenazines from lapachol, ?-lapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo. Bioorg. Med. Chem. Lett. 2004, 14, 1145-1149. (Pubitemid 38229844)
4. de Moura, K.C.G.; Emery, F.S.; Pinto, C.N.; Pinto, M.C.F.R.; Dantas, A.P.; Salomão, K.; de Castro, S.L.; Pinto, A.V. Trypanocidal activity of isolated naphthoquinones from Tabebuia and some heterocyclic derivatives: A review from an interdisciplinary study. J. Braz. Chem. Soc. 2001, 12, 325-338.
5. Lima, N.M.F.; Correia, C.S.; Leon, L.L.; Machado, G.M.C.; Madeira, M.F.; Santana, A.E.G.; Goulart, M.O.F. Antileishmanial activity of lapachol analogues. Mem. Inst. Oswaldo Cruz 2004, 99, 757-761. (Pubitemid 40278172)
6. da Silva Júnior, E.N.; Guimarães, T.T.; Menna-Barreto, R.F.S.; Pinto, M.C.F.R.; de Simone, C.A.; Pessoa, C.; Cavalcanti, B.C.; Sabino, J.R.; Andrade, C.K.Z.; Goulart, M.O.F.; et al. The evaluation of quinonoid compounds against Trypanosoma cruzi: Synthesis of imidazolic anthraquinones, nor-?-lapachone derivatives and ?-lapachone-based 1,2,3-triazoles. Bioorg. Med. Chem. 2010, 18, 3224-3230.
7. da Silva Júnior, E.N.; de Deus, C.F.; Cavalcanti, B.C.; Pessoa, C.; Costa-Lotufo, L.V.; Montenegro, R.C.; de Moraes, M.O.; Pinto, M.C.F.R.; de Simone, C.A.; Ferreira, V.F.; et al. 3-Arylamino and 3-alkoxy-nor-?-lapachone derivatives: synthesis and cytotoxicity against cancer cell lines. J. Med. Chem. 2010, 53, 504-508.
8. Tonholo, J.; Freitas, L.R.; de Abreu, F.C.; Azevedo, D.C.; Zani, C.L.; de Oliveira, A.B.; Goulart, M.O.F. Electrochemical properties of biologically active heterocyclic naphthoquinones. J. Braz. Chem. Soc. 1998, 9, 163-169. (Pubitemid 128539782)
9. Hillard, E.A.; Abreu, F.C.; Ferreira, D.C.M.; Jaouen, G.; Goulart, M.O.F.; Amatore, C. Electrochemical parameters and techniques in drug development, with an emphasis on quinones and related compounds. Chem. Commun. 2008, 2612-2628. (Pubitemid 351795574)
10. Ferraz, P.A.L.; de Abreu, F.C.; Pinto, A.V.; Glezer, V.; Tonholo, J.; Goulart, M.O.F. Electrochemical aspects of the reduction of biologically active 2-hydroxy-1,4-naphthoquinones. J. Electroanal. Chem. 2001, 507, 275-286. (Pubitemid 32639251)
11. Bodini, M.E.; Arancibia, V. Manganese complexes with 2-hydroxy-3(3- methyl-2-butenyl)-1,4- naphthoquinone (Lapachol). Redox chemistry and spectroscopy in dimethylsulphoxide. Polyhedron 1989, 8, 1407-1412.
12. Sawhney, S.S.; Vohra, N.; Chandel, S.K. Formation constants and thermodynamic functions of Cd(II), Zn(II), Pb(II), VO2+ and Ce(IV) with Lapachol. Thermochim. Acta 1982, 52, 349-350.
13. Sawhney, S.S.; Bains, S.S. Thermal and pH-metric studies on complexes of Hg(II) and Er(III) with 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone (lapachol). Thermochim. Acta 1983, 71, 381-386.
14. Hernández-Molina, R.; Kalinina, I.; Esparza, P.; Sokolov, M.; Gonzalez-Platas, J.; Estévez-Braun, A.; Pérez-Sacau, E. Complexes of Co(II), Ni(II) and Cu(II) with lapachol. Polyhedron 2007, 26, 4860-4864.
15. Caruso, F.; Martýnez, M.; Rossi, M.; Goldberg, A.; ChaconVillalba, M.E.; Aymonin, P.J. Crystal and molecular structure of manganese(II) lapacholate, a novel polymeric species undergoing temperature-reversible metal to ligand electron transfer. Inorg. Chem. 2009, 48, 3529-3534.
16. Ge, R.; Sun, H. Bioinorganic chemistry of bismuth and antimony: Target sites of metallodrugs. Acc. Chem. Res. 2007, 40, 267-274.
17. Frézard, F.; Demicheli, C.; Ribeiro, R.R. Pentavalent antimonials: New perspectives for old drugs. Molecules 2009, 14, 2317-2336.
18. Tiekink, E.R. Antimony and bismuth compounds in oncology. Crit. Rev. Oncol. Hematol. 2002, 42, 217-224. (Pubitemid 34618518)
19. Sharma, P.; Perez, D.; Cabrera, A.; Rosas, N.; Arias, J.L. Perspectives of antimony compounds in oncology. Acta Pharmacol. Sin. 2008, 29, 881-890.
20. Silvestru, C.; Socaciu, C.; Bara, A.; Haiduc, I. The first organoantimony(III) compounds possessing antitumor properties: Diphenylantimony(III) derivatives of dithiophosphorus ligands. Anticancer Res. 1990, 10, 803-804. (Pubitemid 20237836)
21. Bara, A.; Socaciu, C.; Silvestru, C.; Haiduc, I. Antitumour organometallics. I. Activity of some diphenyltin(IV) and diphenylantimony(III) derivatives on in vitro and in vivo Ehrlich ascites tumor. Anticancer Res. 1991, 11, 1651-1655.
22. Carraher, C.E., Jr.; Nass, M.D.; Giron, D.J.; Cerutis, D.R. Structural and biological characterization of antimony(V) polyamines. J. Macromol. Sci. Chem. 1983, 19, 1101-1120.
23. Wang, G.C.; Xiao, J.; Lu, Y.; Li, J.S.; Cui, J.R.; Wang, R.Q.; Ran, F.X. Synthesis, crystal structures and in vitro antitumor activities of some arylantimony derivatives of analogues of demethylcantharimide. J. Organomet. Chem. 2004, 689, 1631-1638.
24. Li, J.S.; Ma, Y.Q.; Cui, J.R.; Wang, R.Q. Synthesis and in vitro antitumor activity of some tetraphenylantimony derivatives of exo-7-oxa-bicyclo[2,2,1] heptane (ene)-3-arylamide-2-acid. Appl. Organomet. Chem. 2001, 15, 639-645.
25. Desoize, B. Metals and metal compounds in cancer treatment. Anticancer Res. 2004, 24, 1529-1544. (Pubitemid 38954674)
26. Murafuji, T.; Miyoshi, Y.; Ishibashi, M.; Rahman, A.F.M.M.; Sugihara, Y.; Miyakawa, I.; Uno, H. Antifungal activity of organobismuth compounds against the yeast Saccharomyces cerevisiae: Structure-activity relationship. J. Inorg. Biochem. 2004, 98, 547-552. (Pubitemid 38264271)
27. Agrawal, R.; Sharma, J.; Nandani, D.; Batra, A.; Singh, Y. Triphenylarsenic(V) and -antimony(V) derivatives of multidentate Schiff bases: Synthesis, characterization, and antimicrobial activities. J. Coord. Chem. 2011, 64, 554-563.
28. Matano, Y.; Nomura, H.; Hisanaga, T.; Nakano, H.; Shiro, M.; Imahori, H. Diverse structures and remarkable oxidizing ability of triarylbismuthane oxides. Comparative study on the structure and reactivity of a series of triarylpnictogen oxides. Organometallics 2004, 23, 5471-5480.
29. Yamamoto, Y.; Ohdoi, K.; Chen, X.; Kitano, M.; Akiba, K. Synthesis and structure of six-coordinated organobismuth compounds with bidentate ligands (12-Bi-6). Organometallics 1993, 12, 3297-3303.
30. Campi, E.M.; Deacon, G.B.; Jackson, W.R.; Skelton, B.W.; Smith, K.A.; White, A.H. Novel coordination complexes in the bismuth(III)/oxinate system. Z. Anorg. Allg. Chem. 2006, 632, 1483-1486. (Pubitemid 44047491)
31. Dittes, U.; Keppler, B.K.; Nuber, B. Synthesis and structure of seven-coordinate bismuth(V) complexes with benzenoid and non-benzenoid arene ligands: Tri(aryl)tropolonatobismuth(V) complexes. Angew. Chem. Int. Ed. 1996, 35, 67-68. (Pubitemid 126665467)
32. Enraf-Nonius. Collect; Nonius BV: Delft, The Netherlands, 1997-2000.
33. Otwinowski, Z.; Minor, W. Processing of X-ray diffraction data collected in oscillation mode. In Methods in Enzymology; Carter, C.W., Jr., Sweet, R.M., Eds.; Academic Press: New York, NY, USA, 1997, Volume 276, pp. 307-326. (Pubitemid 27085611)
34. Sheldrick, G.M. SHELXS-97. Program for crystal structure resolution. University of Göttingen, Göttingen, Germany, 2008.
35. Farrugia, L.J. ORTEP-3 for Windows-A version of ORTEP-III with a Graphical User Interface (GUI). J. Appl. Crystallogr. 1997, 30, 565. (Pubitemid 127791756)
36. Farrugia, L.J. WinGX suite for small-molecule single-crystal crystallography. J. Appl. Crystallogr. 1999, 32, 837-838. (Pubitemid 129794704)