Synthesis and characterization of di-phenyl-tinIV-salicyliden-ortho-aminophenols: Analysis of in vitro antitumor/antioxidant activities and molecular structures

Journal of Inorganic Biochemistry

Volumn 101, Issue 7, 2007, Pages 1070-1085

  Beltrán, Hiram I ^a   Damian Zea, Carlos ^a   Hernández Ortega, Simón ^a   Nieto Camacho, Antonio ^a   Ramírez Apan, Maria Teresa ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Antioxidant; Antitumor; Di phenyl tinIV; Molecular design; QSAR; X ray structures

Indexed keywords

2 AMINOPHENOL; 2,2 DIPHENYL 6 AZA 1,3 DIOXA 15 CHLORO 2 STANNA[D,H]DIBENZOCYCLONONENE; 2,2 DIPHENYL 6 AZA 1,3 DIOXA 15 METHYL 2 STANNA[D,H]DIBENZOCYCLONONENE; 2,2 DIPHENYL 6 AZA 1,3 DIOXA 15 NITRO 2 STANNA[D,H]DIBENZOCYCLONONENE; 2,2 DIPHENYL 6 AZA 1,3 DIOXA 15 TERT BUTYL 2 STANNA[D,H]DIBENZOCYCLONONENE; 2,2 DIPHENYL 6 AZA 1,3 DIOXA 16 METHYL 2 STANNA[D,H]DIBENZOCYCLONONENE; 2,2 DIPHENYL 6 AZA 1,3 DIOXA 16 NITRO 2 STANNA[D,H]DIBENZOCYCLONONENE; 2,2 DIPHENYL 6 AZA 1,3 DIOXA 2 STANNA[D,H]DIBENZOCYCLONONENE; ALCOHOL DERIVATIVE; BUTYLCRESOL; CISPLATIN; DIPHENYL TIN OXIDE; QUERCETIN; SALICYLALDEHYDE; THIOBARBITURIC ACID REACTIVE SUBSTANCE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BRAIN HOMOGENATE; CANCER CELL CULTURE; CELL SPECIFICITY; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DOSE RESPONSE; DRUG DESIGN; DRUG INHIBITION; DRUG SUBSTITUTION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN TISSUE; IC 50; INFRARED SPECTROSCOPY; MALE; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ONE POT SYNTHESIS; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; TUMOR CELL LINE; X RAY DIFFRACTION;

AMINOPHENOLS; ANIMALS; ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; BRAIN; CELL LINE; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; CISPLATIN; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; INHIBITORY CONCENTRATION 50; K562 CELLS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; QUERCETIN; RATS; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; STRUCTURE-ACTIVITY RELATIONSHIP; THIOBARBITURIC ACID REACTIVE SUBSTANCES;

RATTUS;

EID: 34250183056     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2007.04.002     Document Type: Article

References (68)

1. Ball P. Nature 431 (2004) 624-626
2. Abrams M.J., and Murrer B.A. Science 261 (1993) 725-730
3. Gielen M. Appl. Organomet. Chem. 16 (2002) 481-494
4. Tian L.J., Yu Q.S., Zheng X.L., Shang Z.C., Liu X.L., and Qian B.C. Appl. Organomet. Chem. 19 (2005) 672-676
5. Samuel P.M., de Vos D., Raveendra D., Sarma J., and Roy S. Bioorg. Med. Chem. Lett. 12 (2002) 61-64
6. Saxena A.K., and Huber F. Coord. Chem. Rev. 95 (1989) 109-123
7. Atsushi A., Hisada K., and Ando I. Radioisotopes 22 (1973) 7-11
8. Yamaguchi M., Sugii K., and Okada S. J. Toxicol. Sci. Jpn. 5 (1981) 238-242
9. Lascourreges J.F., Caumette P., and Donard O.F.X. Appl. Organomet. Chem. 14 (2000) 98-107
10. Olzynska A., Przybylo M., Gabrielska J., Trela Z., Przestalski S., and Langner M. Appl. Organomet. Chem. 19 (2005) 1073-1078
11. Miszta A., Gabrielska J., Przestalski S., and Langner M. Appl. Organomet. Chem. 19 (2005) 736-741
12. Langner M., Gabrielska J., and Przestalski S.A. Appl. Organomet. Chem. 14 (2000) 25-33
13. Burda K., Lekki J., Cieslak J., Kruk J., Lekka M., Dubiel S., Stanek J., and Stachura Z. Appl. Organomet. Chem. 16 (2002) 148-154
14. M. Gielen, R. Willem, M. Biesemans, M. Kemmer, D. de Vos, Tin polyoxaalkanecarboxylates and compositions containing them., in US Patent 0039270A1. 2001, U.S.
15. Gielen M. J. Braz. Chem. Soc. 14 (2003) 870-877
16. Han G.Y., and Yang P. J. Inorg. Biochem. 91 (2002) 230-236
17. Kemmer M., Ghys L., Gielen M., Biesemans M., Tiekink E.R.T., and Willem R. J. Organomet. Chem. 582 (1999) 195-203
18. Berg C.P., Rothbart A., Lauber K., Stein G.M., Engels I.H., Belka C., Janicke R.U., Schulze-Osthoff K., and Wesselborg S. Oncogene 22 (2003) 775-780
19. Fiers W., Beyaert R., Declercq W., and Vandenabeele P. Oncogene 18 (1999) 7719-7730
20. Jan C.R., Jiann B.P., Lu Y.C., Chang H.T., Su W.R., Chen W.C., Yu C.C., and Huang J.K. Life Sci. 70 (2002) 1337-1345
21. Hoti N., Ma J., Tabassum S., Wang Y., and Wu M. J. Biochem. 134 (2003) 521-528
22. von Ballmoos C., Brunner J., and Dimroth P. Proc. Natl. Acad. Sci. USA. 101 (2004) 11239-11244
23. Ueno H., Suzuki T., Kinosita K., and Yoshida M. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 1333-1338
24. Bragadin M., and Marton D. J. Inorg. Biochem. 68 (1997) 75-78
25. Bragadin M., Marton D., Manente S., Scutari G., and Toninello A. Inorg. Chim. Acta 348 (2003) 225-228
26. Gielen M. Coord. Chem. Rev. 151 (1996) 41-51
27. In: Gielen M.F. (Ed). Tin-based Antitumour Drugs (1990), Springer-Verlag, Berlin
28. In: Gielen M.F., and Tiekink E.R.T. (Eds). Metallotherapeutic Drugs and Metal-based Diagnostic Agents: The Use of Metals in Medicine (2005), Wiley, Chichester, West Sussex
29. In: Gielen M.F. (Ed). Metal-based Anti-tumour Drugs (1988), Freund Pub. House, London
30. Tian L.J., Shang Z.C., Zheng X.L., Sun Y.X., Yu Y., Qian B.C., and Liu X.L. Appl. Organomet. Chem. 20 (2006) 74-80
31. Casas J.S., Castineiras A., Rodriguez-Arguelles M.C., Sanchez A., Sordo J., Lopez A.V., Pinelli S., Lunghi P., Ciancianaini P., Bonati A., Dall'Aglio P., and Albertini R. J. Inorg. Biochem. 76 (1999) 277-284
32. Ronconi L., Marzano C., Russo U., Sitran S., Graziani R., and Fregona D. Appl. Organomet. Chem. 17 (2003) 9-16
33. Ronconi L., Marzano C., Russo U., Sitran S., Graziani R., and Fregona D. J. Inorg. Biochem. 91 (2002) 413-420
34. Zamudio-Rivera L.S., George-Tellez R., Lopez-Mendoza G., Morales-Pacheco A., Flores E., Hopfl H., Barba V., Fernandez F.J., Cabirol N., and Beltran H.I. Inorg. Chem. 44 (2005) 5370-5378
35. Li Q.S., da Silva M., and Pombeiro A.L.L. Chem. Eur. J. 10 (2004) 1456-1462
36. Ali A., Flora S.J.S., Saxena G., Kolehmainen E., Mahieu B., and Rao C.P. J. Inorg. Biochem. 100 (2006) 206-213
37. Rozycka-Roszak B., Pruchnik H., and Kaminski E. Appl. Organomet. Chem. 14 (2000) 465-472
38. Saxena A., Tandon J.P., and Crowe A.J. Polyhedron 4 (1985) 1085-1089
39. Saxena A., and Tandon J.P. Cancer Lett. 19 (1983) 73-76
40. Tian L.J., Sun Y.X., Qian B.C., Yang G.M., Yu Y., Shang Z.C., and Zheng X.L. Appl. Organomet. Chem. 19 (2005) 1127-1131
41. Tian L.J., Qian B.C., Sun Y.X., Zheng X.L., Yang M., Li H.J., and Liu X.L. Appl. Organomet. Chem. 19 (2005) 980-987
42. Boualam M., Biesemans M., Meunierpiret J., Willem R., and Gielen M. Appl. Organomet. Chem. 6 (1992) 197-205
43. Gielen M., Biesemans M., Willem R., and Tiekink E.R.T. Eur. J. Inorg. Chem. (2004) 445-451
44. Gomez E., Contreras-Ordonez G., and Ramirez-Apan T. Chem. Pharm. Bull. 54 (2006) 54-57
45. Barba V., Vega E., Luna R., Höpfl H., Beltrán H.I., and Zamudio-Rivera L.S. J. Organomet. Chem. 692 (2007) 731-739
46. Beltran H.I., Zamudio-Rivera L.S., Mancilla T., Santillan R., and Farfan N. Chem. Eur. J. 9 (2003) 2291-2306
47. Farfan N., Mancilla T., Santillan R., Gutierrez A., Zamudio-Rivera L.S., and Beltran H.I. J. Organomet. Chem. 689 (2004) 3481-3491
48. Diamantis A.A., Gulbis J.M., Manikas M., and Tiekink E.R.T. Phosphorus Sulfur Silicon Relat. Elem. 151 (1999) 251-259
49. Reyes H., Garcia C., Farfan N., Santillan R., Lacroix P.G., Lepetit C., and Nakatani K. J. Organomet. Chem. 689 (2004) 2303-2310
50. Du J.A., Daniels D.H., Asbury C., Venkataraman S., Liu J.R., Spitz D.R., Oberley L.W., and Cullen J.J. J. Biol. Chem. 281 (2006) 37416-37426
51. Chen M.F., Chen W.C., Wu C.T., Lin P.Y., Shau H., Liao S.K., Yang C.T., and Lee K.D. Int. J. Radiat. Oncol. Biol. Phys. 66 (2006) 1461-1472
52. Beevi S.S., Rasheed M.H., and Geetha A. Clin. Chim. Acta 375 (2007) 119-123
53. SAINT-NT, 2001, Bruker Analytical X-ray Systems: Karlsruhe, Germany.
54. SHELXTL-NT, 2000, Bruker Analytical X-ray Systems: Karlsruhe, Germany.
55. Farrugia L. J. Appl. Crystallogr. 32 (1999) 837-838
56. Farrugia L. J. Appl. Crystallogr. 30 (1997) 565-566
57. Monks A., Scudiero D., Skehan P., Shoemaker R., Paull K., Vistica D., Hose C., Langley J., Cronise P., Vaigrowolff A., Graygoodrich M., Campbell H., Mayo J., and Boyd M. J. Natl. Cancer Inst. 83 (1991) 757-766
58. Protección ambiental - Salud ambiental - Residuos peligrosos biológico-infecciosos - Clasificación y especificaciones de manejo, 2002, Diario Oficial de la Federación, México.
59. Rossato J.I., Ketzer L.A., Centuriao F.B., Silva S.J.N., Ludtke D.S., Zeni G., Braga A.L., Rubin M.A., and Rocha J.B.T. Neurochem. Res. 27 (2002) 297-303
60. Lowry O.H., Rosebrough N.J., Farr A.L., and Randall R.J. J. Biol. Chem. 193 (1951) 265-275
61. Ng T.B., Liu F., and Wang Z.T. Life Sci. 66 (2000) 709-723
62. Ohkawa H., Ohishi N., and Yagi K. Anal. Biochem. 95 (1979) 351-358
63. Esterbauer H., and Cheeseman K.H. Methods Enzymol. 186 (1990) 407-421
64. Luna-Garcia R., Damian-Murillo B.M., Barba V., Hopfl H., Beltran H.I., and Zamudio-Rivera L.S. Chem. Commun. (2005) 5527-5529
65. Boschi D., Tron G.C., Lazzarato L., Chegaev K., Cena C., Di Stilo A., Giorgis M., Bertinaria M., Fruttero R., and Gasco A. J. Med. Chem. 49 (2006) 2886-2897
66. Govindarajan R., Rastogi S., Vijayakumar M., Shirwaikar A., Rawat A.K.S., Mehrotra S., and Pushpangadan P. Biol. Pharm. Bull. 26 (2003) 1424-1427
67. Fremont L., Gozzelino M.T., Franchi M.P., and Linard A. J. Nutr. 128 (1998) 1495-1502
68. In: Johnson C.D. (Ed). The Hammett Equation (1980), Cambridge University Press, New York