Synthesis, crystal structure and biological activities of copper(II) complexes with chelating bidentate 2-substituted benzimidazole ligands

Journal of Inorganic Biochemistry

Volumn 100, Issue 8, 2006, Pages 1389-1398

  Saczewski, Franciszek ^a   Dziemidowicz Borys, Ewa ^a   Bednarski, Patrick J ^b   Grünert, Renate ^b   Gdaniec, Maria ^c   Tabin, Piotr ^a  

^a MEDICAL UNIVERSITY OF GDANSK   (Poland)

^b UNIVERSITY OF GREIFSWALD   (Germany)

^c ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

2 Substituted benzimidazoles; Antitumor activity; Copper(II) complexes; Superoxide dismutase mimicking activity; X ray structure analysis

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; COPPER COMPLEX; COPPER ZINC SUPEROXIDE DISMUTASE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER GROWTH; CANCER INHIBITION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG ACTIVITY; DRUG INHIBITION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; GROWTH INHIBITION; HUMAN; HUMAN CELL; IC 50; MOLECULAR WEIGHT; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; BENZIMIDAZOLES; CELL LINE, TUMOR; COPPER; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; LIGANDS; MODELS, MOLECULAR; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; SUPEROXIDE DISMUTASE;

EID: 33745594575     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2006.04.002     Document Type: Article

References (50)

1. Spasov A.A., Yozhitsa I.N., Bugaeva L.I., and Anisimova V.A. Pharm. Chem. J. 33 (1999) 232-243
2. Bucknall R.A., and Carter S.B. Nature (1967) 1099-1101
3. Gumus F., Algul O., Eren G., Eroglu H., Diril N., Gur S., and Ozkul A. Eur. J. Med. Chem. 38 (2003) 473-480
4. Gocke M., Utku S., Gur S., Rozkul A., and Gumus F. Eur. J. Med. Chem. 40 (2005) 135-141
5. Bharti N., and Shailendra M.T. Bioorg. Med. Chem. Lett. 12 (2002) 869-871
6. Vaidynathan V.G., and Nair B.U. J. Inorg. Biochem. 91 (2002) 405-412
7. Wang J., Shuai L., Xiao X., Zeng Y., Li Z., and Matsumura-Inoe T. J. Inorg. Biochem. 99 (2005) 883-885
8. Coyle B., Kiusella P., McCann M., Devereux D., O'Connor R., Clynes M., and Kavanagh K. Toxicol. in Vitro 18 (2004) 63-70
9. Devereux M., McCann M., O Shea D., Kelly R., Egan D., Deegan C., Kavanagh K., McKee V., and Finn G. J. Inorg. Biochem. 98 (2004) 1023-1031
10. Pederson T.C., and Aust S.D. Biochem. Biophys. Res. Commun. 52 (1973) 1071-1073
11. Oberley L.W., and Buettner G.R. Cancer. Res. 39 (1979) 1141-1150
12. Sorenson R.J. Chem. Br. 16 (1984) 1110-1112
13. R.K. Gouch, T.W. Kensler, L.W. Oberley, J.R.J. Sorenson, in: K.D. Karlin, J. Zubieta (Eds.), Biochemical and Inorganic Copper Chemistry, vol. 1, Adenine, New York, 1986, pp. 139-156.
14. Farmer K.J., and Sohal R.S. Free Radic. Biol. Med. 7 (1989) 23-31
15. Rusting R.L. Sci. Am. 267 (1992) 88
16. Grisham M.B. TiPS 21 (2000) 119-120
17. Bhirud R.G., and Srivastava T.S. Inorg. Chim. Acta 173 (1990) 121-125
18. Bhirud R.J., and Srivastava T.S. Inorg. Chim. Acta 179 (1991) 125-131 and references cited herein
19. Easmon J., Purstinger G., Heinish G., Roth T., Fiebig H.H., Holzer W., Jager W., Jenny M., and Hofmann J. J. Med. Chem. 44 (2001) 2164-2171
20. Liang F., Wu C., Lin H., Li T., Gao D., Li Z., Wei J., Zheng C., and Sun M. Bioorg. Med. Chem. Lett. 13 (2003) 2469-2472
21. Rodriguez-Arguelles M.C., Ferrari M.B., Bisceglie F., Pelizzi C., Pelosi G., Pinelli S., and Sassi M. J. Inorg. Biochem. 98 (2004) 313-321
22. Ferrari M.B., Bisceglie F., Pelosi G., Tarasconi P., Albertini R., Dall'Aglio P.P., Pinelli S., Bergamo A., and Sava G. J. Inorg. Biochem. 98 (2004) 301-312
23. Sharma S., Athar F., Maurya M.R., Naqvi F., and Azam A. Eur. J. Med. Chem. 40 (2005) 557-562
24. Cramer F., Pawelzik K., and Baldauf H.J. Chem. Ber. 91 (1958) 1049-1054
25. Holan G., Samuel E.L., Ennis B.C., and Hinde R.W. J. Chem. Soc. (C) (1967) 20-25
26. Ennis B., Holan G., and Samuel E.L. J. Chem. Soc. (C) (1967) 33-39
27. Foks H., and Janowiec M. Acta Polon. Pharm. XXXV (1978) 281-288
28. Biedrzycki A., and Przeworski G. Ber. Dtsch. Chem. Ges. 45 (1912) 3455-3483
29. McCord J.M., and Fridovich I. Superoxide dismutase. J. Biol. Chem. 22 (1969) 6049-6055
30. Bienvenue E., Choua S., Lobo-Recio M.-A., Marzin C., Pacheco P., Seta P., and Tarrago G. J. Inorg. Biochem. 57 (1995) 157-168
31. Bracht K., Boubakari, Grünert R., and Bednarski P.J. Anticancer Drugs 17 (2006) 41-51
32. Oxford Diffraction, Crysalis CCD and RED, ver. 1.171, Oxford Diffraction, Oxfordshire, UK, 2004.
33. Sheldrick G.M. SHELXS-97: Program for a Crystal Structure Solution (1997), University of Göttingen, Germany
34. Sheldrick G.M. SHELXL-97: Program for the Refinement of a Crystal Structure from Diffraction Data (1997), University of Göttingen, Germany
35. Singh B., and Mishra H. J. Indian Chem. Soc. 63 (1986) 692-698
36. Deacon G.B., and Phillips R.J. Coord. Chem. Rev. 33 (1980) 227-243
37. Deacon G.B., Huber F., and Phillips P.J. Inorg. Chim. Acta 104 (1985) 41-45
38. Siemens. Stereochemical Workstation Operation Manual, Release 3.4 (1989), Siemens Analytical X-Ray Intsruments, Inc., Madison, WI, USA
39. Allen F.H. Acta Cryst. B 58 (2002) 380-386
40. Addison A.W., Rao T.N., Reedijck J., and van Rijn J. J. Chem. Soc., Dalton Trans. (1984) 1349-1355
41. Pardo O., Tomas A., Mazurier A., Nguyen-Huy D., and Viossat B. Z. Kristallogr.- New Cryst. St. 215 (2000) 111-112
42. Carballo R., Castineiras A., Hiller W., and Strahle J. J. Coord. Chem. 40 (1996) 253-271
43. Rettig S.J., Storr A., and Trotter J. Can. J. Chem. 77 (1999) 434-438
44. Weser U., Schubotz L.M., and Longfelder E. J. Mol. Catal. 13 (1981) 249-255
45. Gonzalez-Alvarez M., Alzuet G., Borras J., Aguado L.C., Montejo-Bernardo J.M., and Garcia-Granada S. J. Biol. Inorg. Chem. 8 (2003) 112-130
46. Ohtsu H., Shimazaki Y., Odani A., Yamauchi O., Mori W., Itoh S., and Fukuzumi S. J. Am. Chem. Soc. 122 (2000) 5733-5741
47. Casanova J., Alzuet G., Latorre J., and Borras J. Inorg. Chem. 36 (2000) 2052-2058
48. Casanova J., Alzuet G., Ferrer S., Latorre J., Ramirez J.A., and Borras J. Inorg. Chim. Acta 304 (2000) 170-177
49. Szilagyi I., Labadi I., Hernadi K., Palinko I., Nagy N.V., Korecz L., Rockenbauer A., Kele Z., and Kiss T. J. Inorg. Biochem. 99 (2005) 1619-1629
50. Patel R.N., Kumar S., and Pandeya K.B. J. Inorg. Biochem 89 (2002) 61-68