Synthesis, structural and spectroscopic characterization and biomimetic properties of new copper, manganese, zinc complexes: Identification of possible superoxide-dismutase mimics bearing hydroxyl radical generating/scavenging abilities

Journal of Inorganic Biochemistry

Volumn 104, Issue 8, 2010, Pages 820-830

  Lupidi, Giulio ^a   Marchetti, Fabio ^a   Masciocchi, Norberto ^b   Reger, Daniel L ^c   Tabassum, Sartaj ^d   Astolfi, Paola ^e   Damiani, Elisabetta ^e   Pettinari, Claudio ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

^b UNIVERSITY OF INSUBRIA   (Italy)

^c UNIVERSITY OF SOUTH CAROLINA   (United States)

^d ALIGARH MUSLIM UNIVERSITY   (India)

^e UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 [2 [4 [[2,2,2 TRI(1H PYRAZOL 1 YL)ETHOXY]METHYL]BENZYLOXY] 1,1 DI(1H PYRAZOL 1 YL]ETHYL] 1H PYRAZOLE; ACETIC ACID DERIVATIVE; BIS(3,5 DIMETHYLPYRAZOLYL)ACETATE; BIS(PYRAZOLYL)ACETATE; BORIC ACID; COPPER COMPLEX; HYDRIDOTRIS(3 PHENYL 5 METHYLPYRAZOLYL)BORATE; HYDROXYL RADICAL; IMIDAZOLE DERIVATIVE; MANGANESE DERIVATIVE; PEROXYNITRITE; PYRAZOLE DERIVATIVE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG; ZINC COMPLEX;

ANTIOXIDANT ACTIVITY; ARTICLE; BIOMIMETICS; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; FLUORESCENCE; IC 50; OXIDATION; SPECTROSCOPY; STRUCTURE ANALYSIS; X RAY POWDER DIFFRACTION;

COPPER; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICAL SCAVENGERS; MANGANESE; OXIDATION-REDUCTION; PEROXYNITROUS ACID; PYRAZOLES; STEREOISOMERISM; SUPEROXIDES; ZINC;

EID: 77953609136     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2010.03.013     Document Type: Article

References (61)

1. de Grey A.D. Free Radic. Res. 2006, 40:1244-1249.
2. Johnson F., Giulivi C. Mol. Aspects. Med. 2005, 26:340-352.
3. Sorenson J.R.J. Curr. Med. Chem. 2002, 9:639-662.
4. Salvemini D., Wang Z.-Q., Zweier J.L., Samouilov A., Macarthur H., Misko T.P., Currie M.G., Cuzzocrea S., Sikorski J.A., Riley D.P. Science 1999, 286:304-306.
5. Zhang C.X., Lippard S.J. Curr. Op. Chem. Biol. 2003, 7:481-489.
6. Riley D.P. Chem. Rev. 1999, 99:2573-2588.
7. Sakurai H., Kojlwe Y., Yoshikawa Y., Kewebe K., Yosul H. Coord. Chem. Rev. 2002, 226:167-178.
8. Day B.J. Antioxid. Redox Signal 2008, 10:355-370.
9. Afonso V., Champy R., Mitrovic D., Collin P., Lomri A. Joint Bone Spine. 2007, 74:324-329.
10. Potapov A.S., Nudnova E.A., Domina G.A., Kirpotina L.N., Quinn M.T., Khlebnikov A.I., Schepetkin I.A. Dalton Trans. 2009, 23:4488-4498.
11. Cejuedo M., Alzuet S., Ferrer S., Borra J., Castineiras A., Mozzani A., Casella L. Inorg. Chem. 2004, 43:6805-6814.
12. Sprakel V.S., Feiters M.C., Meyer-Klaucke W., Klopstra M., Brinksma J., Feringa B.L., Karlin K.D., Nolte R.J. Dalton Trans 2005, 3522-3527.
13. Tabassum S., Parveen S., Arjmand F. Indian J. Chem. 2004, 43A:270-277.
14. Tabassum S., Parveen S., Arjmand F. Trans. Met. Chem. 2005, 30:196-204.
15. Arjmand F., Parveen S., Tabassum S. Trans. Met. Chem. 2005, 30:128-135.
16. Schepetkin I., Potapov A., Klebnikov A., Korotkova E., Lukina A., Malovichko G., Kirpotina L., Quinn M.T. J. Biol. Inorg. Chem. 2006, 11:499-513.
17. Chen P., Fujisawa K., Solomon E.I. J. Am. Chem. Soc. 2000, 122:10177-10193.
18. Parkin G. Chem. Rev. 2004, 104:699-768.
19. Singh U.P., Sharma A.K., Tyagi P., Upreti S., Singh R.K. Polyhedron 2006, 25:3628-3638.
20. Schofield A.D., Barros M.L., Cushion M.G., Schwarz A.D., Mountford P. Dalton Trans. 2009, 85-96.
21. Beck A., Weibert B., Burzlaff N. Eur. J. Inorg. Chem. 2001, 521-527.
22. Hegelmann I., Beck A., Eichhorn C., Weibert B., Burzlaff N. Eur. J. Inorg. Chem. 2003, 339-347.
23. Hammes B.S., Kieber-Emmons M.T., Letizia J.A., Shirin Z., Carrano C.J., Zakharov L.N., Rheingold A.L. Inorg. Chim. Acta 2002, 346:227-238.
24. Kozlevčar B., Gamez P., de Gelder R., Driessen W.L., Reedijk J. Eur. J. Inorg. Chem. 2003, 47-50.
25. Santillan G.A., Carrano C.J. Inorg. Chem. 2007, 46:1751-1759.
26. Santillan G.A., Carrano C.J. Dalton Trans 2008, 3995-4005.
27. Santillan G.A., Carrano C.J. Inorg. Chem. 2008, 47:930-939.
28. Kozlevčar B., Golobič A., Gamez P., Koval I.A., Driessen W.L., Reedijk J. Inorg. Chim. Acta 2005, 358:1135-1140.
29. Pellei M., Gioia Lobbia G., Santini C., Spagna R., Camalli M., Fedeli D., Falcioni G. Dalton Trans 2004, 2822-2828.
30. Peters L., Hübner E., Haas T., Heinemann F.W., Burzlaff N. J. Organomet.Chem 2009, 694:2319-2327.
31. Hübner E., Haas T., Burzlaff N. Eur. J. Inorg. Chem. 2006, 4989-4997.
32. Burzlaff N., Hegelmann I., Weibert B. J. Organomet. Chem. 2001, 626:16-23.
33. Burzlaff N. Tripodal N,N,O-Ligands For Metalloenzyme Models And Organometallics. Adv. Inorg. Chem. 2008, Vol. 60:101-165. Elsevier, London. R. van Eldik (Ed.).
34. Otero A., Fernández-Baeza J., Lara-Sánchez A., Tejeda J., F: Sánchez-Barba L. Eur. J. Inorg. Chem 2008, 5309-5326.
35. Uppu R.M., Squadrito G.L., Cueto R., Pryor W.A. Methods Enzymol. 1996, 269:311-312.
36. Senko M.W. IsoPro Isotopic Abundance Simulator, v. 2.1 1994, National High Magnetic Field Laboratory, Los Alamos National Laboratory, Los Alamos, NM.
37. Reger D.L., Wright T.D., Semeniuc R.F., Grattan T.C., Smith M.D. Inorg. Chem. 2001, 40:6212-6219.
38. Yang K.-W., Wang Y.-Z., Huang Z.-X., Sun J. Polyhedron 1997, 16:109.
39. Marchetti F., Pellei M., Pettinari C., Pettinari R., Rivarola E., Santini C., Skelton B.W., White A.H. J. Organomet. Chem. 2005, 690:1878-1888.
40. Kopf H., Pietraszuk C., Hübner E., Burzlaff N. Organometallics 2006, 25:2533-2546.
41. Sheldrick G.M. SHELXL-97: Crystal Structure Refinement Program 1997, University of Göttingen, Germany.
42. Version 3.0, Bruker AXS, 2005, Karlsruhe, Germany.
43. 1 were derived from the experimentally determined crystal structure of a ruthenium dimer. Crystal Growth Des. 2006, 6:1068-1070.
44. Valentão P., Fernes E., Carvalho F., Andrade P.B., Seabra R.M., Bastos M.L., Agric J. Food Chem. 2001, 49:3476-3479.
45. Paya M., Halliwell B., Hoult J.R.S. Biochem. Pharmacol. 1992, 44:205-214.
46. Zhang H., Gurney J.M., Becker D., Kalyanaraman B. J. Biol. Chem. 2002, 277:1013-1020.
47. Geary W.J. Coord. Chem. Rev. 1971, 7:81-122.
48. Nakamoto K. Infrared and Raman Spectra of Inorganic and Coordination Compounds 2009, 62-67. John Wiley & Sons, Hoboken, New Jersey, and references reported therein. 6th Ed., Part B.
49. Pettinari C. Scorpionates II: Chelating Borate Ligands 2008, Imperial College Press, London.
50. Pettinari C., Marchetti F., Pettinari R., Marinelli A., Crispini A., Bellusci A. Inorg. Chim. Acta 2009, 362:4593-4598.
51. Finkelstein E., Rosen G.M., Raukman E.J. J. Am. Chem. Soc 1980, 102:4994-4999.
52. Fielden E.M., Roberts P.B., Bray B.C., Lowe D.J., Mautner G.N., Rotilio G., Calabrese L. Biochem. J. 1974, 139:49-60.
53. Offer T., Russo A., Samuni A. FASEB J. 2000, 14:1215-1223.
54. Formigari A., Irato P., Santon A. Comp. Biochem. Physiol., Part C 2007, 146:443-459.
55. Bagchi D., Bagchi M., Stohs S.J. Gen. Pharmac. 1997, 28:85-91.
56. Wang Q., Wang Y., Yang Z. Chem. Pharm. Bull. 2008, 56:1018-1021.
57. Li T.R., Yang Z.Y., Wang B.D. Chem. Pharm. Bull. 2007, 55:26-32.
58. Qin D., Yang Z., Qi G. Spectrochim. Acta A 2009, 74:415-420.
59. Muscoli C., Cuzzocrea S., Riley D.P., Zweier J.L., Thiemermann C., Wang Z.Q., Salvemini D. Br. J. Pharmacol. 2003, 140:445.
60. Esposito E., Cuzzocrea S. Front. Biosci. 2009, 14:263.
61. Xu Y., Liu B., Zweie J.L., He G. J. Pharmacol. Exp. Ther. 2008, 327:402.