Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed to design kojic acid derivatives with new perspectives

Journal of Inorganic Biochemistry

Volumn 104, Issue 5, 2010, Pages 560-569

  Nurchi, Valeria Marina ^a   Crisponi, Guido ^a   Lachowicz, Joanna Izabela ^a   Murgia, Sergio ^a   Pivetta, Tiziana ^a   Remelli, Maurizio ^b   Rescigno, Antonio ^a   Niclós Gutíerrez, Juan ^c   González Pérez, Josefa María ^c   Domínguez Martín, Alicia ^c   Castiñeiras, Alfonso ^d   Szewczuk, Zbigniew ^e  

^a UNIVERSITY OF CAGLIARI   (Italy)

^b UNIVERSITY OF FERRARA   (Italy)

^c UNIVERSITY OF GRANADA   (Spain)

^d UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^e UNIVERSITY OF WROC AW   (Poland)

Author keywords

Al(III); Fe(III); Kojic acid; Molecular modeling; PFe; Solution equilibria; Synthesis; Thermodynamic measurements; X ray structure

Indexed keywords

6 (5 HYDROXY 2 HYDROXYMETHYL PYRAN 4 ONE) 5 HYDROXY 2 HYDROXYMETHYL PYRAN 4 ONE; ALUMINUM COMPLEX; IRON COMPLEX; KOJIC ACID; METAL COMPLEX; METAL ION; MONOPHENOL MONOOXYGENASE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CALORIMETRY; COMPLEX FORMATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; ENZYME INHIBITION; IONIC STRENGTH; POTENTIOMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; QUANTUM CHEMISTRY; SPECTROPHOTOMETRY; STRUCTURE ANALYSIS; THERMODYNAMICS; X RAY ANALYSIS;

ALUMINUM; ANTIOXIDANTS; CHELATING AGENTS; CRYSTALLOGRAPHY, X-RAY; HUMANS; IRON; LIGANDS; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; MONOPHENOL MONOOXYGENASE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRONES;

EID: 77950689019     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2010.01.007     Document Type: Article

References (59)

1. Bentley R. Nat. Prod. Rep. 2006, 23:1046-1062.
2. Thomson K.H., Barta C.A., Orwig C. Chem. Soc. Rev. 2006, 35:545-556.
3. Yabuta T. J. Chem. Soc. 1924, 125:575-587.
4. Burdock F.A., Soni M.G., Carabin I.G. Reg. Toxicol. Pharmacol. 2001, 33(1):80-101.
5. R. Fukusawa, H. Wakabayashi, T. Natori, Japanese Patent 5740875, 1982.
6. Kahn V., Ben-Shalom N., Zakin V. J. Agric. Food Chem. 1997, 45(11):4460-4465.
7. Beelik A. Adv. Carbohydr. Chem. 1956, 11:145-183.
8. Wiley J.W., Tyson G.N., Steller J.S. J. Am. Chem. Soc. 1942, 64:963-964.
9. Crisponi G., Remelli M. Coord. Chem. Rev. 2008, 252:1225-1240.
10. Kalinowski D.S., Richardson D.R. Pharmacol. Rev. 2005, 57:547-583.
11. Crichton R.R., Ward R.J. Curr. Med. Chem. 2003, 10:997-1004.
12. Hider R.C., Liu Z.D. Curr. Med. Chem. 2003, 10:1051-1064.
13. Santos A. Coord. Chem. Rev. 2002, 228:187-203.
14. Perl D.P., Gajdusek D.C., Yanagihara R.T., Gibbs C.J. Science 1982, 217:1053-1055.
15. Dayde S., Filella M., Berthon G. J. Inorg. Biochem. 1990, 38:241-259.
16. Ohman L.O., Martin R.B. Clin. Chem. 1994, 40:598-601.
17. Fox R.C., Taylor P.D. Bioorg. Med. Chem. Lett. 1998, 8:443-446.
18. Crisponi G., Nurchi V.M., Pivetta T. J. Inorg. Biochem. 2008, 102:209-215.
19. Crisponi G., Nurchi V.M., Pivetta T., Galezowska J., Gumienna-Kontecka E., Bailly T., Burgada R., Kozlowski H. J. Inorg. Biochem. 2008, 102:1486-1494.
20. Nurchi V.M., Pivetta T., Lachowicz J.I., Crisponi G. J. Inorg. Biochem. 2009, 103:227-236.
21. Nurchi V.M., Crisponi G., Pivetta T., Tramontano E., Cesare Marincola F., Lachowicz J.I. Polyhedron 2009, 28:763-768.
22. Nurchi V.M., Crisponi G., Pivetta T., Donatoni M., Remelli M. J. Inorg. Biochem. 2008, 102:684-692.
23. Albert A., Serjant E.P. The Determination of Ionization Constants 1984, Chapman and Hall, London, (Chapter 2).
24. Marongiu B., Piras A., Porcedda S., Tuveri E., Sanjust E., Meli M., Sollai F., Zucca P., Rescigno A. J. Agric. Food Chem. 2007, 55:10022-10027.
25. Rescigno A., Zucca P., Flurkey A., Inlow J., Flurkey W.H. Enzyme Microb. Technol. 2007, 41:620-627.
26. Crisponi G., Caredda A., Cristiani F., Diaz A., Nurchi V.M., Pinna R., Pivetta T., Silvagni R. Ann. Chim. (Rome) 2004, 94:147-153.
27. Gran G. Analyst 1952, 77:661-671.
28. Zekany L., Nagypal I. Computational Methods for the Determination of Formation Constants 1985, Plenum Press, New York, (Chapter 8). D.J. Legget (Ed.).
29. Gans P., Sabatini A., Vacca A. Talanta 1996, 43:1739-1753.
30. Gampp H., Maeder M., Meyer Ch.J., Zuberbuhler A.D. Talanta 1985, 32:1133-1139.
31. Gampp H., Maeder M., Meyer Ch.J., Zuberbuhler A.D. Talanta 1986, 33:943-951.
32. Gampp H., Maeder M., Meyer Ch.J., Zuberbuhler A.D. Anal. Chim. Acta 1987, 193:287-293.
33. Glasoe P.K., Long F. J. Phys. Chem. 1960, 60:188-190.
34. Hansen L.D., Jensen T.E., Mayne S., Eatough D.J., Izatt R.M., Christensen J.J. J. Chem. Thermodyn. 1975, 7:919-926.
35. Gans P., Sabatini A., Vacca A. J. Solut. Chem. 2008, 37:467-476.
36. Vacca A., Sabatini A., Bologni L. J. Chem. Soc., Dalton Trans. 1981, 1246-1250.
37. Bruker, APEX2 Software, V2.0-1, Bruker AXS Inc., Madison, Wisconsin, USA, 2005.
38. Sheldrick G.M. SADABS, Program for Empirical Absorption Correction of Area Detector Data 1997, University of Goettingen, Germany.
39. Sheldrick G.M. Acta Crystallogr. A 1990, 46:467-473.
40. Sheldrick G.M. SHELXL-97. Program for the Refinement of Crystal Structures 1997, University of Goettingen, Germany.
41. Wilson A.J.C. International Tables for Crystallography, vol. 1 1995, Kluwer Academic Publishers, Dordrecht, The Netherlands.
42. Spek A.L. PLATON, A Multipurpose Crystallographic Tool 2003, Utrecht University, Utrecht, The Netherlands.
43. E. Keller, SCHAKAL-97. A Computer Program for the Graphic Representation of Molecular and Crystallographyic Models, University of Freiburg i. Br., Germany, 1997.
44. Paul M.A., Long P.A. Chem. Rev. 1957, 57:1-45.
45. Pettit L.D., Powell K.J. The IUPAC Stability Constants Database, Ver. 5.7 2001, Academic Software and IUPAC, Otley, UK.
46. Petrola R. Finn. Chem. Lett. 1985, 12:201-206.
47. Murakami Y. Chem. Soc. Jpn. 1962, 35:52-56.
48. Naik D. Anal. Chim. Acta 1979, 106:147-150.
49. Crisponi G., Lai A., Monduzzi M., Saba G. Inorg. Chim. Acta 1983, 80:85-88.
50. Baes Ch.F., Mesmer R.E. The Hydrolysis of Cations 1986, R.E. Kreiger Publishing, Malabar, FL.
51. McBryde W., Atkinson G. Can. J. Chem. 1961, 39:510-525.
52. Sommer L., Losmanova A. Collec. Czech. Chem. Commun. 1961, 26:2781-2805.
53. Murakami Y. J. Inorg. Nucl. Chem. 1962, 24:679-688.
54. Sima J., Sipos R., Izakovic M., Valigura D., Tarapcik P. Polish J. Chem. 2006, 80:1991-1999.
55. Odoko M., Yamamoto K., Okabe N. Acta Crystallogr. C 2002, 58C:m469-m470.
56. Zalemba K., Lasocha W., Adamski A., Stanek J., Pattek-Janczyk A. J. Coord. Chem. 2007, 60:1537-1546.
57. Lockhart T.P., Davidson F. Organometallics 1987, 6:2471-2478.
58. de A.G., Fernandes A., da P.I., Maia S., de Souza E.J., Lemos S.S., Batista A.A., Abram U., Ellena J., Castellano E.E., Deflon V.M. Polyhedron 2008, 27:2983-2989.
59. Lord S.J., Epstein N.A., Paddock R.L., Vogels C.M., Hennigar T.L., Zaworotko M.J., Taylor N.J., Driedzik W.R., Broderick T.L., Westcott S.A. Can. J. Chem. 1999, 77:1249-1261.