New glycoside derivatives of carnosine and analogs resistant to carnosinase hydrolysis: Synthesis and characterization of their copper(II) complexes

Journal of Inorganic Biochemistry

Volumn 105, Issue 2, 2011, Pages 181-188

  Lanza, Valeria ^a   Bellia, Francesco ^a   D'Agata, Roberta ^a   Grasso, Giuseppe ^a   Rizzarelli, Enrico ^a   Vecchio, Graziella ^a  

^a UNIVERSITY OF CATANIA   (Italy)

Author keywords

Carnosinase; Carnosine; Carnosine amide; Copper(II) complexes; Glucose; Lactose

Indexed keywords

AMIDE; ANTIOXIDANT; CARNOSINE; CARNOSINE DERIVATIVE; CHELATING AGENT; COPPER COMPLEX; DIPEPTIDASE; DIPEPTIDE; GLUCOSE; GLYCOSIDE; HISTIDINE; LACTOSE; LIGAND; METAL ION; SUGAR; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CHELATION; CIRCULAR DICHROISM; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; ENZYME ACTIVITY; HOMEOSTASIS; HYDROLYSIS; INORGANIC CHEMISTRY; MUSCLE; NERVOUS TISSUE; NONHUMAN; OXIDATIVE STRESS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THERMODYNAMICS; ULTRAVIOLET RADIATION;

CARNOSINE; CHELATING AGENTS; CIRCULAR DICHROISM; COORDINATION COMPLEXES; COPPER; DIPEPTIDASES; GLYCOSIDES; HUMANS; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA;

EID: 78649601269     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2010.10.014     Document Type: Article

References (78)

1. P.J. Quinn, A.A. Boldyrev, and V.E. Formazuyk Mol. Aspects Med. 13 1992 379 444
2. C.K.B. Ferrari Biogerontology 5 2004 275 290
3. C.K.B. Ferrari, and E.A.F.S. Torres Biomed. Pharmacother. 57 2003 251 260
4. R.D. Shytle, J. Ehrhart, J. Tan, J. Vila, M. Cole, C.D. Sanberg, P.R. Sanberg, and P.C. Bickford Rejuvenation Res. 10 2007 173 178
5. A.R. Hipkiss Adv. Food Nutr. Res. 57 2009 87 154
6. A. Decker, S.A. Livisay, and S. Zhou Biochemistry (Mosc) 65 2000 766 770
7. J.H. Kang, K.S. Kim, S.Y. Choi, H.Y. Kwon, M.H. Won, and T.-C. Kang Mol. Cells 13 2002 498 502
8. A.R. Hipkiss, V.C. Worthington, D.T.J. Himsworth, and W. Herwig Biochim. Biophys. Acta 1380 1998 46 54
9. T. Nagasawa, T. Yonekura, N. Nishizawa, and D.D. Kitts Mol. Cell. Biochem. 225 2001 29 34
10. R. Kohen, Y. Yamamoto, K.C. Cundy, and B.N. Ames Proc. Natl Acad. Sci. USA 85 1988 3175 3179
11. S. Cuzzocrea, T. Genovese, M. Failla, G. Vecchio, M. Fruciano, E. Mazzon, R. Di Paola, C. Muia, C. La Rosa, N. Crimi, E. Rizzarelli, and C. Vancheri Am. J. Physiol. Lung Cell. Mol. Physiol. 292 2007 L1095 L1104
12. A.A. Fouad, M.A.-A. El-Rehany, and H.K. Maghraby Eur. J. Pharmacol. 572 2007 61 68
13. Baran E.J. Biochemistry (Mosc) 65 2000 789 797
14. K.J. Barnham, and A.I. Bush Curr. Opin. Chem. Biol. 12 2008 222 228
15. Q. Fu, H. Dai, W. Hu, Y. Fan, Y. Shen, W. Zhang, and Z. Chen Cell. Mol. Neurobiol. 28 2008 307 316
16. P.Q. Trombley, M.S. Horning, and L.J. Blakemore Biochemistry (Mosc) 65 2000 807 816
17. M. Di Donato, H.F. Hsu, S. Narindrasorak, L. Que, and B. Sarkar Biochemistry 39 2000 1890 1896
18. S. Katayama, K. Nishizawa, M. Hirano, S. Yamamura, and Y. Momose J. Pharm. Pharm. Sci. 3 2000 114 117
19. Matsukura T., and Tanaka H. Biochemistry (Mosc) 65 2000 817 823
20. M.C. Jackson, C.M. Kucera, and J.F. Lenney Clin. Chim. Acta 196 1991 193 205
21. J.F. Lenney, R.P. George, A.M. Weiss, C.M. Kucera, P.W. Chan, and G.S. Rinzler Clin. Chim. Acta 123 1982 221 231
22. M. Teufel, V. Saudek, J.-P. Ledig, A. Bernhardt, S. Boularand, A. Carreau, N.J. Cairns, C. Carter, D.J. Cowley, D. Duverger, A.J. Ganzhorn, C. Guenet, B. Heintzelmann, V. Laucher, C. Sauvage, and T. Smirnova J. Biol. Chem. 278 2003 6521 6531
23. J.F. Lenney, S.C. Peppers, C.M. Kucera-Orallo, and R.P. George Biochem. J. 228 1985 653 660
24. H. Otani, N. Okumura, A. Hashida-Okumura, and K. Nagai J. Biochem. (Tokyo) 137 2005 167 175
25. R.P. Bonomo, V. Bruno, E. Conte, G. De Guidi, D. La Mendola, G. Maccarrone, F. Nicoletti, E. Rizzarelli, S. Sortino, and G. Vecchio J. Chem. Soc., Dalton Trans. 2003 4406 4415
26. P. Mineo, D. Vitalini, D. La Mendola, E. Rizzarelli, E. Scamporrino, and G. Vecchio J. Inorg. Biochem. 98 2004 254 265
27. D. La Mendola, E. Rizzarelli, and G. Vecchio Eur. Pat. Appl. 2002 University of Catania EP 1176154
28. G. Vecchio, D. La Mendola, and E. Rizzarelli J. Supramol. Chem. 1 2001 87 95
29. E. Rizzarelli, G. Vecchio, G. Lazzarino, A.M. Amorini, and F. Bellia Eur. Pat. Appl. 2007 Universita' Degli Studi di Catania Italy EP 1860116
30. A.M. Amorini, F. Bellia, V. Di Pietro, B. Giardina, D. La Mendola, G. Lazzarino, S. Sortino, B. Tavazzi, E. Rizzarelli, and G. Vecchio Eur. J. Med. Chem. 42 2007 910 920
31. D. La Mendola, S. Sortino, G. Vecchio, and E. Rizzarelli Helv. Chim. Acta 85 2002 1633 1643
32. F. Bellia, A.M. Amorini, D. La Mendola, G. Vecchio, B. Tavazzi, B. Giardina, V. Di Pietro, G. Lazzarino, and E. Rizzarelli Eur. J. Med. Chem. 43 2008 373 380
33. A. Boldyrev, E. Bulygina, T. Leinsoo, I. Petrushanko, S. Tsubone, and H. Abe Comp. Biochem. Physiol. Biochem. Mol. Biol. 137 2004 81 88
34. J. Almkvist, and A. Karlsson Glycoconjugate J. 19 2004 575 581
35. H.J. Gabius Eur. J. Biochem. 243 1997 543 576
36. S. Elgavish, and B. Shaanan Trends Biochem. Sci. 22 1997 462 467
37. R. D'Agata, G. Grasso, G. Iacono, G. Spoto, and G. Vecchio Org. Biomol. Chem. 4 2006 610 612
38. M. Hashida, K. Akamatsu, M. Nishikawa, F. Yamashita, and Y. Takakura J. Control. Release 62 1999 253 262
39. M. Hashida, H. Hirabayashi, M. Nishikawa, and Y. Takakura J. Control. Release 46 1997 129 137
40. M. Nishikawa, H. Hirabayashi, Y. Takakura, and M. Hashida Pharm. Res. 12 1995 209 214
41. C. Li, and W.-T. Wong Tetrahedron Lett. 43 2002 3217 3220
42. F.J. Muňoz, J. Pérez, Á. Rumbero, J.I. Santos, F.J. Caňada, S. André, H.-J. Gabius, J.S. Jiménez-Barbero, J.V. Sinisterra, and M.A.J. Hernáiz Bioconjug. Chem. 20 2009 673 682
43. G. Grasso, R. D'Agata, E. Rizzarelli, G. Spoto, L. D'Andrea, C. Pedone, A. Picardi, A. Romanelli, M. Fragai, and K.J. Yeo J. Mass Spectrom. 40 2005 1565 1571
44. G. Grasso, M. Fragai, E. Rizzarelli, G. Spoto, and K.J. Yeo J. Am. Soc. Mass Spectrom. 18 2007 961 969
45. F. Bellia, V. Calabrese, F. Guarino, M. Cavallaro, C. Cornelius, V. De Pinto, and E. Rizzarelli Antioxid. Redox Signal. 11 2009 2759 2775
46. N. Schaschke, I. Assfalg-Machleidt, W. Machleidt, T. Lassleben, C.P. Sommerhoff, and L. Moroder Bioorg. Med. Chem. Lett. 10 2000 677 680
47. C. Pean, A. Wijkhuisen, F. Djedaini-Pilard, J. Fischer, S. Doly, M. Conrath, J.Y. Couraud, J. Grassi, B. Perly, and C. Creminon Biochim. Biophys. Acta 1541 2001 150 160
48. V. Cucinotta, F. D'Alessandro, G. Impellizzeri, G. Pappalardo, E. Rizzarelli, and G. Vecchio J. Chem. Soc., Chem. Commun. 1991 293 294
49. B. Di Blasio, V. Pavone, F. Nastri, C. Isernia, M. Saviano, C. Pedone, V. Cucinotta, G. Impellizzeri, E. Rizzarelli, and G. Vecchio Proc. Natl Acad. Sci. USA 89 1992 7218 7221
50. C.E. Brown, and W.E. Antholine J. Phys. Chem. 83 1979 3314 3319
51. P.G. Daniele, E. Prenesti, V. Zelano, and G. Ostacoli Spectrochim. Acta Pt. A-Molec. Biomol. Spectr. 49 1993 1299 1306
52. S. Velez, N.G. Nair, and V.P. Reddy Colloids Surf., B: Biointerfaces 66 2008 291 294
53. P. Mineo, D. Vitalini, D.L. Mendola, E. Rizzarelli, E. Scamporrino, and G. Vecchio Rapid Commun. Mass Spectrom. 16 2002 722 729
54. P.G. Daniele, P. Amico, and G. Ostacoli Inorg. Chim. Acta 66 1982 65 70
55. Brookes G., and Pettit L.D. J. Chem. Soc., Dalton Trans. 1975 2112 2116
56. Agarwal R.P., and Pettit L.D. J. Chem. Soc., Dalton Trans. 1975 268 272
57. F. Bellia, D. La Mendola, G. Maccarrone, P. Mineo, D. Vitalini, E. Scamporrino, S. Sortino, G. Vecchio, and E. Rizzarelli Inorg. Chim. Acta 360 2007 945 954
58. J.L. Gómez-Ariza, T. GarcIa-Barrera, F. Lorenzo, V. Bernal, M.J. Villegas, and V. Oliveira Anal. Chim. Acta 524 2004 15 22
59. V.B.D. Marco, and G.G. Bombi Mass Spectrom. Rev. 25 2006 347 379
60. V.S.K. Kolli, and R. Orlando J. Am. Soc. Mass Spectrom. 6 1995 234 241
61. G. Grasso, P. Mineo, E. Rizzarelli, and G. Spoto Int. J. Mass Spectrom. 282 2009 50 55
62. G. Maccarrone, R. Caruso, A. Contino, A. Giuffrida, M. Messina, and V. Cucinotta Eur. J. Inorg. Chem. 2009 2009 2612 2620
63. O. Yamauchi, Y. Nakao, and A. Nakahara Bull. Chem. Soc. Jpn 46 1979 3749 3752
64. J.M. Tsangaris, and R.B. Martin J. Am. Chem. Soc. 92 1970 4255 4260
65. H. Lavanant, H. Virelizier, and Y. Hoppilliard J. Am. Soc. Mass Spectrom. 9 1998 1217 1221
66. A.T. Blades, P. Jayaweera, M.G. Ikonomou, and P. Kebarle Int. J. Mass Spectrom. Ion Processes 102 1990 251 267
67. X. Yaodong, Z. Xin, A.L. Yergey, and J. Am Soc. Mass Spectrom. 7 1996 25 29
68. D. La Mendola, P. Mineo, E. Rizzarelli, E. Scamporrino, G. Vecchio, and D. Vitalini J. Supramol. Chem. 1 2001 147 151
69. F. Bellia, D. La Mendola, C. Pedone, E. Rizzarelli, M. Saviano, and G. Vecchio Chem. Soc. Rev. 38 2009 2756 2781 and reference therein
70. E. Rizzarelli, and G. Vecchio Coord. Chem. Rev. 188 1999 343 364 and reference therein
71. V.V. Mossine, and T.P. Mawhinney J. Agric. Food Chem. 55 2007 10373 10381
72. H. Sigel, and R.B. Martin Chem. Rev. 82 1982 385 426
73. E.W. Wilson, M.H. Kasperian, and R.B. Martin J. Am. Chem. Soc. 92 1970 5365 5372
74. J.M. Tsangaris, J.W. Chang, and R.B. Martin J. Am. Chem. Soc. 91 1969 726 731
75. B. Gyurcsik, I. Vosekalna, and E. Larsen Acta Chem. Scand. 51 1997 49 58
76. L. Casella, and M. Gullotti Inorg. Chem. 22 1983 242 249
77. T. Wang, and Z. Guo Curr. Med. Chem. 13 2006 525 537
78. L.E. Scott, and C. Orvig Chem. Rev. 109 2009 4885 4910