A new triferrocenyl-tris(hydroxymethyl)aminomethane derivative as a highly sensitive electrochemical marker of biomolecules: Application to the labelling of PNA monomers and their electrochemical characterization

Chemistry - A European Journal

Volumn 12, Issue 15, 2006, Pages 4091-4100

  Baldoli, Clara ^a   Rigamonti, Clara ^b   Maiorana, Stefano ^b   Licandro, Emanuela ^b   Falciola, Luigi ^b   Mussini, Patrizia Romana ^b  

^a CNR   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

Bioorganometallic chemistry; Electrochemistry ferrocene; Metallocenes peptide nucleic acids

Indexed keywords

BIOORGANOMETALLIC CHEMISTRY; ELECTROCHEMISTRY FERROCENE; METALLOCENES PEPTIDE NUCLEIC ACIDS;

BIOASSAY; BIOMARKERS; DERIVATIVES; ELECTROCHEMISTRY; MONOMERS; ORGANOMETALLICS; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

BIOLOGICAL MARKER; DRUG DERIVATIVE; FERROCENE; FERROUS ION; PEPTIDE NUCLEIC ACID; TROMETAMOL;

ARTICLE; CHEMISTRY; ELECTROCHEMISTRY; STAINING;

BIOLOGICAL MARKERS; ELECTROCHEMISTRY; FERROUS COMPOUNDS; PEPTIDE NUCLEIC ACIDS; STAINING AND LABELING; TROMETHAMINE;

EID: 33646818318     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501466     Document Type: Article

References (46)

1. P. E. Nielsen, M. Egholm, R. H. Berg, O. Buchardt, Science 1991, 254, 1497-1500.
2. Peptide Nucleic Acids: Protocols and Applications (Ed.: P. E. Nielsen), 2nd ed., Horizon Bioscience (UK), 2004.
3. S. Tomac, M. Sarkar, T. Ratilainen, P. Wittung, P. E. Nielsen, B. Nordén, J. Am. Chem. Soc. 1996, 118, 5544-5552.
4. a) E. Uhlmann, A Peyman, G. Breipohl, W. D. Will, Angew. Chem. 1998, 110, 2954-2983;
5. Angew. Chem. Int. Ed. 1998, 37, 2796-2823;
6. b) U. Giesen, W. Kleider, C. Berding, A. Geiger, H. Ørum, P. E. Nielsen, Nucleic Acids Res. 1998, 26, 5004-5006.
7. T. Ratilainen, A. Holmén, E. Tuite, P. E Nielsen, B. Nordén, Biochemistry 2000, 39, 7781-7791.
8. K. Kerman, D. Ozkan, P. Kara, A. Erden, B. Meric, P. E. Nielsen, M. Ozsoz, Electroanalysis 2003, 15, 667-670.
9. A. Basile, A. Giuliani, G. Pirri, M. Chiari, Electrophoresis 2002, 23, 926-929.
10. R Corradini, G. Feriotto, S. Sforza, R. Marchelli, R. Gambari, J. Mol. Recognit. 2004, 17, 76-84.
11. S. Sforza, R. Corradini, S. Ghirardi, A. Dossena, R. Marchelli, Eur. J. Org. Chem. 2000, 16, 2905-2913.
12. S. Sforza, G. Galaverna, A. Dossena, R. Corradini, R. Marchelli, Chirality 2002, 14, 591-598.
13. M. Pooga, U. Soomets, M. Hallbrink, A. Valkna, K. Saar, K. Rezaei, U. Kahl, J.-X. Hao, X.-J. Xu, Z. Wiesenfeld-Hallin, Nat. Biotechnol. 1998, 16, 857-861.
14. a) B. M. Tyler, D. J. McCormick, C. V. Hoshall, C. L. Douglas, K. Jansen, B. W. Lacy, B. Cusack, E. Richelson, FEBS Lett. 1998, 421, 280-284;
15. b) L. Good, P. E. Nielsen, Nat. Biotechnol. 1998, 16, 355-368.
16. J. L. Harris, N. Winssinger, Chem. Eur. J. 2005, 11, 6792-6801.
17. a) Bioorganometallics (Ed.: G. Jaouen), Wiley-VCH, Weinheim, 1st ed., 2005;
18. b) R. H. Fish, G. Jaouen, Organometallics 2003, 22, 2166-2177;
19. c) See also special issues in J. Organomet. Chem.
20. on bioorganometallic chemistry: J. Organomet. Chem. 2004, 689, 25;
21. J. Organomet. Chem. 2003, 668, 1-2.
22. a) C. Baldoli, P. Cerea, C. Giannini, E. Licandro, C. Rigamonti, S. Maiorana, Synlett 2005, 1984-1994;
23. b) C. Baldoli, L. Falciola, E. Licandro, S. Maiorana, P. Mussini, P. Ramani, C. Rigamonti, G. Zinzalla, J. Organomet. Chem. 2004, 689, 4791-4802.
24. a) A. R. Pike, L. C. Ryder, B. R. H. Horrocks, W. Clegg, B. A. Connolly, A. Houlton, Chem. Eur. J. 2005, 11, 344-353;
25. b) P. de-los-Santos Álvarez, M. J. Lobo-Castañón, A. J. Miranda-Ordieres, P. Tuñón-Blanco, Anal. Bioanal. Chem. 2004, 78, 104-118;
26. c) J. Wang, Nucleic Acids Res. 2000, 28, 3011-3016.
27. J. Wang, Bioesens. Bioelectron. 1998, 13, 757-762.
28. a) D. R. Van Stavaren, N. Metzler-Nolte, Chem. Rev. 2004, 104, 5931-5985;
29. b) T. S. Zatsepin, S. Y. Andreev, T. Hianik, T. S. Oretskaya, Russ. Chem. Rev. 2003, 72, 537-554.
30. a) J. C. Verheijen, G. A van der Marel, J. H. van Boom, N. Metzler-Nolte, Bioconjugate Chem. 2000, 11, 741-743;
31. b) A. Hess, N. Metzler-Nolte, J. Chem. Soc. Chem. Commun. 1999, 885-886.
32. A. Maurer, H. B. Kraatz, N. Metzler-Nolte, Eur. J. Inorg. Chem. 2005, 3207-3210.
33. a) C. Baldoli, E. Licandro, S. Maiorana, D. Resemini, C. Rigamonti, L. Falciola, M. Longhi, P. Mussini, J. Electroanal. Chem. 2005, 585, 197-205;
34. b) C. Baldoli, S. Maiorana, P. R. Mussini, C. Rigamonti, Patent MI-2004 A001427, deposited 15/07/04. PCT estension deposited 15/07/05.
35. P. R. Ashton, S. E. Boyd, C. L. Brown, N. Jayaram, S. A. Nepogodiev, J. F. Stoddart, Chem. Eur. J. 1996, 2, 1115-1128.
36. The ferrocene group is not stable to acid hydrolysis conditions.
37. H. J. Knölker, T. Braxmeier, G. Schlechtingen, Angew. Chem. 1995, 107, 2746-2749;
38. Angew. Chem. Int. Ed. Engl. 1995, 34, 2497-2500.
39. A further example for the use of 2 for labelling amino acids is reported in reference [21a].
40. A. J. Bard, L.R Faulkner, Electrochemical Methods. Fundamentals and Applications, Wiley, New York 2002, pp. 228-232.
41. A. J. Bard, L.R Faulkner, Electrochemical Methods. Fundamentals and Applications, Wiley, New York 2002, pp. 458-464.
42. Prof. D. Astruc private discussion.
43. A. J. Bard, L.R Faulkner, Electrochemical Methods. Fundamentals and Applications, Wiley, New York 2002, pp. 648-650.
44. G. Gritzner, J. Kuta, Pure Appl. Chem. 1984, 56, 461-466.
45. A. J. Bard, L.R Faulkner, Electrochemical Methods. Fundamentals and Applications, Wiley, New York 2002, pp. 247-252.
46. M. Egholm, O. Buchardt, P. E. Nielsen, J. Org. Chem. 1994, 59, 5767-5773.