New peptide labels containing covalently bonded platinum(II) centers as diagnostic biomarkers and biosensors

Organic Letters

Volumn 2, Issue 22, 2000, Pages 3461-3464

  Albrecht, Martin ^a   Rodríguez, Gema ^a   Schoenmaker, Jeroen ^a   Van Koten, Gerard ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL MARKER; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PEPTIDE; PLATINUM; PLATINUM COMPLEX; VALINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GENETIC PROCEDURES; SYNTHESIS;

BIOLOGICAL MARKERS; BIOSENSING TECHNIQUES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; ORGANOPLATINUM COMPOUNDS; PEPTIDES; PLATINUM; VALINE;

EID: 0034597526     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006484l     Document Type: Article

References (42)

1. Fersht, A. Enzyme Structure and Mechanism, 2nd ed.; W. H. Freeman and Company: New York, 1985.
2. Dill, K. A. Biochemistry 1990, 29, 7133.
3. Tuchscherer, G.; Scheibler, L.; Dumy, P.; Mutter, M. Biopolymers (Peptide Science) 1998, 47, 63.
4. Nonradioactive labeling and Detection of Biomolecules; Kessler, C. A., Ed.; Springer: Berlin, 1992.
5. (a) Severin, K.; Bergs, R.; Beck, W. Angew. Chem. 1998, 110, 1722; Angew. Chem., Int. Ed. 1998, 37, 1635.
6. (a) Severin, K.; Bergs, R.; Beck, W. Angew. Chem. 1998, 110, 1722; Angew. Chem., Int. Ed. 1998, 37, 1635.
7. (b) Ryabov, A. D. Angew. Chem. 1991, 103, 945; Angew. Chem., Int. Ed. Engl. 1991, 30, 931.
8. (b) Ryabov, A. D. Angew. Chem. 1991, 103, 945; Angew. Chem., Int. Ed. Engl. 1991, 30, 931.
9. (c) Jaouen, G.; Vessières, A. Acc. Chem. Res. 1993, 26, 361.
10. Collman, J. P.; Hegedus, S. L.; Norton, J. R.; Fink, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
11. (a) Jaroch, S.; Schwarz, T.; Steglich, W.; Zistler, P. Angew. Chem. 1993, 105, 1803; Angew. Chem., Int. Ed. Engl. 1993, 32, 1771.
12. (a) Jaroch, S.; Schwarz, T.; Steglich, W.; Zistler, P. Angew. Chem. 1993, 105, 1803; Angew. Chem., Int. Ed. Engl. 1993, 32, 1771.
13. (b) Gleichmann, A. J.; Wolff, J. M.; Sheldrick, W. S. J. Chem. Soc., Dalton Trans. 1995, 1549.
14. (c) Krämer, B. Angew. Chem. 1996, 108, 1287; Angew. Chem., Int. Ed. Engl. 1996, 35, 1197.
15. (c) Krämer, B. Angew. Chem. 1996, 108, 1287; Angew. Chem., Int. Ed. Engl. 1996, 35, 1197.
16. For organometallic peptide labeling at the N-terminus, see, for example: (a) Eckert, H.; Forster, B.; Seidel, C. Z. Naturforsch. B 1991, 46, 339.
17. (b) Amiens, C.; Balavoine, G.; Guibé, F. J. Organomet. Chem. 1993, 443, 207.
18. (c) Hungate, R. W.; Miller, F.; Goodman, M. S. Tetrahedron Lett. 1988, 27, 4273. For labeling of the C-terminus, see, for example:
19. (d) Brosch, O.; Weyhermüller, T.; Metzler-Nolte, N. Eur. J. Inorg. Chem. 2000, 323.
20. van Koten, G. Pure Appl. Chem. 1989, 61, 1681.
21. (a) Ismail, I. M. Sadler, P. J. In Platinum, Gold, and Other Metal Chemotherapeutic Agents; Lippard, S. J., Ed.; ACS Symposium Series 209; American Chemical Society: Washington, D.C., 1983; p 171.
22. (b) Pregosin, P. S. Coord. Chem. Rev. 1982, 44, 247.
23. (a) Albrecht, M.; Gossage, R. A.; Lutz, M.; Spek, A. L.; van Koten, G. Chem. Eur. J. 2000, 6, 1431.
24. (b) Albrecht, M.; van Koten, G. Adv. Mater. 1999, 11, 171.
25. (c) Albrecht, M.; Gossage, R. A.; Spek, A. L.; van Koten, G. Chem. Commun. 1998, 1003.
26. (a) Ford, A.; van Koten, G. Submitted,
27. (b) Rodríguez, G.; Albrecht, M.; Spek, A. L.; van Koten, G. Manuscript in preparation.
28. Bodanszky, M. Principles of Peptide Synthesis; Springer: Heidelberg, 1984.
29. Bourne, G. T.; Meutermans, W. D. F.; Alewood, P. F.; McGeary, R. P.; Scanlon, M.; Watson, A. A.; Smythe, M. L. J. Org. Chem. 1999, 64, 3095.
30. (a) Canty, A. J.; Patel, J.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 2000, 599, 195.
31. (b) Steele, B. R.; Vrieze, K. Transition Met. Chem. 1977, 2, 140.
32. Albrecht, M.; Lutz, M.; Spek, A. L.; van Koten, G. Nature 2000, 406, 970.
33. Darensbourg, D. J.; Robertson, J. B.; Larkins, D. L.; Reibenspies, J. H. Inorg. Chem. 1999, 38, 2473.
34. Mingos, D. M. P. Transition Met. Chem. 1978, 3, 1.
35. Albrecht, M.; Gossage, R. A.; Frey, U.; Ehlers, A. W.; Baerends, E. J.; Merbach, A. E.; van Koten, G. Submitted.
36. (a) Ryan, R. R.; Kubas, G. J.; Moody, D. C.; Eller, P. G. Struct. Bonding (Berlin) 1981, 46, 47.
37. (b) Muijsers, J. C.; Niemantsverdriet, J. W.; Wehman-Ooyevaar, I. C. M.; Grove, D. M.; van Koten, G. Inorg. Chem. 1992, 31, 3143.
38. 2 concentration, which is a particularly important characteristic in view of sensor applications in complex systems.
39. Okpodu, C. M.; Alscher, R. G.; Grabau, E. A.; Cramer, C. L. J. Plant Physiol. 1996, 148, 309.
40. Lippard, S. J.; Berg, J. M. Principles of Bioinorganic Chemistry; University Science Books: Mill Valley, CA, 1994.
41. A similar strategy using organometallic sites for the selective gas recognition has been recently applied for the fabrication of (irreversible) NO sensors, see: Franz, K. J.; Singh, N.; Lippard, S. J. Angew. Chem. 2000, 112, 2194; Angew. Chem., Int. Ed. 2000, 39, 2120.
42. A similar strategy using organometallic sites for the selective gas recognition has been recently applied for the fabrication of (irreversible) NO sensors, see: Franz, K. J.; Singh, N.; Lippard, S. J. Angew. Chem. 2000, 112, 2194; Angew. Chem., Int. Ed. 2000, 39, 2120.