An Expedient Synthesis of Cationic Rhodamine Fluorescent Probes Suitable for Conjugation to Amino Acids and Peptides

Synthesis

Volumn , Issue 17, 2003, Pages 2647-2654

  Afonso, Carlos A M ^a   Santhakumar, V ^b   Lough, Alan ^b   Batey, Robert A ^b  

^a UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

Amino acid derivatives; Fluorescent probes; Peptides; Rhodamines

Indexed keywords

AMINO ACIDS; CHROMATOGRAPHY; DYES; FLUORESCENCE; SYNTHESIS (CHEMICAL);

CATIONIC FLUORESCENT PROBES;

AROMATIC COMPOUNDS;

AMINO ACID DERIVATIVE; FLUORESCENT DYE; RHODAMINE; RHODAMINE 6G;

ARTICLE; CONJUGATION; FLUORESCENCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0346753437     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42475     Document Type: Article

References (38)

1. Valeur, B. Molecular Fluorescence: Principles and Applications; Wiley-VCH: Weinheim, 2002.
2. (a) Haugland, R. P. Handbook of Fluorescent Probes and Research Products; Molecular Probes, Inc.: Eugene, 2001, and references cited therein.
3. (b) Probe Design and Chemical Sensing, In Topics in Fluorescence Spectroscopy, Vol. 4; Lakowicz, J. R., Ed.; Plenum Press: New York, 1994.
4. (c) Scala-Valéro, C.; Doizi, D.; Guillaumet, G. Tetrahedron Lett. 1999, 40, 4803.
5. (a) Rahavendran, S.V.; Karnes, H. T. Anal. Chem. 1996, 68, 3763.
6. (b) Soper, S. A.; McGown, L. B.; Warner, I. M. Anal. Chem. 1994, 66, 428R.
7. (a) Finney, N. S. Curr. Opin. Drug Discovery Dev. 1998, 1, 98.
8. (b) Lescrinier, T.; Hendrix, C.; Kerremans, L.; Rozenski, J.; Link, A.; Samyn, B.; Aerschot, A. V.; Lescrinier, E.; Eritja, R.; Beeumen, J. V.; Herdewijn, P. Chem.-Eur. J. 1998, 4, 425
9. . (5) (a) Mitchison, T. J.; Sawin, K. E.; Theriot, J. A.; Gee, K.; Mallavarapu, A. Caged Compounds, In Methods in Enzymology, Vol. 291; Marriott, G., Ed.; Academic Press: New York, 1998, 63.
10. (b) Boturyn, D.; Boudali, A.; Constant, J.-F.; Defrancq, E.; L'homme, J. Tetrahedron 1997, 53, 5485.
11. (c) Harapanhalli, R. S.; Roy, A. M.; Adelstein, S. J.; Kassis, A. J. Med. Chem. 1998, 41, 2111.
12. (d) Mayer, A.; Neuenhofer, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 1044.
13. (e) Kojima, H.; Hirotani, M.; Urano, Y.; Kikuchi, K.; Higuchi, T.; Nagano, T. Tetrahedron Lett. 2000, 41, 69.
14. Davie, E.; Morris, J. H.; Smith, E. Org. Mass Spectrom. 1974, 763.
15. Cai, S. X.; Zhang, H.-Z.; Guastella, J.; Drewe, J.; Yang, W.; Weber, E. Bioorg. Med. Chem. Lett. 2001, 11, 39.
16. (a) Bain, A. J.; Chandna, P.; Butcher, G.; Bryant, J. J. Chem. Phys. 2000, 772, 10435.
17. (b) Byassee, T. A.; Chan, W. C.; Nie, S. Anal. Chem. 2000, 72, 5606.
18. (c) Fang, X.; Tan, W. Anal. Chem. 1999, 71, 3101.
19. (d) Mandala, M.; Serck-Hanssen, G.; Martino, G.; Helle, K. B. Anal. Biochem. 1999, 274, 1.
20. (e) Nie, S.; Chiu, D. T.; Zare, R. N. Science 1994, 266, 1018.
21. (f) Matsumoto, Y.; Sasaoka, N.; Tsuchida, T.; Fujiwara, T.; Nagao, S.; Ohmoto, T. J. Neurooncol. 1992, 13, 217.
22. (g) Choi, K. J.; Turkevich, L. A.; Loza, R. J. Phys. Chem. 1988, 92, 2248.
23. (h) Kuzela, S.; Joste, V.; Nelson, B. D. Eur. J. Biochem. 1986, 154, 553.
24. Heilporn, S.; Broeders, F.; Daloze, D.; Braekman, J. C.; Boeynaems, J. M. Bull. Soc. Chim. Belg. 1994, 103, 309.
25. Gallo, E. A.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 9774.
26. For a similar linking strategy for peptides to fluoresceins and their application as fluorescent reporters, see: Chen, C.-A.; Yeh, R.-H.; Lawrence, D. S. J. Am. Chem. Soc. 2002, 124, 3840.
27. (a) Adamczyk, M.; Grote, J. Bioorg. Med. Chem. Lett. 2000, 10, 1539.
28. (b) See also: Cincotta, L.; Foley, J. W. U.S. Patent 4,290,955, 1981.
29. (a) Mayer, U.; Oberlinner, A. U.S. Patent 4,647,675, 1987.
30. (b) Arnost, M. J.; Meneghini, F. A.; Palumbo, P. S.; Stroud, S. G. U.S. Patent 4,900,686, 1990.
31. (c) Mayer, U.; Oberlinner, A. U.S. Patent 4,935,059, 1990.
32. (d) Haugland, R. P.; Singer, V. L.; Yue, S. T. U.S. Patent 6,399,392, 2002.
33. Wakamiya, T.; Saruta, K.; Yasuoka, J.-I.; Kusumoto, S. Bull. Chem. Soc. Jpn. 1995, 68, 2699.
34. 18 for the method used).
35. 17). Non-hydrogen atoms were assigned anisotropic thermal parameters. Hydrogen atoms were included in calculated positions and treated as riding atoms. The refinement which included 469 parameters, converged with R1 [I>2σ(I)] = 0.0375 (for 8449 reflections with I>2σ(I)) and wR2 (all unique data) = 0.0970. Atomic coordinates and further crystallographic details have been deposited at the Cambridge Crystallographic Data Centre, deposition number CCDC-191818, and copies of this data can be obtained in application to CCDC, 12, Union Road, Cambridge CB2 1EZ, UK. [Fax: 444(1223)336033; E-mail: deposit@ccdc.cam.ac.uk].
36. Sheldrick, G. M. SHELXTL/PC Version 5.1, Windows NT Version, Bruker AXS Inc., Madison, USA.
37. Parker, C. A. Photoluminescence of Solutions; Elsevier: Amsterdam, 1968.
38. Kohno, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 322.