Synthesis of a New Class of Sol vent-Sensitive Fluorescent Labels

Angewandte Chemie - International Edition

Volumn 37, Issue 3, 1998, Pages 325-329

  La Clair, James J ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Dyes; Fluorescence labeling; Solvatochromism

Indexed keywords

EID: 0032536570     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980216)37:3<325::AID-ANIE325>3.0.CO;2-L     Document Type: Article

References (26)

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11. This can be circumvented through use of two- or multi-photon excitation, see C. Xu, W. W. Webb, J. Opt. Soc. Am. B, 1996, 13, 481.
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13. J. J. La Clair, Proc. Natl. Acad. Sci. USA. 1997, 94, 1623. For studies on similar materials
14. see a) D. M. Shin, D. G. Whitten, J. Phys. Chem. 1988, 92, 2945; b) S. Akiyama, K. Tajima, S. Nakatsuji, K. Nakashima, K. Abiru, M. Watanabe, Bull. Chem. Soc. Jpn. 1995, 65, 2043.
15. see a) D. M. Shin, D. G. Whitten, J. Phys. Chem. 1988, 92, 2945; b) S. Akiyama, K. Tajima, S. Nakatsuji, K. Nakashima, K. Abiru, M. Watanabe, Bull. Chem. Soc. Jpn. 1995, 65, 2043.
16. Piperazine 4 was prepared by allowing N-phenylpiperazine to react with di-terf-butyl dicarbonate, triethylamine, and DMAP in dichloromethane. For an alternative route, see M. Ferez, P. Potier, S. Halazy, Tetrahedon Lett. 1996, 37, 8487.
17. Compound 9 was converted into 10 to increase the yield in subsequent manipulations.
18. The extent of hydrolysis was determined by monitoring the loss in absorption at 400 nm after 5 h of dialysis at the designated pH.
19. For the assignment of K and B bands, see A. Burawoy, Ber. Dtsch. Chem. Ges. 1930, 63, 3155. Enhancement of the B band was significantly greater in protic (54-63%) than in aprotic media (14-47%).
20. One possible explanation is that this is due to the lack of additional twisted intramolecular charge-transfer (TICT) states through minimization of rotation about the aryl-piperidine bond. For work describing TICT states see: a) Z. Grabowski, K. Rotkiewicz, A. Siemiarczuk, D. J. Cowley, W. Buumann, Nouv. J. Chim. 1979, 3, 443; b) W. Rettig, Angew. Chem. 1986, 98, 969; Angew. Chem. Int. Ed. Engl. 1986, 25, 971; c) C. Rulliere, Z. R. Grabowski, J. Dobkowski, Chem. Phys. Lett. 1987, 137, 408; d) M. Vogel, W. Rettig, Ber. Bunsenges. Phys. Chem. 1985, 137, 408.
21. One possible explanation is that this is due to the lack of additional twisted intramolecular charge-transfer (TICT) states through minimization of rotation about the aryl-piperidine bond. For work describing TICT states see: a) Z. Grabowski, K. Rotkiewicz, A. Siemiarczuk, D. J. Cowley, W. Buumann, Nouv. J. Chim. 1979, 3, 443; b) W. Rettig, Angew. Chem. 1986, 98, 969; Angew. Chem. Int. Ed. Engl. 1986, 25, 971; c) C. Rulliere, Z. R. Grabowski, J. Dobkowski, Chem. Phys. Lett. 1987, 137, 408; d) M. Vogel, W. Rettig, Ber. Bunsenges. Phys. Chem. 1985, 137, 408.
22. One possible explanation is that this is due to the lack of additional twisted intramolecular charge-transfer (TICT) states through minimization of rotation about the aryl-piperidine bond. For work describing TICT states see: a) Z. Grabowski, K. Rotkiewicz, A. Siemiarczuk, D. J. Cowley, W. Buumann, Nouv. J. Chim. 1979, 3, 443; b) W. Rettig, Angew. Chem. 1986, 98, 969; Angew. Chem. Int. Ed. Engl. 1986, 25, 971; c) C. Rulliere, Z. R. Grabowski, J. Dobkowski, Chem. Phys. Lett. 1987, 137, 408; d) M. Vogel, W. Rettig, Ber. Bunsenges. Phys. Chem. 1985, 137, 408.
23. One possible explanation is that this is due to the lack of additional twisted intramolecular charge-transfer (TICT) states through minimization of rotation about the aryl-piperidine bond. For work describing TICT states see: a) Z. Grabowski, K. Rotkiewicz, A. Siemiarczuk, D. J. Cowley, W. Buumann, Nouv. J. Chim. 1979, 3, 443; b) W. Rettig, Angew. Chem. 1986, 98, 969; Angew. Chem. Int. Ed. Engl. 1986, 25, 971; c) C. Rulliere, Z. R. Grabowski, J. Dobkowski, Chem. Phys. Lett. 1987, 137, 408; d) M. Vogel, W. Rettig, Ber. Bunsenges. Phys. Chem. 1985, 137, 408.
24. One possible explanation is that this is due to the lack of additional twisted intramolecular charge-transfer (TICT) states through minimization of rotation about the aryl-piperidine bond. For work describing TICT states see: a) Z. Grabowski, K. Rotkiewicz, A. Siemiarczuk, D. J. Cowley, W. Buumann, Nouv. J. Chim. 1979, 3, 443; b) W. Rettig, Angew. Chem. 1986, 98, 969; Angew. Chem. Int. Ed. Engl. 1986, 25, 971; c) C. Rulliere, Z. R. Grabowski, J. Dobkowski, Chem. Phys. Lett. 1987, 137, 408; d) M. Vogel, W. Rettig, Ber. Bunsenges. Phys. Chem. 1985, 137, 408.
25. Single-molecule studies were conducted with an Eigen - Rigler confocal fluorescence correlation spectrometer. All samples were excited at 457 nm (0.5 W) with an argon ion laser (Lexel, Waldbronn, Germany). The laser beam was passed through a water-immersible objective (Zeiss Plan Neofluar 40 × 0.9) and directed toward a droplet of the material attached through a drop of water and a hanging cover slip (Fisher 12-5454-101). The samples were contained in a 20-μL gold well and were filtered through a porous glass filter immediately prior to use. Fluorescence was collected through the same objective and filtered with a 545-nm cutoff filter, a) M. Eigen, R. Rigler, Proc. Natl. Acad. Sci. USA 1994, 91, 5740;
26. b) R. Rigler, J. Biotech. 1995, 41, 177.