Ion conductors derived from biogenic amines, bile acids, and amino acids

Bioconjugate Chemistry

Volumn 13, Issue 6, 2002, Pages 1314-1318

  Bandyopadhyay, Punam ^a   Bandyopadhyay, Prasun ^a   Regen, Steven L ^a  

^a LEHIGH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; IONS; RATE CONSTANTS;

AMINO-ACIDS; BILE ACID; BIOGENIC AMINES; CHOLIC ACIDS; DESIGN PRINCIPLES; ION CONDUCTORS; PHOSPHOCHOLINE; SARCOSINE; SYNTHESISED; Γ-AMINOBUTYRIC ACID;

AMINO ACIDS;

EID: 0036861026     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc0255539     Document Type: Article

References (29)

1. (a) Stadler, E., Dedek, P., Yamashita, K., and Regen, S. L. (1994) J. Am. Chem. Soc. 116, 6677.
2. (b) Sadownik, A., Deng, G., Janout, V., Bernard, E. M., Kikuchi, K., Armstrong, D., and Regen, S. L. (1995) J. Am. Chem. Soc. 117, 6138.
3. (c) Yamashita, K., Janout, V., Bernard, E. M., Armstrong, D., and Regen, S. L. (1995) J. Am. Chem. Soc. 117, 6249.
4. (d) Deng, G., Merritt, M., Yamashita, K., Janout, V., Sadownik, A., and Regen, S. L. (1996) J. Am. Chem. Soc. 118, 3307.
5. (e) Deng, G., Dewa, T., and Regen, S. L. (1996) J. Am. Chem. Soc. 118, 8975.
6. (f) Kikuchi, K., Bernard, E. M., Sadownik, A., Regen, S. L., and Armstrong, D. (1997) Antimicrob. Agents Chemother. 41, 1433.
7. (g) Merritt, M., Lanier, M., Deng, G., and Regen, S. (1998) L. J. Am. Chem. Soc. 120, 8494.
8. (h) Otto, S., Osifchin, M., and Regen, S. L. (1999) J. Am. Chem. Soc. 121, 7276.
9. (i) Otto, S., Osifchin, M., and Regen, S. L. (1999) J. Am. Chem. Soc. 121, 10440.
10. (j) DiGiorgio, A. F., Otto, S., Bandyopadhyay, P., and Regen, S. L. (2000) J. Am. Chem. Soc. 122, 11029.
11. (k) Bandyopadhyay, P., Janout, V., Zhang, L., Sawko, J. A., and Regen, S. L. (2000) J. Am. Chem. Soc. 122, 12888.
12. (l) Bandyopadhyay, P., Janout, V., Zhang, L., and Regen, S. L. (2001) J. Am. Chem. Soc. 123, 7691.
13. For general reviews on nonpeptide ion channels and channel models, see: (a) Kobuke, Y. (1997) in Advances in Supramolecular Chemistry (G. W. Gokel, Ed.) Vol. 4, p 163, JAI, Greenwich, London. (b) Koert, U. (1997) Chem. Unserer Z. 31, 20. (c) Gokel, G. W., and Murillo, O. (1996) Acc. Chem. Res. 29, 425.
14. For general reviews on nonpeptide ion channels and channel models, see: (a) Kobuke, Y. (1997) in Advances in Supramolecular Chemistry (G. W. Gokel, Ed.) Vol. 4, p 163, JAI, Greenwich, London. (b) Koert, U. (1997) Chem. Unserer Z. 31, 20. (c) Gokel, G. W., and Murillo, O. (1996) Acc. Chem. Res. 29, 425.
15. For general reviews on nonpeptide ion channels and channel models, see: (a) Kobuke, Y. (1997) in Advances in Supramolecular Chemistry (G. W. Gokel, Ed.) Vol. 4, p 163, JAI, Greenwich, London. (b) Koert, U. (1997) Chem. Unserer Z. 31, 20. (c) Gokel, G. W., and Murillo, O. (1996) Acc. Chem. Res. 29, 425.
16. For selected examples of other ion conductors from the recent literature, see: (a) Sakai, N., Gerard, D., and Matile, S. (2001) J. Am. Chem. Soc. 123, 2517. (b) Renkes, T., Schafer, H. J., Siemens, P. M., and Neumann, E. (2000) Angew. Chem., Int. Ed. 39, 25112. (c) Forman, S. L., Fettinger, J. C., Pieraccini, S., Gottarelli, G., and Davis, J. T. (2000) J. Am. Chem. Soc. 122, 4060. (d) Perez, C., Espinola, C. G., Foces-Foces, C., Nunez-Coello, P., Carrasco, H., and Martin, J. D. (2000) Org. Lett. 2, 1185. (e) Das, S., Kurok, P., Jedlinski, Z., and Reusch, R. N. (1999) Macromolecules 32, 8781. (f) Abel, E., Maguire, G. E. M., Murillo, O., Suzuki, I., De Wall, S. L., and Gokel, G. W. (1999) J. Am. Chem. Soc. 121, 9043. (g) Qi, Z., Sokabe, M., Donowaki, K., and Ishida, H. (1999) Biophys. J. 76, 631. (h) Hall, C. D., Kirkovits, G. J., and Hall, A. C. (1999) Chem. Commun. 1897. (i) Fritz, M. G., Walde, P., and Seebach, D. (1999) Macromolecules 32, 574. (j) Fyles, T. M., Hu, C., and Knoy, R. (2001) Org. Lett. 3, 1335.
17. For selected examples of other ion conductors from the recent literature, see: (a) Sakai, N., Gerard, D., and Matile, S. (2001) J. Am. Chem. Soc. 123, 2517. (b) Renkes, T., Schafer, H. J., Siemens, P. M., and Neumann, E. (2000) Angew. Chem., Int. Ed. 39, 25112. (c) Forman, S. L., Fettinger, J. C., Pieraccini, S., Gottarelli, G., and Davis, J. T. (2000) J. Am. Chem. Soc. 122, 4060. (d) Perez, C., Espinola, C. G., Foces-Foces, C., Nunez-Coello, P., Carrasco, H., and Martin, J. D. (2000) Org. Lett. 2, 1185. (e) Das, S., Kurok, P., Jedlinski, Z., and Reusch, R. N. (1999) Macromolecules 32, 8781. (f) Abel, E., Maguire, G. E. M., Murillo, O., Suzuki, I., De Wall, S. L., and Gokel, G. W. (1999) J. Am. Chem. Soc. 121, 9043. (g) Qi, Z., Sokabe, M., Donowaki, K., and Ishida, H. (1999) Biophys. J. 76, 631. (h) Hall, C. D., Kirkovits, G. J., and Hall, A. C. (1999) Chem. Commun. 1897. (i) Fritz, M. G., Walde, P., and Seebach, D. (1999) Macromolecules 32, 574. (j) Fyles, T. M., Hu, C., and Knoy, R. (2001) Org. Lett. 3, 1335.
18. For selected examples of other ion conductors from the recent literature, see: (a) Sakai, N., Gerard, D., and Matile, S. (2001) J. Am. Chem. Soc. 123, 2517. (b) Renkes, T., Schafer, H. J., Siemens, P. M., and Neumann, E. (2000) Angew. Chem., Int. Ed. 39, 25112. (c) Forman, S. L., Fettinger, J. C., Pieraccini, S., Gottarelli, G., and Davis, J. T. (2000) J. Am. Chem. Soc. 122, 4060. (d) Perez, C., Espinola, C. G., Foces-Foces, C., Nunez-Coello, P., Carrasco, H., and Martin, J. D. (2000) Org. Lett. 2, 1185. (e) Das, S., Kurok, P., Jedlinski, Z., and Reusch, R. N. (1999) Macromolecules 32, 8781. (f) Abel, E., Maguire, G. E. M., Murillo, O., Suzuki, I., De Wall, S. L., and Gokel, G. W. (1999) J. Am. Chem.. Soc. 121, 9043. (g) Qi, Z., Sokabe, M., Donowaki, K., and Ishida, H. (1999) Biophys. J. 76, 631. (h) Hall, C. D., Kirkovits, G. J., and Hall, A. C. (1999) Chem. Commun. 1897. (i) Fritz, M. G., Walde, P., and Seebach, D. (1999) Macromolecules 32, 574. (j) Fyles, T. M., Hu, C., and Knoy, R. (2001) Org. Lett. 3, 1335.
19. For selected examples of other ion conductors from the recent literature, see: (a) Sakai, N., Gerard, D., and Matile, S. (2001) J. Am. Chem. Soc. 123, 2517. (b) Renkes, T., Schafer, H. J., Siemens, P. M., and Neumann, E. (2000) Angew. Chem., Int. Ed. 39, 25112. (c) Forman, S. L., Fettinger, J. C., Pieraccini, S., Gottarelli, G., and Davis, J. T. (2000) J. Am. Chem. Soc. 122, 4060. (d) Perez, C., Espinola, C. G., Foces-Foces, C., Nunez-Coello, P., Carrasco, H., and Martin, J. D. (2000) Org. Lett. 2, 1185. (e) Das, S., Kurok, P., Jedlinski, Z., and Reusch, R. N. (1999) Macromolecules 32, 8781. (f) Abel, E., Maguire, G. E. M., Murillo, O., Suzuki, I., De Wall, S. L., and Gokel, G. W. (1999) J. Am. Chem. Soc. 121, 9043. (g) Qi, Z., Sokabe, M., Donowaki, K., and Ishida, H. (1999) Biophys. J. 76, 631. (h) Hall, C. D., Kirkovits, G. J., and Hall, A. C. (1999) Chem. Commun. 1897. (i) Fritz, M. G., Walde, P., and Seebach, D. (1999) Macromolecules 32, 574. (j) Fyles, T. M., Hu, C., and Knoy, R. (2001) Org. Lett. 3, 1335.
20. For selected examples of other ion conductors from the recent literature, see: (a) Sakai, N., Gerard, D., and Matile, S. (2001) J. Am. Chem. Soc. 123, 2517. (b) Renkes, T., Schafer, H. J., Siemens, P. M., and Neumann, E. (2000) Angew. Chem., Int. Ed. 39, 25112. (c) Forman, S. L., Fettinger, J. C., Pieraccini, S., Gottarelli, G., and Davis, J. T. (2000) J. Am. Chem. Soc. 122, 4060. (d) Perez, C., Espinola, C. G., Foces-Foces, C., Nunez-Coello, P., Carrasco, H., and Martin, J. D. (2000) Org. Lett. 2, 1185. (e) Das, S., Kurok, P., Jedlinski, Z., and Reusch, R. N. (1999) Macromolecules 32, 8781. (f) Abel, E., Maguire, G. E. M., Murillo, O., Suzuki, I., De Wall, S. L., and Gokel, G. W. (1999) J. Am. Chem. Soc. 121, 9043. (g) Qi, Z., Sokabe, M., Donowaki, K., and Ishida, H. (1999) Biophys. J. 76, 631. (h) Hall, C. D., Kirkovits, G. J., and Hall, A. C. (1999) Chem. Commun. 1897. (i) Fritz, M. G., Walde, P., and Seebach, D. (1999) Macromolecules 32, 574. (j) Fyles, T. M., Hu, C., and Knoy, R. (2001) Org. Lett. 3, 1335.
21. For selected examples of other ion conductors from the recent literature, see: (a) Sakai, N., Gerard, D., and Matile, S. (2001) J. Am. Chem. Soc. 123, 2517. (b) Renkes, T., Schafer, H. J., Siemens, P. M., and Neumann, E. (2000) Angew. Chem., Int. Ed. 39, 25112. (c) Forman, S. L., Fettinger, J. C., Pieraccini, S., Gottarelli, G., and Davis, J. T. (2000) J. Am. Chem. Soc. 122, 4060. (d) Perez, C., Espinola, C. G., Foces-Foces, C., Nunez-Coello, P., Carrasco, H., and Martin, J. D. (2000) Org. Lett. 2, 1185. (e) Das, S., Kurok, P., Jedlinski, Z., and Reusch, R. N. (1999) Macromolecules 32, 8781. (f) Abel, E., Maguire, G. E. M., Murillo, O., Suzuki, I., De Wall, S. L., and Gokel, G. W. (1999) J. Am. Chem. Soc. 121, 9043. (g) Qi, Z., Sokabe, M., Donowaki, K., and Ishida, H. (1999) Biophys. J. 76, 631. (h) Hall, C. D., Kirkovits, G. J., and Hall, A. C. (1999) Chem. Commun. 1897. (i) Fritz, M. G., Walde, P., and Seebach, D. (1999) Macromolecules 32, 574. (j) Fyles, T. M., Hu, C., and Knoy, R. (2001) Org. Lett. 3, 1335.
22. For selected examples of other ion conductors from the recent literature, see: (a) Sakai, N., Gerard, D., and Matile, S. (2001) J. Am. Chem. Soc. 123, 2517. (b) Renkes, T., Schafer, H. J., Siemens, P. M., and Neumann, E. (2000) Angew. Chem., Int. Ed. 39, 25112. (c) Forman, S. L., Fettinger, J. C., Pieraccini, S., Gottarelli, G., and Davis, J. T. (2000) J. Am. Chem. Soc. 122, 4060. (d) Perez, C., Espinola, C. G., Foces-Foces, C., Nunez-Coello, P., Carrasco, H., and Martin, J. D. (2000) Org. Lett. 2, 1185. (e) Das, S., Kurok, P., Jedlinski, Z., and Reusch, R. N. (1999) Macromolecules 32, 8781. (f) Abel, E., Maguire, G. E. M., Murillo, O., Suzuki, I., De Wall, S. L., and Gokel, G. W. (1999) J. Am. Chem. Soc. 121, 9043. (g) Qi, Z., Sokabe, M., Donowaki, K., and Ishida, H. (1999) Biophys. J. 76, 631. (h) Hall, C. D., Kirkovits, G. J., and Hall, A. C. (1999) Chem. Commun. 1897. (i) Fritz, M. G., Walde, P., and Seebach, D. (1999) Macromolecules 32, 574. (j) Fyles, T. M., Hu, C., and Knoy, R. (2001) Org. Lett. 3, 1335.
23. For selected examples of other ion conductors from the recent literature, see: (a) Sakai, N., Gerard, D., and Matile, S. (2001) J. Am. Chem. Soc. 123, 2517. (b) Renkes, T., Schafer, H. J., Siemens, P. M., and Neumann, E. (2000) Angew. Chem., Int. Ed. 39, 25112. (c) Forman, S. L., Fettinger, J. C., Pieraccini, S., Gottarelli, G., and Davis, J. T. (2000) J. Am. Chem. Soc. 122, 4060. (d) Perez, C., Espinola, C. G., Foces-Foces, C., Nunez-Coello, P., Carrasco, H., and Martin, J. D. (2000) Org. Lett. 2, 1185. (e) Das, S., Kurok, P., Jedlinski, Z., and Reusch, R. N. (1999) Macromolecules 32, 8781. (f) Abel, E., Maguire, G. E. M., Murillo, O., Suzuki, I., De Wall, S. L., and Gokel, G. W. (1999) J. Am. Chem. Soc. 121, 9043. (g) Qi, Z., Sokabe, M., Donowaki, K., and Ishida, H. (1999) Biophys. J. 76, 631. (h) Hall, C. D., Kirkovits, G. J., and Hall, A. C. (1999) Chem. Commun. 1897. (i) Fritz, M. G., Walde, P., and Seebach, D. (1999) Macromolecules 32, 574. (j) Fyles, T. M., Hu, C., and Knoy, R. (2001) Org. Lett. 3, 1335.
24. For selected examples of other ion conductors from the recent literature, see: (a) Sakai, N., Gerard, D., and Matile, S. (2001) J. Am. Chem. Soc. 123, 2517. (b) Renkes, T., Schafer, H. J., Siemens, P. M., and Neumann, E. (2000) Angew. Chem., Int. Ed. 39, 25112. (c) Forman, S. L., Fettinger, J. C., Pieraccini, S., Gottarelli, G., and Davis, J. T. (2000) J. Am. Chem. Soc. 122, 4060. (d) Perez, C., Espinola, C. G., Foces-Foces, C., Nunez-Coello, P., Carrasco, H., and Martin, J. D. (2000) Org. Lett. 2, 1185. (e) Das, S., Kurok, P., Jedlinski, Z., and Reusch, R. N. (1999) Macromolecules 32, 8781. (f) Abel, E., Maguire, G. E. M., Murillo, O., Suzuki, I., De Wall, S. L., and Gokel, G. W. (1999) J. Am. Chem. Soc. 121, 9043. (g) Qi, Z., Sokabe, M., Donowaki, K., and Ishida, H. (1999) Biophys. J. 76, 631. (h) Hall, C. D., Kirkovits, G. J., and Hall, A. C. (1999) Chem. Commun. 1897. (i) Fritz, M. G., Walde, P., and Seebach, D. (1999) Macromolecules 32, 574. (j) Fyles, T. M., Hu, C., and Knoy, R. (2001) Org. Lett. 3, 1335.
25. For selected examples of other ion conductors from the recent literature, see: (a) Sakai, N., Gerard, D., and Matile, S. (2001) J. Am. Chem. Soc. 123, 2517. (b) Renkes, T., Schafer, H. J., Siemens, P. M., and Neumann, E. (2000) Angew. Chem., Int. Ed. 39, 25112. (c) Forman, S. L., Fettinger, J. C., Pieraccini, S., Gottarelli, G., and Davis, J. T. (2000) J. Am. Chem. Soc. 122, 4060. (d) Perez, C., Espinola, C. G., Foces-Foces, C., Nunez-Coello, P., Carrasco, H., and Martin, J. D. (2000) Org. Lett. 2, 1185. (e) Das, S., Kurok, P., Jedlinski, Z., and Reusch, R. N. (1999) Macromolecules 32, 8781. (f) Abel, E., Maguire, G. E. M., Murillo, O., Suzuki, I., De Wall, S. L., and Gokel, G. W. (1999) J. Am. Chem. Soc. 121, 9043. (g) Qi, Z., Sokabe, M., Donowaki, K., and Ishida, H. (1999) Biophys. J. 76, 631. (h) Hall, C. D., Kirkovits, G. J., and Hall, A. C. (1999) Chem. Commun. 1897. (i) Fritz, M. G., Walde, P., and Seebach, D. (1999) Macromolecules 32, 574. (j) Fyles, T. M., Hu, C., and Knoy, R. (2001) Org. Lett. 3, 1335.
26. (a) Degani, H., and Elgavish, G. A. (1978) FEBS Lett. 90, 357.
27. (b) Gupta, R. K., and Gupta, P. (1982) J. Magn. Reson. 47, 344.
28. (c) Pike, M. M., Simon, S. R., Balschi, J. A., and Springer, C. S., Jr. (1982) Proc. Natl Acad. Sci. U.S.A. 79, 810.
29. (d) Pregel, M. J., Jullien, L., and Lehn, J. M. (1992) Angew. Chem., Int. Ed. Engl. 31, 1637.