Synthesis of fluorescence-labeled peptidocalix[4]arene library and its peptide sensing ability

Tetrahedron Letters

Volumn 43, Issue 44, 2002, Pages 7949-7952

  Hioki, Hideaki ^a   Kubo, Miwa ^a   Yoshida, Hiroko ^a   Bando, Motohiko ^a   Ohnishi, Yumiko ^a   Kodama, Mitsuaki ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

Calixarenes; Chemosensors; Combinatorial library; Fluorescence change

Indexed keywords

FLUORESCENT DYE; LEUCINE ENKEPHALIN DERIVATIVE; PEPTIDE; PEPTIDOCALIX[4]ARENE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION (PARAMETERS); FLUORESCENCE; SENSOR; SYNTHESIS;

ARENE;

EID: 0037190858     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01861-0     Document Type: Article

References (23)

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2. For selected reviews of chemosensors, see: (a) Czarnik, A. W. Fluorescent Chemosensors for Ion and Molecule Recognition; American Chemical Society: Washington DC, 1992; (b) Prasanna de Silva, A.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566; (c) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 197-202; (d) Bissel, R. A.; Prasanna de Silva, A.; Gunaratne, H. Q. N.; Lynch, P. L. M.; Maguire, G. E. M.; Sandanayake, K. R. A. S. Chem. Soc. Rev. 1992, 187-195; (e) Diamond, D.; McKervey, M. A. Chem. Soc. Rev. 1996, 15-24; (f) Lockhart, J. C. Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 1, pp. 605-634.
3. For selected reviews of chemosensors, see: (a) Czarnik, A. W. Fluorescent Chemosensors for Ion and Molecule Recognition; American Chemical Society: Washington DC, 1992; (b) Prasanna de Silva, A.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566; (c) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 197-202; (d) Bissel, R. A.; Prasanna de Silva, A.; Gunaratne, H. Q. N.; Lynch, P. L. M.; Maguire, G. E. M.; Sandanayake, K. R. A. S. Chem. Soc. Rev. 1992, 187-195; (e) Diamond, D.; McKervey, M. A. Chem. Soc. Rev. 1996, 15-24; (f) Lockhart, J. C. Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 1, pp. 605-634.
4. For selected reviews of chemosensors, see: (a) Czarnik, A. W. Fluorescent Chemosensors for Ion and Molecule Recognition; American Chemical Society: Washington DC, 1992; (b) Prasanna de Silva, A.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566; (c) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 197-202; (d) Bissel, R. A.; Prasanna de Silva, A.; Gunaratne, H. Q. N.; Lynch, P. L. M.; Maguire, G. E. M.; Sandanayake, K. R. A. S. Chem. Soc. Rev. 1992, 187-195; (e) Diamond, D.; McKervey, M. A. Chem. Soc. Rev. 1996, 15-24; (f) Lockhart, J. C. Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 1, pp. 605-634.
5. For selected reviews of chemosensors, see: (a) Czarnik, A. W. Fluorescent Chemosensors for Ion and Molecule Recognition; American Chemical Society: Washington DC, 1992; (b) Prasanna de Silva, A.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566; (c) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 197-202; (d) Bissel, R. A.; Prasanna de Silva, A.; Gunaratne, H. Q. N.; Lynch, P. L. M.; Maguire, G. E. M.; Sandanayake, K. R. A. S. Chem. Soc. Rev. 1992, 187-195; (e) Diamond, D.; McKervey, M. A. Chem. Soc. Rev. 1996, 15-24; (f) Lockhart, J. C. Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 1, pp. 605-634.
6. For selected reviews of chemosensors, see: (a) Czarnik, A. W. Fluorescent Chemosensors for Ion and Molecule Recognition; American Chemical Society: Washington DC, 1992; (b) Prasanna de Silva, A.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566; (c) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 197-202; (d) Bissel, R. A.; Prasanna de Silva, A.; Gunaratne, H. Q. N.; Lynch, P. L. M.; Maguire, G. E. M.; Sandanayake, K. R. A. S. Chem. Soc. Rev. 1992, 187-195; (e) Diamond, D.; McKervey, M. A. Chem. Soc. Rev. 1996, 15-24; (f) Lockhart, J. C. Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 1, pp. 605-634.
7. Examples of chemosensors for peptides or saccharides sensors: (a) Chen, C.-T.; Wagner, H.; Still, W. C. Science 1998, 279, 851-853; (b) Iorio, E. J.; Shao, Y.; Chen, C.-T.; Wagner, H.; Still, W. C. Bioorg. Med. Chem. Lett. 2001, 11, 1635-1638; (c) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1910-1922; (d) Davis, C. J.; Lewis, P. T.; McCarroll, M. E.; Read, M. W.; Cueto, R.; Strongin, R. M. Org. Lett. 1999, 1, 331-334; (e) Wang, W.; Gao, S.; Wang, B. Org. Lett. 1999, 1, 1209-1212.
8. Examples of chemosensors for peptides or saccharides sensors: (a) Chen, C.-T.; Wagner, H.; Still, W. C. Science 1998, 279, 851-853; (b) Iorio, E. J.; Shao, Y.; Chen, C.-T.; Wagner, H.; Still, W. C. Bioorg. Med. Chem. Lett. 2001, 11, 1635-1638; (c) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1910-1922; (d) Davis, C. J.; Lewis, P. T.; McCarroll, M. E.; Read, M. W.; Cueto, R.; Strongin, R. M. Org. Lett. 1999, 1, 331-334; (e) Wang, W.; Gao, S.; Wang, B. Org. Lett. 1999, 1, 1209-1212.
9. Examples of chemosensors for peptides or saccharides sensors: (a) Chen, C.-T.; Wagner, H.; Still, W. C. Science 1998, 279, 851-853; (b) Iorio, E. J.; Shao, Y.; Chen, C.-T.; Wagner, H.; Still, W. C. Bioorg. Med. Chem. Lett. 2001, 11, 1635-1638; (c) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1910-1922; (d) Davis, C. J.; Lewis, P. T.; McCarroll, M. E.; Read, M. W.; Cueto, R.; Strongin, R. M. Org. Lett. 1999, 1, 331-334; (e) Wang, W.; Gao, S.; Wang, B. Org. Lett. 1999, 1, 1209-1212.
10. Examples of chemosensors for peptides or saccharides sensors: (a) Chen, C.-T.; Wagner, H.; Still, W. C. Science 1998, 279, 851-853; (b) Iorio, E. J.; Shao, Y.; Chen, C.-T.; Wagner, H.; Still, W. C. Bioorg. Med. Chem. Lett. 2001, 11, 1635-1638; (c) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1910-1922; (d) Davis, C. J.; Lewis, P. T.; McCarroll, M. E.; Read, M. W.; Cueto, R.; Strongin, R. M. Org. Lett. 1999, 1, 331-334; (e) Wang, W.; Gao, S.; Wang, B. Org. Lett. 1999, 1, 1209-1212.
11. Examples of chemosensors for peptides or saccharides sensors: (a) Chen, C.-T.; Wagner, H.; Still, W. C. Science 1998, 279, 851-853; (b) Iorio, E. J.; Shao, Y.; Chen, C.-T.; Wagner, H.; Still, W. C. Bioorg. Med. Chem. Lett. 2001, 11, 1635-1638; (c) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1910-1922; (d) Davis, C. J.; Lewis, P. T.; McCarroll, M. E.; Read, M. W.; Cueto, R.; Strongin, R. M. Org. Lett. 1999, 1, 331-334; (e) Wang, W.; Gao, S.; Wang, B. Org. Lett. 1999, 1, 1209-1212.
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17. 5Leu enkephalin derivatives by combinatorial approach has been reported: (a) Boyce, R.; Li, G.; Nestler, H. P.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 7955-7956.; (b) Cheng Y.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813-1814.
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19. . The analytes 2, 3 and 4 were synthesized by general Fmoc solid-phase peptide synthesis, see: Chan W.C., White P.D. Fmoc Solid-Phase Peptide Synthesis: A Practical Approach. 2000;Oxford University Press, New York.
20. Starting from dimethoxycalix[4]arene, 5 was prepared by solution-phase synthesis via O-alkylation by N-Boc protected aminoethylated chloroacetamide followed by Fmoc peptide synthesis and capping with 1-pyrenebutyric acid.
21. -3. The result indicates that the emission at 470 nm is assigned to intramolecular excimer.
22. Compound 1a on the beads was not stained red after incubation with 3a or 4a, which indicates that both 3b and 4b do not bind sensor 5.
23. Connors K.A. Binding Constants. 1987;141 Wiley-Interscience.