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Publicly Available Published by De Gruyter April 29, 2012

Progress toward red and near-infrared (NIR) emitting saccharide sensors

  • Martha Sibrian-Vazquez , Jorge O. Escobedo , Mark Lowry and Robert M. Strongin

Red-shifted and near-infrared (NIR)-active rhodamine analogs and their boronic acid derivatives were synthesized and studied. These latter compounds function as fluorogenic NIR active substrates for sugar sensing. The effects of benzannulation and boronic acid functionalization on fluorophore optical and sensing properties are described.


Conference

International Meeting on Boron Chemistry (IMEBORON-XIV), International Symposium on Boron Chemistry, IMEB, Boron Chemistry, 14th, Niagara Falls, Canada, 2011-09-11–2011-09-15


References

1 10.1021/jo980219k, T. S. Fabre, W. D. Treleaven, T. D. McCarley, C. L. Newton, R. M. Landry, M. C. Saraiva, R. M. Strongin. J. Org. Chem.63, 3522 (1998).Search in Google Scholar

2 10.1021/ol000204k, M. W. Read, J. O. Escobedo, D. M. Willis, P. A. Beck, R. M. Strongin. Org. Lett.2, 3201 (2000).Search in Google Scholar PubMed

3a 10.1021/jo9709965, P. T. Lewis, C. J. Davis, M. C. Saraiva, W. D. Treleaven, T. D. McCarley, R. M. Strongin. J. Org. Chem.62, 6110 (1997).Search in Google Scholar

3b 10.1021/jo9806557, P. T. Lewis, R. M. Strongin. J. Org. Chem.63, 6065 (1998).Search in Google Scholar PubMed

4 10.1021/ol035978q, K. K. Kim, J. O. Escobedo, N. N. St Luce, O. Rusin, D. Wong, R. M. Strongin. Org. Lett.5, 5007 (2003).Search in Google Scholar PubMed PubMed Central

5 10.1021/ol990105a, C. J. Davis, P. T. Lewis, M. E. McCarroll, M. W. Read, R. Cueto, R. M. Strongin. Org. Lett.1, 331 (1999).Search in Google Scholar PubMed

6 10.1021/ja017713h, M. He, R. J. Johnson, J. O. Escobedo, P. A. Beck, K. K. Kim, N. N. St Luce, C. J. Davis, P. T. Lewis, F. R. Fronczek, B. J. Melancon, A. A. Mrse, W. D. Treleaven, R. M. Strongin. J. Am. Chem. Soc.124, 5000 (2002).Search in Google Scholar PubMed PubMed Central

7a T. D. James, K. Sandanayake, S. Shinkai. Angew. Chem., Int. Ed.35, 1910 (1996).10.1002/anie.199619101Search in Google Scholar

7b 10.1351/pac199668061207, K. Sandanayake, T. D. James, S. Shinkai. Pure Appl. Chem.68, 1207 (1996).Search in Google Scholar

8 10.1039/c1cc11343g, S. Lim, J. O. Escobedo, M. Lowry, R. M. Strongin. Chem. Commun.47, 8295 (2011).Search in Google Scholar PubMed PubMed Central

9 10.1021/ja063651p, S. Jiang, J. O. Escobedo, K. K. Kim, O. Alptürk, G. K. Samoei, S. O. Fakayode, I. M. Warner, O. Rusin, R. M. Strongin. J. Am. Chem. Soc.128, 12221 (2006).Search in Google Scholar PubMed PubMed Central

10 10.1016/S0040-4020(02)00489-1, G. Springsteen, B. H. Wang. Tetrahedron58, 5291 (2002).Search in Google Scholar

11a 10.1021/ja055817c, L. Zhu, S. H. Shabbir, M. Gray, V. M. Lynch, S. Sorey, E. V. Anslyn. J. Am. Chem. Soc.128, 1222 (2006).Search in Google Scholar

11b 10.1021/jo900187a, B. E. Collins, S. Sorey, A. E. Hargrove, S. H. Shabbir, V. M. Lynch, E. V. Anslyn. J. Org. Chem.74, 4055 (2009).Search in Google Scholar

12 10.1021/ja807872s, T. L. Halo, J. Appelbaum, E. M. Hobert, D. M. Balkin, A. Schepartz. J. Am. Chem. Soc.131, 438 (2008).Search in Google Scholar

13 10.1071/CH11328, S. Lim, M. Lowry, R. M. Strongin. Aust. J. Chem.64, 1470 (2011).Search in Google Scholar

14 10.1016/0003-2697(91)90237-N, J. E. Whitaker, R. P. Haugland, F. G. Prendergast. Anal. Biochem.194, 330 (1991).Search in Google Scholar

15 10.1073/pnas.0710341105, Y. J. Yang, M. Lowry, X. Y. Xu, J. O. Escobedo, M. Sibrian-Vazquez, L. Wong, C. M. Schowalter, T. J. Jensen, F. R. Fronczek, I. M. Warner, R. M. Strongin. Proc. Natl. Acad. Sci. USA105, 8829 (2008).Search in Google Scholar PubMed PubMed Central

16 10.1002/cyto.990100206, L. G. Lee, G. M. Berry, C.-H. Chen. Cytometry10, 151 (1989).Search in Google Scholar PubMed

17 10.1039/b817228e, K. Furukawa, H. Abe, J. Wang, M. Uda, H. Koshino, S. Tsuneda, Y. Ito. Org. Biomol. Chem.7, 671 (2009).Search in Google Scholar PubMed

18a 10.1039/c39940000477, T. D. James, K. Sandanayake, S. Shinkai. J. Chem. Soc., Chem. Commun. 477 (1994).Search in Google Scholar

18b 10.1021/ja00140a013, T. D. James, K. Sandanayake, R. Iguchi, S. Shinkai. J. Am. Chem. Soc.117, 8982 (1995).Search in Google Scholar

19 S. P. Leytus, L. L. Melhado, W. F. Mangel. Biochem. J.209, 299 (1983).10.1042/bj2090299Search in Google Scholar

20 10.1021/ol015560x, S. P. Draffin, P. J. Duggan, S. A. M. Duggan. Org. Lett.3, 917 (2001).Search in Google Scholar PubMed

Online erschienen: 2012-4-29
Erschienen im Druck: 2012-4-30

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