Abstract
A dicarboxylate-based fluorescent receptor has been synthesized for the recognition of the guanidinium ion and guanidine-containing biomolecules in aqueous medium to address the issue of biomolecular interaction. The acyclic receptor binds to guests in a 1: 2 mode due to the flexibility of its binding motifs. The host-guest binding behavior was studied by means of UV and fluorescence titration. The binding of the host with the guanidinium ion was found to be stronger than with the other guanidine-containing guests.
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(a) Fujisawa, K., Humbert-Droz, M., Letrun, R., Vauthey, E., Wesolowski, T.A., Sakai, N., and Matile, S., J. Am. Chem. Soc., 2015, vol. 137, p. 11047. (b) Wang, X., Sarycheva, O.V., Koivisto, B.D., McKie, A.H. and Hof, F., Org. Lett., 2008, vol. 10, p. 297.
(a) Balakrishnan, S., Scheuermann, M. J., and Zondlo, N.J., ChemBioChem, 2012, vol. 13, p. 259. (b) Chen, H., Gu, L., Yin, Y., Koh, K., and Lee, J., Int. J. Mol. Sci., 2011, vol. 12, p. 2315.
Guinovart, T., Hernandez-Alonso, D., Adriaenssens, L., Blondeau, P., Martinez-Belmonte, M., Rius, F.X., Andrade, F. J., and Ballester, P., Angew. Chem. Int. Ed., 2016, vol. 55, p. 2435.
Bell, T.W., Khasanov, A.B., and Drew, M.G.B., J. Am. Chem. Soc., 2002, vol. 124, p. 14092.
Fokkens, M., Schrader, T., and Klarner, F.-G., J. Am. Chem. Soc., 2005, vol. 127, p. 14415.
Potocky, T.B., Silvius, J., Menon, A.K., and Gellman, S.H., ChemBioChem, 2007, vol. 8, p. 917.
Schug, K.A. and Lindner, W., Chem. Rev., 2005, vol. 105, p. 67.
Wender, P.A., Galliher, W.C., Goun, E.A., Jones, L.R., and Pillow, T.H., Adv. Drug Delivery Rev., 2008, vol. 60, p. 452.
Mueller, N., Pasternak, A.O., Klaver, B., Cornelissen, M., Berkhout, B., and Das, A.T., J. Virol., 2018, vol. 92, p. e01855–17.
Hammond, J.A., Zhou, L., Lamichhane, R., Chu, H.-Y., Millar, D.P., Gerace, L., and Williamson, J.R., J. Mol. Biol., 2018, vol. 430, p. 537.
Lee, S.D., Yu, K.L., Park, S.H., Jung, Y.M., Kim, M.J., and You, J.C., BMB Rep., 2018, vol. 51, p. 388.
(a) Best, M.D., Tobey, S.L., and Anslyn, E.V., Coord. Chem. Rev., 2003, vol. 240, p. 3. (b) Leow, D., and Tan, C.H., Chem. Asian J., 2009, vol. 4, p. 488. (c) Blondeau, P., Segura, M., Prez-Fernndez, R., and de Mendoza, J., Chem. Soc. Rev., 2007, vol. 36, p. 198. (d)Schmuck, C., Coord. Chem. Rev., 2006, vol. 250, p. 3053.
Gokel, G.W., Leevy, M., and Weber, M.E., Chem. Rev., 2004, vol. 104, p. 2723.
(a) James, L.I., Beaver, J.E., Rice, N.W. and Waters, M.L., J. Am. Chem. Soc., 2013, vol. 135, p. 6450. (b) Zhou, X., Jin, X., Li, D., and Wu, X. Chem. Commun., 2011, vol. 47, p. 3921.
Barrow, S.J., Kasera, S., Rowland, M.J., del Barrio, J., and Scherman, O.A., Chem. Rev., 2015, vol. 115, p. 12320.
Chen, H., Gu, L., Yin, Y., Koh, K., and Lee, J., Int. J. Mol. Sci., 2011, vol. 12, p. 2315.
Späth, A., and König, B., Beilstein J. Org. Chem., 2010, vol. 6, no. 32. doi 10.3762/bjoc.6.32; (b) Gersthagen, T., Schmuck, C., and Schrader, T. Supramol. Chem., 2010, vol. 22, p. 853.
(a) Oshovsky, G.V., Reinhoudt, D.N., and Verboom, W., Angew. Chem. Int. Ed., 2007, vol. 46, p. 2366. (b) Zhao, Y., Chem. Eur. J., 2018, vol. 24, p. 14001.
So, S.M., Moozeh, K., Lough, A.J., and Chin, J., Angew. Chem. Int. Ed., 2014, vol. 53, p. 829.
(a) Marcotte, N., Fery-Forgues, S., and Lavabre, D., J. Phys. Chem. A, 1999, vol. 103, p. 3163. (b) Marcotte, N., and Fery-Forgues, S., J. Chem. Soc., Perkin Trans. 2, 2000, p. 1711.
The minimization of energy was carried out by MMX (PC MODEL by Serena Software)
(a) Connors K.A., Binding Constant: The Measurement of Molecular Complex Stability, New York: John Wiley & Sons, 1987. (b) Benesi, H. and Hildebrand, J.H., J. Am. Chem. Soc., 1949, vol. 71, p. 2703.
(a) Hargrove, A.E., Zhong, Z., Sessler, J.L., Anslyn, E.V., New J. Chem., 2010, vol. 34, p. 348. (b) Thordarson, P., Chem. Soc. Rev., 2011, vol. 40, p. 1305.
Gel’man, N.E., Terent’eva, E.A., Shanina, T.M., Kipa-renko, L.M., and Rezl, V., Metody kolichestvennogo orga-nicheskogo elementnogo mikroanaliza (The Methods of Quantitative Organic Elemental Microanalysis), Moscow: Khimiya, 1987.
Acknowledgments
Subrata Jana thanks to MPCST, Govt. of Madhya Pradesh, India for financial support. Kishor Kumar Suryavanshi thanks to Indira Gandhi National Tribal University (Central University), Amarkantak, M.P., India for research fellowship.
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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 5, pp. 818.
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Jana, S., Suryavanshi, K.K. Recognition and Sensing of Guanidine-containing Biomolecules in Aqueous Medium. Russ J Org Chem 55, 707–715 (2019). https://doi.org/10.1134/S1070428019050208
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DOI: https://doi.org/10.1134/S1070428019050208