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Synthesis and photochemistry of pH-sensitive GFP chromophore analogs |
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| Authors: | Alan R Katritzky Megumi Yoshioka-Tarver Bahaa El-Dien M El-Gendy C Dennis Hall |
| Institution: | a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611, USA b Cotton Chemistry and Utilization, Southern Regional Research Center, USDA—ARS, New Orleans, Louisiana 70124, USA c Department of Chemistry, Faculty of Science, Benha University, Benha, Egypt |
| Abstract: | GFP chromophore analogs (7a-e, 8, and 10a,b) containing 2-thienyl-, 5-methyl-2-furyl-, 2-pyrryl, and 6-methyl-2-pyridyl-groups were synthesized and their fluorescence spectra recorded in the pH range 1-7. NMR studies showed that protonation of 8 (2-thienyl system) inhibited photoisomerization (Z-E) about the exocyclic double bond but that protonation of 7c (E + Z) (2-pyrryl system) gave only 7cE. Fluorescence studies revealed enhancement of fluorescence intensity of 7c and 7b,e (furyl system) below pH 2.5 and gave a similar result for 10a (pyridyl system) below pH 6. Quantum yields at pH 1 were low, probably due to excited state proton transfer (ESPT). |
| Keywords: | GFP chromophores Fluorescence Photoisomerization Hydrogen bonding 15N NMR |
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