Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 21, Issue 24, Pages 7964-7970Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2013.09.058
Keywords
Peptidyl sensor; Fluorescence; Selective; Hg(II); Chemosensor; Peptide sensor
Funding
- Basic Research Program of the National Research Foundation [2012R1AB3000574]
- Korea Environmental Industry and Technology Institute [201200054 0013]
- Korea Environmental Industry & Technology Institute (KEITI) [ARQ201202034002] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
- National Research Foundation of Korea [2012R1A1B3000574] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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A novel peptidyl chemosensor (PySO2-His-Gly-Gly-Lys(PySO2)-NH2, 1) was synthesized by incorporation of two pyrene (Py) fluorophores into the tetrapeptide using sulfonamide group. Compound 1 exhibited selective fluorescence response towards Hg(II) over the other metal ions in aqueous buffered solutions. Furthermore, 1 with the potent binding affinity (K-d = 120 nM) for Hg(II) detected Hg(II) without interference of other metal ions such as Ag(I), Cu(II), Cd(II), and Pb(II). The binding mode of 1 with Hg(II) was investigated by UV absorbance spectroscopy, H-1 NMR titration experiment, and pH titration experiment. The addition of Hg(II) induced a significant decrease in both excimer and monomer emissions of the pyrene fluorescence. Hg(II) interacted with the sulfonamide groups and the imidazole group of His in the peptidyl chemosensor and then two pyrene fluorophores were close to each other in the peptide. The decrease of both excimer and monomer emission was mainly due to the excimer/ monomer emission change by dimerization of two pyrene fluorophores and a quenching effect of Hg(II). (C) 2013 Elsevier Ltd. All rights reserved.
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