TY - JOUR
T1 - Pteridine-based fluorescent pH sensors designed for physiological applications
AU - Saleh, Na'Il
AU - Graham, John
AU - Afaneh, Akef
AU - Al-Soud, Yaseen A.
AU - Schreckenbach, Georg
AU - Esmadi, Fatima T.
N1 - Funding Information:
N.S. would like to acknowledge the Office of Research Support and Sponsored Projects (RSSP) at the United Arab Emirates University for their financial support of this project under grant number 21S041 within the framework of National Research Foundation funding program (NRF). G.S. and A.A. gratefully acknowledge financial support from the Natural Sciences and Engineering Research Council of Canada (NSERC) .
PY - 2012/11/1
Y1 - 2012/11/1
N2 - New derivatives of pteridine, namely 6,7-diphenyl-2-morpholinylpterin (DMPT) and 6-thienyllumazine (TLM) were designed and easily synthesized in a rational way for pH-fluorescence sensing near physiological pH. The dual-excitation ratiometric sensing was based on the distinct spectral properties of the fluorophore in its neutral and deprotonated states. Density Functional Theory (DFT) calculations were used to determine structures, gas phase acidities and pK a values for the new dyes. Substitutions on pterin (PT) and lumazine (LM) structures with phenyl, thienyl or morpholinyl groups enhanced the acidity of the new dyes. DMPT displays visible turn-on emission signals from blue to cyan (bluish-green) upon changing the pH from acidic to basic around pK a of 7.2. The advantages of the new pteridine dyes over those previously known pH sensors are discussed in details in terms of their facile preparation and functionalization, pK a tuning strategy, wide responsive and resolved signal around physiological pH, photostability, water solubility, and adequacy for intracellular pH measurements.
AB - New derivatives of pteridine, namely 6,7-diphenyl-2-morpholinylpterin (DMPT) and 6-thienyllumazine (TLM) were designed and easily synthesized in a rational way for pH-fluorescence sensing near physiological pH. The dual-excitation ratiometric sensing was based on the distinct spectral properties of the fluorophore in its neutral and deprotonated states. Density Functional Theory (DFT) calculations were used to determine structures, gas phase acidities and pK a values for the new dyes. Substitutions on pterin (PT) and lumazine (LM) structures with phenyl, thienyl or morpholinyl groups enhanced the acidity of the new dyes. DMPT displays visible turn-on emission signals from blue to cyan (bluish-green) upon changing the pH from acidic to basic around pK a of 7.2. The advantages of the new pteridine dyes over those previously known pH sensors are discussed in details in terms of their facile preparation and functionalization, pK a tuning strategy, wide responsive and resolved signal around physiological pH, photostability, water solubility, and adequacy for intracellular pH measurements.
KW - DFT calculations
KW - Fluorescent pH sensors
KW - Physiological pH
KW - Protonation/deprotonation
KW - Pteridine
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U2 - 10.1016/j.jphotochem.2012.08.002
DO - 10.1016/j.jphotochem.2012.08.002
M3 - Article
AN - SCOPUS:84866173670
SN - 1010-6030
VL - 247
SP - 63
EP - 73
JO - Journal of Photochemistry and Photobiology A: Chemistry
JF - Journal of Photochemistry and Photobiology A: Chemistry
ER -