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A new simple phthalimide-based fluorescent probe for highly selective cysteine and bioimaging for living cells
Youming Shen1, Xiangyang Zhang2, Youyu Zhang3
1Hunan Province Cooperative Innovation Center for The Construction & Development of Dongting Lake Ecological Economic Zone, College of Chemistry and Materials Engineering, Hunan University of Arts and Science, Changde, 415000, PR China; Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, PR China; Key Laboratory of Preparation and Application of Environmentally Friendly Materials (Jilin Normal University), Ministry of Education, Changchun 130103, PR China.
Abstract:
A new turn-on phthalimide fluorescent probe has designed and synthesized for sensing cysteine (Cys) based on excited state intramolecular proton transfer (ESIPT) process. It is consisted of a 3-hydroxyphthalimide derivative moiety as the fluorophore and an acrylic ester group as a recognition receptor. The acrylic ester acts as an ESIPT blocking agent. Upon addition of cystein, intermolecular nucleophilic attack of cysteine on acrylic ester releases the fluorescent 3-hydroxyphthalimide derivative, thereby enabling the ESIPT process and leading to enhancement of fluorescence. The probe displays high sensitivity, excellent selectivity and with large Stokes shift toward cysteine. The linear interval range of the fluorescence titration ranged from 0 to 1.0×10-5M and detection limit is low (6×10-8M). In addition, the probe could be used for bio-imaging in living cells.
