title: Thiol-chromene click chemistry: a coumarin-based derivative and its use as regenerable thiol probe and in bioimaging applications.
abstract: The synthesis and characterization of a coumarin-chromene (8, 9-dihydro-2H-cyclopenta[b]pyrano[2,3-f]chromene-2,10(7aH)-dione) (1) derivative and its use for thiol chemosensing in water was reported. Experimental details showed 1 acts as a probe for the detection of thiols including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), whereas amino acids which do not contain thiols induced no changes in UV-vis spectra and fluorescence emission properties of 1. A possible detection mechanism is a nucleophilic attack of thiols to the α,β-unsaturated ketone in 1 that resulted in a fluorescent coumarin derivative. Further studies showed that 1-thiol derivatives can be applied to the design of regenerative chemodosimeters for Cu(2+), Hg(2+) and Cd(2+) in water based on M(n+)-promoted desulfurization and recovery of 1. Furthermore, the optical properties of the probe and its Cys-addition product were theoretically studied. The ability of probe 1 to detect thiols in living cells (HepG2 cells) via an enhancement of the fluorescence was proved. Moreover, the applicability of 1 for the direct determination of biorelevant thiols in a complex matrix such as human plasma was also demonstrated.
authors.affiliation: Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Institute of Molecular Science, Shanxi University, Taiyuan 030006, China.
authors.forename: Yutao
authors.initials: Y
authors.lastname: Yang
authors.forename: Fangjun
authors.initials: F
authors.lastname: Huo
authors.forename: Caixia
authors.initials: C
authors.lastname: Yin
authors.forename: Anmin
authors.initials: A
authors.lastname: Zheng
authors.forename: Jianbin
authors.initials: J
authors.lastname: Chao
authors.forename: Yingqi
authors.initials: Y
authors.lastname: Li
authors.forename: Zongxiu
authors.initials: Z
authors.lastname: Nie
authors.forename: Ramón
authors.initials: R
authors.lastname: Martínez-Máñez
authors.forename: Diansheng
authors.initials: D
authors.lastname: Liu
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry*; D057930:Click Chemistry; D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry; D005978:Glutathione / Q000737:chemistry; D056945:Hep G2 Cells; D006801:Humans; D057054:Molecular Imaging; D015394:Molecular Structure; D013439:Sulfhydryl Reagents / Q000737:chemistry
chemical_list: D001578:Benzopyrans; D003374:Coumarins; D005456:Fluorescent Dyes; D013439:Sulfhydryl Reagents; C030123:coumarin; D005978:Glutathione; D003545:Cysteine