title: Novel chemosensors for detection of glutathione by reduction or substitution of naphthalimide derivatives containing sulfoxide or sulfone substituents.
abstract: A series of compounds, naphthalimide derivatives containing sulfoxide or sulfone substituents, were easily synthesized and characterized, which can be used for detection of glutathione. The detailed spectral studies demonstrated that the compounds displayed high selectivity for glutathione over cysteine, homocysteine and other biological molecules. Further studies suggested that reduction or nucleophilic substitution of sulfoxide or sulfone substituents of naphthalimide compounds by thiols induced ICT process in the chemosensors, and then resulted in fluorescence intensity enhancement. Also, the compounds were proved to be useful for imaging GSH in living cells. The nucleophilic substitution mechanism further revealed that the compounds were potential reagents for labeling sulfhydryl protein.
authors.affiliation: Collaborative Innovation Center for Birth Defect Research and Transformation of Shandong Province, Jining Medical University, Jining 272067, People's Republic of China.
authors.forename: Ruijiao
authors.initials: R
authors.lastname: Chen
authors.forename: Hai
authors.initials: H
authors.lastname: Lu
authors.forename: Chuanxin
authors.initials: C
authors.lastname: Liu
authors.forename: Qingsheng
authors.initials: Q
authors.lastname: Kong
mesh_terms: D005456:Fluorescent Dyes / Q000737:chemistry* / Q000378:metabolism; D005978:Glutathione / Q000032:analysis* / Q000378:metabolism; D006367:HeLa Cells; D006801:Humans; D053644:Naphthalimides / Q000737:chemistry* / Q000378:metabolism; D010084:Oxidation-Reduction; D013450:Sulfones / Q000737:chemistry* / Q000378:metabolism; D013454:Sulfoxides / Q000737:chemistry* / Q000378:metabolism
chemical_list: D005456:Fluorescent Dyes; D053644:Naphthalimides; D013450:Sulfones; D013454:Sulfoxides; D005978:Glutathione