title: A fluorescence enhancement probe based on BODIPY for the discrimination of cysteine from homocysteine and glutathione.
abstract: Herein, a fluorescent probe BODIPY-based glyoxal hydrazone (BODIPY-GH) (1) for cysteine based on inhibiting of intramolecular charge transfer (ICT) quenching process upon reaction with the unsaturated aldehyde has been synthesized, which exhibits longer excitation wavelength, selective and sensitive colorimetric and fluorimetric response toward cysteine in natural media. The probe shows highly selectivity towards cysteine over homocysteine and glutathione as well as other amino acids with a significant fluorescence enhancement response within 15min In the presence of 50 equiv. of homocysteine, the emission increased slightly within 15min and completed in 2.5h to reach its maximum intensity. Therefore, the discrimination of cysteine from homocysteine and glutathione can be achieved through detection of probe 1. It shows low cytotoxicity and excellent membrane permeability toward living cells, which was successfully applied to detect and image intracellular cysteine effectively by confocal fluorescence imaging.
authors.affiliation: Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province and State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
authors.forename: Deyan
authors.initials: D
authors.lastname: Gong
authors.affiliation: Institute of Urology, The Second Hospital of Lanzhou University, Lanzhou, Gansu Province, China.
authors.forename: Yuejun
authors.initials: Y
authors.lastname: Tian
authors.affiliation: Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province and State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
authors.forename: Chengduan
authors.initials: C
authors.lastname: Yang
authors.affiliation: Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province and State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
authors.forename: Anam
authors.initials: A
authors.lastname: Iqbal
authors.affiliation: Institute of Urology, The Second Hospital of Lanzhou University, Lanzhou, Gansu Province, China.
authors.forename: Zhiping
authors.initials: Z
authors.lastname: Wang
authors.affiliation: Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province and State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
authors.forename: Weisheng
authors.initials: W
authors.lastname: Liu
authors.affiliation: Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province and State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China. Electronic address: qinww@lzu.edu.cn.
authors.forename: Wenwu
authors.initials: W
authors.lastname: Qin
authors.affiliation: State Key Laboratory of Veterinary Etiological Biology and Key Laboratory of Animal Virology of Ministry of Agriculture, Lanzhou Veterinary Research Institute, Chinese Academy of Agricultural Sciences, Xujiaping 1, Lanzhou, Gansu 730046, China.
authors.forename: Xiangtao
authors.initials: X
authors.lastname: Zhu
authors.affiliation: State Key Laboratory of Veterinary Etiological Biology and Key Laboratory of Animal Virology of Ministry of Agriculture, Lanzhou Veterinary Research Institute, Chinese Academy of Agricultural Sciences, Xujiaping 1, Lanzhou, Gansu 730046, China. Electronic address: ghch-2004@hotmail.com.
authors.forename: Huichen
authors.initials: H
authors.lastname: Guo
mesh_terms: D000818:Animals; D015374:Biosensing Techniques / Q000379:methods; D001896:Boron Compounds / Q000737:chemistry*; D002460:Cell Line; D003545:Cysteine / Q000032:analysis*; D005456:Fluorescent Dyes / Q000737:chemistry*; D005978:Glutathione / Q000032:analysis*; D006710:Homocysteine / Q000032:analysis*; D006801:Humans; D007668:Kidney / Q000737:chemistry / Q000166:cytology; D008856:Microscopy, Fluorescence / Q000379:methods; D061848:Optical Imaging / Q000379:methods*; D013050:Spectrometry, Fluorescence / Q000379:methods; D013552:Swine
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D006710:Homocysteine; D005978:Glutathione; D003545:Cysteine
keywords: BODIPY; Bioimaging; Cysteine; Fluorescent probes; Living cells