title: An aldehyde group-based P-acid probe for selective fluorescence turn-on sensing of cysteine and homocysteine.
abstract: A highly sensitive and selective turn on fluorescent probe P-acid-aldehyde (P-CHO) is developed for the determination of cysteine (Cys) and homocysteine (Hcy). The probe is designed and synthesized by incorporating the specific functional group aldehyde group for thiols into a stable π-conjugated material 4,4'-(2,5-dimethoxy-1,4-phenylene) bis(ethyne-2,1-diyl) dibenzoic acid (P-acid). The probe fluorescence is quenched through donor photoinduced electron transfer (d-PET) between the fluorophore (P-acid) and the recognition group (aldehyde group). In the presence of thiols, Cys and Hcy can selectively react with aldehyde group of the probe because the inhibition of d-PET between fluorophore and recognition group. Therefore, a turn-on fluorescent sensor was established for the fluorescence recovery. Under the optimized conditions, the fluorescence response of probe is directly proportional to the concentration of Cys in the range of 4-95 NM L(-1), with a detection limit 3.0 nM. In addition, the sensing system exhibits good selectively toward Cys and Hcy in the presence of other amino acids. It has been successfully applied for bioimaging of Cys and Hcy in living cells with low cell toxicity.
authors.affiliation: School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China.
authors.forename: Chunlei
authors.initials: C
authors.lastname: Yang
authors.affiliation: School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China.
authors.forename: Xiu
authors.initials: X
authors.lastname: Wang
authors.affiliation: School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China.
authors.forename: Lei
authors.initials: L
authors.lastname: Shen
authors.affiliation: School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China.
authors.forename: Wenping
authors.initials: W
authors.lastname: Deng
authors.affiliation: School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China.
authors.forename: Haiyun
authors.initials: H
authors.lastname: Liu
authors.affiliation: Shandong Provincial Key Laboratory of Preparation and Measurement of Building Materials, University of Jinan, Jinan 250022, China.
authors.forename: Shenguang
authors.initials: S
authors.lastname: Ge
authors.affiliation: School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China. Electronic address: chm_yanm@126.com.
authors.forename: Mei
authors.initials: M
authors.lastname: Yan
authors.affiliation: Shangdong Provincial Key Laboratory of Radiation Oncology, Shandong Cancer Hospital and Institute, Jinan 250117, China.
authors.forename: Xianrang
authors.initials: X
authors.lastname: Song
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D015374:Biosensing Techniques; D003545:Cysteine / Q000302:isolation & purification*; D005453:Fluorescence; D006710:Homocysteine / Q000302:isolation & purification*; D006801:Humans; D057230:Limit of Detection
chemical_list: D000447:Aldehydes; D006710:Homocysteine; D003545:Cysteine
keywords: Bioimaging; Cysteine; Fluorescent probe; Homocysteine; Photoinduced electron transfer; π-conjugated material