title: Unraveling the Hydrolysis of Merocyanine-Based Probes in Biological Assay.
abstract: Merocyanine dyes, owing to their unique photochemical properties, are widely used to fabricate probes for the detection of biologically active small molecules and bioimaging. In this paper, merocyanine-based probes were proved of undergoing unwanted hydrolysis. To explore the strategies toward avoiding the hydrolysis, the detailed hydrolysis mechanism was first investigated, which was also confirmed by density functional theory (DFT) calculation. Then a series of merocyanine dyes were rationally designed. Influences of molecular structures of the probes, the analytical media such as pH and components of the solution on the hydrolysis were systematically studied. The experimental results suggest that merocyanine based probes with low electron density are more likely to suffer the hydrolysis, which could be exacerbated by the well-accepted strategy for constructing type-II probes. It is worth noting that chemical surroundings could also exert distinctive influence on the hydrolysis. The hydrolysis could be obviously aggravated when fetal calf serum or DMSO was deployed. Our findings will definitely provide an effective and reliable approach for guiding the rational design of highly robust merocyanine-based probes and the optimization of the analytical media, which is helpful in terms of avoiding the hydrolysis of the probes and hydrolysis caused analytical errors.
authors.affiliation: College of Chemistry and Chemical Engineering, Central South University , Changsha, Hunan 410083, P. R. China.
authors.forename: Liqiang
authors.initials: L
authors.lastname: Wang
authors.affiliation: College of Chemistry and Chemical Engineering, Central South University , Changsha, Hunan 410083, P. R. China.|Henan Key Laboratory of Biomolecular Recognition and Sensing, College of Chemistry and Chemical Engineering, Shangqiu Normal University , Shangqiu, Henan 476000, P. R. China.
authors.forename: Yuanqiang
authors.initials: Y
authors.lastname: Hao
authors.affiliation: College of Chemistry and Chemical Engineering, Central South University , Changsha, Hunan 410083, P. R. China.
authors.forename: Jianhan
authors.initials: J
authors.lastname: Huang
authors.affiliation: Key Laboratory of Chemistry in Ethnic Medicine Resource, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University , Kunming, Yunnan 650031, P. R. China.
authors.forename: Yonghui
authors.initials: Y
authors.lastname: He
authors.affiliation: College of Chemistry and Chemical Engineering, Central South University , Changsha, Hunan 410083, P. R. China.
authors.forename: Ke
authors.initials: K
authors.lastname: Zeng
authors.affiliation: College of Chemistry and Chemical Engineering, Central South University , Changsha, Hunan 410083, P. R. China.
authors.forename: Juan
authors.initials: J
authors.lastname: Li
authors.affiliation: College of Chemistry and Chemical Engineering, Central South University , Changsha, Hunan 410083, P. R. China.
authors.forename: Johnny Muya
authors.initials: JM
authors.lastname: Chabu
authors.affiliation: College of Chemistry and Chemical Engineering, Central South University , Changsha, Hunan 410083, P. R. China.
authors.forename: Wansong
authors.initials: W
authors.lastname: Chen
authors.affiliation: College of Chemistry and Chemical Engineering, Central South University , Changsha, Hunan 410083, P. R. China.
authors.forename: Minghui
authors.initials: M
authors.lastname: Yang
authors.affiliation: College of Chemistry and Chemical Engineering, Central South University , Changsha, Hunan 410083, P. R. China.
authors.forename: Liu
authors.initials: L
authors.lastname: Deng
authors.affiliation: College of Chemistry and Chemical Engineering, Central South University , Changsha, Hunan 410083, P. R. China.
authors.forename: You-Nian
authors.initials: YN
authors.lastname: Liu
mesh_terms: D000818:Animals; D001578:Benzopyrans / Q000737:chemistry*; D015374:Biosensing Techniques; D002417:Cattle; D004396:Coloring Agents / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D006868:Hydrolysis; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D011744:Pyrimidinones / Q000737:chemistry*; D011789:Quantum Theory; D044967:Serum / Q000737:chemistry
chemical_list: D001578:Benzopyrans; D004396:Coloring Agents; D007211:Indoles; D011744:Pyrimidinones; C548873:merocyanine; C003954:merocyanine dye; D004121:Dimethyl Sulfoxide