Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Institute of Molecular Science, Shanxi University, Taiyuan 030006, China.
Biosens Bioelectron. 2013 Sep 15;47:300-6. doi: 10.1016/j.bios.2013.03.007. Epub 2013 Mar 17.
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.
报道了香豆素-色烯（8,9-二氢-2H-环戊并[b]吡喃并[2,3-f]色烯-2,10（7aH）-二酮）（1）衍生物的合成与表征及其在水中用于硫醇化学传感的用途。实验细节表明，1 可作为检测巯基包括半胱氨酸（Cys）、同型半胱氨酸（Hcy）和谷胱甘肽（GSH）的探针，而不含巯基的氨基酸不会引起 1 的紫外-可见光谱和荧光发射性质的变化。可能的检测机制是硫醇对 1 中α,β-不饱和酮的亲核攻击，导致荧光香豆素衍生物的形成。进一步的研究表明，1-硫醇衍生物可应用于基于 M(n+)-促进脱硫和 1 的回收的水相 Cu(2+)、Hg(2+)和 Cd(2+)的再生化学传感器的设计。此外，还对探针及其 Cys 加成产物的光学性质进行了理论研究。通过增强荧光，证明了探针 1 具有在活细胞（HepG2 细胞）中检测巯基的能力。此外，还证明了 1 可用于直接测定复杂基质（如人血浆）中的生物相关巯基。
