Istituto per Sintesi Organica e Fotoreattività, Consiglio Nazionale delle Ricerche, Via Gobetti 101, Bologna 40129, Italy.
Molecules. 2012 Jan 18;17(1):910-33. doi: 10.3390/molecules17010910.
This paper summarizes some of our results on the application of oligothiophenes as fluorescent markers for biological studies. The oligomers of thiophene, widely known for their semiconductor properties in organic electronics, are also fluorescent compounds characterized by chemical and optical stability, high absorbance and quantum yield. Their fluorescent emission can be easily modulated via organic synthesis by changing the number of thiophene rings and the nature of side-chains. This review shows how oligothiophenes can be derivatized with active groups such as phosphoramidite, N-hydroxysuccinimidyl and 4-sulfotetrafluorophenyl esters, isothiocyanate and azide by which the (bio)molecules of interest can be covalently bound. This paper also describes how molecules such as oligonucleotides, proteins and even nanoparticles, tagged with oligothiophenes, can be used in experiments ranging from hybridization studies to imaging of fixed and living cells. Finally, a few multilabeling experiments are described.
本文总结了我们在将寡聚噻吩用作荧光标记物进行生物研究方面的一些成果。噻吩的低聚物以其在有机电子学中的半导体特性而广为人知,它们也是具有化学和光学稳定性、高吸收率和量子产率的荧光化合物。通过有机合成改变噻吩环的数量和侧链的性质,可以很容易地调节它们的荧光发射。本综述展示了如何通过磷酰胺、N-羟基琥珀酰亚胺基和 4-磺酰氟苯基酯、异硫氰酸酯和叠氮化物等活性基团对寡聚噻吩进行衍生化,从而可以将感兴趣的(生物)分子通过共价键连接。本文还描述了如何使用标记有寡聚噻吩的分子,如寡核苷酸、蛋白质甚至纳米粒子,进行从杂交研究到固定和活细胞成像的实验。最后,还描述了一些多标记实验。