Oligonucleotides (ONs) modified with 2′-O-(pyren-1-yl)methylribonucleotides have been explored for a range of applications in molecular biology, nucleic acid diagnostics, and materials science for more than 25 years. The first part of this review provides an overview of synthetic strategies toward 2′-O-(pyren-1-yl)methylribonucleotides and is followed by a summary of biophysical properties of nucleic acid duplexes modified with these building blocks. Insights from structural studies are then presented to rationalize the reported properties. In the second part, applications of ONs modified with 2′-O-(pyren-1-yl)methyl-RNA monomers are reviewed, which include detection of RNA targets, discrimination of single nucleotide polymorphisms, formation of self-assembled pyrene arrays on nucleic acid scaffolds, the study of charge transfer phenomena in nucleic acid duplexes, and sequence-unrestricted recognition of double-stranded DNA. The predictable binding mode of the pyrene moiety, coupled with the microenvironment-dependent properties and synthetic feasibility, render 2′-O-(pyren-1-yl)methyl-RNA monomers as a promising class of pyrene-functionalized nucleotide building blocks for new applications in molecular biology, nucleic acid diagnostics, and materials science.

中文翻译：

---

25年并且仍保持坚挺：2'- O-（pyren-1-yl）methylribonucleotides –用于分子生物学，诊断学和材料科学的多功能构建基块

用2' - O-（pyren -1-yl）methylribonucleotides修饰的寡核苷酸（ONs）在分子生物学，核酸诊断和材料科学中的广泛应用已有25年以上的历史了。本综述的第一部分概述了针对2' - O-（吡喃-1-基）甲基核糖核苷酸的合成策略，然后概述了用这些构件修饰的核酸双链体的生物物理特性。然后提出结构研究的见解，以合理化所报告的属性。在第二部分中，用2'- O修饰的ON的应用-（pyren-1-yl）methyl-RNA单体进行了综述，其中包括RNA靶标的检测，单核苷酸多态性的识别，核酸支架上自组装pyr阵列的形成，核酸双链体中电荷转移现象的研究，以及对双链DNA的序列无限制识别。moiety部分的可预测结合模式，加上微环境依赖性和合成可行性，使得2' - O-（pyren-1-yl）methyl-RNA单体成为新的pyr功能化核苷酸构建模块在分子生物学，核酸诊断和材料科学中的应用。