Hrdlicka Patrick J, Karmakar Saswata
Department of Chemistry, University of Idaho, Moscow, Idaho 83843, USA.
Org Biomol Chem. 2017 Nov 29;15(46):9760-9774. doi: 10.1039/c7ob02152f.
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.
2'-O-(芘-1-基)甲基核糖核苷酸修饰的寡核苷酸（ONs）已在分子生物学、核酸诊断和材料科学等一系列应用中得到了超过25年的探索。本综述的第一部分概述了合成2'-O-(芘-1-基)甲基核糖核苷酸的策略，随后总结了用这些结构单元修饰的核酸双链体的生物物理性质。接着呈现结构研究的见解，以解释所报道的性质。在第二部分中，综述了用2'-O-(芘-1-基)甲基-RNA单体修饰的ONs的应用，包括RNA靶标的检测、单核苷酸多态性的区分、在核酸支架上形成自组装芘阵列、核酸双链体中电荷转移现象的研究以及双链DNA的序列无限制识别。芘部分可预测的结合模式，加上微环境依赖性性质和合成可行性，使2'-O-(芘-1-基)甲基-RNA单体成为一类有前途的芘功能化核苷酸结构单元，可用于分子生物学、核酸诊断和材料科学的新应用。
