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Fluorescent Nucleoside Analogs: Probes for Investigating Nucleic Acid Structure and Function
Author(s) -
Tanpure Arun A.,
Pawar Maroti G.,
Srivatsan Seergazhi G.
Publication year - 2013
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.201300010
Subject(s) - chemistry , nucleoside , nucleic acid , oligonucleotide , fluorescence , pyrimidine , combinatorial chemistry , nucleotide , solvatochromism , nucleic acid structure , nucleoside analogue , function (biology) , pyrimidine analogue , oligonucleotide synthesis , biophysics , stereochemistry , biochemistry , dna , rna , biology , physics , quantum mechanics , evolutionary biology , solvent , gene
Base‐modified fluorescent nucleoside analog probes have been very valuable in the study of nucleic acid structure and function. Many of them structurally resemble natural bases, and also display useful properties, such as large Stokes shifts and sensitivity to microenvironment changes. Therefore, unlike traditional fluorescence probes, which mostly report global changes, nucleoside analogs, when incorporated into oligonucleotides, can photophysically report changes that occur around the site of interest, at the nucleotide level. In this review, we provide an overview of various strategies that have been employed to design base‐modified fluorescent nucleoside analogs. Then we review recent developments and applications of new generation fluorescent nucleoside analogs with a particular focus on the synthesis, photophysical characterizations and applications of heterobicycle‐conjugated pyrimidine nucleoside analogs that have been developed by our group. These analogs, which have a minimal effect on the structures of the oligonucleotides into which they are incorporated, show emission in the visible region and excellent fluorescence solvatochromism. Notably, unlike the majority of fluorescent nucleoside analogs developed so far, these analogs retain their fluorescence efficiency when incorporated into oligonucleotides. We anticipate that these nucleoside analogs, with such photophysical properties, would be useful in designing robust biophysical assays to study nucleic acids.