Please use this identifier to cite or link to this item:
Title: Incorporating G-C pair-recognizing Guanidinium into PNAs for sequence and structure specific recognition of dsRNAs over dsDNAs and ssRNAs
Authors: Krishna, Manchugondanahalli S.
Wang, Zhenzhang
Zheng, Liangzhen
Bowry, Jogesh
Ong, Alan Ann Lerk
Mu, Yuguang
Prabakaran, Mookkan
Chen, Gang
Keywords: Science::Biological sciences
Issue Date: 2019
Source: Krishna, M. S., Wang, Z., Zheng, L., Bowry, J., Ong, A. A. L., Mu, Y., Prabakaran, M. & Chen, G. (2019). Incorporating G-C pair-recognizing Guanidinium into PNAs for sequence and structure specific recognition of dsRNAs over dsDNAs and ssRNAs. Biochemistry, 58(36), 3777-3788.
Project: RG152/17
Journal: Biochemistry
Abstract: Recognition of RNAs under physiological conditions is important for the development of chemical probes and therapeutic ligands. Nucleobase-modified dsRNA-binding PNAs (dbPNAs) are promising for the recognition of dsRNAs in a sequence and structure specific manner under near-physiological conditions. Guanidinium is often present in proteins and small molecules for the recognition of G bases in nucleic acids, in cell-penetrating carriers, and in bioactive drug molecules, which might be due to the fact that guanidinium is amphiphilic and has unique hydrogen bonding and stacking properties. We hypothesized that a simple guanidinium moiety can be directly incorporated into PNAs to facilitate enhanced molecular recognition of G-C pairs in dsRNAs and improved bioactivity. We grafted a guanidinium moiety directly into a PNA monomer (designated as R) using a two-carbon linker as guided by computational modeling studies. The synthetic scheme of the PNA R monomer is relatively simple compared to that of the previously reported L monomer. We incorporated the R residue into various dbPNAs for binding studies. dbPNAs incorporated with R residues are excellent in sequence specifically recognizing G-C pairs in dsRNAs over dsDNA and ssRNAs. We demonstrated that the R residue is compatible with unmodified T and C and previously developed modified L and Q residues in dbPNAs for targeting model dsRNAs, the influenza A viral panhandle duplex structure, and the HIV-1 frameshift site RNA hairpin. Furthermore, R residues enhance the cellular uptake of PNAs.
ISSN: 0006-2960
DOI: 10.1021/acs.biochem.9b00608
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Biochemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SBS Journal Articles
SPMS Journal Articles

Citations 50

Updated on Jun 24, 2021

Citations 20

Updated on Jun 29, 2021

Page view(s)

Updated on Oct 24, 2021


Updated on Oct 24, 2021

Google ScholarTM




Items in DR-NTU are protected by copyright, with all rights reserved, unless otherwise indicated.