Preferential targeting of i-motifs and G-quadruplexes by small molecules† †Electronic supplementary information (ESI) available: Experimental details, synthetic procedures, characterization data of compounds, 1H NMR and 13C NMR spectra, FRET melting, TO displacement, smFRET, lifetime data, CD spectr

Content Provider	Semantic Scholar
Author	Debnath, Manish Ghosh, Shirsendu Chauhan, Ajay Paul, Rakesh Bhattacharyya, Kankan Dash, Jyotirmayee
Copyright Year	2017
Abstract	i-Motifs and G-quadruplexes are dynamic nucleic acid secondary structures, which are believed to play key roles in gene expression. We herein report two peptidomimetic ligands (PBP1 and PBP2) that selectively target i-motifs and G-quadruplexes over double-stranded DNA. These peptidomimetics, regioisomeric with respect to the position of triazole/prolinamide motifs, have been synthesized using a modular method involving Cu(i)-catalyzed azide and alkyne cycloaddition. The para-isomer, PBP1 exhibits high selectivity for i-motifs while the meta-isomer PBP2 binds selectively to G-quadruplex structures. Interestingly, these ligands have the ability to induce G-quadruplex or i-motif structures from the unstructured single-stranded DNA conformations, as observed using single molecule Förster resonance energy transfer (smFRET) studies. The quantitative real-time polymerase chain reaction (qRT-PCR), western blot, and dual-luciferase assays indicate that PBP1 upregulates and PBP2 downregulates BCL-2 gene expression in cancer cells.
Starting Page	7448
Ending Page	7456
Page Count	9
File Format	PDF HTM / HTML
DOI	10.1039/c7sc02693e
Alternate Webpage(s)	https://pubs.rsc.org/en/content/articlepdf/2017/sc/c7sc02693e
PubMed reference number	29163897
Alternate Webpage(s)	https://doi.org/10.1039/c7sc02693e
Journal	Medline
Volume Number	8
Journal	Chemical science
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article