Design of a fused triazolyl 2-quinolinone unnatural nucleoside via tandem CuAAC-Ullmann coupling reaction and study of photophysical property. Issue 18 (3rd May 2018)

• Record Type: Journal Article
• Authors: Bag, Subhendu Sekhar; Das, Suman Kalyan; Gogoi, Hiranya
• Is Part Of: Tetrahedron. Volume 74:Issue 18(2018)
• Page Start: 2218
• Page End: 2229
• Publication Date: 2018-05-03
• Subjects: Fused triazolylquinolinone nucleoside -- Fluorescent -- Tandem CuAAC-Ullmann coupling -- Widen nucleo base -- BSA interaction -- Spectroscopy; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.03.037
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: This report presents the design and synthesis of a novel fused triazolyl 2-quinolinone (FTQuon ) nucleoside as a new generation of angularly widened unnatural nucleobase surrogate with two possible H-bonding faces-one H-bond acceptor and another donor. The synthesis via a tandem CuAAC-Ullmann coupling, the study of photophysical properties and theoretical calculation in the context of DNA are the main contents of this report. The newly designed nucleoside shows interesting photphysical property with slight blue shifted solvatochromicity. It also shows pH sensitive emission. All the theoretical DNA duplexes containing theFTQuon show right−handed B-form helicity as revealed from a molecular dynamics simulation using Schrodinger Macromodel. A theoretical (DFT) study indicates a good stabilizing property ofFTQuon via pairing with natural pyrimidine bases. It also shows good interaction property with BSA protein signalled via a switch on fluorescence response. Graphical abstract: Highlights: Sacrificial aromatic π-stacking interaction to pay third H-bond stabilization. Angularly widened hydrophobic base analogue of d(8aza )G with two possible H-bonding faces. Tandem CuAAC-Ullmann reaction to Fused Triazolyl Quinolinone (FTQuon ) nucleoside as third generation of triazolyl nucleoside. Theoretical calculation revealed its potential pyrimidine pairing selectivity, especially, cytosine selectivity with pairing energy much higher than a natural A:T pair. Interesting photphysical property and interaction ability with BSA protein.