Amino‐Acid‐Derived Naphthalenediimides as Versatile G‐Quadruplex Binders. Issue 35 (24th May 2017)

• Record Type: Journal Article
• Authors: Răsădean, Dora M.; Sheng, Bin; Dash, Jyotirmayee; Pantoş, G. Dan
• Is Part Of: Chemistry. Volume 23:Issue 35(2017)
• Page Start: 8491
• Page End: 8499
• Publication Date: 2017-05-24
• Subjects: circular dichroism -- DNA -- G-quadruplex -- naphthalenediimide -- structure–activity relationships; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201700957
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The design and synthesis of water soluble, amino‐acid‐functionalised naphthalenediimides (NDIs) as potential ligands of native G‐quadruplexes is reported. The NDIs were tested on a panel of oncogene promoters, on the human telomeric sequence h‐telo, and on double‐stranded DNA. Out of the ligands tested, NDI3 ( N ϵ ‐Boc‐ l ‐lysine NDI) exhibited a highly discriminating nature by only stabilising the oncogene promoter c‐kit2, which is up‐regulated up to 80 % in ovarian, gastrointestinal, and breast malignancies. Abstract : Selective oncogene stablilisation : Water‐soluble, amino acid functionalised naphthalenediimides are potential ligands of native G‐quadruplexes, and they are tested on a panel of oncogene promoters and against double‐strand DNA. One of the ligands, NDI3, exhibits a highly discriminating nature by stabilising only the oncogene promoter c‐kit2, which is upregulated up to 80 % in ovarian, gastrointestinal, and breast malignancies (see figure).