Amino-Acid-Derived Naphthalenediimides as Versatile G-Quadruplex Binders

Dora-Maria Rasadean; Bin Sheng; Jyotirmayee Dash; G. Dan Pantos

doi:10.1002/chem.201700957

Amino-Acid-Derived Naphthalenediimides as Versatile G-Quadruplex Binders

Dora-Maria Rasadean, Bin Sheng, Jyotirmayee Dash, G. Dan Pantos

Indian Association for the Cultivation of Science

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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, NDI 3 (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.

Original language	English
Pages (from-to)	8491-8499
Number of pages	9
Journal	Chemistry - A European Journal
Volume	23
Issue number	35
Early online date	24 May 2017
DOIs	https://doi.org/10.1002/chem.201700957
Publication status	Published - 23 Jun 2017

Keywords

circular dichroism
DNA
G-quadruplex
naphthalenediimide
structure–activity relationships

ASJC Scopus subject areas

General Chemistry

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10.1002/chem.201700957

Accepted Version
This is the peer reviewed version of the following article:Dora M. Răsădean Bin Sheng Dr. Jyotirmayee Dash Dr. G. Dan Pantoş (2017) Amino‐Acid‐Derived Naphthalenediimides as Versatile G‐Quadruplex Binders. Chemistry - A European Journal, 23(35) which has been published in final form at 10.1002/chem.201700957]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Accepted author manuscript, 1.7 MB

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title = "Amino-Acid-Derived Naphthalenediimides as Versatile G-Quadruplex Binders",

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, NDI 3 (Nϵ-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.",

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AU - Pantos, G. Dan

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AB - 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, NDI 3 (Nϵ-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.

KW - circular dichroism

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KW - G-quadruplex

KW - naphthalenediimide

KW - structure–activity relationships

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Amino-Acid-Derived Naphthalenediimides as Versatile G-Quadruplex Binders

Abstract

Keywords

ASJC Scopus subject areas

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