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

Research output: Contribution to journal › Article › peer-review

26 Citations (SciVal)

376 Downloads (Pure)

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

Access to Document

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

Cite this

@article{c196ce46730b401b9ff8a5ec0cb653f1,

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.",

keywords = "circular dichroism, DNA, G-quadruplex, naphthalenediimide, structure–activity relationships",

author = "Dora-Maria Rasadean and Bin Sheng and Jyotirmayee Dash and Pantos, \{G. Dan\}",

year = "2017",

month = jun,

day = "23",

doi = "10.1002/chem.201700957",

language = "English",

volume = "23",

pages = "8491--8499",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley and Sons Inc.",

number = "35",

}

TY - JOUR

T1 - Amino-Acid-Derived Naphthalenediimides as Versatile G-Quadruplex Binders

AU - Rasadean, Dora-Maria

AU - Sheng, Bin

AU - Dash, Jyotirmayee

AU - Pantos, G. Dan

PY - 2017/6/23

Y1 - 2017/6/23

N2 - 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.

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

KW - DNA

KW - G-quadruplex

KW - naphthalenediimide

KW - structure–activity relationships

UR - https://www.scopus.com/pages/publications/85019869331

UR - http://dx.doi.org/10.1002/chem.201700957

U2 - 10.1002/chem.201700957

DO - 10.1002/chem.201700957

M3 - Article

AN - SCOPUS:85019869331

SN - 0947-6539

VL - 23

SP - 8491

EP - 8499

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 35

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this