The Influence of Chirality on the β-Amino-Acid Naphthalenediimides/G-Quadruplex DNA Interaction

Sam Clowes; Yusuf Ali; Olivia R Astley; Dora M. Răsădean; Dan Pantos

doi:10.3390/molecules28217291

The Influence of Chirality on the β-Amino-Acid Naphthalenediimides/G-Quadruplex DNA Interaction

Sam Clowes, Yusuf Ali, Olivia R Astley, Dora M. Răsădean, Dan Pantos

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

Abstract

G-quadruplexes (G4s) have been identified as a potential alternative chemotherapy target. A series of eight β-amino acid derived naphthalenediimides (NDI) were screened against a series of oncogenic G4 sequences: c-KIT1, h-TELO, and TBA. Three sets of enantiomers were investigated to further our understanding of the effect of point chirality on G4 stabilisation. Enantioselective binding behaviour was observed with both c-KIT1 and h-TELO. Docking studies using GNINA and UV-vis titrations were employed to better understand this selective binding behaviour.

Original language	English
Article number	7291
Number of pages	19
Journal	Molecules
Volume	28
Issue number	21
Early online date	27 Oct 2023
DOIs	https://doi.org/10.3390/molecules28217291
Publication status	Published - 1 Nov 2023

Bibliographical note

Funding: We thank the Engineering and Physical Sciences Research Council (EPSRC) DTA for S.R.C. and D.M.R

Data Availability Statement: All data underlying the findings of this work are available from the corresponding author upon reasonable request.

Keywords

G-quadruplex DNA
chiral recognition
circular dichroism
docking
enantioselectivity

ASJC Scopus subject areas

Drug Discovery
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Physical and Theoretical Chemistry
Pharmaceutical Science
Organic Chemistry

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AU - Pantos, Dan

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AB - G-quadruplexes (G4s) have been identified as a potential alternative chemotherapy target. A series of eight β-amino acid derived naphthalenediimides (NDI) were screened against a series of oncogenic G4 sequences: c-KIT1, h-TELO, and TBA. Three sets of enantiomers were investigated to further our understanding of the effect of point chirality on G4 stabilisation. Enantioselective binding behaviour was observed with both c-KIT1 and h-TELO. Docking studies using GNINA and UV-vis titrations were employed to better understand this selective binding behaviour.

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The Influence of Chirality on the β-Amino-Acid Naphthalenediimides/G-Quadruplex DNA Interaction

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

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