Ruthenium Complex "Light Switches" that are Selective for Different G-Quadruplex Structures

Erin Wachter; Diego Moyá; Sean Parkin; Edith C. Glazer

doi:10.1002/chem.201503203

Ruthenium Complex "Light Switches" that are Selective for Different G-Quadruplex Structures

Erin Wachter, Diego Moyá, Sean Parkin, Edith C. Glazer

Chemistry

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

49 Scopus citations

Abstract

Recognition and regulation of G-quadruplex nucleic acid structures is an important goal for the development of chemical tools and medicinal agents. The addition of a bromo-substituent to the dipyridylphenazine (dppz) ligands in the photophysical "light switch", [Ru(bpy)₂dppz]²⁺, and the photochemical "light switch", [Ru(bpy)₂dmdppz]²⁺, creates compounds with increased selectivity for an intermolecular parallel G-quadruplex and the mixed-hybrid G-quadruplex, respectively. When [Ru(bpy)₂dppz-Br]²⁺ and [Ru(bpy)₂dmdppz-Br]²⁺ are incubated with the G-quadruplexes, they have a stabilizing effect on the DNA structures. Activation of [Ru(bpy)₂dmdppz-Br]²⁺ with light results in covalent adduct formation with the DNA. These complexes demonstrate that subtle chemical modifications of Ru^II complexes can alter G-quadruplex selectivity, and could be useful for the rational design of in vivo G-quadruplex probes.

Original language	English
Pages (from-to)	550-559
Number of pages	10
Journal	Chemistry - A European Journal
Volume	22
Issue number	2
DOIs	https://doi.org/10.1002/chem.201503203
State	Published - Jan 11 2016

Bibliographical note

Funding Information:
This work was supported by the American Cancer Society (RSG-13-079-01-CDD) and the National Institutes of Health (R01M107586). E.W. was supported by the University of Kentucky Research Challenge Trust Fund Fellowship. We would also like to thank the University of Kentucky Environmental Research Training Laboratory (ERTL) for assisting with chemical analysis. The luminescence plate reader experiments were performed on an Instrument in the Center for Molecular Medicine Protein Core, which is funded through NIH/NIGMS COBRE grant P30M110787.

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

G-quadruplexes
light switch
photochemistry
photophysics
ruthenium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201503203

Cite this

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abstract = "Recognition and regulation of G-quadruplex nucleic acid structures is an important goal for the development of chemical tools and medicinal agents. The addition of a bromo-substituent to the dipyridylphenazine (dppz) ligands in the photophysical {"}light switch{"}, [Ru(bpy)2dppz]2+, and the photochemical {"}light switch{"}, [Ru(bpy)2dmdppz]2+, creates compounds with increased selectivity for an intermolecular parallel G-quadruplex and the mixed-hybrid G-quadruplex, respectively. When [Ru(bpy)2dppz-Br]2+ and [Ru(bpy)2dmdppz-Br]2+ are incubated with the G-quadruplexes, they have a stabilizing effect on the DNA structures. Activation of [Ru(bpy)2dmdppz-Br]2+ with light results in covalent adduct formation with the DNA. These complexes demonstrate that subtle chemical modifications of RuII complexes can alter G-quadruplex selectivity, and could be useful for the rational design of in vivo G-quadruplex probes.",

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author = "Erin Wachter and Diego Moy{\'a} and Sean Parkin and Glazer, {Edith C.}",

note = "Funding Information: This work was supported by the American Cancer Society (RSG-13-079-01-CDD) and the National Institutes of Health (R01M107586). E.W. was supported by the University of Kentucky Research Challenge Trust Fund Fellowship. We would also like to thank the University of Kentucky Environmental Research Training Laboratory (ERTL) for assisting with chemical analysis. The luminescence plate reader experiments were performed on an Instrument in the Center for Molecular Medicine Protein Core, which is funded through NIH/NIGMS COBRE grant P30M110787. Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

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AU - Parkin, Sean

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N1 - Funding Information: This work was supported by the American Cancer Society (RSG-13-079-01-CDD) and the National Institutes of Health (R01M107586). E.W. was supported by the University of Kentucky Research Challenge Trust Fund Fellowship. We would also like to thank the University of Kentucky Environmental Research Training Laboratory (ERTL) for assisting with chemical analysis. The luminescence plate reader experiments were performed on an Instrument in the Center for Molecular Medicine Protein Core, which is funded through NIH/NIGMS COBRE grant P30M110787. Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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N2 - Recognition and regulation of G-quadruplex nucleic acid structures is an important goal for the development of chemical tools and medicinal agents. The addition of a bromo-substituent to the dipyridylphenazine (dppz) ligands in the photophysical "light switch", [Ru(bpy)2dppz]2+, and the photochemical "light switch", [Ru(bpy)2dmdppz]2+, creates compounds with increased selectivity for an intermolecular parallel G-quadruplex and the mixed-hybrid G-quadruplex, respectively. When [Ru(bpy)2dppz-Br]2+ and [Ru(bpy)2dmdppz-Br]2+ are incubated with the G-quadruplexes, they have a stabilizing effect on the DNA structures. Activation of [Ru(bpy)2dmdppz-Br]2+ with light results in covalent adduct formation with the DNA. These complexes demonstrate that subtle chemical modifications of RuII complexes can alter G-quadruplex selectivity, and could be useful for the rational design of in vivo G-quadruplex probes.

AB - Recognition and regulation of G-quadruplex nucleic acid structures is an important goal for the development of chemical tools and medicinal agents. The addition of a bromo-substituent to the dipyridylphenazine (dppz) ligands in the photophysical "light switch", [Ru(bpy)2dppz]2+, and the photochemical "light switch", [Ru(bpy)2dmdppz]2+, creates compounds with increased selectivity for an intermolecular parallel G-quadruplex and the mixed-hybrid G-quadruplex, respectively. When [Ru(bpy)2dppz-Br]2+ and [Ru(bpy)2dmdppz-Br]2+ are incubated with the G-quadruplexes, they have a stabilizing effect on the DNA structures. Activation of [Ru(bpy)2dmdppz-Br]2+ with light results in covalent adduct formation with the DNA. These complexes demonstrate that subtle chemical modifications of RuII complexes can alter G-quadruplex selectivity, and could be useful for the rational design of in vivo G-quadruplex probes.

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Ruthenium Complex "Light Switches" that are Selective for Different G-Quadruplex Structures

Abstract

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Keywords

ASJC Scopus subject areas

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