Substituted dipyridophenazine complexes of Cr(III): synthesis, enantiomeric resolution and binding interactions with calf thymus DNA

Suni Vasudevan; Jayden A. Smith; Michal Wojdyla; Thomas McCabe; Nicholas C. Fletcher; Susan J. Quinn; John M. Kelly

doi:10.1039/c000150c

Substituted dipyridophenazine complexes of Cr(III): synthesis, enantiomeric resolution and binding interactions with calf thymus DNA

Suni Vasudevan, Jayden A. Smith, Michal Wojdyla, Thomas McCabe, Nicholas C. Fletcher, Susan J. Quinn, John M. Kelly^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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Abstract

[Cr(phen)₂(X₂dppz)]³⁺ {X = H, Me, or F} have been synthesised, characterised, and chromatographically resolved into their constituent Δ and Λ enantiomers. The DNA-binding interactions of each of the racemic complexes were investigated, with the results of linear dichroism, thermal denaturation, and emission quenching studies indicative of intercalative binding to CT-DNA with a significant electrostatic contribution. UV/Vis absorption titrations suggest strong DNA binding by each of the racemic complexes, with the methylated analogue [Cr(phen)₂(Me₂dppz)]³⁺ exhibiting the largest equilibrium binding constant. Emission quenching and UV-Vis titrations of the enantiomers of [Cr(phen)₂(dppz)]³⁺ imply similar binding affinities for the Δ and Λ isomers, although significant differences between the circular dichroism spectra of the enantiomers in the presence of DNA connote differences in binding orientation and/or conformation between the two.

Original language	English
Pages (from-to)	3990-3998
Number of pages	9
Journal	Dalton Transactions
Issue number	16
DOIs	https://doi.org/10.1039/c000150c
Publication status	Published - 28 Apr 2010

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title = "Substituted dipyridophenazine complexes of Cr(III): synthesis, enantiomeric resolution and binding interactions with calf thymus DNA",

abstract = "[Cr(phen)2(X2dppz)]3+ {X = H, Me, or F} have been synthesised, characterised, and chromatographically resolved into their constituent Δ and Λ enantiomers. The DNA-binding interactions of each of the racemic complexes were investigated, with the results of linear dichroism, thermal denaturation, and emission quenching studies indicative of intercalative binding to CT-DNA with a significant electrostatic contribution. UV/Vis absorption titrations suggest strong DNA binding by each of the racemic complexes, with the methylated analogue [Cr(phen)2(Me2dppz)]3+ exhibiting the largest equilibrium binding constant. Emission quenching and UV-Vis titrations of the enantiomers of [Cr(phen)2(dppz)]3+ imply similar binding affinities for the Δ and Λ isomers, although significant differences between the circular dichroism spectra of the enantiomers in the presence of DNA connote differences in binding orientation and/or conformation between the two.",

author = "Suni Vasudevan and Smith, {Jayden A.} and Michal Wojdyla and Thomas McCabe and Fletcher, {Nicholas C.} and Quinn, {Susan J.} and Kelly, {John M.}",

year = "2010",

month = apr,

day = "28",

doi = "10.1039/c000150c",

language = "English",

pages = "3990--3998",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

number = "16",

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TY - JOUR

T1 - Substituted dipyridophenazine complexes of Cr(III): synthesis, enantiomeric resolution and binding interactions with calf thymus DNA

AU - Vasudevan, Suni

AU - Smith, Jayden A.

AU - Wojdyla, Michal

AU - McCabe, Thomas

AU - Fletcher, Nicholas C.

AU - Quinn, Susan J.

AU - Kelly, John M.

PY - 2010/4/28

Y1 - 2010/4/28

N2 - [Cr(phen)2(X2dppz)]3+ {X = H, Me, or F} have been synthesised, characterised, and chromatographically resolved into their constituent Δ and Λ enantiomers. The DNA-binding interactions of each of the racemic complexes were investigated, with the results of linear dichroism, thermal denaturation, and emission quenching studies indicative of intercalative binding to CT-DNA with a significant electrostatic contribution. UV/Vis absorption titrations suggest strong DNA binding by each of the racemic complexes, with the methylated analogue [Cr(phen)2(Me2dppz)]3+ exhibiting the largest equilibrium binding constant. Emission quenching and UV-Vis titrations of the enantiomers of [Cr(phen)2(dppz)]3+ imply similar binding affinities for the Δ and Λ isomers, although significant differences between the circular dichroism spectra of the enantiomers in the presence of DNA connote differences in binding orientation and/or conformation between the two.

AB - [Cr(phen)2(X2dppz)]3+ {X = H, Me, or F} have been synthesised, characterised, and chromatographically resolved into their constituent Δ and Λ enantiomers. The DNA-binding interactions of each of the racemic complexes were investigated, with the results of linear dichroism, thermal denaturation, and emission quenching studies indicative of intercalative binding to CT-DNA with a significant electrostatic contribution. UV/Vis absorption titrations suggest strong DNA binding by each of the racemic complexes, with the methylated analogue [Cr(phen)2(Me2dppz)]3+ exhibiting the largest equilibrium binding constant. Emission quenching and UV-Vis titrations of the enantiomers of [Cr(phen)2(dppz)]3+ imply similar binding affinities for the Δ and Λ isomers, although significant differences between the circular dichroism spectra of the enantiomers in the presence of DNA connote differences in binding orientation and/or conformation between the two.

U2 - 10.1039/c000150c

DO - 10.1039/c000150c

M3 - Article

SN - 1477-9226

SP - 3990

EP - 3998

JO - Dalton Transactions

JF - Dalton Transactions

IS - 16

ER -

Substituted dipyridophenazine complexes of Cr(III): synthesis, enantiomeric resolution and binding interactions with calf thymus DNA

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