Δ-cis-α-[Ru(RR-picchxnMe2 )(phen)]2+ shows minor groove AT selectivity with oligonucleotides

Proudfoot, Emma M.; Mackay, Joel P.; Vagg, Robert S.; Vickery, Kymberley; Williams, Peter A.; Karuso, Peter

doi:10.1039/a704001f

Cited by 17 publications

(15 citation statements)

References 12 publications

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“…However, an optically active ternary octahedral ruthenium complex, D-cis-a-[Ru(RR-picchxnMe 2 )(phen)] 2? (picchxnMe 2 = N,N 0 -dimethyl-N, N 0 -di(2-picolyl)-1,2-diaminocyclohexane), was shown via NMR study to bind with AT selectivity in the minor groove of d(CGCGATCGCG) 2 and d(ATATCGA TAT) 2 duplexes without intercalation of the phen ligand (Proudfoot et al 1997). On the other hand, recognition of zinc(II)-cyclen derivatives for AT-rich regions involve the zinc atom covalently bonding to N(3)-deprotonated anionic form of the thymine and the stacking interaction of the aromatic substituent group(s) at the cyclen with aromatic ring of proximal nucleobase (Kikuta et al 2000).…”

Section: Dna Binding Studymentioning

confidence: 97%

Crystal structure, DNA binding studies, nucleolytic property and topoisomerase I inhibition of zinc complex with 1,10-phenanthroline and 3-methyl-picolinic acid

et al. 2009

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Crystal structure analysis of the zinc complex establishes it as a distorted octahedral complex, bis(3-methylpicolinato-kappa(2) N,O)(2)(1,10-phenanthroline-kappa(2) N,N)-zinc(II) pentahydrate, [Zn(3-Me-pic)(2)(phen)]x5H(2)O. The trans-configuration of carbonyl oxygen atoms of the carboxylate moieties and orientation of the two planar picolinate ligands above and before the phen ligand plane seems to confer DNA sequence recognition to the complex. It cannot cleave DNA under hydrolytic condition but can slightly be activated by hydrogen peroxide or sodium ascorbate. Circular Dichroism and Fluorescence spectroscopic analysis of its interaction with various duplex polynucleotides reveals its binding mode as mainly intercalation. It shows distinct DNA sequence binding selectivity and the order of decreasing selectivity is ATAT > AATT > CGCG. Docking studies lead to the same conclusion on this sequence selectivity. It binds strongly with G-quadruplex with human tolemeric sequence 5'-AG(3)(T(2)AG(3))(3)-3', can inhibit topoisomerase I efficiently and is cytotoxic against MCF-7 cell line.

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Section: Dna Binding Studymentioning

confidence: 97%

Crystal structure, DNA binding studies, nucleolytic property and topoisomerase I inhibition of zinc complex with 1,10-phenanthroline and 3-methyl-picolinic acid

et al. 2009

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“…/ to function as stereoand enantiodiscriminatory intercalating probes of DNA structures [6,[12][13][14]. In these complexes, the tetradentate is chosen to have characteristics which allow it to govern binding selectivity through helical groove interactions, thereby providing a molecular recognition function.…”

Section: Introductionmentioning

confidence: 99%

DNA Binding of Some Chiral Metallointercalators Derived From9,10‐Phenanthrenediamine

et al. 1998

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A study of the interaction with calf thymus DNA is described of a novel set of chiral ternary complex cations of general form [Ru(N4-tet)(phdi)]2+ (where N4 -tet is the chiral linear tetradentate R*R*-picchxn or R*-picchxnMe2). Individual equilibrium binding constants (KB) have been determined from spectroscopic titrations employing the hypochromism induced in the visible absorbance of the cations on interaction with the nucleic acid. These demonstrate both stereo- and enantioselectivity in the binding interactions. These KB data, together with induced circular dichroism and DNA thermal denaturation results, are all indicative of selective intercalation of the bidentate components of the cations into the nucleobase stack of the duplex. Supportive evidence for a secondary binding mode for the picchxn complexes is provided by the different mutagenicity profiles obtained for related cations.

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“…Yet, it experiences a small shift (+0.04 ppm) upon K-isomer binding not enough to be interpreted as an effect of hydrogen bonding. It can be due to the formation of a hydrogen bond, bifurcated and longer than normal or actually Van der Waals interaction between peptide backbone or side chains and the G 2 /C 11 exocyclic amino group [41]. In a similar manner, the groove binding of the drug Distamycin A to d(CGCGAATTCGCG) 2 induces small downfield shifts to both the adenine ring protons and the drug pyrrole NH groups [41].…”

Section: Interaction Of K-and D-[ru(bpy) 2 (M-bpy-7p)] 2+ With D(gcgcmentioning

confidence: 94%

Synthesis and characterization of the diastereomers Λ- and Δ-[Ru(bpy)2(m-bpy-l-Arg-Gly-l-Asn-l-Ala-l-His-l-Glu-l-Arg)]Cl2

Myari¹,

Hadjiliadis²,

Garoufis³

2005

Journal of Inorganic Biochemistry

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Δ-cis-α-[Ru(RR-picchxnMe2 )(phen)]2+ shows minor groove AT selectivity with oligonucleotides

Abstract: NMR studies show that the ternary octahedral D-cis-a-[Ru(RR-picchxnMe 2 )(phen)] 2+ cation binds with AT selectivity in the minor groove of [d(CGCGATCGCG) 2 ] and [d(ATATCGATAT) 2 ] duplexes through a non-intercalative interaction.

Cited by 17 publications

References 12 publications

Crystal structure, DNA binding studies, nucleolytic property and topoisomerase I inhibition of zinc complex with 1,10-phenanthroline and 3-methyl-picolinic acid

Crystal structure, DNA binding studies, nucleolytic property and topoisomerase I inhibition of zinc complex with 1,10-phenanthroline and 3-methyl-picolinic acid

DNA Binding of Some Chiral Metallointercalators Derived From9,10‐Phenanthrenediamine

Synthesis and characterization of the diastereomers Λ- and Δ-[Ru(bpy)2(m-bpy-l-Arg-Gly-l-Asn-l-Ala-l-His-l-Glu-l-Arg)]Cl2

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