Tuning the DNA binding and cleavage of bpa Cu(II) complexes by ether tethers with hydroxyl and methoxy groups

Tjakraatmadja, Airlangga Arya Janitra Sudarga; Lüdtke, Carsten; Kulak, Nora

doi:10.1016/j.ica.2016.02.034

Cited by 8 publications

(6 citation statements)

References 40 publications

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“…C2 > C1 ; C4 > C3 ). The beneficial role of methoxy groups in pyridyl‐based ligands for hydrolytic DNA cleavage has been observed by us before …”

Section: Resultsmentioning

confidence: 79%

“…Many mononuclear Cu II , Co II , Zn II and Fe II complexes which were derived from a wide range of ligands of varied skeletal structures and geometrical environments have been extensively used as catalysts for DNA cleavage . Model systems incorporating multi‐nuclear 3d metal(II) complexes and sometimes hetero‐dinuclear metal ions were also employed , .…”

Section: Introductionmentioning

confidence: 99%

“…The oxidative cleavage occurs via reactive oxygen species (ROS: reactive singlet oxygen, 1 O 2 ; superoxide, O 2 – ; hydroxyl radical, OH · ). This mechanism requires a redox‐active metal and an external co‐reactant such as an oxidizing or reducing agent, or light in order to initiate the cleavage , , , , , , , . The ROS generate DNA fragments that cannot be re‐ligated and thus hamper their use in vivo.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Efficient Artificial Nucleases for Mediating DNA Cleavage Based on Tuning the Steric Effect in the Pyridyl Derivatives of Tripod Tetraamine‐Cobalt(II) Complexes

et al. 2018

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Four cobalt(II) complexes [Co(L 1 )Cl]PF 6 /ClO 4 (C1-PF 6 / C1-ClO 4 ), [Co(L 2 )Cl]PF 6 (C2-PF 6 ), [Co(L 3 )Cl]PF 6 /ClO 4 ·H 2 O·CH 3 OH (C3-PF 6 /C3-ClO 4 ·H 2 O·CH 3 OH) and [Co(L 4 [bis(3,5-dimethyl-4methoxy-2-pyridylmethyl)-(2-pyridylmethyl)]amine and {[bis-(3,4-dimethoxy-2-pyridyl)methyl]-(2-pyridylmethyl)}amine, respectively, were synthesized and structurally characterized. Single-crystal X-ray crystallography confirmed the trigonal bipyramidal geometries of the complexes. In aqueous acetonitrile solution, the green complexes dissolve with the formation of a yellow solution with biphasic kinetic behavior. In 60 % H 2 O/ [a]

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“…C2 > C1 ; C4 > C3 ). The beneficial role of methoxy groups in pyridyl‐based ligands for hydrolytic DNA cleavage has been observed by us before …”

Section: Resultsmentioning

confidence: 79%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Efficient Artificial Nucleases for Mediating DNA Cleavage Based on Tuning the Steric Effect in the Pyridyl Derivatives of Tripod Tetraamine‐Cobalt(II) Complexes

et al. 2018

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“…As it can be derived from the molecular structures of the inactive complexes 4-Cl and 5-Cl (Figure 1), the methoxy substituents at the pyridine moieties might hinder and/or suppress the intercalation of the complexes with DNA and hence their DNA cleavage activity. Previous results showed that increasing number of methoxy substituents at the pyridine moieties of pyridyl-derived ligand systems improves the hydrolytic DNA cleavage activity, but this trend could not be confirmed with the current ligands [3,11]. In addition, the molecular structure of complex 6-ClO 4 , which does not show DNA cleavage activity, indicates that the Cu(II) center is sterically shielded [47] and hence not easily accessible for neither hydrolytic (cleavage of the phosphate ester backbone) nor oxidative (reaction with O 2 for ROS generation) DNA cleavage reactions.…”

Section: Reactive Oxygen Species (Ros)mentioning

confidence: 61%

Copper(II) Complexes with Tetradentate Piperazine-Based Ligands: DNA Cleavage and Cytotoxicity

et al. 2021

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Five-coordinate Cu(II) complexes, [Cu(Ln)X]ClO4/PF6, where Ln = piperazine ligands bearing two pyridyl arms and X = ClO4− for Ln = L1 (1-ClO4), L2 (2-ClO4), L3 (3-ClO4), and L6 (6-ClO4) as well as [Cu(Ln)Cl]PF6 for Ln = L1 (1-Cl), L4 (4-Cl), and L5 (5-Cl) have been synthesized and characterized by spectroscopic techniques. The molecular structures of the last two complexes were determined by X-ray crystallography. In aqueous acetonitrile solutions, molar conductivity measurements and UV-VIS spectrophotometric titrations of the complexes revealed the hydrolysis of the complexes to [Cu(Ln)(H2O)]2+ species. The biological activity of the Cu(II) complexes with respect to DNA cleavage and cytotoxicity was investigated. At micromolar concentration within 2 h and pH 7.4, DNA cleavage rate decreased in the order: 1-Cl ≈ 1-ClO4 > 3-ClO4 ≥ 2-ClO4 with cleavage enhancements of up to 23 million. Complexes 4-Cl, 5-Cl, and 6-ClO4 were inactive. In order to elucidate the cleavage mechanism, the cleavage of bis(4-nitrophenyl)phosphate (BNPP) and reactive oxygen species (ROS) quenching studies were conducted. The mechanistic pathway of DNA cleavage depends on the ligand’s skeleton: while an oxidative pathway was preferable for 1-Cl/1-ClO4, DNA cleavage by 2-ClO4 and 3-ClO4 predominantly proceeds via a hydrolytic mechanism. Complexes 1-ClO4, 3-ClO4, and 5-Cl were found to be cytotoxic against A2780 cells (IC50 30–40 µM). In fibroblasts, the IC50 value was much higher for 3-ClO4 with no toxic effect.

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“…6) Furthermore, secondary amine substitutions in BPA can be used to increase the types of metals to which the complex can coordinate and/or to introduce bioactive structures. 7,8) Several studies have reported metal-complexed BPA derivatives for DNA cleavage activity, 9) including photocleavage. 10) Since the metal atom itself exhibits poor directivity toward DNA, target-directivity in vivo is ligand-dependent.…”

Section: Introductionmentioning

confidence: 99%

Structural Characterization of Zinc(II)/Cobalt(II) Complexes of Chiral N-(Anthracen-9-yl)methyl-N,N-bis(2-picolyl)amine and Evaluation of DNA Photocleavage Activity

Ichimaru

Kato

Nakatani

et al. 2023

CHEMICAL & PHARMACEUTICAL BULLETIN

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We designed and synthesized a chiral ligand N-(anthracen-9-ylmethyl)-1-(pyridin-2-yl)-N-(pyridin-2ylmethyl)ethanamine (APPE) DNA photocleavage agent to investigate the effects of chirality of bis(2-picolyl)-amine on the DNA photocleavage activity of metal complexes. The structures of Zn II and Co II complexes in APPE were analyzed via X-ray crystallography and fluorometric titration. APPE formed metal complexes with a 1 : 1 stoichiometry in both the crystalline and solution states. Fluorometric titration was used to show that the Zn II and Co II association constants of these complexes (log K a s) were 4.95 and 5.39, respectively. The synthesized complexes were found to cleave pUC19 plasmid DNA when irradiated at 370 nm. The DNA photocleavage activity of the Zn II complex was higher than that of the Co II complex. The absolute configuration of the methyl-attached carbon did not affect DNA cleavage activity and, unfortunately, an achiral APPE derivative without the methyl group (ABPM) was found to perform DNA photocleavage more effectively than APPE. One reason for this may be that the methyl group suppressed the structural flexibility of the photosensitizer. These results will be useful for the design of new photoreactive reagents.

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Tuning the DNA binding and cleavage of bpa Cu(II) complexes by ether tethers with hydroxyl and methoxy groups

Cited by 8 publications

References 40 publications

Efficient Artificial Nucleases for Mediating DNA Cleavage Based on Tuning the Steric Effect in the Pyridyl Derivatives of Tripod Tetraamine‐Cobalt(II) Complexes

Efficient Artificial Nucleases for Mediating DNA Cleavage Based on Tuning the Steric Effect in the Pyridyl Derivatives of Tripod Tetraamine‐Cobalt(II) Complexes

Copper(II) Complexes with Tetradentate Piperazine-Based Ligands: DNA Cleavage and Cytotoxicity

Structural Characterization of Zinc(II)/Cobalt(II) Complexes of Chiral <i>N</i>-(Anthracen-9-yl)methyl-<i>N</i>,<i>N</i>-bis(2-picolyl)amine and Evaluation of DNA Photocleavage Activity

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