Synthesis and pH-sensitive redox properties of 1,10-phenanthroline-5,6-dione complexes

Kou, Yingying; Xu, Guang-Jun; Gu, Wen; Tian, Jin‐Lei; Yan, Shi‐Ping

doi:10.1080/00958970802010575

Cited by 6 publications

(4 citation statements)

References 14 publications

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“…The redox couples C 1 /A 1 and C 2 /A 2 observed for [Cu(TPMA)(PD)] 2+ at the DNA biosensor were initially much smaller in magnitude than redox peaks observed with the other complexes (Figure 5a). The C 1 /A 1 redox wave was recorded at similar potentials to those at the bare gold electrode (C 1 at −0.08 V and A 1 at −0.04 V vs. SCE) and can be associated with the electrochemical reduction of the complex [48], directed by PD electronic characteristics.…”

Section: Electrochemical Characterisation Of [Cu(tpma)(nn′)] 2+ Complexes At the Dna Biosensormentioning

confidence: 92%

“…In measurements performed on [Cu(TPMA)(PD)] 2+ , it was determined that the C 1 /A 1 redox coupled is ascribed to the 'Cu(PD) character' of the complex and C 3 /A 3 can be associated with the reversible oxidation of the 1,10-phen-5,6-dione (PD) ligand. Transition metal PD complexes can undergo a two-step 2 electron reduction [46][47][48], while the reduction of the free PD ligand in aqueous solution, from quinone to semiquinone and further to hydroquinone, has also been reported [49,50] (S-3, Figure S7, SM). Moreover, the C 2 peak, also common to the other complexes at −0.4 V, is linked to the A 2 oxidation processes and describes the electroactivity of the reorganised complex ('Cu(TPMA) character').…”

Section: Electrochemical Characterisation Of Copper Complexes At Gold Electrodesmentioning

confidence: 96%

“…According to the literature, some quinones can covalently bind to DNA bases, creating DNA adducts [59,60]. associated with the electrochemical reduction of the complex [48], directed by PD electronic characteristics. The C2/A2 redox couple, the '[Cu(TPMA)] 2+ character' of the complex, was evident −0.42/−0.33 V vs. SCE.…”

Section: Electrochemical Characterisation Of [Cu(tpma)(nn′)] 2+ Complexes At the Dna Biosensormentioning

confidence: 99%

“…S1 and S2: Electrochemical parameters for the copper complexes obtained at the DNA biosensors; Figure S11: Washing of the DNA layer after interaction with [Cu(TPMA)(PD)] 2+ ; Figures S12-S15: The relationship between the oxidation and reduction wave peak currents versus the scan rate, and the square root of the scan rate, at the DNA biosensor; Figures S16-S19: The stability of the complexes at the DNA biosensor; Tables S3-S6: DNA nuclease efficacy of copper complexes. References [17,37,[45][46][47][48][49][50]52,61,64,65] have been cited in the Supplementary Materials.…”

Section: Supplementary Materialsmentioning

confidence: 99%

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Mapping the DNA Damaging Effects of Polypyridyl Copper Complexes with DNA Electrochemical Biosensors

et al. 2022

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Several classes of copper complexes are known to induce oxidative DNA damage that mediates cell death. These compounds are potentially useful anticancer agents and detailed investigation can reveal the mode of DNA interaction, binding strength, and type of oxidative lesion formed. We recently reported the development of a DNA electrochemical biosensor employed to quantify the DNA cleavage activity of the well-studied [Cu(phen)2]2+ chemical nuclease. However, to validate the broader compatibility of this sensor for use with more diverse—and biologically compatible—copper complexes, and to probe its use from a drug discovery perspective, analysis involving new compound libraries is required. Here, we report on the DNA binding and quantitative cleavage activity of the [Cu(TPMA)(N,N)]2+ class (where TPMA = tris-2-pyridylmethylamine) using a DNA electrochemical biosensor. TPMA is a tripodal copper caging ligand, while N,N represents a bidentate planar phenanthrene ligand capable of enhancing DNA interactions through intercalation. All complexes exhibited electroactivity and interact with DNA through partial (or semi-) intercalation but predominantly through electrostatic attraction. Although TPMA provides excellent solution stability, the bulky ligand enforces a non-planar geometry on the complex, which sterically impedes full interaction. [Cu(TPMA)(phen)]2+ and [Cu(TPMA)(DPQ)]2+ cleaved 39% and 48% of the DNA strands from the biosensor surface, respectively, while complexes [Cu(TPMA)(bipy)]2+ and [Cu(TPMA)(PD)]2+ exhibit comparatively moderate nuclease efficacy (ca. 26%). Comparing the nuclease activities of [Cu(TPMA)(phen)] 2+ and [Cu(phen)2]2+ (ca. 23%) confirms the presence of TPMA significantly enhances chemical nuclease activity. Therefore, the use of this DNA electrochemical biosensor is compatible with copper(II) polypyridyl complexes and reveals TPMA complexes as a promising class of DNA damaging agent with tuneable activity due to coordinated ancillary phenanthrene ligands

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Section: Electrochemical Characterisation Of [Cu(tpma)(nn′)] 2+ Complexes At the Dna Biosensormentioning

confidence: 92%

Section: Electrochemical Characterisation Of Copper Complexes At Gold Electrodesmentioning

confidence: 96%

Section: Electrochemical Characterisation Of [Cu(tpma)(nn′)] 2+ Complexes At the Dna Biosensormentioning

confidence: 99%

Section: Supplementary Materialsmentioning

confidence: 99%

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Mapping the DNA Damaging Effects of Polypyridyl Copper Complexes with DNA Electrochemical Biosensors

et al. 2022

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Mn-carbonyl molecular catalysts containing a redox-active phenanthroline-5,6-dione for selective electro- and photoreduction of CO2 to CO or HCOOH

Stanbury

Compain

Trejo

et al. 2017

Electrochimica Acta

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Synthesis, structure and magnetic properties of a binuclear Co(II)-pyrophosphate complex, [Co2(phenanthroline-dione)4(P2O7)]

et al. 2019

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Synthesis and pH-sensitive redox properties of 1,10-phenanthroline-5,6-dione complexes

Cited by 6 publications

References 14 publications

Mapping the DNA Damaging Effects of Polypyridyl Copper Complexes with DNA Electrochemical Biosensors

Mapping the DNA Damaging Effects of Polypyridyl Copper Complexes with DNA Electrochemical Biosensors

Mn-carbonyl molecular catalysts containing a redox-active phenanthroline-5,6-dione for selective electro- and photoreduction of CO2 to CO or HCOOH

Synthesis, structure and magnetic properties of a binuclear Co(II)-pyrophosphate complex, [Co2(phenanthroline-dione)4(P2O7)]

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