DNA Binding and Oxidative Cleavage by a Water‐soluble Carboxyl Manganese(III) Corrole

Zhang, Yang; Wang, Qi; Wen, Jinyan; Wang, Xiang-Li; Mahmood, Mian Hr; Ji, Liang‐Nian; Liu, Haiyang

doi:10.1002/cjoc.201300488

Cited by 18 publications

(18 citation statements)

References 64 publications

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“…To further elucidate the binding mode between 1 and ct-DNA, the viscosity was measured, which is regarded as the least ambiguous for probing the binding mode of small molecule to DNA in the absence of crystallographic and NMR data [12,56]. An obvious increase in viscosity of DNA can be observed if a small molecule interacts with DNA in an intercalative mode, because the DNA helix would lengthen upon insertion of intercalator (EB, Fig.…”

Section: Dna Bindingmentioning

confidence: 99%

“…R 0 is the critical distance when the transfer efficiency (E) is 50% and it may be calculated by Equation 12. K 2 is the spatial orientation factor describing the relative orientation in space of the donor-acceptor transition dipoles, K 2 = 2/3, N is the refraction index of the medium, F is the fluorescence quantum yield in the absence of energy transfer, J is the overlap integral between the fluorescence emission spectrum of donor and the absorption spectrum of acceptor.…”

Section: Hsa Bindingmentioning

confidence: 99%

“…DMSO and t-BuOH are hydroxyl radical ( · OH) scavengers. L-histidine and DABCO are scavengers for singlet oxygen ( 1 O 2 ) [11,12]. The addition of DMSO and t-BuOH (Lanes 6 and 7) can effectively inhibit DNA cleavage.…”

Section: Nuclease Activity Studiesmentioning

confidence: 99%

“…Serum albumin (SA) is the most abundant carrier protein whose in vivo binding to drugs could significantly affect the pharmaceutical process and toxicity of drugs [9]. The interactions of DNA or serum albumin (SA) with porphyrinoids, such as corroles [10][11][12][13][14], phthalocyanines [15] and porphyrins [16][17][18][19] have drawn much attention for their potential clinical uses.…”

Section: Introductionmentioning

confidence: 99%

“…It is well-known that the transition-metal complexes of porphyrinoids, such as manganese porphyrins and manganese corroles [10][11][12]19] as nuclease mimics, exhibit excellent catalytic activity for oxidative DNA cleavage. The transition-metal complexes of N-confused porphyrin have been demonstrated to be potent catalysts in cyclopropanation of styrene with high trans-selectivity [33,34] and oxygen atom transfer reactions [35].…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

The magnetic properties, DNA/HSA binding and nuclease activity of manganese N-confused porphyrin

Peng

Ali

et al. 2016

J. Porphyrins Phthalocyanines

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The first oxidative cleavage of DNA by manganese N-confused porphyrin [chloro(2aza-2-methyl-5,10,15,20-tetrakis(p-chlorophenyl)-21-carbaporphyrin)manganese(III), 1] using H 2 O 2 as oxidant agent and its magnetic, calf thymus DNA(ct-DNA)-and human serum albumin (HSA) binding properties were investigated. The magnitude of the axial (D) zero-field splitting for the mononuclear Mn(III) center in 1 was determined to be approximately 2.71 cm -1 by paramagnetic susceptibility measurements. The DNA-and HSA binding experimental results showed that 1 bound to ct-DNA via an outside groove binding mode and the hydrophobic cavity located in subdomain IIA of HSA with the binding constant of 4.144 × 10 5 M -1 and ~10 6 M -1 , respectively. Thermodynamic parameters revealed that both DNA-and HSA binding were spontaneous process. The main driven forces were the hydrogen bond and van der Waals for the former, but hydrophobic interaction for the latter, which were further confirmed by molecular docking modeling. Manganese N-confused porphyrin 1 could cleave the supercoiled plasmid DNA efficiently in the presence of hydrogen peroxide. Hydroxyl radical ( · OH) was found the active species for oxidative damage of DNA.

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Section: Dna Bindingmentioning

confidence: 99%

Section: Hsa Bindingmentioning

confidence: 99%

Section: Nuclease Activity Studiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

The magnetic properties, DNA/HSA binding and nuclease activity of manganese N-confused porphyrin

Peng

Ali

et al. 2016

J. Porphyrins Phthalocyanines

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DNA binding and nuclease activity of cationic iron(IV) and manganese(III) corrole complexes

Zhang

Wen

Wang

et al. 2014

Applied Organom Chemis

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Cationic meso(4-N-methylpyridyl)-based metallocorroles, μ-oxo iron corrole dimer (1b) and manganese corrole monomer (2b), were synthesized and characterized. The interactions of these two metal corrole complexes with CT-DNA were studied by UVvisible, fluorescence and circular dichroism spectroscopic methods, as well as by viscosity measurements. The results revealed that 1b interacts with CT-DNA in a difunctional binding mode, i.e. non-classical intercalation and outside groove binding with H-aggregation, while 2b can interact with CT-DNA via an outside groove binding mode only. The binding constants K b of 1b and 2b were 4.71 × 10 5 M À1 and 2.17 × 10 5 M À1 , respectively, indicating that 1b can bind more tightly to CT-DNA than 2b. Furthermore, both complexes may cleave the supercoiled plasmid DNA efficiently in the presence of hydrogen peroxide or tert-butyl hydroperoxide (TBHP), albeit 1b exhibited a little higher efficiency. The inhibitor tests suggested that singlet oxygen and high-valent (oxo)iron(VI) corrole or (oxo)manganese(V) corrole might be the active intermediates responsible for the oxidative DNA scission. Figure 2. UV-visible spectral changes of 1b in 5 mM Tris-HCl/50 mM NaCl buffer (pH 5), t = 0 (dashed line), 5, 10, 15 and 30 min.Figure 10. Absorption spectra of (a) 1b (20 μM) and (b) 2b (20 μM) in 50 mM Tris-HCl/18 mM NaCl buffer (pH 7.2) in the presence of TBHP or H 2 O 2 at different times. (a) [H 2 O 2 ] = [TBHP] = 10 μM; (b) [H 2 O 2 ] = [TBHP] = 20 mM.

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Photocytotoxicity and G‐quadruplex DNA interaction of water‐soluble gallium(III) tris(N‐methyl‐4‐pyridyl)corrole complex

Zhang

Wen

et al. 2015

Applied Organom Chemis

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A water-soluble cationic gallium corrole, 5,10,15-tris(N-methyl-4-pyridyl)corrolatogallium(III) (3), was prepared and characterized. The photocytotoxicity of 3 was investigated using Hep G2 cancer cell line. Upon treatment with corrole 3 and irradiation, fragmentation of tumor cell nuclei was observed, which led to apoptosis. Flow cytometric analysis clearly showed the efficient induction of apoptotic cell death, and corrole 3 exhibited high photocytotoxicity towards Hep G2 cancer cells (IC 50 = 60 nM). Furthermore, the binding behavior of corrole 3 with c-MYC G-quadruplex DNA, a potent target for antitumor drugs, was investigated using spectroscopic methods and molecular docking simulation.

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DNA Binding and Oxidative Cleavage by a Water‐soluble Carboxyl Manganese(III) Corrole

Cited by 18 publications

References 64 publications

The magnetic properties, DNA/HSA binding and nuclease activity of manganese N-confused porphyrin

The magnetic properties, DNA/HSA binding and nuclease activity of manganese N-confused porphyrin

DNA binding and nuclease activity of cationic iron(IV) and manganese(III) corrole complexes

Photocytotoxicity and G‐quadruplex DNA interaction of water‐soluble gallium(III) tris(N‐methyl‐4‐pyridyl)corrole complex

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