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1.
Metallomics ; 13(4)2021 04 24.
Artigo em Inglês | MEDLINE | ID: mdl-33765148

RESUMO

A novel optically pure dinuclear copper(II) complex of a rosin derivative dehydroabietic acid (DHA, HL) was synthesized and fully characterized. The in vitro antitumor activities of the copper(II) complex Cu2(µ2-O)(L)4(DMF)2 (1) were explored and compared with those of a trinuclear iron(III) complex [Fe3(µ3-O)(L)6(CH3OH)2(CH3O)]·H2O (2). 1 was more cytotoxic than 2, and the in vitro cytotoxicity of 1 was comparable to that of cisplatin and oxaliplatin. The metal coordination improved the cytotoxicity of DHA. 1 could arrest cycle in G1 phase and induce apoptosis in MCF-7 cell. 1 increased reactive oxygen species level, GSSG/GSH ratio, and Ca2+ production, and caused the loss of mitochondrial membrane potential (Δψm) in MCF-7 cells. The up-regulated Bax and down-regulated Bcl-2 expression levels, caspase-9/caspase-3 activation, and the release of Cyt c demonstrate that 1 triggered mitochondria-mediated intrinsic apoptosis in MCF-7 cells. Caspase-8/caspase-4 activation and up-regulated Fas expression indicate that death receptor-mediated extrinsic apoptosis was included. Comet assay and up-regulated γ-H2AX and p53 expressions confirmed that 1 caused DNA damage in MCF-7 cells. Moreover, 1 led to enhancement of the biomarker of lipid peroxidation and the indicator of protein carbonylation in MCF-7 cells. All the results suggest that 1 could kill MCF-7 cells by generating oxidative stress, impairing DNA, promoting lipid peroxidation and protein carbonylation, and inducing apoptosis and autophagy. Furthermore, 1 also displayed antimetastatic activities with inhibition of cell invasion and migration, together with antiangiogenesis properties. On the whole, copper complex based on rosin derivatives is worth developing as metal-based antitumor drugs.


Assuntos
Abietanos/química , Antineoplásicos/farmacologia , Complexos de Coordenação/farmacologia , Cobre/química , Ferro/química , Neoplasias/patologia , Resinas Vegetais/química , Antineoplásicos/química , Apoptose , Ciclo Celular , Movimento Celular , Complexos de Coordenação/química , Dano ao DNA , Humanos , Peroxidação de Lipídeos , Potencial da Membrana Mitocondrial , Mitocôndrias/efeitos dos fármacos , Mitocôndrias/metabolismo , Mitocôndrias/patologia , Neoplasias/tratamento farmacológico , Neoplasias/metabolismo , Estresse Oxidativo , Carbonilação Proteica , Espécies Reativas de Oxigênio/metabolismo , Células Tumorais Cultivadas , Cicatrização
2.
Spectrochim Acta A Mol Biomol Spectrosc ; 246: 118944, 2021 Feb 05.
Artigo em Inglês | MEDLINE | ID: mdl-33007643

RESUMO

To explore the biological properties of rosin derivatives, two dehydroabietic acid derivatives N-(5-dehydroabietyl-1,3,4-thiadiazole)-yl-pyridine-2-carboxamide (DTPC) and di-N-(5-dehydroabietyl-1,3,4-thiadiazole)-yl-pyridine-2,6-carboxamide (DDTPC) with 1,3,4-thiadiazole, pyridine and amide moieties were designed and synthesized according to superposition principle of activity group. They interact with calf thymus DNA (CT DNA) via intercalation based on the results of circular dichroism (CD) and fluorescence spectroscopy, DNA denaturation and viscosity studies. Fluorescence and CD spectral experiments indicate that they might be transported and stored by protein like bovine serum albumin (BSA). MTT assay was further carried out to examine their cytotoxicity, they both showed selective cytotoxicity and DTPC exhibited better cytotoxicity. The antiproliferative effect of DTPC toward A431 cell line was stronger than that of clinically used cisplatin and oxaliplatin. In addition, the cytotoxicity of DTPC and DDTPC was closely related with their DNA binding ability.


Assuntos
Antineoplásicos , Complexos de Coordenação , Abietanos , Animais , Antineoplásicos/farmacologia , Bovinos , Cisplatino , DNA/metabolismo , Ligação Proteica , Soroalbumina Bovina/metabolismo
3.
Dalton Trans ; 48(41): 15646-15656, 2019 Oct 22.
Artigo em Inglês | MEDLINE | ID: mdl-31465061

RESUMO

Two optically pure chiral binuclear copper(ii) complexes [Cu2(µ-Cl)2L2]·CH2Cl2 (1) and Cu2L4 (2) based on the natural product rosin derivative N-(5-dehydroabietyl-1,3,4-thiadiazole)-2-substituted pyridinecarboxamide (HL) were prepared, fully characterized and their biological activities were evaluated. The circular dichroism (CD), fluorescence spectroscopy, and DNA melting studies indicate that 1 and 2 interact with calf thymus DNA (CT DNA) via intercalation. It can be concluded that 1 and 2 have a strong affinity to bovine serum albumin (BSA) based on the fluorescence and CD spectral evidence. The MTT assay illustrates that the selective cytotoxic activity of 1 is better than that of HL, 2, cisplatin and oxaliplatin. The exposure of 1 to MCF-7 cells resulted in cell cycle arrest in the G1 phase, apoptosis, mitochondrial dysfunction and an elevated ROS level. The western blot analysis results indicate that 1 might induce apoptosis through intrinsic and extrinsic pathways, autophagy and DNA damage in MCF-7 cells. Furthermore, the down-regulated VEGFR2, MMP-2 and MMP-9 expression levels indicate that 1 should have the ability to resist metastasis and angiogenesis. Thus, based on the above described results 1 has high potential value for anticancer applications.


Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Complexos de Coordenação/química , Complexos de Coordenação/farmacologia , Cobre/química , Resinas Vegetais/química , Animais , Antineoplásicos/metabolismo , Apoptose/efeitos dos fármacos , Bovinos , Ciclo Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Complexos de Coordenação/metabolismo , DNA/metabolismo , Eletroquímica , Humanos , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Modelos Moleculares , Conformação Molecular , Espécies Reativas de Oxigênio/metabolismo , Soroalbumina Bovina/metabolismo , Albumina Sérica Humana/metabolismo
4.
J Hazard Mater ; 340: 326-335, 2017 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-28728111

RESUMO

The first 3D heteropoly blue Ba2Na4[SiW4VW8VIO40]·19H2O (1) as heterogeneous Fenton-like catalyst and flocculent was hydrothermally synthesized and fully characterized by various methods 1 was an efficient Fenton-like catalyst for degradation of phenol with degradation rate of 92.1% (visible light irradiation), and 89.0% (no light) in 90min, respectively. The degradation efficiency of anionic dye methyl orange was 97.0% in 5min, when 1 was used as photo-Fenton-like catalyst under visible light. And 1 was a nice flocculent for cationic dyes methylene blue and rhodamine B, the removal rates were both above 95%. Moreover, 1 could degrade methyl orange and flocculate rhodamine B at the same time, but the degradation rate decreased from 100% to 77.5% in 60min, while the flocculation of RhB in 10min was not affected.

5.
J Photochem Photobiol B ; 142: 77-85, 2015 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-25528191

RESUMO

The first chiral trinuclear iron(III) complex [Fe3(µ3-O)(L)6(CH3OH)2(CH3O)]⋅H2O (2) of a natural rosin product dehydroabietic acid (HL, 1) was synthesized and fully characterized. The interactions of 1 and 2 with salmon sperm DNA were investigated by viscosity measurements, UV, fluorescence and circular dichroism (CD) spectroscopic techniques. Absorption spectral (Kb=1.30×10(5)M(-1) (1), 1.40×10(5)M(-1)(2)), emission spectral (KSV=1.19×10(4)M(-1) (1), 1.79×10(4)M(-1) (2)) and viscosity measurements reveal that 1 and 2 interacted with DNA through intercalation and 2 exhibited a slight higher DNA binding ability. The Stern-Volmer quenching constant (KSV) and corresponding thermodynamic parameters (ΔG, ΔH and ΔS) of the binding processes were determined. The negative ΔH and ΔG values indicate that the binding reactions were exothermic and spontaneous. 1 and 2 were also screened for their cytotoxic ability and 1 demonstrated higher growth inhibition of the selected cancer cells at concentrations of 25µM and 50µM, this result was not identical with their DNA binding ability order. Thus, the involvement of Fe(III) centers had positive effect on DNA binding ability and negative effect on cytotoxicity.


Assuntos
Complexos de Coordenação/química , DNA/química , Compostos Férricos/química , Resinas Vegetais/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Dicroísmo Circular , Complexos de Coordenação/metabolismo , Complexos de Coordenação/toxicidade , Cristalografia por Raios X , DNA/metabolismo , Células HeLa , Humanos , Células MCF-7 , Conformação Molecular , Espectrometria de Fluorescência , Estereoisomerismo , Termodinâmica , Viscosidade
6.
J Photochem Photobiol B ; 132: 36-44, 2014 Mar 05.
Artigo em Inglês | MEDLINE | ID: mdl-24583369

RESUMO

A chiral Schiff base HL N-(5-bromo-salicylaldehyde)dehydroabietylamine (1) and its chiral dinuclear copper complex [Cu2L4]·4DMF (2) have been synthesized and fully characterized. The interactions of 1 and 2 with salmon sperm DNA have been investigated by viscosity measurements, UV, fluorescence and circular dichroism (CD) spectroscopic techniques. Absorption spectral (Kb=3.30 × 10(5)M(-)(1) (1), 6.63 × 10(5)M(-)(1)(2)), emission spectral (Ksv=7.58 × 10(3)M(-)(1) (1), 1.52 × 10(4)M(-)(1) (2)), and viscosity measurements reveal that 1 and 2 interact with DNA through intercalation and 2 exhibits a higher DNA binding ability. In addition, CD study indicates 2 cause a more evident perturbation on the base stacking and helicity of B-DNA upon binding to it. In fluorimetric studies, the enthalpy (ΔH>0) and entropy (ΔS>0) changes of the reactions between the compounds with DNA demonstrate hydrophobic interactions. 1 and 2 were also screened for their cytotoxic ability and 2 demonstrates higher growth inhibition of the selected cancer cells at concentration of 50 µM, this result is identical with their DNA binding ability order. All the experimental results show that the involvement of Cu (II) centers has some interesting effect on DNA binding ability and cytotoxicity of the chiral Schiff base.


Assuntos
Abietanos/toxicidade , Apoptose/efeitos dos fármacos , Complexos de Coordenação/metabolismo , Cobre/química , DNA/metabolismo , Bases de Schiff/toxicidade , Abietanos/química , Abietanos/metabolismo , Linhagem Celular Tumoral , Complexos de Coordenação/síntese química , Complexos de Coordenação/química , Cristalografia por Raios X , DNA/química , Células HeLa , Células Hep G2 , Humanos , Íons/química , Células MCF-7 , Conformação Molecular , Bases de Schiff/química , Bases de Schiff/metabolismo , Estereoisomerismo , Termodinâmica , Viscosidade
7.
J Photochem Photobiol B ; 125: 32-41, 2013 Aug 05.
Artigo em Inglês | MEDLINE | ID: mdl-23727617

RESUMO

Two novel copper-2,2'-bipyridine complexes [Cu(SAL)(2,2'-bipy)ClO4]2 (1) and [Cu(µ2-O)(2,2'-bipy)NO3]2 (2) (HSAL=salicylaldehyde) were synthesized and characterized by X-ray single-crystal diffraction, elemental analysis and IR spectra. The interactions of the complexes with salmon sperm DNA were investigated by viscosity analysis, UV, fluorescence and circular dichroism (CD) spectroscopic techniques. Absorption spectral (Kb=3.00×10(5)M(-1) (1), 3.49×10(5)M(-1)(2)), emission spectral ((Ksv) 3.33×10(4)M(-1) (1), 3.40×10(4)M(-1) (2)), and viscosity measurements reveal that 1 and 2 interact with DNA through intercalation. In fluorimetric studies, the enthalpy (ΔH>0) and entropy (ΔS>0) changes of the reactions between the Cu (II) complexes with DNA demonstrate hydrophobic interactions. In addition, CD study indicates the Cu (II) complexes cause a more B-like to a more A-like conformational change upon binding DNA. All the experimental results show that the interaction mode of the two complexes was greatly affected by the coordination environments of Cu (II) centers. Their in vitro cytotoxicity towards five selected tumor cell lines HepG-2, HeLa, NCI-H460, MCF-7 and HL-60 has been evaluated by MTT method, and 2 exhibits higher growth inhibition of the selected cell lines at concentration of 50 µM, this result is identical with their DNA binding ability order.


Assuntos
2,2'-Dipiridil/química , Antineoplásicos/farmacologia , Cobre/farmacologia , Compostos Organometálicos/farmacologia , Antineoplásicos/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Cobre/química , DNA/química , DNA/metabolismo , Humanos , Compostos Organometálicos/química
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