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ANALYTICAL AND BIOANALYTICAL CHEMISTRY · 2023 ·Vol. 415 ·期 12 ·2249-2260 · IF 4.3

Electrochemical detection of the oxidative damage of a potential pyrimido[5,4-g]pteridine-derived antitumor agent toward DNA

Guo Fei-Fei,Li Tong,Mu Xi-Ping,Zhang Xue,Xu Zhi-Hao,Sun Ping,Yu Ri-Lei,Xia Ya-Mu,Gao Wei-Wei

In this work, we design and synthesize 2,2′-(7,9-dimethyl-2,4,6,8-tetraoxo-6,7,8,9-tetrahydropyrimido[5,4-g]pteridine-1,3(2H,4H)-diyl)bis( N,N -bis(2-chloroethyl)acetamide) (PT-MCA) as a novel DNA intercalator and potential antitumor agent. Electrochemical analysis reveals the redox process of PT-MCA on the electrode surface. The bioelectrochemical sensors are obtained by modifying the surface of GCE with calf thymus DNA (ctDNA), poly (dG), poly (dA), and G-quadruplex, respectively. The DNA oxidative damage induced by PT-MCA is investigated by comparing the peak intensity change of dGuo and dAdo and monitoring the peaks of the oxidation products of guanine and/or adenine (8-oxoGua and/or 2,8-oxoAde). UV–vis absorption and fluorescence spectra and gel electrophoresis are further employed to understand the intercalation of PT-MCA into DNA base pairs. Moreover, PT-MCA is proved to exhibit stronger anti-proliferation activity than mitoxantrone against both 4T1 and B16-F10 cancer cells. At last, the oxidative damage of PT-MCA toward ctDNA is not interfered by the coexistence of ions and also can be detected in real serums. Graphical abstract

CAS / MDL: 64-17-5 6642-31-5 111-42-2 141-82-2

研究领域: 药物化学 · 生物化学 · 癌症研究 · 电化学 · 分子生物学

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BIOORGANIC CHEMISTRY · 2024 · IF 4.5

Rational design and synthesis of triazene-amonafide derivatives as novel potential antitumor agents causing oxidative damage towards DNA through intercalation mode

Ping Sun,Na Xu,Xue Zhang,Yun-Fei Gao,Jia-Yin Zhang,Qi-Ming Zhang,Chen Liang,Ri-Lei Yu,Ya-Mu Xia,Wei-Wei Gao

In this work, we rationally designed and synthesized two novel triazene-amonafide derivatives 2-(2-(diisopropylamino)ethyl)-5-(3,3-dimethyltriaz-1-en-1-yl)-1H-benzo[ de ]isoquinoline-1,3(2H)-dione ( D-11 ) and 5-(3,3-diethyltriaz-1-en-1-yl)-2-(2-(diisopropylamino)ethyl)-1H-benzo[ de ]isoquinoline-1,3(2H)-dione ( D-12 ) as potential antitumor agents. The DNA damage induced by the intercalation mode of D-11 ( D-12 ) towards DNA was electrochemically detected through the construction of efficient biosensors. The consecutive processes of reversible redox of naphthylimide ring and irreversible oxidation of triazene moiety were elucidated on the surface of glassy carbon electrode (GCE) by CV, SWV, and DPV methods. Electrochemical biosensors were obtained through the immobilization of ct DNA, G-quadruplexes, poly(dG), and poly(dA), respectively, on the clean surface of GCE. After the incubation of biosensors with D-11 or D-12 , the peaks of dGuo and dAdo decreased prominently, and the peak of 8-oxoGua appeared at +0.50 V, suggesting that the interaction between D-11 ( D-12 ) and DNA could result in the oxidative damage of guanine. Unexpected, the as-prepared DNA biosensor possessed satisfactory anti-interference property and good practicability in real samples. UV–vis and fluorescence spectra, and gel electrophoresis assays were employed to further confirm the intercalation mode of D-11 ( D-12 ) towards DNA base pairs. Moreover, D-11 was proved to exhibit stronger anti-proliferation activity than mitionafide and amonafide against both A549 and HeLa cell lines.

CAS / MDL: 50-81-7 63-91-2

研究领域: 药物化学 · 生物化学 · 分子生物学 · 癌症研究

✓ 已验证产品关联 DOI PubMed 高影响因子

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SENSORS AND ACTUATORS B-CHEMICAL · 2021 · IF 7.46

Label-free electrochemical detection of genetic damage induced by the interaction of a novel potential aminoanthraquinone-derived antitumor agent with DNA modified electrode

Kai-Xin Song,Dong Chen,Zi-Yang Liao,Xuan Yu,Fei-Fei Guo,Ri-Lei Yu,Meng-Zhen Xu,Ya-Mu Xia,Wei-Wei Gao

In this work, an efficient electrochemical biosensor for the detection of DNA damage induced by the interaction of a novel antitumor agent AD-NU was investigated by CV , DPV and SWV methods. The GCE was modified with calf thymus DNA, G-quadruplexes, poly dA and poly dG, respectively. Among all the candidates, compound AD-NU was the optimum ligand because of the minimum energy when binding to DNA or TOP II by molecular docking. The electrochemical analysis revealed the redox mechanism of AD-NU on the GCE surface, which included two consecutive reversible processes of 9,10-diquinone and irreversible redox of nitroso group . The DNA damage caused by AD-NU was investigated by comparing the intensity changes of dGuo and dAdo oxidation peaks in DNA strands, and monitoring the appearance of peak for oxidative product 8-oxoGua. Further confirmation for the interaction between AD-NU and DNA was performed by UV–vis absorption and fluorescence titration, which implied the intercalation of AD-NU into DNA base pairs with a high affinity constant ( K b = 13.7 ×10 5 M −1 ). The electrophoresis also revealed the potency of AD-NU to cleave and unwind DNA strands. Finally, AD-NU was proved to have good antiproliferative activity toward tumor cells, with IC 50 values of 3.0 μmol ∙ L −1 for A549 cell lines and 3.3 μmol ∙ L −1 for Hela cell lines, superior to MTZ reference.

研究领域: 电化学 · 生物传感器 · 分子生物学 · 癌症研究 · 分析化学 · 药理学

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Electrochemical detection of the oxidative damage of a potential pyrimido[5,4-g]pteridine-derived antitumor agent toward DNA

Rational design and synthesis of triazene-amonafide derivatives as novel potential antitumor agents causing oxidative damage towards DNA through intercalation mode

Label-free electrochemical detection of genetic damage induced by the interaction of a novel potential aminoanthraquinone-derived antitumor agent with DNA modified electrode