Design, synthesis and biological evaluation of novel ferrocene-pyrazole derivatives containing nitric oxide donors as COX-2 inhibitors for cancer therapy

Ren, Shen-Zhen; Wang, Zhongchang; Zhu, Dan; Zhu, Xiaohua; Shen, Fa-Qian; Wu, Song-Yu; Chen, Jinjin; Xu, Chen; Zhu, Hai‐Liang

doi:10.1016/j.ejmech.2018.08.048

Cited by 49 publications

(18 citation statements)

References 31 publications

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“…The cytotoxicity was studied using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay according to previous reports with some modification. 54 Briefly, HeLa, MCF-7, and 293T cells (7 × 10 4 cells) were seeded in 96-well plates and incubated for 12 h. Then, the cells were incubated with gradient concentrations of blank and DOXloaded vesicles for 24 or 48 h. Afterward, the cytotoxicity was measured by the standard MTT assay. The cytotoxicities of different formulations of nanocarriers were calculated as follows:…”

Section: Methodsmentioning

confidence: 99%

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Nanoscale Metal–Organic-Frameworks Coated by Biodegradable Organosilica for pH and Redox Dual Responsive Drug Release and High-Performance Anticancer Therapy

Ren

Zhu

et al. 2019

ACS Appl. Mater. Interfaces

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Responsive nanocarriers with biocompatibility and precise drug releasing capability have emerged as a prospective candidate for anticancer treatment. However, the challenges imposed by the complicated preparation process and limited loading capacities have seriously impeded the development of novel multifunctional drug delivery systems. Here, we developed a novel and dual-responsive nanocarrier based on a nanoscale ZIF-8 core and an organosilica shell containing disulfide bridges in its frameworks through a facile and efficient strategy. The prepared ZIF-8@DOX@organosilica nanoparticles (ZDOS NPs) exhibited a well-defined structure and excellent doxorubicin (DOX) loading capability (41.2%) with pH and redox dual-sensitive release properties. The degradation of the organosilica shell was observed after 12 h incubation with a 10 mM reducing agent. Confocal imaging and flow cytometry analysis further proved that the nanocarriers can efficiently enter cells and complete intracellular DOX release under the low pH and high glutathione concentrations, which resulted in an enhanced cytotoxicity of DOX for cancer cells. Meanwhile, subcellular localization experiments revealed that the ZDOS NPs entered cells mainly by endocytosis and then escaped from lysosomes into the cytosol. Moreover, in vivo assays also demonstrated that the ZDOS NPs exhibited negligible systemic toxicity and significantly enhanced anticancer efficiencies compared with free DOX. In summary, our prepared pH and redox dual-responsive nanocarriers provide a potential platform for controlled release and cancer treatment.

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Section: Methodsmentioning

confidence: 99%

“…The cell apoptosis and ROS analysis of different DOX-loaded vesicles were investigated according to our previous reports. , …”

Section: Methodsmentioning

confidence: 99%

Nanoscale Metal–Organic-Frameworks Coated by Biodegradable Organosilica for pH and Redox Dual Responsive Drug Release and High-Performance Anticancer Therapy

Ren

Zhu

et al. 2019

ACS Appl. Mater. Interfaces

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“…They show, for example, biological activities possessing antimicrobial, anti-inflammatory, or antitumor properties [ 48 , 49 , 50 , 51 , 52 , 53 , 54 ]. In this respect, it was found that ferrocenyl-functionalization of pyrazoles enhances their biological activities [ 55 , 56 , 57 , 58 , 59 ]. Facile synthesis methods of ferrocenyl-substituted pyrazoles were reported [ 60 , 61 , 62 , 63 , 64 , 65 , 66 ], with only a brief comment about the parent diferrocenyl NH-pyrazole in 1963 [ 66 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Electrochemistry of Diferrocenyl β-Diketones, -Diketonates, and Pyrazoles

Lehrich

Mahrholdt²,

Korb³

et al. 2020

Molecules

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The synthesis of FcC(O)CH(R)C(O)Fc (Fc = Fe(η5-C5H4)(η5-C5H5); R = H, 5; nBu, 7; CH2CH2(OCH2CH2)2OMe, 9), [M(κ2O,O′-FcC(O)CHC(O)Fc)n] (M = Ti, n = 3, 10; M = Fe, n = 3, 11; M = BF2, n = 1, 12), and 1-R’-3,5-Fc2-cC3HN2 (R’ = H, 13; Me, 14; Ph, 15) is discussed. The solid-state structures of 5, 7, 9, 12, 13, 15, and 16 ([TiCl2(κ2O,O′-PhC(O)CHC(O)Ph)2]) show that 7 and 9 exist in their β-diketo form. Compound 13 crystallizes as a tetramer based on a hydrogen bond pattern, including one central water molecule. The electrochemical behavior of 5–7 and 9–16 was studied by cyclic and square-wave voltammetry, showing that the ferrocenyls can separately be oxidized reversibly between −50 and 750 mV (5–7, 9, 12–15: two Fc-related events; 10, 11: six events, being partially superimposed). For complex 10, Ti-centered reversible redox processes appear at −985 (TiII/TiIII) and −520 mV (TiIII/TiIV). Spectro-electrochemical UV-Vis/NIR measurements were carried out on 5, 6, and 12, whereby only 12 showed an IVCT (intervalence charge-transfer) band of considerable strength (νmax = 6250 cm−1, Δν½ = 4725 cm−1, εmax = 240 L·mol−1·cm−1), due to the rigid C3O2B cycle, enlarging the coupling strength between the Fc groups.

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“…Трехкомпонентную каскадную конденсацию формилферроцена, ароматических аминов и циклических β-дикарбонильных соединений проводили кипячением в бутаноле (схема 32). Полученные соединения проявили значительную цитотоксическую активность в отношении клеточной линии аденокарциномы толстой кишки LS174T[68].Реакции 1,3-диполярного циклоприсоединения широко используются для синтеза производных ферроцена с фрагментами изоксазола, пиразола[62, 69,70]. Некоторые из производных ферроценпиразолсульфонамида 86 проявили сильное ингибирующее действие к циклооксигеназe COХ-2 и антипролиферативную активность в отношении клеток рака шейки матки Hela, сравнимую с препаратом Целекоксибом[70].…”

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“…Полученные соединения проявили значительную цитотоксическую активность в отношении клеточной линии аденокарциномы толстой кишки LS174T[68].Реакции 1,3-диполярного циклоприсоединения широко используются для синтеза производных ферроцена с фрагментами изоксазола, пиразола[62, 69,70]. Некоторые из производных ферроценпиразолсульфонамида 86 проявили сильное ингибирующее действие к циклооксигеназe COХ-2 и антипролиферативную активность в отношении клеток рака шейки матки Hela, сравнимую с препаратом Целекоксибом[70]. Ферроценилпиразолы 87 продемонстрировали высокую антимикробную активность (схема 33) [71].…”

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Chemical modification of different compounds with nitrogen-containing heterocycles

Акишина

Дикусар

2021

Vescì Akademìì navuk Belarusì. Seryâ himičnyh navuk

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Heterocyclic compounds have an extremely important practical application, since many heterocycles are the basis of the most valuable medicinal substances, both natural (vitamins, enzymes, alkaloids, etc.) and synthetic biologically active compounds. The work mainly considers the most relevant directions for various purposes drugs search by modifying known bioactive natural, organoelement and framework compounds with 1,2-azole, oxazole, oxadiazole, thiazole, triazole, pyridine, pyrimidine heterocycles over the past 10 years. Chemical modification makes it possible to increase the water solubility of the compounds, which is important when choosing the pathways for the most rational drug introduction into the body, to reduce the toxicity of the corresponding substances, to increase the breadth of the therapeutic action, and also to give new valuable medicinal properties, thus significantly expanding their application in medicine and agriculture.

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Design, synthesis and biological evaluation of novel ferrocene-pyrazole derivatives containing nitric oxide donors as COX-2 inhibitors for cancer therapy

Cited by 49 publications

References 31 publications

Nanoscale Metal–Organic-Frameworks Coated by Biodegradable Organosilica for pH and Redox Dual Responsive Drug Release and High-Performance Anticancer Therapy

Nanoscale Metal–Organic-Frameworks Coated by Biodegradable Organosilica for pH and Redox Dual Responsive Drug Release and High-Performance Anticancer Therapy

Synthesis, Characterization, and Electrochemistry of Diferrocenyl β-Diketones, -Diketonates, and Pyrazoles

Chemical modification of different compounds with nitrogen-containing heterocycles

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