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A Dy(iii)–organic framework as a fluorescent probe for highly selective detection of picric acid and treatment activity on human lung cancer cells

  • Shi-Jie Fan , Ren Sun EMAIL logo , Yu-Bo Yan , Hao-Bo Sun , Sai-Nan Pang and Shi-Dong Xu
Published/Copyright: August 29, 2020
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Open Chemistry
From the journal Open Chemistry Volume 18 Issue 1

Abstract

A dysprosium(iii) organic framework, {[Dy(H2O)(BTCTB)]·2H2O}n (1, H3BTCTB = 3,3′,3′′-[1,3,5-benzenetriyltris(carbonylimino)]tris-benzoic acid), was synthesized through the hydrothermal reaction of Dy(NO3)3 with the C3-symmetric organic ligand H3BTCTB at 160°C for 96 h. At the same time, the sensitivity of picric acid in water medium was tested with material 1 as the fluorescent sensor. The detection limit was 0.71 µM and KSV of this experiment was 8.55 × 104 M−1, which might be attributed to the presence of abundant amide groups in the framework of 1. In addition, the treatment effect of compound 1 against the NCI-H292 lung cancer cells was evaluated. The Cell Counting Kit-8 (CCK-8) method was conducted to measure the viability of cancer cell after treated through the compound 1. The DCFH-DA was applied for the determination of ROS. The relative expression of the inflammatory genes was measured with RT-PCR. The western blotting was conducted to detect the effect of the compound against MDM-2 levels in NCI-H292 lung cancer cells. The possible binding interactions in terms of binding poses are probed by performing molecular docking simulations.

Keywords: Dy–MOF; C3-symmetric organic ligand; picric acid sensor; lung cancer; molecular docking

1 Introduction

In modern medicine, metal ions and their complexes have been used for decades [1]. Cisplatin is an effective cancer drug and its discovery promotes the development of inorganic chemistry of drugs. In the current research and development system of anticancer drugs, platinum complexes have always been the focus of attention [2]. In the redox environment, there is a cell-level program to enhance the drug function. This discovery makes it possible to replace cisplatin with tunable metal complexes as a new anticancer drug. For example, research work on copper complexes has been completed, that is, endogenous metals are less harmful to normal cells except cancer cells [3]. In addition, Wilson and his team also claim that cobalt(iii) complexes may contribute to the development of new anticancer drugs [4].

Metallic organic skeletons (MOFs or PCPs) are often referred to as porous coordination polymers. These materials have the advantages of controllable pore size and a strong functional pore structure, so they have attracted much attention in many fields such as gas storage, catalytic reaction, drug conduction, separation, proton flow, magnetic pole, optics, and conduction [5,6,7,8,9,10]. At the same time, because of the crystallinity, adjustable porosity, and special electronic structure of MOFs, they are widely used in the field of fluorescent sensors. Recently, a variety of MOFs have been combined with nitroaromatic hydrocarbons to produce luminous probes for the determination of picric acids (PAs) in water solutions [11,12,13,14]. In these MOFs, those compounds based on lanthanide metal centers have become a new research object due to their unique characteristics of long emission life, high color purity, and a large displacement of stokes. Nevertheless, it is challenging to synthesize the Ln–MOFs because they possess a high number of coordinations and they have a tendency to coordinate with the ligand of oxygen donor that contains more flexibility and higher number of coordinations [15,16,17]. In addition, some Ln–MOFs could not keep their integrality framework in water, which restricts their further applications. The C3-symmetric ligand 3,3′,3′′-[1,3,5-benzenetriyltris(carbonylimino)]tris-benzoic acid (H3BTCTB) should be an excellent selection for generating the Ln–MOF sensors that contain outstanding detection properties and high skeleton stability. First, the stability of Ln–MOF sensors was improved by adding the rigid benzoic acid group bound to metal ions. Second, three amide bonds attached to ligands can be utilized at the hydrogen bond position and the Lewis base position to increase conductivity in aqueous media. Based on the above considerations, a novel Dy(iii)–MOF has been fabricated hydrothermally, and its chemical formula is {[Dy(H2O)(BTCTB)]·2H2O}n (1), which was detected in depth through the analysis of element, TGA, the diffraction of single-crystal X-ray as well as the PXRD. Due to its strong fluorescent emission and high water stability, complex 1 was studied as the fluorescent sensor to determine the PA in the water. In the bio-study, the inhibition of compound 1 against the NCI-H292 lung cancer cells was measured. First of all, the viability of NCI-H292 cells after treatment was assessed by the CCK-8 method, and the obtained results revealed that the cancer cell viability could be significantly reduced by the compound 1 exposure. In addition to this, the cell apoptosis and ROS accumulation were determined and the data indicated that the compound 1 has the ability to induce cancer cell apoptosis by triggering the ROS production. Next, the relative expression of the inflammatory genes revealed that the compound 1 could also inhibit the inflammatory response in the cancer cells. The MDM-2 levels in the NCI-H292 lung cancer cells were obviously decreased by the compound treatment. The possible binding poses are studied in detail by using molecular docking simulations, which could provide evidence for the experimental hypothesis from the molecular level.

2 Experimental

2.1 Chemicals and measurements

All the chemicals used in the experiment could be acquired from market and they were utilized without additional purification. The analysis of elements for nitrogen, hydrogen, and carbon was carried out using a PerkinElmer 240C analyzer. The infrared spectrum from 4,000 cm−1 to 400 cm−1 obtained by the solid reagent was recorded on a Bruker ALPHA spectrometer. Using a Bruker-D8-Advance X-ray diffractometer to collect the PXRD data, we find that λ is 1.5418 Å and the range of 2θ is 5° to 50°. In order to conduct the thermogravimetric analyses, set the LABSYS Evo thermal analyzer in nitrogen environment which increases 5°C every minute, and the temperature is in the range of 25–800°C. The ultraviolet-visible absorption spectrum in the range of 200–800 nm was collected by a ultraviolet spectrophotometer. The photoluminescence spectrum was measured on the FLS1000 Photoluminescence Spectrophotometer of Edinburgh instrument.

2.2 Preparation and characterization for {[Dy(H2O)(BTCTB)]·2H2O}n (1)

We mixed the 0.1 mmol and 45 mg of Dy(NO3)3·6H2O, 0.05 mmol and 28.4 mg of H3BTCTB, and 30 µL and 0.01 mmol L−1 of water NaOH solution with doubly deionized 30 µL and 0.01 mmol L−1 of water NaOH solution with the 10.0 mL doubly deionized water to generate a mixture, and stored the obtained mixture into the 23.0 mL autoclave lined with Teflon. Afterward, we heated the autoclave for four days at 160°C under autogenous pressure. After cooling the above mixture slowly at the rate of 3.0°C h−1 to the ambient temperature, we can directly acquire the colorless crystals with a block shape of the complex 1 which are fit for single-crystal X-ray diffraction, cleaned by utilizing water, and then dried in air with a yield of 87% (on the basis of H3BTCTB). Anal. calcd for C30H24DyN3O12: N, 5.38%; H, 3.10 and C, 46.14. Found: N 5.44 %; H 3.15 and C 46.76. FT-IR (KBr): ν˜=513(w), 588 (w), 676 (m), 731 (w), 771 (m), 829 (w), 910 (w), 1,081 (w), 1,165 (w), 1,242 (m), 1,292 (w), 1,396 (s), 1,435 (m), 1,534 (s), 1,583 (s), 1,623 (s), 1,669 (s), 3,361 (br) cm−1.

We utilized the Oxford XcaliburE diffractometer to get the X-ray data. Statistical analysis of various strength data was performed using CrysAlisPro software and the results were converted into the HKL format. The SHELXS program was used to create the model directly, and the least square method was used to adjust the model. All of the non-hydrogen atoms contain a number of different parameters of the opposite sex. With the AFIX command, the H atom is pinned to the C atom to which it is attached. According to Table 1, we can see the experimental details of complex 1 and the final crystal data.

Table 1

The crystallographic parameters and the refinement for the complex 1

Empirical formula C30H24DyN3O12
Formula weight 781.02
Temperature/K293(2)
Crystal systemTriclinic
Space group P1¯
a/Å 8.69540(16)
b/Å 11.1362(2)
c/Å 15.69870(14)
α/° 70.5695(12)
β/° 78.012(3)
γ/° 77.3710(13)
Volume/Å31383.77(4)
Z2
ρcalc (g/cm3)1.874
µ/mm−115.115
Data/restraints/parameters 4,929/0/415
Goodness-of-fit on F21.023
Final R indexes [I ≥ 2σ(I)]R1 = 0.0332, ωR2 = 0.0766
Final R indexes [all data] R1 = 0.0374, ωR2 = 0.0792
Largest diff. peak/hole/e Å−31.62/−1.14
CCDC1985897

2.3 Cell counting assay

Taking the NCI-H292 lung cancer cells as an example, the CCK-8 method was used to test the antiproliferation effect of the complex, and appropriate modifications were made at the same time. NCI-H292 cells in the growing stage were placed in the 100 µL of DMEM at 1 × 103 cells each well concentration. The culture medium was added with 10% FBS and 1% solution of penicillin–streptomycin. The culture medium was placed at 37°C with a 5% carbon dioxide content overnight. When 80% of the cell population was mixed, the compounds with different concentrations of 1, 2, 4, 8, 10, 20, 40, and 80 µM were left to remain idle for 24 h. Then, the original medium was replaced by 10 µL of CCK-8 solution and placed in a dark environment at 37°C for 1 h. Finally, BioTek ELx808 Absorbance Microplate Reader was used to measure the absorbance at 450 nm. According to the results of the experiment, the cell survival rate can be obtained. The cell survival rate is equal to the result of OD treatment minus OD blank divided by the OD control result minus the blank of OD.

2.4 Intracellular ROS measurement

The ROS content in the NCI-H292 lung cancer cells was determined by using the 2′,7′-dichlorofluorescein diacetate test kit. First of all, the NCI-H292 cells were kept in a 6-well plate for 6 h and then a certain concentration of compounds was added for treatment. Then 20 µM DCFH-DA solution was poured in and placed in a dark environment at 37°C for half an hour. After cleaning the cells with PBS, flow cytometry was utilized for the analysis of cell absorbance in different experimental groups.

2.5 ELISA

After treated through compound 1, the inflammatory response level in the NCI-H292 lung cancer cells was determined by the ELISA test of the TNF-α and IL-1β content. This assay was performed strictly according to the instructions. In short, the NCI-H292 cells in the logarithmic growth stage were inoculated into 6-well plates for half a day, and after that, we added compound 1 for cell treatment at the indicated concentration. After treatment, the cell supernatant was harvested and the TNF-α and IL-1β content was measured with the ELISA test kit. This test is needed to be implemented three times or more.

2.6 Western blotting detection

The western blotting was performed in this current study to assess the MDM-2 protein expression levels in the NCI-H292 lung cancer cells, as well as the influence of the compound on the MDM-2 relative expression. All the performances in this research were accomplished under manufacturer’s guidance with slight changes [18,19]. In short, the NCI-H292 lung cancer cells were harvested and then inoculated in the 6-well plates with cells’ ultimate density of 1 × 106 cells each well concentration. The plates were kept in the cell incubator at 5% CO2 and 37°C environment. After culturing for 12 h, the compound was added for treatment with 1× IC50 and 3× IC50. Next, the cells were harvested and then lysed by utilizing RIPA buffer for the overall extraction of protein. The BCA Protein Assay kit (23225, Pierce, USA) was recommended to evaluate the protein samples’ quality and quantity. After that, the protein samples were divided into equal amounts and loaded onto 10% SDS-PAGE denaturing gels, followed by transfer onto PVDF membranes. All of the PVDF membranes were sealed with non-fat milk of 5% for 120 min under ambient temperature and then inoculated at the 4°C overnight utility with the proper primary antibody toward MDM2 or glyceraldehyde-3-phosphate dehydrogenase. Subsequently, the secondary antibody bound to horseradish peroxidase was added for incubation for another 60 min. Ultimately, the MDM-2 proteins were visualized by utilizing the increased ECL test kit and quantified with the ImageJ software (BIO-RAD).

2.7 Simulation details

To perform the molecular docking simulation, the complex and the probe protein were prepared by AutoDockTools, after which the simulation was performed by AutoDock4. The MDM-2 protein was selected as the probe protein, and the protein structure was downloaded from the protein database. The PDB ID of MDM-2 protein is 4UD7. On the other hand, the complex contains the organic moiety as well as the Eu metal core. The complex has been treated as the semiflexible ligand. The coordinate of the grid center is −4.166, 2.034, 19.229.

The length of the grid box is 80. The unit of length is angstrom. The maximum allowed number of poses for scoring is 20. The visualizations have been complemented by PyMol.

  1. Ethical approval: The conducted research work is not related to either human or animal use.

3 Results and discussion

3.1 Molecular structure

With sodium hydroxide as the pH regulator, the Dy(NO3)3·6H2O reacts with H3BTCTB for four days in water to afford white crystals of 1 with a yield of 87%. The addition of NaOH could not only control the pH value of the reaction system, but could also facilitate the deprotonation of the H3BTCTB ligand. The single-crystal X-ray analysis reflects that the complex 1 is crystallized in the triclinic space group of P1¯ (Table 1), displaying a (4,8)-linked skeleton that contains the paddle wheel subunits {Dy2(COO)4} extended through the 4-linked linkages of BTCTB3−. The complex 1’s asymmetric unit contains a Dy(iii) ion, a triple H-removed anion of BTCTB3− for the compensation of charge, two lattice molecules of water as well as a terminal aqua ligand. As illustrated in Figure 1a, the Dy(iii) ion local coordination surroundings are detected through six carboxylic acid oxygens (O9E, O8E, O6D, O5C, O2A, and O1), a coordinated molecule of water (O12W), and an amide oxygen donor (of O4B) in five deprotonated ligands of BTCTB3−. The lengths of the Dy(iii)–O bond vary from 2.292 to 2.553 Å. The distinctive Dy(iii) ions are octacoordinated. CShM = 1.241 is calculated through the SHAPE software, and the mode of coordination is the micro distorted double triangular prism. By contrast, the sole ligand of BTCTB3− in the complex 1 uses the pattern of µ6-η1:η1:η1:η1:η1:η1:η1:η0:η0 to complex to six Dy(iii) ions via an amide oxygen donor and six carboxylic acids (Figure 1b), displaying an uncommon heptadentate ligand. The BTCTB3− ligand with six-coordination pattern makes the central phenyl ring not coplanar with three benzolyl groups, and the dihedral angles of the central phenyl ring and each carboxylic acid group, respectively, are 6.7°, 26.5°, and 74.8°. Two pairs of carboxylic acid groups in four symmetrically related ligands of BTCTB3− aggregated two independent Dy(iii) ions into the subunit {Dy2(COO)4} with a paddle wheel-shape, and the distance from metal to metal is 4.3362(2) Å (Figure 1c). Each of the subunits {Dy2(COO)4} is surrounded periodically by eight anions of µ6-BTCTB3−, acting as the 8-linked node in topology. On the contrary, because of the extra coordination of the amide oxygen atom with the Dy(iii) ion, the C3-symmetric ligand of BTCTB3− links with four subunits {Dy2(COO)4} unexpectedly, which leads to the tripod linker evolve to the 4-linked node. The 8-linked subunits {Dy2(COO)4} and 4-linked ligands BTCTB3− are interlinked, generating a fresh 4,8-linked skeleton (Figure 1d).

Figure 1 (a) The coordination environment of the Dy(iii) ion view in the complex 1. (b) The coordination fashion for ligand. (c) The complex 1’s three-dimensional network. (d) The complex 1’s 4,8-linked skeleton.
Figure 1

(a) The coordination environment of the Dy(iii) ion view in the complex 1. (b) The coordination fashion for ligand. (c) The complex 1’s three-dimensional network. (d) The complex 1’s 4,8-linked skeleton.

The purity of the complex 1 can be checked by X-ray diffraction patterns. According to Figure 2a, the experimental results and PXRD simulation results have been consistent, indicating that the final crystal is a perfect reactant. The difference between the two results may depend on the quality of the experimental samples. In order to test the degradation of PA in the water, it is essential to detect complex 1’s stability in the water. Compared with the original sample, the difference between the two results reflects its stability in water. The results show that complex 1 is quite stable. At the same time, we put 1 in a 25–800°C environment, increased 10°C every minute and carried out thermogravimetric analysis in nitrogen environment to judge its thermal stability. Figure 2b shows that the first weightlessness occurs between 20 and 220°C, when coordination water molecules and lattice water molecules are released. Then, place 1 in the environment below 500°C. Further heating, we can see that 1 is in the second weightlessness process, structure collapse, and gradual decomposition of ligands. The experimental results show that the stability of 1 is very good, which meets the important preconditions for its application. In the infrared spectrum, the wide absorption band centered at 3,360 cm−1 is attributed to the O–H stretching vibration, suggesting the presence of water molecules. There is no peak at 1,735 cm−1, which means that the organic ligands are deprotonated completely. Accordingly, there are several strong bands of symmetric and asymmetric stretching vibrations for the carboxylic acid group at 1,621, 1,670, 1,534 and 1,582, 1,396, and 1,434 cm−1. These data mentioned above proved that there is an effective coordination behavior between the Dy(iii) ion and the triply deprotonated ligand of BTCTB3−.

Figure 2 (a) The complex 1’s diagrams of PXRD. (b) The TGA curve for the complex 1.
Figure 2

(a) The complex 1’s diagrams of PXRD. (b) The TGA curve for the complex 1.

3.2 Fluorescence behavior and selective detection of nitroaromatic compounds

The luminescent MOF based on Dy(iii) has an excellent luminous performance. As shown in Figures 1 and 3a, it shows a strong characteristic transition at 393, 467, and 561 nm of the fluorescence spectrum. The coordination of Dy(iii) ions leads to π to π* transition, which leads to 393 nm emission spectrum. 4F9/2 to 6H15/2 leads to 467 nm emission spectrum. 4F9/2 to 6H13/2 leads to 561 nm emission spectrum. In order to determine the PA content, fluorescence quenching titration was used. In order to study the sensing ability of 1, PA, 1,4-dinitrobenzene (1,4-DNB), 4-nitrotoluene (4-NT) and 3-nitrotoluene (3-NT), 3-chloronitrobenzene (Cl-NB), nitrobenzene (NB) as well as 2,4-dinitrotoluene (2,4-DNT) were selected for analysis. In order to investigate the effect of the complex 1 against the aromatic nitro group, the luminescent performances of other compounds were tested. By continuously increasing the concentration of PA and recording the emission spectrum, we can study the influence of 1 on the conductivity of PA in water. As the PA amount changed from 20 to 200 µL (1.0 mM), 95.5% of 1 was quenched by ultraviolet-visible emission, and the quenching efficiency of all substances, such as NB, Cl-NB, PA, 3-NT, 2,4-DNT, 1,4-DNB, and 4-NT, ranged from high to low (Figure 3b). It is found that the aromatic compounds have a unique effect on the fluorescence intensity of 1 in water. After the addition of other substances, the fluorescence of 1 in water shows no change. After the addition of PA, the fluorescence is greatly weakened, which shows that 1 is very easy to perceive the electron defective analyte (Figure 3c). In conclusion, 1 can be used as a nitroaromatic sensor. The uniqueness of PA compared with those of other substances is very important in practical applications. By adding 4-NT, 3-NT, PA, 2,4-DNT and 1,4-DNB, NB as well as Cl-NB, the linearity of quenching can be observed by comparing PA with other nitroaromatics. When the amount of analyte added is consistent with the PA solution, the fluorescence intensity is immediately quenched.

Figure 3 (a) The luminescent quenching of the complex 1 dispersed in the water solution, after adding the PA to the water solution. (b) The quenching rates of the compound 1 in the presence of some other analytes. (c) The luminescent quenching of the complex 1 dispersed in the water solution, after adding some other analytes and adding the PA. (d) The SV diagram for a variety of nitro-analytes.
Figure 3

(a) The luminescent quenching of the complex 1 dispersed in the water solution, after adding the PA to the water solution. (b) The quenching rates of the compound 1 in the presence of some other analytes. (c) The luminescent quenching of the complex 1 dispersed in the water solution, after adding some other analytes and adding the PA. (d) The SV diagram for a variety of nitro-analytes.

In order to determine the complex 1’s quenching rate, we use the SV equation of I0/I = KSV[Q] + 1, in which the I0 refers to the fluorescence strength in the absence of the analyte, the I refers to the fluorescence intensity when the analyte is added, the KSV represents the quenching constant, and the [Q] represents the analyte’s molar concentration. According to the SV diagram in Figure 3d, PA is low concentration state and inclines upward when it reaches the critical point, while other analytes are always linear. The unique performance of PA may be due to the energy transfer between the PA and the complex or its own absorption of energy. The quenching constant of PA is 8.55 × 104 M−1, which shows that 1 is very strong for PA (Figure 4a). At the same time, the quenching constant of PA in water is higher than the original value [20,21,22]. In order to detect the sensitivity of 1, the low concentration PA was quenched. Use 3σ/slope to calculate the detection limit (Figure 4b). The σ was acquired from the fluorescence strength test without PA. According to the fitting curve for the concentration of PA and fluorescence strength, the slope can be obtained. The calculation shows that the LOD of the sensor is 0.71 µM, so the sensor is very sensitive to PA in water.

Figure 4 (a) Fluorescence quenching of compound 1 through a variety of PA concentrations, where the I and I0, respectively, represent the fluorescence signal strengths for sensing material in the presence and absence of analyte. I0/I = KSV[PA] + 1 (correlation coefficient, R2 = 0.983). (b) The relation between the fluorescence intensity and PA added into the suspension of 1 and their linear fit curve for the estimation of LOD (R2 = 0.987).
Figure 4

(a) Fluorescence quenching of compound 1 through a variety of PA concentrations, where the I and I0, respectively, represent the fluorescence signal strengths for sensing material in the presence and absence of analyte. I0/I = KSV[PA] + 1 (correlation coefficient, R2 = 0.983). (b) The relation between the fluorescence intensity and PA added into the suspension of 1 and their linear fit curve for the estimation of LOD (R2 = 0.987).

3.3 Compound 1 inhibits the viability of NCI-H292 lung cancer cells

After synthesizing the compound 1 with a fresh structure, the antiviability effect of the compound 1 toward the NCI-H292 lung cancer cells was measured through the CCK-8 method. According to the results illustrated in Figure 5, after the exposure of the compound 1 for one day, the viability results of the lung cancer cells were detected and then plotted. We find that the compound 1 inhibited the NCI-H292 lung cancer cells with the dose-dependent pattern. The complex 1’s IC50 value against the NCI-H292 cells was 2.78 ± 0.09 µg/mL, which was calculated based on the results of CCK-8. The obtained results suggested that the compound 1 may be a good candidate anticancer drug for the treatment of lung cancer.

Figure 5 The viability of the NCI-H292 cells was decreased with the dose-dependent pattern after treated through the compound 1. The NCI-H292 cells were treated through the indicated compound 1’s high dilutions for one day. After this treatment, the absorbance was determined and the diagram of the cell viability was plotted and the compound’s IC50 value was calculated. This research study is needed to be implemented three times or more.
Figure 5

The viability of the NCI-H292 cells was decreased with the dose-dependent pattern after treated through the compound 1. The NCI-H292 cells were treated through the indicated compound 1’s high dilutions for one day. After this treatment, the absorbance was determined and the diagram of the cell viability was plotted and the compound’s IC50 value was calculated. This research study is needed to be implemented three times or more.

3.4 Compound 1 induces ROS accumulation and inflammatory cytokine release in NCI-H292 lung cancer cells

The inflammatory response level of cells is crucial for the survival of cells, and the inflammatory response level is commonly displayed as the ROS accumulation level and the release of inflammatory cytokines. Therefore, DCFH-DA is needed to measure the ROS in the NCI-H292 cells. According to the results, we can see that the higher the compound 1 dose, the higher the ROS content in NCI-H292 cells (Figure 6a). When the concentration of the compound 1 was 1× IC50, the ROS positive cells were 12.74%, but when the concentration of the compound 1 was 3× IC50, the ROS positive cells increased to 83.67%, suggesting that there was a dose–response relationship between the compound treatment and ROS accumulation in the cancer cells. In addition to this, ELISA was further exploited to determine the TNF-α and IL-1β level released from the NCI-H292 cells after compound 1 treatment. In Figure 6b, we can see that compound 1 treatment obviously reduced the TNF-α and IL-1β content with the dose-dependent pattern. This result is in accordance with the above-mentioned results of ROS, suggesting that the compound 1 has an outstanding antitumor activity on the NCI-H292 lung cancer cells.

Figure 6 Reduced ROS accumulation and inflammatory cytokine release in NCI-H292 cells after treated through the compound 1. The NCI-H292 cells were treated with a series of indicated complex 1’s dilutions (3× IC50 and 1× IC50) for one day. (a) The ROS level in the NCI-H292 cells was measured by the detection kit. (b) The TNF-α and IL-1β content in the NCI-H292 cells was measured by the ELISA test kit.
Figure 6

Reduced ROS accumulation and inflammatory cytokine release in NCI-H292 cells after treated through the compound 1. The NCI-H292 cells were treated with a series of indicated complex 1’s dilutions (3× IC50 and 1× IC50) for one day. (a) The ROS level in the NCI-H292 cells was measured by the detection kit. (b) The TNF-α and IL-1β content in the NCI-H292 cells was measured by the ELISA test kit.

3.5 Compound 1 regulates the expression levels of the MDM-2 protein in NCI-H292 lung cancer cells

In the former research work, we have confirmed that the compound 1 has an outstanding inhibition against the proliferation of the NCI-H292 lung cancer cells and promotes the ROS accumulation in the cells. In this section, a further study was performed on the exploration of an anticancer mechanism. The MDM-2 is highly expressed in the NCI-H292 lung cancer cells, and its expression level is correlated with clinical symptoms, which also participate in the occurrence, growth, invasion, and lymph node metastasis of NCI-H292 lung cancer. The expression levels of MDM-2 have been widely used as indicatory symptoms of lung cancer development. According to the results illustrated in Figure 7, we find that there was an obviously higher level of the MDM-2 levels in the NCI-H292 lung cancer, in comparison with the BEAS-2B human normal lung epithelial cells. After treated through the compound at the concentrations of 3× IC50 and 1× IC50, the MDM-2 expression levels in the NCI-H292 lung cancer cells were decreased significantly and dose-dependently (Figure 7a). The quantification of the protein expression is shown in Figure 7b.

Figure 7 The inhibited MDM2 protein expression levels in the NCI-H292 lung cancer cells after compound treatment. The NCI-H292 cells were treated through the indicated distinct complex 1’s concentrations (3× IC50 and 1× IC50) for one day. The expression level of the MDM2 protein was measured with the western blotting assay (a). The quantification of figure a (b).
Figure 7

The inhibited MDM2 protein expression levels in the NCI-H292 lung cancer cells after compound treatment. The NCI-H292 cells were treated through the indicated distinct complex 1’s concentrations (3× IC50 and 1× IC50) for one day. The expression level of the MDM2 protein was measured with the western blotting assay (a). The quantification of figure a (b).

3.6 Molecular docking

In order to understand if the tumor antiproliferation were due to suppression of MDM-2 gene expression alone or due to a combination with MDM-2 inhibition, a molecular docking study was carried out. A major challenge in the identification of the binding site is because of the protein flexibility. It has been shown in a previous study that the MDM-2 protein has two novel binding sites, that is why it has been chosen as the probe protein in the current study. It is obvious that the Dy(iii) complex has multiple “–NH–CO–” functional groups, which have been suggested from the experimental results that these functional groups could be the source of the binding interactions. In order to explain the experimental hypothesis, the energy favorable binding poses have been shown in Figure 8. From here, we can see that the complex indeed has multiple interactions to the protein, and almost all of the identified interactions are formed by the “–NH–CO–” functional groups from the complex. The corresponding binding energies are −8.63 (7a), −8.13 (7b), −8.07 (7c), and −7.95 (7d) kcal/mol.

Figure 8 The energy favorable binding poses indicate multiple binding interactions between the complex and the probe protein, and the binding energies are −8.63 (1a), −8.13 (1b), −8.07 (1c), and −7.95 (1d) kcal/mol. The cyan moieties indicate the synthesized Eu complex, whereas the green moieties present the interacting residues.
Figure 8

The energy favorable binding poses indicate multiple binding interactions between the complex and the probe protein, and the binding energies are −8.63 (1a), −8.13 (1b), −8.07 (1c), and −7.95 (1d) kcal/mol. The cyan moieties indicate the synthesized Eu complex, whereas the green moieties present the interacting residues.

Although from Figure 8 the binding interactions can be observed, it is relatively unclear as to what are the interacting residues and non-interacting residues that are surrounding the complex. In order to see the binding interactions in a more detailed way, the binding poses that have been obtained from the molecular docking simulation have been converted to 2-dimensional presentations by using the ligplus. The results are shown in Figure 9. In Figure 9a, the complex is shown to have three binding interactions, all of which are from the nitrogen atoms on the complex, and the involved residues are Ala21 (3.17), Asn111 (2.75), and Thr26 (2.81). In Figure 9b, not only is the nitrogen atom found to form the binding interaction, but the oxygen atom on “–NH–CO–” functional group is also found to form the binding interaction. The interacting residues are Gln24 (2.94) and Thr26 (2.93). There are other binding interactions in Figure 9b, which are mainly from the oxygen atoms near the metal core, which shows less importance. In Figure 9c, Ser17 (2.39) and Thr26 (2.81) are found to be the interacting residues. In Figure 9d, three binding interactions are formed and only Thr26 is involved. As such, the experimental observations have been confirmed and the interacting forms are shown at the molecular level. The molecular docking studies support the hypothesis that compound 1 also inhibits MDM-2. The in vitro studies are in progress and will be reported in due course.

Figure 9 2-Dimensional binding poses that have been presented in Figure 8, from which the interacting and non-interacting residues can be seen clearly. Their residue names as well as the binding distances are shown to guide the eye.
Figure 9

2-Dimensional binding poses that have been presented in Figure 8, from which the interacting and non-interacting residues can be seen clearly. Their residue names as well as the binding distances are shown to guide the eye.

4 Conclusion

In conclusion, we have synthesized a Dy(iii)–MOF by hydrothermal reaction of Dy(NO3)3 with the C3-symmetric organic ligand H3BTCTB at 160°C for 96 h. The crystal structure analysis of 1 by single-crystal X-ray diffraction reflects that the complex 1 is a three-dimensional skeleton structure on the basis of the subunits {Dy2(COO)4} with a paddle wheel-shape and displays the 4,8-linked network. At the same time, the sensitivity of PA in water medium was tested with material 1 as a fluorescent sensor. The detection limit was 0.71 µM and KSV of this experiment was 8.55 × 104 M−1, which might be attributed to the presence of abundant amide groups in the framework of 1. In the bio-research, the inhibition of the complex 1 against the NCI-H292 lung cancer cells was assessed. First of all, the CCK-8 method was conducted and the data showed that the viability for the NCI-H292 cells was decreased obviously after treated through the compound 1. Afterward, the DCFH-DA results reflected that the ROS production in the NCI-H292 cells was significantly inhibited. The inflammatory genes’ relative expression was also inhibited by the compound 1 exposure, which is confirmed by the RT-PCR assay, and the MDM-2 levels in the NCI-H292 lung cancer cells were obviously decreased via the compound treatment. The molecular docking study also proved the interaction between the MDM-2 and the synthetic compound 1.

  1. Conflict of interest: The authors declare that there is no conflict of interest regarding the publication of this paper.

  2. Data availability: The data used to support the findings of this study are included within the article.

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Received: 2020-02-24
Revised: 2020-06-05
Accepted: 2020-06-08
Published Online: 2020-08-29

© 2020 Shi-Jie Fan et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/chem-2020-0141
Keywords for this article
Dy–MOF; C3-symmetric organic ligand; picric acid sensor; lung cancer; molecular docking
Creative Commons
BY 4.0

Articles in the same Issue

  1. Regular Articles
  2. Electrochemical antioxidant screening and evaluation based on guanine and chitosan immobilized MoS2 nanosheet modified glassy carbon electrode (guanine/CS/MoS2/GCE)
  3. Kinetic models of the extraction of vanillic acid from pumpkin seeds
  4. On the maximum ABC index of bipartite graphs without pendent vertices
  5. Estimation of the total antioxidant potential in the meat samples using thin-layer chromatography
  6. Molecular dynamics simulation of sI methane hydrate under compression and tension
  7. Spatial distribution and potential ecological risk assessment of some trace elements in sediments and grey mangrove (Avicennia marina) along the Arabian Gulf coast, Saudi Arabia
  8. Amino-functionalized graphene oxide for Cr(VI), Cu(II), Pb(II) and Cd(II) removal from industrial wastewater
  9. Chemical composition and in vitro activity of Origanum vulgare L., Satureja hortensis L., Thymus serpyllum L. and Thymus vulgaris L. essential oils towards oral isolates of Candida albicans and Candida glabrata
  10. Effect of excess Fluoride consumption on Urine-Serum Fluorides, Dental state and Thyroid Hormones among children in “Talab Sarai” Punjab Pakistan
  11. Design, Synthesis and Characterization of Novel Isoxazole Tagged Indole Hybrid Compounds
  12. Comparison of kinetic and enzymatic properties of intracellular phosphoserine aminotransferases from alkaliphilic and neutralophilic bacteria
  13. Green Organic Solvent-Free Oxidation of Alkylarenes with tert-Butyl Hydroperoxide Catalyzed by Water-Soluble Copper Complex
  14. Ducrosia ismaelis Asch. essential oil: chemical composition profile and anticancer, antimicrobial and antioxidant potential assessment
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  16. Influence of Chemical Osmosis on Solute Transport and Fluid Velocity in Clay Soils
  17. A New fatty acid and some triterpenoids from propolis of Nkambe (North-West Region, Cameroon) and evaluation of the antiradical scavenging activity of their extracts
  18. Antiplasmodial Activity of Stigmastane Steroids from Dryobalanops oblongifolia Stem Bark
  19. Rapid identification of direct-acting pancreatic protectants from Cyclocarya paliurus leaves tea by the method of serum pharmacochemistry combined with target cell extraction
  20. Immobilization of Pseudomonas aeruginosa static biomass on eggshell powder for on-line preconcentration and determination of Cr (VI)
  21. Assessment of methyl 2-({[(4,6-dimethoxypyrimidin-2-yl)carbamoyl] sulfamoyl}methyl)benzoate through biotic and abiotic degradation modes
  22. Stability of natural polyphenol fisetin in eye drops Stability of fisetin in eye drops
  23. Production of a bioflocculant by using activated sludge and its application in Pb(II) removal from aqueous solution
  24. Molecular Properties of Carbon Crystal Cubic Structures
  25. Synthesis and characterization of calcium carbonate whisker from yellow phosphorus slag
  26. Study on the interaction between catechin and cholesterol by the density functional theory
  27. Analysis of some pharmaceuticals in the presence of their synthetic impurities by applying hybrid micelle liquid chromatography
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  29. Incorporation of silver stearate nanoparticles in methacrylate polymeric monoliths for hemeprotein isolation
  30. Development of ultrasound-assisted dispersive solid-phase microextraction based on mesoporous carbon coated with silica@iron oxide nanocomposite for preconcentration of Te and Tl in natural water systems
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  32. Determination of the content of selected trace elements in Polish commercial fruit juices and health risk assessment
  33. Diorganotin(iv) benzyldithiocarbamate complexes: synthesis, characterization, and thermal and cytotoxicity study
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  35. Anticancer, antioxidant, and acute toxicity studies of a Saudi polyherbal formulation, PHF5
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  37. Comparative studies of two vegetal extracts from Stokesia laevis and Geranium pratense: polyphenol profile, cytotoxic effect and antiproliferative activity
  38. Fragmentation pattern of certain isatin–indole antiproliferative conjugates with application to identify their in vitro metabolic profiles in rat liver microsomes by liquid chromatography tandem mass spectrometry
  39. Investigation of polyphenol profile, antioxidant activity and hepatoprotective potential of Aconogonon alpinum (All.) Schur roots
  40. Lead discovery of a guanidinyl tryptophan derivative on amyloid cascade inhibition
  41. Physicochemical evaluation of the fruit pulp of Opuntia spp growing in the Mediterranean area under hard climate conditions
  42. Electronic structural properties of amino/hydroxyl functionalized imidazolium-based bromide ionic liquids
  43. New Schiff bases of 2-(quinolin-8-yloxy)acetohydrazide and their Cu(ii), and Zn(ii) metal complexes: their in vitro antimicrobial potentials and in silico physicochemical and pharmacokinetics properties
  44. Treatment of adhesions after Achilles tendon injury using focused ultrasound with targeted bFGF plasmid-loaded cationic microbubbles
  45. Synthesis of orotic acid derivatives and their effects on stem cell proliferation
  46. Chirality of β2-agonists. An overview of pharmacological activity, stereoselective analysis, and synthesis
  47. Fe3O4@urea/HITh-SO3H as an efficient and reusable catalyst for the solvent-free synthesis of 7-aryl-8H-benzo[h]indeno[1,2-b]quinoline-8-one and indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine derivatives
  48. Adsorption kinetic characteristics of molybdenum in yellow-brown soil in response to pH and phosphate
  49. Enhancement of thermal properties of bio-based microcapsules intended for textile applications
  50. Exploring the effect of khat (Catha edulis) chewing on the pharmacokinetics of the antiplatelet drug clopidogrel in rats using the newly developed LC-MS/MS technique
  51. A green strategy for obtaining anthraquinones from Rheum tanguticum by subcritical water
  52. Cadmium (Cd) chloride affects the nutrient uptake and Cd-resistant bacterium reduces the adsorption of Cd in muskmelon plants
  53. Removal of H2S by vermicompost biofilter and analysis on bacterial community
  54. Structural cytotoxicity relationship of 2-phenoxy(thiomethyl)pyridotriazolopyrimidines: Quantum chemical calculations and statistical analysis
  55. A self-breaking supramolecular plugging system as lost circulation material in oilfield
  56. Synthesis, characterization, and pharmacological evaluation of thiourea derivatives
  57. Application of drug–metal ion interaction principle in conductometric determination of imatinib, sorafenib, gefitinib and bosutinib
  58. Synthesis and characterization of a novel chitosan-grafted-polyorthoethylaniline biocomposite and utilization for dye removal from water
  59. Optimisation of urine sample preparation for shotgun proteomics
  60. DFT investigations on arylsulphonyl pyrazole derivatives as potential ligands of selected kinases
  61. Treatment of Parkinson’s disease using focused ultrasound with GDNF retrovirus-loaded microbubbles to open the blood–brain barrier
  62. New derivatives of a natural nordentatin
  63. Fluorescence biomarkers of malignant melanoma detectable in urine
  64. Study of the remediation effects of passivation materials on Pb-contaminated soil
  65. Saliva proteomic analysis reveals possible biomarkers of renal cell carcinoma
  66. Withania frutescens: Chemical characterization, analgesic, anti-inflammatory, and healing activities
  67. Design, synthesis and pharmacological profile of (−)-verbenone hydrazones
  68. Synthesis of magnesium carbonate hydrate from natural talc
  69. Stability-indicating HPLC-DAD assay for simultaneous quantification of hydrocortisone 21 acetate, dexamethasone, and fluocinolone acetonide in cosmetics
  70. A novel lactose biosensor based on electrochemically synthesized 3,4-ethylenedioxythiophene/thiophene (EDOT/Th) copolymer
  71. Citrullus colocynthis (L.) Schrad: Chemical characterization, scavenging and cytotoxic activities
  72. Development and validation of a high performance liquid chromatography/diode array detection method for estrogen determination: Application to residual analysis in meat products
  73. PCSK9 concentrations in different stages of subclinical atherosclerosis and their relationship with inflammation
  74. Development of trace analysis for alkyl methanesulfonates in the delgocitinib drug substance using GC-FID and liquid–liquid extraction with ionic liquid
  75. Electrochemical evaluation of the antioxidant capacity of natural compounds on glassy carbon electrode modified with guanine-, polythionine-, and nitrogen-doped graphene
  76. A Dy(iii)–organic framework as a fluorescent probe for highly selective detection of picric acid and treatment activity on human lung cancer cells
  77. A Zn(ii)–organic cage with semirigid ligand for solvent-free cyanosilylation and inhibitory effect on ovarian cancer cell migration and invasion ability via regulating mi-RNA16 expression
  78. Polyphenol content and antioxidant activities of Prunus padus L. and Prunus serotina L. leaves: Electrochemical and spectrophotometric approach and their antimicrobial properties
  79. The combined use of GC, PDSC and FT-IR techniques to characterize fat extracted from commercial complete dry pet food for adult cats
  80. MALDI-TOF MS profiling in the discovery and identification of salivary proteomic patterns of temporomandibular joint disorders
  81. Concentrations of dioxins, furans and dioxin-like PCBs in natural animal feed additives
  82. Structure and some physicochemical and functional properties of water treated under ammonia with low-temperature low-pressure glow plasma of low frequency
  83. Mesoscale nanoparticles encapsulated with emodin for targeting antifibrosis in animal models
  84. Amine-functionalized magnetic activated carbon as an adsorbent for preconcentration and determination of acidic drugs in environmental water samples using HPLC-DAD
  85. Antioxidant activity as a response to cadmium pollution in three durum wheat genotypes differing in salt-tolerance
  86. A promising naphthoquinone [8-hydroxy-2-(2-thienylcarbonyl)naphtho[2,3-b]thiophene-4,9-dione] exerts anti-colorectal cancer activity through ferroptosis and inhibition of MAPK signaling pathway based on RNA sequencing
  87. Synthesis and efficacy of herbicidal ionic liquids with chlorsulfuron as the anion
  88. Effect of isovalent substitution on the crystal structure and properties of two-slab indates BaLa2−xSmxIn2O7
  89. Synthesis, spectral and thermo-kinetics explorations of Schiff-base derived metal complexes
  90. An improved reduction method for phase stability testing in the single-phase region
  91. Comparative analysis of chemical composition of some commercially important fishes with an emphasis on various Malaysian diets
  92. Development of a solventless stir bar sorptive extraction/thermal desorption large volume injection capillary gas chromatographic-mass spectrometric method for ultra-trace determination of pyrethroids pesticides in river and tap water samples
  93. A turbidity sensor development based on NL-PI observers: Experimental application to the control of a Sinaloa’s River Spirulina maxima cultivation
  94. Deep desulfurization of sintering flue gas in iron and steel works based on low-temperature oxidation
  95. Investigations of metallic elements and phenolics in Chinese medicinal plants
  96. Influence of site-classification approach on geochemical background values
  97. Effects of ageing on the surface characteristics and Cu(ii) adsorption behaviour of rice husk biochar in soil
  98. Adsorption and sugarcane-bagasse-derived activated carbon-based mitigation of 1-[2-(2-chloroethoxy)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea-contaminated soils
  99. Antimicrobial and antifungal activities of bifunctional cooper(ii) complexes with non-steroidal anti-inflammatory drugs, flufenamic, mefenamic and tolfenamic acids and 1,10-phenanthroline
  100. Application of selenium and silicon to alleviate short-term drought stress in French marigold (Tagetes patula L.) as a model plant species
  101. Screening and analysis of xanthine oxidase inhibitors in jute leaves and their protective effects against hydrogen peroxide-induced oxidative stress in cells
  102. Synthesis and physicochemical studies of a series of mixed-ligand transition metal complexes and their molecular docking investigations against Coronavirus main protease
  103. A study of in vitro metabolism and cytotoxicity of mephedrone and methoxetamine in human and pig liver models using GC/MS and LC/MS analyses
  104. A new phenyl alkyl ester and a new combretin triterpene derivative from Combretum fragrans F. Hoffm (Combretaceae) and antiproliferative activity
  105. Erratum
  106. Erratum to: A one-step incubation ELISA kit for rapid determination of dibutyl phthalate in water, beverage and liquor
  107. Review Articles
  108. Sinoporphyrin sodium, a novel sensitizer for photodynamic and sonodynamic therapy
  109. Natural products isolated from Casimiroa
  110. Plant description, phytochemical constituents and bioactivities of Syzygium genus: A review
  111. Evaluation of elastomeric heat shielding materials as insulators for solid propellant rocket motors: A short review
  112. Special Issue on Applied Biochemistry and Biotechnology 2019
  113. An overview of Monascus fermentation processes for monacolin K production
  114. Study on online soft sensor method of total sugar content in chlorotetracycline fermentation tank
  115. Studies on the Anti-Gouty Arthritis and Anti-hyperuricemia Properties of Astilbin in Animal Models
  116. Effects of organic fertilizer on water use, photosynthetic characteristics, and fruit quality of pear jujube in northern Shaanxi
  117. Characteristics of the root exudate release system of typical plants in plateau lakeside wetland under phosphorus stress conditions
  118. Characterization of soil water by the means of hydrogen and oxygen isotope ratio at dry-wet season under different soil layers in the dry-hot valley of Jinsha River
  119. Composition and diurnal variation of floral scent emission in Rosa rugosa Thunb. and Tulipa gesneriana L.
  120. Preparation of a novel ginkgolide B niosomal composite drug
  121. The degradation, biodegradability and toxicity evaluation of sulfamethazine antibiotics by gamma radiation
  122. Special issue on Monitoring, Risk Assessment and Sustainable Management for the Exposure to Environmental Toxins
  123. Insight into the cadmium and zinc binding potential of humic acids derived from composts by EEM spectra combined with PARAFAC analysis
  124. Source apportionment of soil contamination based on multivariate receptor and robust geostatistics in a typical rural–urban area, Wuhan city, middle China
  125. Special Issue on 13th JCC 2018
  126. The Role of H2C2O4 and Na2CO3 as Precipitating Agents on The Physichochemical Properties and Photocatalytic Activity of Bismuth Oxide
  127. Preparation of magnetite-silica–cetyltrimethylammonium for phenol removal based on adsolubilization
  128. Topical Issue on Agriculture
  129. Size-dependent growth kinetics of struvite crystals in wastewater with calcium ions
  130. The effect of silica-calcite sedimentary rock contained in the chicken broiler diet on the overall quality of chicken muscles
  131. Physicochemical properties of selected herbicidal products containing nicosulfuron as an active ingredient
  132. Lycopene in tomatoes and tomato products
  133. Fluorescence in the assessment of the share of a key component in the mixing of feed
  134. Sulfur application alleviates chromium stress in maize and wheat
  135. Effectiveness of removal of sulphur compounds from the air after 3 years of biofiltration with a mixture of compost soil, peat, coconut fibre and oak bark
  136. Special Issue on the 4th Green Chemistry 2018
  137. Study and fire test of banana fibre reinforced composites with flame retardance properties
  138. Special Issue on the International conference CosCI 2018
  139. Disintegration, In vitro Dissolution, and Drug Release Kinetics Profiles of k-Carrageenan-based Nutraceutical Hard-shell Capsules Containing Salicylamide
  140. Synthesis of amorphous aluminosilicate from impure Indonesian kaolin
  141. Special Issue on the International Conf on Science, Applied Science, Teaching and Education 2019
  142. Functionalization of Congo red dye as a light harvester on solar cell
  143. The effect of nitrite food preservatives added to se’i meat on the expression of wild-type p53 protein
  144. Biocompatibility and osteoconductivity of scaffold porous composite collagen–hydroxyapatite based coral for bone regeneration
  145. Special Issue on the Joint Science Congress of Materials and Polymers (ISCMP 2019)
  146. Effect of natural boron mineral use on the essential oil ratio and components of Musk Sage (Salvia sclarea L.)
  147. A theoretical and experimental study of the adsorptive removal of hexavalent chromium ions using graphene oxide as an adsorbent
  148. A study on the bacterial adhesion of Streptococcus mutans in various dental ceramics: In vitro study
  149. Corrosion study of copper in aqueous sulfuric acid solution in the presence of (2E,5E)-2,5-dibenzylidenecyclopentanone and (2E,5E)-bis[(4-dimethylamino)benzylidene]cyclopentanone: Experimental and theoretical study
  150. Special Issue on Chemistry Today for Tomorrow 2019
  151. Diabetes mellitus type 2: Exploratory data analysis based on clinical reading
  152. Multivariate analysis for the classification of copper–lead and copper–zinc glasses
  153. Special Issue on Advances in Chemistry and Polymers
  154. The spatial and temporal distribution of cationic and anionic radicals in early embryo implantation
  155. Special Issue on 3rd IC3PE 2020
  156. Magnetic iron oxide/clay nanocomposites for adsorption and catalytic oxidation in water treatment applications
  157. Special Issue on IC3PE 2018/2019 Conference
  158. Exergy analysis of conventional and hydrothermal liquefaction–esterification processes of microalgae for biodiesel production
  159. Advancing biodiesel production from microalgae Spirulina sp. by a simultaneous extraction–transesterification process using palm oil as a co-solvent of methanol
  160. Topical Issue on Applications of Mathematics in Chemistry
  161. Omega and the related counting polynomials of some chemical structures
  162. M-polynomial and topological indices of zigzag edge coronoid fused by starphene
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