Decorated Cu NPs on Lignin coated magnetic nanoparticles: Its performance in the reduction of nitroarenes and investigation of its anticancer activity in A549 lung cancer cells

Yongjie Huang; Yan Kang; Attalla El-kott; Ahmed Ezzat Ahmed; Ahmed Khames; Mohamed Abdellatif Zein

doi:10.1016/j.arabjc.2021.103299

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Original article

2021

:14;

202108

doi:

10.1016/j.arabjc.2021.103299

Decorated Cu NPs on Lignin coated magnetic nanoparticles: Its performance in the reduction of nitroarenes and investigation of its anticancer activity in A549 lung cancer cells

Yongjie Huang^{^a}, Yan Kang^{^b}, Attalla El-kott^{^c,^d,⁎}, Ahmed Ezzat Ahmed^{^c,^e}, Ahmed Khames^{^f}, Mohamed Abdellatif Zein^{^g,^h}

a Department of Geriatric Respiratory and Sleep, The First Affiliated Hospital of Zhengzhou University, Zhengzhou City, Henan Province 450052, China

b Department Two of Respiratory and Critical Care Medicine, The First Affiliated Hospital of Zhengzhou University, Zhengzhou City, Henan Province 450052, China

c Biology Department, College of Science, King Khalid University, Abha, Saudi Arabia

d Zoology Department, College of Science, Damanhour University, Damanhour, Egypt

e Theriogenology Department, College of Veterinary Medicine, South Valley University, 83523 Qena, Egypt

f Department of Pharmaceutics and Industrial Pharmacy, College of Pharmacy, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia

g Chemistry Department, College of Science, Damanhour University, Egypt

h Chemistry Department, College of Alwajh, Tabuk University, Saudi Arabia

⁎Corresponding author. elkottaf@yahoo.com (Attalla El-kott)

Received: 2021-4-9, Accepted: 2021-6-25,

Disclaimer:
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.

Abstract

This work describes an eco-friendly approach for in situ immobilization of Cu nanoparticles on the surface of lignin modified Fe₃O₄ nanoparticles, without using any toxic reducing and capping agents. The structure, morphology, and physicochemical properties were characterized by various analytical techniques such as Fourier transformed infrared spectroscopy (FT-IR), field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), energy dispersive X-ray spectroscopy (EDS), X-ray diffraction (XRD), inductively coupled plasma (ICP) and vibrating sample magnetometer (VSM). The Fe₃O₄/Lignin/Cu NPs was proven to be highly efficient nanocatalyst for reduction of nitroarenes. The reaction was performed in water medium and excellent yields of the products were achieved. The nanocatalyst was easily magnetically recovered and recycled 8 times without any significant loss of catalytic activity. While studying the biological activity, cell viability of Fe₃O₄/Lignin/Cu NPs was very low against A549 lung cancer cells without any cytotoxicity on the normal cell line. The viability of lung cancer cell line reduced dose-dependently in the presence of Fe₃O₄/Lignin/Cu nanocomposite. The IC₅₀ of Fe₃O₄/Lignin/Cu nanocomposite was32 µg/mL against A549 cell line.

Keywords

Fe3O4/lignin/Cu

Reduction

Nitro compounds

A549

Human lung cancer

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1 Introduction

The industrial development has an obvious effect towards the economic advancement of the society. However, this also simultaneously has brought in the environmental pollution and ecological disruption as undesirable consequences (Chong et al., 2010; Zhao et al., 2019). In the past few decades, water, the lifeline of the civilization, has mostly been affected severely. Natural and surface water has become highly noxious due to dumping of drugs, unprocessed organic and inorganic dyes, heavy metals, pharmaceuticals and unsafe chemicals from textile, chemical and dye industries (Cermakova et al., 2017; Zhou et al., 2015; Ayad et al., 2017 ). The insufficient awareness among the people, inadequacy in control managements regarding water treatment and profit making tendencies has made the situation worse. Among the different harmful chemicals, nitroarenes are one of the protagonists. They are extremely fatal for all the living animals upsetting their CNS, kidney and liver. In particular, the nitrophenols, being soluble in water, causes substantive damage to the marine living system. These compounds are so rigid that can’t be also degraded by microbes and bacteria (Shah et al., 2017; Maham et al., 2017; Das et al., 2019; Veisi et al., 2019 ). Amongst the different disposal procedures, catalytic reduction has engrossed the most potential (Dhorabe et al., 2016; Ahmaruzzaman and Gayatri, 2010; Barreca et al., 2014; Chen et al., 2017a, 2017b; Revathy et al., 2018; Roy, 2020; Challagulla et al., 2019 ). The consequential amines are much secured and have widespread relevance in photography, optics, cosmetics, synthesis of intermediates related to dyes, agrochemicals and drugs (Layek et al., 2012; Datta et al., 2017). Interestingly, nanomaterials have proved their potential as effective catalyst in the said transformation (Veisi et al., 2020, 2021).

In the last few years, synthesis and development of advanced functionalized nanomaterials has garnered topmost priority in material science for their increasing demand in diverse fields, particularly in catalysis. These materials own several specific features like shape and site selective physicochemical properties, occurrence of large number of surface atoms which mostly act as active sites, high surface to volume ratio and obviously, their ability to recover and reuse in successive batches (Hemmati et al., 2020; García-Suárez et al., 2013; Fu et al., 2019 ). While concerning about the facile isolation and hassle-free smart work-up, magnetic nanoparticles (MNP), especially the ferrites always got special importance (Naghipour and Fakhri, 2016; Duan et al., 2018; Veisi et al., 2018 ). They also got advantages like high abundance, low cost starting materials, easy preparation, thermal and mechanical stability, non-toxic and biocompatibility (Pinto et al., 2012; Mahasti et al., 2019). In addition, based on the presence of their surface hydroxyl groups, they are frequently used as active material support in catalysis (Maia et al., 2019).

These very characteristics have prompted us to demonstrate a novel Cu NP fabricated and lignin functionalized Fe₃O₄, as an advanced architecture functional materials (AAFM) and also towards an application of greener nanoscience (Anastas and Kirchhoff, 2002; Varzi et al., 2021; Khatami et al., 2021; Nasrollahzadeh et al., 2021 ). The bioengineering of nanomaterials using natural resources towards a biocompatible green modified catalyst is a very recent trend in material science. Lignin is a highly functionalized novel biopolymer being inexpensive and abundant, could easily be available from plant woods. The biomolecular modification of lignin over Fe₃O₄ acts as protective shell to shape it as a core-shell structure. Moreover, the presence of large number of oxygenated functionalities in lignin facilitates to immobilize the incoming Cu²⁺ ions followed by their in-situ green reduction to Cu NPs (Scheme 1). The Fe₃O₄/Lignin/Cu NPs was proven to be highly efficient nanocatalyst for reduction of nitroarenes (Scheme 1). Also, the properties of Fe₃O₄/Lignin/Cu nanocomposite against lung cancer cell lines i.e. normal (HUVECs) and A549 were evaluated.

Designing of Fe3O4/Lignin/Cu nanocomposite and its application in the reduction of nitroarenes.

2 Experimental

2.1

2.1 Materials and methods

A.R grade Cu(OAc)₂, FeCl₃ were purchased from Sigma-Aldrich. The organic nitro substrates, all the solvents and NaBH₄ were procured from Merck. MTT dye was purchased from Fluka. All the reagents were used without further purification. The solvents were used after distillation and dried over 4 Å molecular sieves. UV–Visible spectra were recorded with Cary 100 UV–visible spectrophotometer from Agilent Technologies. Structural morphology was studied using a FESEM-TESCAN MIRA3 microscope equipped with EDX (TSCAN). FT-IR was done on a Bruker VERTEX 80 v spectrophotometer. TEM analysis was performed with a Philips CM10 microscope at an operating voltage of 200 Kv. The powder XRD of the nanostructures were done using Co Kα radiation (λ = 1.78897 Å) with operating at 40 keV, and a cathode current of 40 Ma in the scanning range of 2θ = 5–80°. VSM measurement was recorded in a vibrating sample 244 magnetometer MDKFD at room temperature

2.2

2.2 Synthesis of the Fe₃O₄/Lignin

Fe₃O₄ NPs were prepared following a reported method (Revathy et al., 2018). 0.2 g of lignin was dissolved in 100 mL water by sonication for 20 min and was filtered over Whatman No. 1 paper to remove the undisolved plant residues. Subsequently; 0.5 g of the Fe₃O₄ NPs were dispersed in the lignin solution and sonicated again for 20 min and left stirred for 12 h at ambient conditions. The resulting nanocomposite (Fe₃O₄/Lignin NPs) was isolated by magnetic decantation, washed thoroughly with DI water and dried in air.

2.3

2.3 Synthesis of Fe₃O₄/Lignin/Cu NPs

0.5 g of the Fe₃O₄/Lignin was suspended in H₂O (100 mL) and sonicated for 20 min. A 40 mg Cu(OAc)₂ solution in 20 mL H₂O was then added to the previous suspension and pH of the solution was adjusted to 11.0 (NaOH, 3 wt%). The reaction mixture was kept with stirring at 100 °C for 6 h when the Cu²⁺ ions were reduced in situ to Cu NPs by the oxy-functional groups of lignin. Finally, the resulting solid (Fe₃O₄/Lignin/Cu NPs) was retrieved by an external magnet. It was washed thoroughly with aqueous water and acetone and then dried in air. According to ICP-OES analysis the copper content was 0.32 mmol/g.

2.4

2.4 General procedure for the reduction of nitroarenes

A reaction mixture containing 4‐nitrophenol (1 mmol) and NaBH₄ (3 mmol) was stirred in deionized water (5 mL) till a homogeneous solution is obtained. The solution was degassed with N₂ for 10 min. Then the Fe₃O₄/Lignin/Cu catalyst (0.2 mol% Cu) was added and stirring continued. After completion of the reaction (monitored by TLC, n-hexane/EtOAc: 4/1), the catalyst was isolated magnetically, washed with EtOH/H₂O (1:1) and dried for recycling in further batches and 5 mL water was added to the reaction mixture. The product was extracted with ethyl acetate thrice (5 mL × 3). It was then washed with fresh brine water. The organic layer was finally dried over anhydrous Na₂SO₄ and concentrated to have the crude product. It was further purified by silica column chromatography.

2.5

2.5 Determination of anti-human lung cancer potential of Fe₃O₄/Lignin/Cu catalyst

In this study, A549 human lung cancer cell line was used to investigate the cytotoxicity and human lung anti-cancer effects of the catalyst using the standard MTT assay. The cell culture was performed using penicillin, streptomycin, and Dulbecco’s modified Eagle’s medium (DMEM). The distribution of cells was 10,000 cells/well in 96-well plates. All the catalyst samples were prior incubated in presence of 5% CO₂ at 37 °C for 24 h. Then all the cells were exposed to cytotoxic catalyst samples in variable concentrations (10–100 µg/mL) and incubated again for 24 h. Subsequently, they were sterilized under UV-radiation for 2 h. Finally, the MTT dye was added in all wells at 5 mg/mL concentration, incubated again for 4 h at 37 °C and the UV-absorbance (A) at a wavelength of 570 nm. The % cell viability of samples was determined by the following formula- $C e l l v i a b i l i t y (%) = \frac{S a m p l e A}{C o n t r o l A} \times 100$

2.6

2.6 Qualitative measurement

The obtained results were loaded into the “SPSS-22” program and evaluated by “one-way ANOVA”, accompanied by a “Duncan post-hoc” check (p ≤ 0.01).

3 Results and discussion

3.1

3.1 Analysis of catalyst characterization data

The Fe₃O₄/Lignin/Cu nanocomposite was prepared following a post-synthetic modification approach. The plant biomolecule lignin was initially encapsulated over the core ferrite NPs to provide a green and polar environment. This helps the central Fe₃O₄ NPs to prevent from agglomeration, corrosion and unwanted oxidation. Subsequently, the Cu NPs are adorned in the secondary shell over the primary core-shell nanostructure following green reduction (Scheme 1). No harsh reagent was used in the total preparation of the nanocomposite. The as-synthesized material was then thoroughly characterized with several analytical methods like FT-IR, SEM, TEM, EDX, elemental mapping, XRD, VSM and ICP-OES.

Fig. 1 demonstrates the superposition of FT-IR spectrum of the Fe₃O₄/Lignin/Cu nanocomposite with the individual components like bare Fe₃O₄ and the Fe₃O₄/Lignin intermediate in order to validate the stepwise formation. The characteristic strong absorption peaks of Fe₃O₄ can be seen at 439 and 584 cm^-1 due to octahedral bending and tetrahedral stretching vibrations of Fe—O—Fe. The peak at 632 cm⁻¹ corresponds to the ferrite spinel structure. In the spectrum of Fe₃O₄/Lignin (Fig. 1b) all the peaks of Fe₃O₄ are present with the additional peaks due to lignin, being appeared at 3385, 2926 and 1602 cm⁻¹ related to the O—H, C—H and C⚌O stretching vibrations. All the aromatic bond vibrations due to guaiacyl and syringyl scaffolds appear in the wavenumber region of 1600–1000 cm⁻¹ respectively. Fig. 1c describing the Cu doped final material is almost a clone of Fig. 1b except some shifting of peaks due to strong attachment of Cu NPs with the associated oxygenated functional groups.

FT-IR spectra of Fe3O4 (a), Fe3O4/Lignin (b), and Fe3O4/Lignin/Cu (c).

Fig. 2 represents the apparent morphology and shape of the Fe₃O₄/Lignin/Cu nanocomposite, which determined by SEM analysis. The desired nanostructure is typically quasi-spherical shaped and the particles are individually can be identified. However, the agglomeration is seen due to high concentration during manual sample preparations. The globular particles are of nanometric dimension with the particle sizes between 20 and 35 nm. However, Cu NPs cannot be distinguished separately.

In order to have the idea of chemical composition of the Fe₃O₄/Lignin/Cu NPs, EDX analysis was carried out, and the profile is depicted in Fig. 3. It shows the distinct signals of Cu and Fe as major metallic components. As the sample was pre-treated with Au coatings by vapor deposition, its peak appeared in the profile by default. A strong peak of O is seen indicating the dominance of oxygenated functions. Some small and weak peaks of C and N as constitutional elements are also observed. These non-metals can be attributed to the lignin attachment, and also a good justification to the successful immobilization of lignin and Cu NPs over the ferrite NPs. The elemental information was further extended through mapping study. In so doing, a section of the SEM image was scanned by X-ray and the outcome, as the distribution of the constituent elements, is shown in Fig. 4. Evidently, Fe, Cu and C atoms are uniformly distributed over the surface. The homogeneous distribution definitely has an important role behind its catalytic potential.

Elemental mapping of Fe3O4/Lignin/Cu NPs.

More detailed structural information is obtained by TEM. Fig. 5 describes the corresponding image of Fe₃O₄/Lignin/Cu NPs. In Fig. 5 the particles are in granular form and almost perfectly round shaped. A thin layer over the particle surface can be visible. The dark colored Cu NPs are also globular shaped. The ferrite and Cu NPs are almost of similar size of around 15–20 nm. From the image it seems that the ferrite and Cu NPs are embedded over the lignin fibre layer. Moreover, Fig. 5 (inset) determines the particle size distribution histograms for Fe₃O₄/Lignin/Cu NPs whose average size are approximately 16.2 nm.

TEM image of Fe3O4/Lignin/Cu NPs and its particle size distribution histograms.

The nature of crystalline phases and Bragg's diffraction peaks of Fe₃O₄/Lignin/Cu NPs nanocomposite was established by XRD analysis (Fig. 6). It represents a single phase profile indicating a united entity of the assembled counterparts. The typical diffraction peaks due to Fe₃O₄ are observed at 2θ = 30.2, 35.5, 43.4, 53.6, 57.2, 62.8° corresponding to (2 2 0), (3 1 1), (4 0 0), (4 2 2), (5 1 1) and (4 4 0) Bragg reflection planes respectively (JCPDS file, PDF No. 65-3107). Three additional weak diffraction peaks observed at 2θ = 43.1°, 49.6°, and 75.2° are contributed from cubic crystalline Cu NPs being assigned to the (1 1 1), (2 0 0) and (2 2 0) planes, respectively (Joseph et al., 2016).

Fig. 6

XRD profile of Fe₃O₄/Lignin/Cu NPs.

For iron based materials, study of magnetism through VSM analysis is very important. Fe₃O₄/Lignin/Cu NPs was studied and the corresponding outcome is produced in Fig. 7. The saturation magnetization values (M_s) of the material was counted to be 42.8 emu/g. The Fe₃O₄/Lignin/Cu NPs bear lower magnetism than bare Fe₃O₄. The reduction in magnetic values in the modified material is obvious due to covering the core with non-magnetic biomolecules. The Fe₃O₄/Lignin/Cu has further lower M_s value owing to incorporation of diamagnetic Cu NPs.

3.2

3.2 Catalytic application of Fe₃O₄/Lignin/Cu NPs in the reduction of nitroarenes

After the detailed analytical studies and catalytic data investigations, next we targeted the catalytic exploration. Now, in an attempt to identify the best catalytic conditions, we selected the reduction of 4-nitrophenol as a model reaction being carried out in water as the green media and the effect of different reaction parameters like catalyst, their load and amount of reducing agent etc were imposed thereon. The results are summarized in Table 1. As evident from the first three entries, the reaction was absolutely unsuccessful in the absence of any catalyst or having unmodified Fe₃O₄ or Fe₃O₄/Lignin as catalysts, even after the use of NaBH₄ as reducing agent (3.0 mmol). However, the reaction was fruitful using Fe₃O₄/Lignin/Cu as catalyst. This validates the usefulness of Cu in the nanocomposite. It has very good electrical conductivity and excellent redox properties that facilitates the electron transfer in the reduction of nitro group. The Tiny Cu NPs being uniformly dispersed over the high surface might have a degenerative augmented electronic effect. Just 0.1 mol% Cu load was sufficient to afford 80% conversion towards the reduced product. The best result was obtained when 0.2 mol% Cu loaded catalyst was employed in presence of 3.0 mmol of NaBH₄ (entry 6). It resulted 98% of the reduced product in just 30 min of reaction at room temperature. Further variation in the catalyst load or amount of NaBH₄ could not produce better results than the entry 6 (entries 7–9).

After getting the optimized results in the reduction of nitroarenes over Fe₃O₄/Lignin/Cu catalyst, it was the turn for investigating their scope and generality. Consequently, a wide range of aromatic nitro compounds bearing different functions were reduced in water using NaBH₄ as the reductant and the corresponding outcomes are documented in Table 2. Both the electron donating (OMe, OH, NH₂) and withdrawing groups (Cl, Br, NO₂, COOH) in the system were very much compatible under the reaction protocol resulting excellent yields in short times. Interestingly, while reducing the dinitro compounds, we found partially reduced product with 1,3-substrate but got full reduction with 1,2-substrates (entry 8–9). All the substrates were reduced to corresponding amines within 2 h (entry 1–12).

3.3

3.3 Study of reusability and leaching test of Fe₃O₄/Lignin/Cu NPs catalyst

For any heterogeneous catalysis, study of its reusability is a ubiquitous event. It was investigated with the probe reaction starting with a larger batch size (2.0 mmol) under the standard conditions. On completion of a fresh batch, the catalyst was recovered magnetically, washed thoroughly for several times with EtOH/H₂O (1:1), dried at 60 °C to regenerate and used in the subsequent runs. Noticeably, we could reuse it for 8 successive runs without considerable decrease in its activity (Fig. 8). A leaching test was carried out as well in order to prove the robustness of our catalyst. After the isolation of the catalyst from reaction mixture, an ICP-OES analysis was performed with the reaction filtrate. It was gratifying to ensure that only a marginal amount of Cu has been leached out. After the 8th run, the Cu content in the nanocomposite was 0.296 mmol/g. The slight decrease in yield in the 8th cycle is probably due to this loss of Cu and the adsorption of product (4-AP) over the catalyst surface (Lin and Doong, 2011).

Study of reusability of Fe3O4/Lignin/Cu NPs catalyst in reduction of 4‐nitrophenol.

3.4

3.4 Exclusivity of our results

We demonstrated the catalytic comparison of our protocol with literature in the reduction of 4-nitrophenol which is shown in Table 3. It specifically shows that the Fe₃O₄/Lignin/Cu NPs nanocomposite catalyzes the reaction with a better performance over the others, in terms of reaction rate and isolated yield.

Table 3 Comparison of various catalysts in the reduction of 4‐nitrophenol.

Entry	Catalyst (mol%)	Conditions	Time (min)	Yield (%)	Refs.
1	Au/MTA	NaBH₄, EtOH, RT	180	90	(Fountoulaki et al., 2014)
2	TiO2-G1%	H₂, Oxalic acid, UV	60	95	(Xu et al., 2013)
3	Pd NPs/RGO	NaBH₄, EtOH:H₂O, 50 °C	90	97	(Nasrollahzadeh et al., 2016)
4	Fe₃O₄@C@Pt	H₂, EtOH, RT	60	98	(Xie et al., 2013)
5	TiO₂/CoFe₂O₄	NaBH₄, H₂O, RT	35	94	(Ibrahim et al., 2019)
6	Cu nanosphere	NaBH₄, H₂O, RT	60	94	(Patra et al., 2010)
7	Ag–Pt/MWCNTs/PM	NaBH₄, H₂O, RT	350	95	(Esquivel-Peña et al., 2019)
8	Rh–Fe₃O₄ nanocrystals	N₂H₄, EtOH, 80 °C	60	99	(Shokouhimehr et al., 2013)
9	Fe₃O₄/Pd@C NC	NaBH₄, H₂O, RT	60	85	(Wang et al., 2020)
10	Fe₃O₄@Fritillaria/Pd	N₂H₄·H₂O, EtOH:H₂O (1:2), 80 °C	30	98	(Veisi et al., 2021)
11	PdCu/graphene	NaBH₄·H₂O, EtOH:H₂O (1:2), 80 °C	90	98	(Feng et al., 2014)
12	Fe₃O₄/Lignin/Cu NPs	NaBH₄, H₂O, 25 °C	30	98	This work

3.5

3.5 Cytotoxicity effect of Fe₃O₄/Lignin/Cu NPs against A549 lung cancer cells

In our study, the cell viability of HUVEC (normal cell line) and A549 (lung cell line) under different concentration of Fe₃O₄/Lignin and Fe₃O₄/Lignin/Cu NPs were evaluated using the MTT method. As shown in the Fig. 9b, with increasing the concentration of Fe₃O₄/Lignin/Cu NPs the cell viability was reduced. The IC₅₀ of Fe₃O₄/Lignin/Cu NPs was calculated to be around 32 μg/ml while the Fe₃O₄/Lignin could not reach the IC₅₀. As the results show (Fig. 9a), Fe₃O₄/Lignin/Cu NPs do not significant effect on the viability of normal cells, which is consistent with the results of other researchers.

In vitro cytotoxicity analysis of Fe3O4/Lignin and Fe3O4/Lignin/Cu NPs on HUVEC (a) and A549 (b) cells.

The anticancer effect of Fe₃O₄/Lignin/Cu NPs against lung cancer cell (A549) lines was performed. The results show the good cytotoxic activity against the cancer cells (Fig. 9). The concentration of copper nanoparticles plays an important role in the anticancer activity. The copper nanoparticles are having the good results against A549 in that 100 µg show fine results followed by 80 µg, 40 µg, 20µgand 10 µg. The lowest inhibitory action was observed form the concentration of ∼30 µg. In this report, the anticancer activity was observed and that the prepared Fe₃O₄/Lignin/Cu NPs induce a dose dependent inhibition activity against lung cells.

4 Conclusion

In this study, an eco-friendly approach for in situ immobilization of Cu nanoparticles on the surface of lignin modified-Fe₃O₄ nanoparticles, without using any toxic reducing and capping agents. The structure, morphology, and physicochemical properties were characterized. The Fe₃O₄/Lignin/Cu NPs was proven to be highly efficient nanocatalyst for reduction of nitroarenes with good yield. The nanocatalyst was easily magnetically recovered and recycled 8 times without any significant loss of catalytic activity. Also, Fe₃O₄/Lignin/Cu NPs have good cytotoxicity effect against A549 lung cancer cells without any cytotoxicity on the normal cell line.

Acknowledgments

The authors extend their appreciation to the deanship of Scientific Research at King Khalid University, Abha, KSA for supporting this work under grant number (R.G.P.2/122/42), and the work was supported by the Taif University Researchers Supporting Project Number (TURSP-2020/68), Taif University, Taif, Saudi Arabia.

Declaration of Competing Interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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Varzi Z., Esmaeili M.S., Ledari R.T., Maleki A., . Inorg. Chem. Commun.. 2021;125:108465
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Veisi H., Karmakar B., Tamoradi T., Tayebee R., Sajjadifar S., Lotfi S., Maleki B., Hemmati S., . Sci. Rep.. 2021;11:1-15.
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Entry	Catalyst	Cat. Loading (Cu mol%)	NaBH₄ (mmol)	Time (min)	Yield (%)^b
1	–	–	3.0	240	–
2	Fe₃O₄	–	3.0	240	–
3	Fe₃O₄/Lignin	–	3.0	240	–
4	Fe₃O₄/Lignin/Cu	0.20	1.0	60	70
5	Fe₃O₄/Lignin/Cu	0.20	2.0	45	80
6	Fe₃O₄/Lignin/Cu	0.20	3.0	30	98
7	Fe₃O₄/Lignin/Cu	0.20	4.0	30	98
8	Fe₃O₄/Lignin/Cu	0.30	3.0	25	98
9	Fe₃O₄/Lignin/Cu	0.10	3.0	60	80

Entry	Nitroarene	Time (min)	Yield (%)^b
1	Nitrobenzene	60	95
2	4-Nitrophenol	30	98
3	4-Methoxynitrobenzene	30	96
4	4-Chloronitrobenzene	40	92
5	4-Bromonitrobenzene	45	92
6	4-Nitroaniline	30	98
7	3-Chloronitrobenzene	60	90
8	1,3-Dinitrobenzene	90	90
9	1,2-Dinitrobenzene	60	92
10	2-Nitrophenol	90	90
11	2-Nitroaniline	120	92
12	4-Nitrobenzoic acid	120	80

Decorated Cu NPs on Lignin coated magnetic nanoparticles: Its performance in the reduction of nitroarenes and investigation of its anticancer activity in A549 lung cancer cells

Abstract

Keywords

Fe3O4/lignin/Cu

Reduction

Nitro compounds

A549

Human lung cancer

1 Introduction

2 Experimental

2.1 Materials and methods

2.2 Synthesis of the Fe3O4/Lignin

2.3 Synthesis of Fe3O4/Lignin/Cu NPs

2.4 General procedure for the reduction of nitroarenes

2.5 Determination of anti-human lung cancer potential of Fe3O4/Lignin/Cu catalyst

2.6 Qualitative measurement

3 Results and discussion

3.1 Analysis of catalyst characterization data

3.2 Catalytic application of Fe3O4/Lignin/Cu NPs in the reduction of nitroarenes

3.3 Study of reusability and leaching test of Fe3O4/Lignin/Cu NPs catalyst

3.4 Exclusivity of our results

3.5 Cytotoxicity effect of Fe3O4/Lignin/Cu NPs against A549 lung cancer cells

4 Conclusion

Acknowledgments

Declaration of Competing Interest

References

Suggested read for related articles:

2.2 Synthesis of the Fe₃O₄/Lignin

2.3 Synthesis of Fe₃O₄/Lignin/Cu NPs

2.5 Determination of anti-human lung cancer potential of Fe₃O₄/Lignin/Cu catalyst

3.2 Catalytic application of Fe₃O₄/Lignin/Cu NPs in the reduction of nitroarenes

3.3 Study of reusability and leaching test of Fe₃O₄/Lignin/Cu NPs catalyst

3.5 Cytotoxicity effect of Fe₃O₄/Lignin/Cu NPs against A549 lung cancer cells