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Research about Vital Organic Chelates and Metal Ion Complexes

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A special issue of Crystals (ISSN 2073-4352). This special issue belongs to the section "Organic Crystalline Materials".

Deadline for manuscript submissions: closed (30 April 2022) | Viewed by 29873

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Prof. Dr. Moamen S. Refat

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Department of Chemistry, College of Science, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia
Interests: charge-transfer complexes; metal–acid complexes; schiff base complexes; metal–drug interactions; metal–dye complexes; crystal structures
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Prof. Dr. Younes Hanifehpour

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Department of Chemistry, Sayyed Jamaleddin Asadabadi University, Asadabad 6541861841, Iran
Interests: coordination polymer; metal-organic framework; nanocatalyst; Lanthanide-doped semiconductor and advanced materials for wastewater remediation
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Dr. Ashraf El-Bindary

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Chemistry Department Faculty of Science Damietta University Damietta 34517, Egypt
Interests: coordination chemistry; polymer chemistry; potentiometry; thermodynamics; adsorption; photocatalytic degradation of organic pollutants; biological activities

Dr. Abdel Majid A. Adam

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Department of Chemistry, College of Science, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia
Interests: metal complexes; charge-transfer complexes; metal-acid complexes; schiff base complexes; metal drug interactions; metal-dye complexes; crystal structures
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Dr. Ahmed M Naglah

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Drug Exploration and Development Chair (DEDC), Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
Interests: drug delivery; metal drug interactions; biological activities; crystal structures
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Special Issue Information

Dear Colleagues,

Metal ion complexes is a rapidly developing field with enormous potential for applications that provides new possibilities for the pharmaceutical industry. It is expected that the increasing knowledge about the role of minerals in biochemistry will provide an area for designing new drugs in many other areas as well, for example neuropharmacology and anti-potency agents. Advances in coordination chemistry rely heavily on an understanding of not only the thermodynamics of reactions, but also the kinetics of mineral complexes under biologically relevant conditions. Metals are essential cellular components that nature chooses to function in many biochemical processes that are indispensable to living organisms. Transition metal complexes are important in catalysis, material synthesis, photochemistry, and biological systems. Inorganic medicinal chemistry can exploit the unique properties of metal ions to design new drugs. The use of metals and their complexes for medicinal purposes has been present throughout history. With advances in inorganic chemistry, the role of transition metal complexes as therapeutic compounds is becoming increasingly important. Recent advances in inorganic chemistry have made it possible to form a few transition metal complexes of organic interest that can be used as therapeutic agents. This review clarifies the role of metals and recent advances in medicinal organic biochemistry with new approaches to the design and application of innovative metal-based drugs.

Prof. Dr. Moamen S. Refat
Prof. Dr. Younes Hanifehpour
Dr. Ashraf El-Bindary
Dr. Abdel Majid A. Adam
Dr. Ahmed M Naglah
Guest Editors

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Keywords

Metal complexes
Metal-based drugs
Medicinal inorganic chemistry
Crystals
Nanomaterials and applications
Composites

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Published Papers (10 papers)

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Research

13 pages, 1603 KiB

Open AccessArticle

Synthesis, Spectroscopic, and Biological Assessments on Some New Rare Earth Metal Adrenaline Adducts

by Sulaiman A. Al Yousef, Asma S. Al-Wasidi, Ibtisam I. S. AlZahrani, Hotoun I. Thawibaraka, Ahmed M. Naglah, Shaima A. El-Mowafi, Omar B. Ibrahim, Moamen S. Refat and Ahmed Gaber

Crystals 2021, 11(12), 1536; https://doi.org/10.3390/cryst11121536 - 9 Dec 2021

Viewed by 2140

Abstract

Adrenaline (Adr) reacts with chlorides of Y³⁺, Ce³⁺, Nd³⁺ and Sm³⁺ in methanol at 60 °C to yield metal ion adducts of definite composition. These compounds are characterized by elemental analyses, molar conductivity, UV-Vis., ¹H–NMR, Raman laser, scanning electron microscopy, energy-dispersive X-ray spectroscopy (EDX), and mid infrared spectral measurement investigations. The adducts are found to have the formulae [Y₂(Adr)₂(H₂O)₈]Cl₃.8H₂O, [Ce(Adr)₂(H₂O)₂]Cl₃.10H₂O, [Nd(Adr)₂(H₂O)₂]Cl₃.6H₂O, and [Sm(Adr)₂(H₂O)₂]Cl₃.12H₂O, respectively. The two phenolic groups of the catechol moiety are linked to central metal ions based on the infrared and Raman laser spectra. The new compounds were tested against five gram-positive and two-gram negative bacteria, in addition to two Aspergillus strains. Metal adducts were shown to have stronger antibacterial and antifungal properties than free adrenaline compounds. Full article

(This article belongs to the Special Issue Research about Vital Organic Chelates and Metal Ion Complexes)

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11 pages, 3169 KiB

Open AccessEditor’s ChoiceArticle

Characterization of Structural Defects in (Cd,Zn)Te Crystals Grown by the Travelling Heater Method

by Jiaona Zou, Alex Fauler, Alexander S. Senchenkov, Nikolai N. Kolesnikov, Lutz Kirste, Merve Pinar. Kabukcuoglu, Elias Hamann, Angelica Cecilia and Michael Fiederle

Crystals 2021, 11(11), 1402; https://doi.org/10.3390/cryst11111402 - 18 Nov 2021

Cited by 4 | Viewed by 2602

Abstract

Structural defects and compositional uniformity remain the major problems affecting the performance of (Cd, Zn)Te (CZT) based detector devices. Understanding the mechanism of growth and defect formation is therefore fundamental to improving the crystal quality. In this frame, space experiments for the growth of CZT by the Travelling Heater Method (THM) under microgravity are scheduled. A detailed ground-based program was performed to determine experimental parameters and three CZT crystals were grown by the THM. The structural defects, compositional homogeneity and resistivity of these ground-based crystals were investigated. A ZnTe content variation was observed at the growth interface and a high degree of stress associated with extensive dislocation networks was induced, which propagated into the grown crystal region according to the birefringence and X-ray White Beam Topography (XWBT) results. By adjusting the growth parameters, the ZnTe variations and the resulting stress were efficiently reduced. In addition, it was revealed that large inclusions and grain boundaries can generate a high degree of stress, leading to the formation of dislocation slip bands and subgrain boundaries. The dominant defects, including grain boundaries, dislocation networks and cracks in the interior of crystals, led to the resistivity variation in the crystals. The bulk resistivity of the as-grown crystals ranged from 10⁹ Ωcm to 10¹⁰ Ωcm. Full article

(This article belongs to the Special Issue Research about Vital Organic Chelates and Metal Ion Complexes)

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19 pages, 11232 KiB

Open AccessArticle

Structural and Spectroscopic Characteristics of Ni^II and Cu^II Complexes with Poly (Vinyl Alcohol-Nicotinic Acid) Copolymers for Photocatalytic Degradation of Indigo Carmine Dye

by Ibraheem O. Ali, Hisham S. Nassar, Ahmed M. Naglah, Laila M. Al-Harbi and Ahmed A. Elhenawy

Crystals 2021, 11(10), 1244; https://doi.org/10.3390/cryst11101244 - 14 Oct 2021

Cited by 2 | Viewed by 2043

Abstract

Poly-vinyl-alcohol (PVA) has been cross-linked chemically with nicotinic-acid (NA) in an aqueous medium. The copolymers were complexed with Ni^II and Cu^II ions. The complexes and copolymers were analyzed using FT-IR and UV–Visible spectroscopy, XRD and TGA, but copolymers were extra analyzed with nuclear magnetic resonance (¹H NMR). FT-IR spectra of copolymer revealed the presence of C=O & C–N groups due to the esterification of PVA-NA. The Cu/NA-PVA formed via bidentate interaction of the pyridinyl and carboxyl of NA. EPR/UV-vis data shows the square-planar geometry for Ni^II and Cu^II complexes. The adsorption of IC dye onto Cu^II/NA-PVA complex was noticeably greater (90%) in 35 min than Ni^II/NA-PVA. The DFT\B3LYP with 6- 311G* quantum chemical calculations were carried out for tested compounds. The DFT was conducted to examine an interaction mode of the target compounds with the reaction system. The QSPR was calculated as: optimization geometries, (FMOs), chemical-reactivities and NLO for the copolymers. The (MEPs) were figured to predict the interaction behavior of the ligand and its complexes. Full article

(This article belongs to the Special Issue Research about Vital Organic Chelates and Metal Ion Complexes)

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17 pages, 10912 KiB

Open AccessArticle

Preparation and Characterization of New CrFeO₃-Carbon Composite Using Environmentally Friendly Methods to Remove Organic Dye Pollutants from Aqueous Solutions

by Abdel Majid A. Adam, Hosam A. Saad, Ahmed A. Atta, Mohammed Alsawat, Mohamed S. Hegab, Moamen S. Refat, Tariq A. Altalhi, Eid H. Alosaimi and Ayman A. O. Younes

Crystals 2021, 11(8), 960; https://doi.org/10.3390/cryst11080960 - 16 Aug 2021

Cited by 21 | Viewed by 2531

Abstract

Globally, environmental pollution is an important issue. Various pollutants present in water resources, such as bacteria, heavy-metal ions, and organic pollutants, cause serious problems to the environment, animals, plants, and human health. Among the water resources, pollutants, dyestuff, which is discharged from dyeing, textile, and other industrial processes, is an important class of pollutants. Removing these dye pollutants from water resources and wastewater is vital and important due to their toxicity. In this work, a CrFeO₃-carbon nanotube (CNT) adsorbent was synthesized using environmentally friendly methods. The synthesized CrFeO3-CNT adsorbent was characterized stoichiometrically, spectroscopically, and morphologically. The synthesized CrFeO₃-CNT adsorbent was tested for the removal of two dyes: Methyl violet 2B (MV) and Azocarmine G2 (AC) from an aqueous solution. Crushing CrFeO₃ composite with multi-walled fullerene CNT to prepare CrFeO₃-CNT adsorbent improved the adsorption performance of free multi-walled fullerene CNT towards MV dye by 30% and towards AC dye by 33.3%. Full article

(This article belongs to the Special Issue Research about Vital Organic Chelates and Metal Ion Complexes)

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16 pages, 4496 KiB

Open AccessArticle

An Environmentally Friendly Method for Removing Hg(II), Pb(II), Cd(II) and Sn(II) Heavy Metals from Wastewater Using Novel Metal–Carbon-Based Composites

by Abdel Majid Adam, Hosam A. Saad, Ahmed A. Atta, Mohammed Alsawat, Mohamed S. Hegab, Tariq A. Altalhi and Moamen S. Refat

Crystals 2021, 11(8), 882; https://doi.org/10.3390/cryst11080882 - 29 Jul 2021

Cited by 34 | Viewed by 3398

Abstract

Rapid economic and industrial development and population growth have made water contamination a serious environmental problem and a major threat to public health worldwide. Heavy metals are extensively used in numerous industrial applications and are some of the most important environmental contaminants. The impacts of heavy metals on the health of humans, animals, and plants make their removal from wastewater and water resources an important and vital issue. In this study, a simple and environmentally friendly method is proposed for the synthesis of a ZnFe₂O₄-carbon nanotube (CNT) adsorbent material. SEM/EDX analysis and Fourier-transform infrared spectrophotometry (FTIR) are used to characterize the synthesized adsorbent material. We test the synthesized adsorbent material’s ability to recover four heavy metals (Hg(II), Pb(II), Cd(II) and Sn(II) ions) from an aqueous solution. We show that crushing fullerene CNTs with the ZnFe₂O₄ composite improves the adsorption properties of free fullerene CNTs towards the investigated heavy metal ions by 25%. Full article

(This article belongs to the Special Issue Research about Vital Organic Chelates and Metal Ion Complexes)

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17 pages, 5330 KiB

Open AccessArticle

Simultaneous Hydrolysis and Detection of Organophosphate by Benzimidazole Containing Ligand-Based Zinc(II) Complexes

by Gaber A. M. Mersal, Hamdy S. El-Sheshtawy, Mohammed A. Amin, Nasser Y. Mostafa, Amine Mezni, Sarah Alharthi, Rabah Boukherroub and Mohamed M. Ibrahim

Crystals 2021, 11(6), 714; https://doi.org/10.3390/cryst11060714 - 21 Jun 2021

Cited by 6 | Viewed by 2344

Abstract

The agricultural use of organophosphorus pesticides is a widespread practice with significant advantages in crop health and product yield. An undesirable consequence is the contamination of soil and groundwater by these neurotoxins resulting from over application and run-off. Here, we design and synthesize the mononuclear zinc(II) complexes, namely, [Zn(AMB)₂Cl](ClO₄) 1 and [Zn(AMB)₂(OH)](ClO₄) 2 (AMB = 2-aminomethylbenzimidazole), as artificial catalysts inspired by phosphotriesterase (PTE) for the hydrolysis of organophosphorus compounds (OPs) and simultaneously detect the organophosphate pesticides such as fenitrothion and parathion. Spectral and DFT (B3LYP/Lanl2DZ) calculations revealed that complexes 1 and 2 have a square-pyramidal environment around zinc(II) centers with coordination chromophores of ZnN₄Cl and ZnN₄O, respectively. Both 1 and 2 were used as a modifier in the construction of a biomimetic sensor for the determination of toxic OPs, fenitrothion and parathion, in phosphate buffer by square wave voltammetry. The hydrolysis of OPs using 1 or 2 generates p-nitrophenol, which is subsequently oxidized at the surface of the modified carbon past electrode. The catalytic activity of 2 was higher than 1, which is attributed to the higher electronegativity of the former. The oxidation peak potentials of p-nitrophenol were obtained at +0.97 V (vs. Ag/AgCl) using cyclic voltammetry (CV) and +0.88 V (vs. Ag/AgCl) using square wave voltammetry. Several parameters were investigated to evaluate the performance of the biomimetic sensor obtained after the incorporation of zinc(II) complex 1 and 2 on a carbon paste electrode (CPE). The calibration curve showed a linear response ranging between 1.0 μM (0.29 ppm) and 5.5 μM (1.6 ppm) for fenitrothion and 1.0 μM (0.28 ppm) and 0.1 μM (0.028 ppm) for parathion with a limit of detection (LOD) of 0.08 μM (0.022 ppm) and 0.51 μM (0.149 ppm) for fenitrothion and parathion, respectively. The obtained results clearly demonstrated that the CPE modified by 1 and 2 has a remarkable electrocatalytic activity towards the hydrolysis of OPs under optimal conditions. Full article

(This article belongs to the Special Issue Research about Vital Organic Chelates and Metal Ion Complexes)

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16 pages, 6497 KiB

Open AccessArticle

Ultrasound-Assisted Synthesis and DFT Calculations of the Novel 1D Pb (II) Coordination Polymer with Thiosemicarbazone Derivative Ligand and Its Use for Preparation of PbO Clusters

by Jaber Dadashi, Younes Hanifehpour, Babak Mirtamizdoust, Mehdi Abdolmaleki, Elham Mohammadi Jegarkandi, Mahboubeh Rezaei and Sang Woo Joo

Crystals 2021, 11(6), 682; https://doi.org/10.3390/cryst11060682 - 14 Jun 2021

Cited by 9 | Viewed by 3002

Abstract

In the present work, using a sonochemical method, a new lead (II) coordination 1D polymer, [Pb(L)₂(CH₃COO)]_n (L = pyridine-4-carbaldehyde thiosemicarbazone) (1) was prepared. It was characterized structurally with different spectroscopic methods, such as SEM, IR spectroscopy, XRD, and elemental analysis. The coordination compound becomes a stair-step one-dimensional polymer in solid mode. The lead (II) ions have the coordination number of six (PbNS₃O₂) with two oxygen atoms from acetate anion and three sulfur atoms and one nitrogen atom from organic ligand. It contains a stereo-chemically active lone electron pair and the hemidirected coordination sphere. The high-intensity ultrasound is considered a flexible, environmentally friendly, and easy synthetic tool for the coordination compounds. PbO clusters was achieved with thermolyzing 1 at 180 ˚C with oleic acid (as a surfactant). Furthermore, the size and morphology of the created PbO clusters were assessed via SEM. The estimated gap of HOMO and LUMO is 3.275 eV based on DFT calculations. Full article

(This article belongs to the Special Issue Research about Vital Organic Chelates and Metal Ion Complexes)

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11 pages, 3772 KiB

Open AccessArticle

Facile Charge Transfer between Barbituric Acid and Chloranilic Acid over g-C₃N₄: Synthesis, Characterization and DFT Study

by Gaber A. M. Mersal, Mohamed M. Ibrahim, Mohammed A. Amin, Amine Mezni, Nasser Y. Mostafa, Sarah Alharthi, Rabah Boukherroub and Hamdy S. El-Sheshtawy

Crystals 2021, 11(6), 636; https://doi.org/10.3390/cryst11060636 - 2 Jun 2021

Cited by 4 | Viewed by 3153

Abstract

The molecular complexes between barbituric acid (BU) and chloranilic acid (ChA) over graphitic nitride (g-C₃N₄) are investigated. The molecular complexes and the nanocomposite were investigated both in solid state and in methanol. The solid complexes and the corresponding nanocomposite were investigated using FTIR, TGA, and UV-Vis spectroscopy. The structures were explored using DFT calculations using wB97XD/ and def2-TZVP basis set. The DFT calculations revealed the formation of hydrogen-bonded complexes, which initiate the proton transfer from ChA to BU. Immobilization of the BUChA complex over the g-C₃N₄ sheet was stabilized by weak non-covalent interactions, such as π–π interactions. g-C₃N₄ facilitated the charge transfer process, which is beneficial for different applications. Full article

(This article belongs to the Special Issue Research about Vital Organic Chelates and Metal Ion Complexes)

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12 pages, 1823 KiB

Open AccessArticle

Synthesis of 1-[(Aryl)(3-amino-5-oxopyrazolidin-4-ylidene) methyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic Acid Derivatives and Their Breast Anticancer Activity

by Ahmed Gaber, Walaa F. Alsanie, Majid Alhomrani, Abdulhakeem S. Alamri, Ibrahim M. El-Deen and Moamen S. Refat

Crystals 2021, 11(5), 571; https://doi.org/10.3390/cryst11050571 - 20 May 2021

Cited by 4 | Viewed by 2740

Abstract

This research aimed to produce new 1-[(aryl)(3-amino-5-oxopyrazolidin-4-ylidene) methyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic acid derivatives and check their anticancer effect against the breast cancer MCF-7 cell line. The 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (4) compound was obtained by hydrolyzing ethyl 2-oxo-1,2-dihydroquinoline-3-carboxylate (2) with thiourea and anhydrous potassium carbonate ethanol, which was then treated with ethyl 3-substituted 2-cyanoacrylates (6) in the presence of triethylamine in diethyl formamide to give 1-[2-(ethoxy)carbonyl-2-cyano-1-arylvinyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic (7a,d). Cyclization of compound 7 with hydrazine hydrate ethanol inferred the association of 1-[(aryl)(3 amino-5-oxopyrazolidin-4-ylidene)methyl-2-oxo-1,2-dihydroquinol-3-carboxylates (8a,d). Spectroscopic and micro-analytical techniques such as IR, NMR, and elemental analysis were used to validate the structure of the synthesized organic compounds. The anticancer effects of the synthesized compounds 7a–d and 8a–d were tested by using the MTT assay on the MCF-7 cell line. When compared to the reference compound Dox, the compounds 7b,c and 8a–c demonstrated strong anticancer activity against the MCF-7 cell line. The anticancer effects of the synthesized compounds 7a–d and 8a–d were tested against the MCF-7 cell line, using MTT assay. The compounds 7b,c and 8a–c showed significant anticancer activity compared to the reference compound Dox against the MCF-7 cell line. Full article

(This article belongs to the Special Issue Research about Vital Organic Chelates and Metal Ion Complexes)

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13 pages, 1860 KiB

Open AccessArticle

Synthesis and Characterization of Some New Coumarin Derivatives as Probable Breast Anticancer MCF-7 Drugs

by Ahmed Gaber, Walaa F. Alsanie, Majid Alhomrani, Abdulhakeem S. Alamri, Ibrahim M. El-Deen and Moamen S. Refat

Crystals 2021, 11(5), 565; https://doi.org/10.3390/cryst11050565 - 19 May 2021

Cited by 6 | Viewed by 4714

Abstract

This study aimed to synthesize quinolinone derivatives and investigate their cytotoxic activity. The compound 1-azacoumarin-3-carboxylic acid (2-oxo-1H-quinoline-3-carboxylic acid) was obtained via the cyclocondensation of 2-hydroxybenzaldehyde with diethyl malonate in base catalyst to give ethyl coumarin-3-carboxylate, followed by the ammonolysis of ester (ethyl coumarin-3-carboxylate) with ammonia in the presence of anhydrous potassium carbonate. Treatment of 2-oxo-1H-quinoline-3-carboxylic acid with acetic anhydride, cinnamaldehyde, cinnamic acid and methyl 5-phenyl-2-cyano-2,4-pentadienoate under different conditions led to the formation of 1 (substituted) aza coumarin-3-carboxylic acids (1-N-(acetyl)-azacoumarin-3-carboxylic acid, 1-N-(2-Formyl-1-phenyl) vinyl-azacoumarin-3-carboxylic acids, 1-N-[2-(Hydroxy) carbonyl-1-(Phenyl) vinyl]-azacoumarin-3-carboxylic acid and 1-N-(4-Cyano-5-methoxy-5-oxo-1-Phenylpenta-1,3-diene-1-y)-azacoumarin-3-carboxylic 284 acid), respectively. The structures of synthesized 1-(substituted) azacoumarin-3-carboxylic acids were confirmed based on spectroscopic methods (IR and NMR), along with elemental analyses. Interestingly compound 6 demonstrated probable impacts as an anti-cancer drug against the MCF-7 cell line. The mechanism of action was assessed using a flow cytometric assay. The outcomes revealed that compound 6 could arrest the cell cycle at G2/M phase and pre-G1 apoptosis. Full article

(This article belongs to the Special Issue Research about Vital Organic Chelates and Metal Ion Complexes)

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