Synthesis, Characterization, Antiglycation Evaluation, Molecular Docking, and ADMET Studies of 4-Thiazolidinone Derivatives.

The design and development of new small-molecule glycation inhibitors are essential for preventing various chronic diseases, including diabetes mellitus, immunoinflammation, cardiovascular, and neurodegenerative diseases. 4-Thiazolidinone or thiazolidine-4-one is a well-known heterocyclic compound with the potential to inhibit the formation of advanced glycation end products. In the present work, we report the synthesis and characterization of four new 5-arylidene 3-cyclopropyl-2-(phenylimino)thiazolidin-4-one (1-4) compounds and their human serum albumin glycation inhibitory activity. One of the compounds 5-(2H-1,3-benzodioxol-5-ylmethylidene)-3-cyclopropyl-2-(phenylimino)-1,3-thiazolidin-4-one (3) showed potent inhibition in the synthesis of initial, intermediary, and final products of glycation reactions. Besides, conformational changes in the α-helix and ß-sheet (due to hyperglycemia) were also found to be reversed upon the addition of (3). Experimental findings were complemented by computational [molecular docking, ADME/Tox, and density functional theory (DFT)] studies. The docking scores of the compounds were in order 1 > 3 > 2 > 4, indicating the importance of the polar group at the 5-arylidene moiety. The results of ADME/Tox and DFT calculations revealed the safe nature of the compounds with high drug-likeness and stability. Overall, we speculate that the results of this study could provide valuable insights into the biological activity of 4-thiazolidinones.

In silico evaluation of 4-thiazolidinone-based inhibitors against the receptor for advanced glycation end products (RAGE).

Non-enzymatic glycation of biomolecules by reducing sugars led to several products, including the advanced glycation end products (AGEs), the accumulation of which has been linked to various life-threatening diseases. The binding of AGEs to their respective protein receptors for advanced glycation end products (RAGE) can initiate a cascade of reactions, which may alter physiological conditions. The present work investigates the potential of 4-thiazolidinones as RAGE inhibitors. We performed an extensive computational study to identify the structural requirements needed to act as RAGE inhibitors. To achieve this goal, 4-thiazolidinone-based compounds available in PubChem, ZINC15, ChEMBL, and ChEBI databases were screened against RAGE (PDB: 4LP5), leading to the identification of top five drug-like candidates with a high binding affinity to RAGE V-domain catalytic region. Drug likeness, absorption, distribution, metabolism, excretion, and toxicity (ADMET) of the top-scoring compounds have been studied and discussed. Global molecular descriptors, chemical reactivity, hardness, softness, etc., have been estimated. Finally, molecular dynamics (MD) simulations at 100 ns were carried out to check the stability and other properties. Overall, we believe that the identified compounds can potentially attenuate RAGE-AGE interactions.Communicated by Ramaswamy H. Sarma.

Synthesis, Characterization, and Application of Dichloride (5,10,15,20-Tetraphenylporphyrinato) Antimony Functionalized Pectin Biopolymer to Methylene Blue Adsorption.

In this work, pectin biopolymers were functionalized with dichloride (5,10,15,20-tetraphenylporphyrinato) antimony [Sb(TPP)Cl2] at various compositions (0.5%, 1%, and 2%). The prepared compounds were characterized with several analytical methods, including X-ray fluorescence (XRF) spectrometry, Fourier-transform infrared spectroscopy (FT-IR), electrospray ionization mass spectrometry (EIS), scanning electron microscope (SEM), X-ray diffraction (XRD), and thermogravimetric-differential thermal (TGA/DTG) analysis. The XRF technique evidenced the presence of Sb metal in the composite beads. FT-IR suggested that the interaction between pectin and the [Sb(TPP)Cl2] complex was assured by inter- and intramolecular C-H⋯O, C-H⋯Cl hydrogen bonds and weak C-H⋯Cg π interactions (Cg is the centroid of the pyrrole and phenyl rings). The morphological features of the prepared polymeric beads were affected by the addition of [Sb(TPP)Cl2] particles, and the surface became rough. The thermal residual mass for the composite beads (29%) was more important than that of plain beads (23%), which confirmed the presence of inorganic matter in the modified polymeric beads. At 20 °C, the highest adsorption amounts of methylene blue were 39 mg/g and 68 mg/g for unmodified pectin and pectin-[Sb(TPP)Cl2] beads, respectively. The adsorption mechanism correlated well with the kinetic equation of the second order and the isotherm of Freundlich. The prepared polymeric beads were characterized as moderate-to-good adsorbents. The calculated thermodynamic parameters demonstrated an exothermic and thermodynamically nonspontaneous mechanism.

Chemical modification of microcrystalline cellulose with polyethyleneimine and hydrazine: Characterization and evaluation of its adsorption power toward anionic dyes.

Functionalization and various applications of biomaterials have progressively gained a major interest due to the cost-effectiveness, renewability, and biodegradability of these substrates. The current work focalized on the functionalization of microcrystalline cellulose with polyethyleneimine solution (3 %, 5 %, and 10 %) and hydrazine sulfate salt (1:1, 1:2, 2:1) using an impregnation method. Untreated and treated samples were characterized using FT-IR, SEM, XRD, TGA, and DTA analyses. The crystallinity index values for control microcrystalline cellulose, cellulose-polyethyleneimine, and cellulose-hydrazine were 57.13.8 %, 57.29 %, and 52.62 %, respectively. Cellulose-polyethyleneimine (5 %) and cellulose-hydrazine (1:1) displayed the highest adsorption capacities for calmagite (an anionic dye). At equilibrium, the maximum adsorption capacities for calmagite achieved 104 mg/g for cellulose-polyethyleneimine (5 %), 45 mg/g for cellulose-hydrazine (1:1), and only 12.4 mg/g for untreated cellulose. Adsorption kinetics complied well with the pseudo-second-order kinetic model. The adsorption isotherm fitted well with the Langmuir isotherm. Overall, the functionalized cellulosic samples could be considered potential materials for the treatment of contaminated waters.

Characterization and application of ligno-cellulosic fibers derived from Robinia Pseudoacacia for the bio-sorption of methylene blue from water.

Ligno-cellulosic biomasses had been recognized for their potential use to produce chemicals and biomaterials. The current study focused on the use of a new cellulosic Robinia Pseudoacacia fiber and extracted lignin as adsorbents for methylene blue (a cationic dye). The biomaterials were analyzed using FT-IR spectroscopy, SEM, XRD, and TGA-DTA techniques. The surface of Robinia fibers was rough and porous. The crystallinity index (CrI) value for Robinia fibers was found to be 32%. The ability of the studied samples to remove methylene blue from water was assessed under the variation of time, pH, dye concentration, temperature, and NaCl concentration. The maximum adsorption capacity of methylene blue reached 191 mg/g for Robinia fibers and it achieved 22 mg/g for the extracted lignin (T = 20 °C, pH = 6, and time = 90 min). The adsorption data complied with the pseudo second-order kinetic model and both Langmuir and Freundlich isotherms. Based on these findings, the process suggested the occurrence of many physicochemical interactions between methylene blue molecules and the studied biomaterials. The adsorption mechanism was exothermic, non-spontaneous, and it was described by the decrease of the disorder. Adsorption results proved that Robinia fiber was an attractive candidate for the removal of cationic dyes from water.

A low-cost and abundant Robinia Pseudoacacia fiber and its extracted lignin are characterized and further studied as adsorbents for cationic dyes under the change of the experimental conditions.

Synthesis and characterization of a new meso-tetrakis (2,4,6-trimethylphenyl) porphyrinto) zinc(II) supported sodium alginate gel beads for improved adsorption of methylene blue dye.

Chemical modification of a biopolymer offers a simple strategy to realize new materials with added benefits. In this paper, meso-tetrakis(2,4,6-trimethylphenyl) porphyrinto) zinc(II) supported sodium alginate gel beads were successfully prepared, characterized, and used for the removal of a cationic dye from aqueous solution. The chemical structure of the prepared composite beads was confirmed by FT-IR, SEM, XRD and TGA/DTG techniques. Analytical data suggested that the sodium alginate beads and meso-tetrakis(2,4,6-trimethylphenyl) porphyrinto) zinc(II) complex interacted via non-covalent interaction (H-bonding) mode. The morphological micrographs showed spherical and smooth composite beads. The crosslinking of hydroxyl and carboxylate groups of the biopolymer with calcium ions and the incorporation of meso-tetrakis(2,4,6-trimethylphenyl) porphyrinto) zinc(II) into alginate matrix resulted in a small decrease of residual mass. The maximum adsorption capacities of methylene blue, at 20 °C, were found to be 52.3 mg/g and 34.8 mg/g for sodium alginate composite beads (3%) and plain sodium alginate beads, respectively. The adsorption process followed Freundlich isotherm and pseudo second order kinetics. The thermodynamic study displayed an exothermic and non-spontaneous process.

Synthesis, characterization, anticancer and in silico studies of a pyrazole-tethered thiazolidine-2,4-dione derivative.

A new pyrazole-tethered thiazolidine-2,4-dione derivative (8) has been synthesized by the Knoevenagel condensation of 3-(4-nitrophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (4) and 3-(2,4-dioxothiazolidin-3-yl)propanenitrile (7). The structure of the final compound was confirmed by standard spectroscopic techniques including IR spectroscopy, 1H-NMR spectroscopy, and ESI-MS mass spectrometry. Molecular features including frontier molecular orbital (HOMO-LUMO) energies, reactivity descriptors and molecular electrostatic potential (ESP) of the title molecule were determined using density functional theory (DFT) calculation. The in vitro cytotoxicity of both the intermediate (4) and final (8) compounds were investigated against cancerous (SW-480 and MCF-7) and normal (HEK-293) cell lines by MTT assay. Compound (8) displayed higher activity than (4) with higher sensitivity against breast cancer cell line and lesser toxicity. The experimental data were further complemented by docking and absorption, distribution, metabolism, and excretion (ADME) studies.Communicated by Ramaswamy H. Sarma.

Synthesis of copper oxide nanoparticles using Pergularia tomentosa leaves and decolorization studies.

In this investigation, Pergularia tomentosa leaves were used as a promising source of bioproducts for the reduction of copper sulfate into copper oxide nanoparticles. The prepared nanoparticles were characterized using Fourier-transform infrared spectroscopy (FT-IR), X-Ray Diffraction (XRD), Scanning Electron Microscopy (SEM), Transmission electron microscopy (TEM), and Thermogravimetric analysis (TGA). FI-IR showed the presence of hydroxyl, ester, and aromatic groups, which are characteristics of phenolics and other bioproducts. SEM features exhibited spherical and agglomerated particles. In EDX data, the peak at 1 Kev, is an index of metallic nanoparticles of copper. The signals related to C and O peaks indicated the presence of phytochemicals in the studied extract. The synthesized copper oxide nanoparticles had a face-centered cubic structure. The size of the nanoparticles varied from 1.7 to 15.2 nm. The adsorption capacity of methylene blue using copper oxide nanoparticles reached 93.2 mg/g (pH = 6, T = 22 °C, adsorbent dose = 0.0125 g). Additionally, methylene blue solution was completely decolorized after 2 min of reaction (pH = 6, 0.0057 mg NaBH4, C0 = 10 mg/L, catalyst = 0.005 g). NOVELTY STATEMENTIn this study, Pergularia tomentosa leaves were used, for the first time, as a biomaterial rich in bioproducts for the reduction of copper sulfate into copper oxide nanoparticles. The prepared particles act as promising materials for the decolorization of contaminated water via both adsorption and degradation processes.

A Cellulosic Fruit Derived from Nerium oleander Biomaterial: Chemical Characterization and Its Valuable Use in the Biosorption of Methylene Blue in a Batch Mode.

Cellulose substrate waste has demonstrated great potential as a biosorbent of pollutants from contaminated water. In this study, Neriumoleander fruit, an agricultural waste biomaterial, was used for the biosorption of methylene blue from synthetic solution. Fourier-transform infrared (FTIR) spectroscopy indicated the presence of the main absorption peak characteristics of cellulose, hemicellulose, and lignin compositions. X-ray diffraction (XRD) pattern exhibited peaks at 2θ = 14.9° and 2θ = 22°, which are characteristics of cellulose I. Scanning electron microscopy (SEM) showed a rough and heterogeneous surface intercepted by some cavities. Thermogravimetric analysis (TGA) showed more than a thermal decomposition point, suggesting that Nerium fruit is composed of cellulose and noncellulosic matters. The pHpzc value of Nerium surface was experimentally determined to be 6.2. Nerium dosage, pH, contact time, dye concentration, and temperature significantly affected the adsorption capacity. The adsorption capacity reached 259 mg/g at 19 °C. The mean free energy ranged from 74.53 to 84.52 KJ mol-1, suggesting a chemisorption process. Thermodynamic parameters define a chemical, exothermic, and nonspontaneous mechanism. The above data suggest that Nerium fruit can be used as an excellent biomaterial for practical purification of water without the need to impart chemical functionalization on its surface.

Tetrakis(ethyl-4(4-butyryl)oxyphenyl)porphyrinato zinc complexes with 4,4'-bpyridin: synthesis, characterization, and its catalytic degradation of Calmagite.

This work reports on the synthesis and characterization of a new porphyrins complex:[Zn(TEBOP)(4,4'-bpy)](4,4'-bipyridine)(5,10,15,20-(tetraethyl-4(4-butyryl)oxyphenyl)porphyrinato)zinc(ii) (3). Single crystal X-ray diffraction, photophysical and electrochemical characteristics were studied. The prepared complex, penta-coordinated zinc(ii) porphyrin derivatives shows moderate ruffling distortion and the zinc atom is nearly planar with the porphyrin core. Tolyl and ethyl-4(4-butyryl)oxyphenyl) moieties at the meso positions present a bathochromic shift of the absorption bands, and a notable increase in the absorption coefficient of the Q(0,0) and Q(0,1) bands was observed with a higher fluorescence quantum yield and lifetime compared with the free base porphyrin. The electrochemical investigation shows a reversible reduction of the synthesized complexes. The catalytic power and the adsorption properties of the prepared complexes were studied for Calmagite degradation, an azoic organic dye. The results reveal that the studied compounds could be used as catalysts for the decolourisation of dyes in the presence of H2O2.

Di-chlorido-(5,10,15,20-tetra-phenyl-porphyrinato-κ(4) N)anti-mony(V) hexa-chlorido-anti-monate(V).

The asymmetric unit of the title compound, [Sb(C44H28N4)Cl2][SbCl6], consists of one half of an anti-mony(V) tetra-phenyl-porphyrin complex cation and one half of an hexa-chlorido-anti-monate(V) anion. In the complex cation, the Sb(V) atom lies on an inversion center and is octa-hedrally coordinated by four N atoms from a macrocyclic tetra-phenyl-porphyrinate ligand and two chloride ions. The complex cation has approximately a planar core with a maximum deviation of 0.018 (5) Šfrom the porphyrin mean plane. The average Sb-N distance is 2.062 (11) Å, while the Sb-Cl distance is 2.355 (1) Å. The Sb(V) atom of the anion is also located on an inversion center. The [SbCl6](-) octa-hedron exhibits rhombic distortion characterized by the Sb-Cl bond lengths [2.311 (3), 2.374 (2) and 2.393 (4) Å]. In the crystal, the cations and anions are linked C-H⋯ Cl hydrogen bonds, forming a layer parallel to (211).

Dichlorido(5,10,15,20-tetra-phenyl-porphyrinato-κ(4)N)anti-mony(V) hemi{di-µ-chlorido-bis-[trichloridoanti-monate(III)]} dichloro-methane monosolvate.

The asymmetric unit of the title complex, [Sb(C(44)H(28)N(4))Cl(2)][Sb(2)Cl(8)](0.5)·CH(2)Cl(2), is composed of a Sb(V) complex cation wherein the Sb atom is hexa-coordinated by four N atoms of the pyrrole rings of the tetra-phenyl-porphyrinate (TPP) ligands and two chloride ions, a half di-µ-chlorido-bis-[trichloridoanti-monate(III)] counter-anion and a dichloro-methane solvent mol-ecule. In the cation, the average Sb-N distance is 2.066 (2) Å, while the Sb-Cl distances are 2.3410 (11) and 2.3639 (12) Å. The central unit of the cation, SbN(4)C(20), is far from being planar, with deviations of atoms from the least-squares plane ranging from -0.110 (4) to 0.124 (4) Å. The Sb-Cl distances in the anion, which is located about an inversion center, lie in the wide range 2.3715 (13)-2.7489 (13) Å, the longest distances being between the Sb and bridging Cl atoms. The crystal structure is stabilized by inter-molecular C-H⋯Cl inter-actions involving the cations, the anions and the solvent mol-ecules. The solvent mol-ecule is disordered over two orientations in a 0.901 (13):0.099 (13) ratio.

Tri-µ-oxido-bis-[(5,10,15,20-tetra-phenyl-porphyrinato-κN)niobium(V)].

In the title dinuclear Nb(V) compound, [Nb(2)(C(44)H(28)N(4))(2)O(3)], each Nb atom is seven-coordinated with three bridging O atoms and four N atoms from a chelating tetra-phenyl-porphyrinate anion. The Nb-O bond lengths range from 1.757 (6) to 2.331 (6) Å, and the average (niobium-pyrrole N atom) distance is 2.239 Å. In the dinuclear mol-ecule, the Nb⋯Nb separation is 2.8200 (8) Å, and the dihedral angle between the two porphyrinate mean planes is 5.4 (1)°. Weak inter-molecular C-H⋯π inter-actions are present in the crystal structure.