Medicinal bismuth: Bismuth-organic frameworks as pharmaceutically privileged compounds

Historically organometallic compounds have been used to cure certain diseases with limited applications. Although bismuth belongs to the category of heavy metals, many of its derivatives have found applications in modern drug discovery research, mainly because of its low toxicity and higher bioavailability. Being an eco-friendly mild Lewis acid, compounds having bismuth as a central atom are capable of binding several proteins in humans and other species. Bismuth complexes demonstrated antibacterial potential in syphilis, diarrhea, gastritis, and colitis. Apart from antibacterial activities, bismuth compounds exhibited anticancer, antileishmanial, and some extent of antifungal and other medicinal properties. This article discusses major synthetic methods and pharmacological potentials of bismuth complexes exhibiting in vitro activity to significant clinical performance in a systematic and timely manner.Copyright © 2022 Elsevier Ltd

Low-Dimensional Compounds Containing Bioactive Ligands. Part XX: Crystal Structures, Cytotoxic, Antimicrobial Activities and DNA/BSA Binding of Oligonuclear Zinc Complexes with Halogen Derivatives of 8-Hydroxyquinoline

Two tetranuclear [Zn4Cl2(ClQ)6]·2DMF (1) and [Zn4Cl2(ClQ)6(H2O)2]·4DMF (2), as well as three dinuclear [Zn2(ClQ)3(HClQ)3]I3 (3), [Zn2(dClQ)2(H2O)6(SO4)] (4) and [Zn2(dBrQ)2(H2O)6(SO4)] (5), complexes (HClQ = 5-chloro-8-hydroxyquinoline, HdClQ = 5,7-dichloro-8-hydroxyquinoline and HdBrQ = 5,7-dibromo-8-hydroxyquinoline) were prepared as possible anticancer or antimicrobial agents and characterized by IR spectroscopy, elemental analysis and single crystal X-ray structure analysis. The stability of the complexes in solution was verified by NMR spectroscopy. Antiproliferative activity and selectivity of the prepared complexes were studied using in vitro MTT assay against the HeLa, A549, MCF-7, MDA-MB-231, HCT116 and Caco-2 cancer cell lines and on the Cos-7 non-cancerous cell line. The most sensitive to the tested complexes was Caco-2 cell line. Among the tested complexes, complex 3 showed the highest cytotoxicity against all cell lines. Unfortunately, all complexes showed only poor selectivity to normal cells, except for complex 5, which showed a certain level of selectivity. Antibacterial potential was observed for complex 5 only. Moreover, the DNA/BSA binding potential of complexes 1–3 was investigated by UV-vis and fluorescence spectroscopic methods.

Ligational behavior of bidentate nitrogen–oxygen donor 8‐quinolinolazodye toward Ni2+ and Zn2+ ions: Preparation, spectral, thermal, experimental, theoretical, and docking studies

The 5‐(4‐aryl azo)‐8‐hydroxyquinolines (L1–L3) and their metal complexes with Ni2+ and Zn2+ have been produced. Various spectroscopic techniques have been employed to analyze the ligand and complexes. The structures of the prepared compounds have been confirmed by Fourier transform infrared (FT‐IR), proton nuclear magnetic resonance (1H NMR), molar conductance, magnetic measurements, thermal gravimetric and differential thermal analyses (TG and DTA), and electronic transition. The FT‐IR spectra showed that the ligands are coordinated to the metal ions in a bidentate manner with donor sites of the azomethine‐N and phenolic‐OH. The FT‐IR and UV–Visible spectra were compared with the calculated results and showed a good agreement. The mass spectra concluded that the ligands' molecular weights and the calculated estimated m/z values match well. The complexes contain coordinated and hydrated water as confirmed by the TG results. The complexes are tetrahedral, trigonal bipyramid, and octahedral geometrical structures and act as non‐electrolytes in dimethylformamide (DMF) solvent. Using density functional theory (DFT) at the B3LYP level of theory and the 6‐311G** basis set for the C, H, N, Cl, and O atoms and the LANL2DZ basis set for the Ni and Zn atoms. Natural bond orbital (NBO) analysis was used to compute and describe the natural charge population and precise electronic configuration. The small energy gap between HOMO and LUMO energies suggests that charge transfer occurs within Ni2+ and Zn2+ complexes. The first‐order hyperpolarizability (β) of the complexes and the anisotropy of polarizability (α) values show promising optical properties. The electronic transitions of the prepared complexes were computed by time‐dependent density functional theory (TD‐DFT/PCM) with the B3LYP method using a 6‐31G** basis set. The ethanol polarizable continuum model (PCM) was used to simulate the solvent effect. Utilizing a computer virtual screening technique through molecular docking, the anticipation of binding of 8‐quinolinolazodye derivatives and their complexes with human CORONA virus protein (PDB ID: 5epw) was done. [ FROM AUTHOR] Copyright of Applied Organometallic Chemistry is the property of John Wiley & Sons, Inc. and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full . (Copyright applies to all s.)

Green adherent spectrophotometric determination of molnupiravir based on computational calculations; application to a recently FDA-approved pharmaceutical dosage form.

Molnupiravir is an oral antiviral drug developed to provide significant benefit in reducing hospitalizations or deaths in mild COVID-19. Integrated green computational spectrophotometric method was developed for the determination of molnupiravir. Theoretical calculations were performed to predict the best coupling agent for efficient diazo coupling of molnupiravir. The binding energy between molnupiravir and various phenolic coupling agents, α-naphthol, ß-naphthol, 8-hydroxyquinoline, resorcinol, and phloroglucinol, was measured using Gaussian 03 software based on the density functional theory method and the basis set B3LYP/6-31G(d). The results showed that the interaction between molnupiravir and 8-hydroxyquinoline was higher than that of other phenolic coupling agents. The method described was based on the formation of a red colored chromogen by the diazo coupling of molnupiravir with sodium nitrite in acidic medium to form a diazonium ion coupled with 8-hydroxyquinoline. The absorption spectra showed maximum sharp peaks at 515 nm. The reaction conditions were optimized. Beer's law was followed over the concentration range of 1-12 µg/ml molnupiravir. Job's continuous variation method was developed and the stoichiometric ratio of molnupiravir to 8-hydroxyquinoline was determined to be 1:1. The described method was successfully applied to the determination of molnupiravir in pure form and in pharmaceutical dosage form. The results showed that the proposed method has minimal environmental impact compared to previous HPLC method.

Therapeutic properties and molecular docking study of some phenolic compounds as anti-human lung cancer potential: A biochemical approach.

Chloroxine (5,7-dichloro-8-hydroxyquinoline) is a molecule utilized in some shampoos for the therapy of seborrheic dermatitis of the scalp and dandruff. In this study, we investigated the inhibition effects of 5,7-dichloro-8-hydroxyquinoline and methyl 3,4,5-trihydroxybenzoate compounds on the 3-hydroxy-3-methylglutaryl coenzyme-A (HMG-CoA Reductase) and urease enzymes. We have obtained results for the HMG-CoA Reductase and urease enzymes at the micromolar level. In our study, inhibition result of 5,7-dichloro-8-hydroxyquinoline and Methyl 3,4,5-trihydroxybenzoate on HMG-CoA reductase showed lower values 2.28 ± 0.78 and 33.25 ± 5.04 µg/ml, respectively. Additionally, inhibition result of 5,7-dichloro-8-hydroxyquinoline and methyl 3,4,5-trihydroxybenzoate on urease showed lower values 6.18 ± 1.38 and 8.51 ± 1.35 µg/ml, respectively. Molecular docking calculations were made for their biological activities were compared. In the present work, the structures of the related compounds (1 and 2) were drawn using Gaussian 09 software and done geometry optimization at DFT/B3LYP/6-31G* basis set with aforementioned program. Cytotoxicity potential of these compounds against human lung cancer demonstrated that these compounds had good cytotoxic effects. Both compounds significantly decreased lung cell viability from low doses. In addition, 100 µM dose of all compounds caused significant reductions in lung cell viability. In general, we can say that of the two tested compounds, 5,7-dichloro-8-hydroxyquinoline and methyl 3,4,5-trihydroxybenzoate have cytotoxic effects in all cell types, and this effect is particularly strong in lung cells. Activities were performed at concentrations of 10, 20, 50, 70, and 100 µl and we achieved good results. Lung cell viability (%) value was better at 100 µl concentration and IC50 of them were 54.28 and 48.05 µM.

Ligational behavior of bidentate nitrogen–oxygen donor 8-quinolinolazodye toward Ni2+ and Zn2+ ions: Preparation, spectral, thermal, experimental, theoretical, and docking studies

The 5-(4-aryl azo)-8-hydroxyquinolines (L1–L3) and their metal complexes with Ni2+ and Zn2+ have been produced. Various spectroscopic techniques have been employed to analyze the ligand and complexes. The structures of the prepared compounds have been confirmed by Fourier transform infrared (FT-IR), proton nuclear magnetic resonance (1H NMR), molar conductance, magnetic measurements, thermal gravimetric and differential thermal analyses (TG and DTA), and electronic transition. The FT-IR spectra showed that the ligands are coordinated to the metal ions in a bidentate manner with donor sites of the azomethine-N and phenolic-OH. The FT-IR and UV–Visible spectra were compared with the calculated results and showed a good agreement. The mass spectra concluded that the ligands' molecular weights and the calculated estimated m/z values match well. The complexes contain coordinated and hydrated water as confirmed by the TG results. The complexes are tetrahedral, trigonal bipyramid, and octahedral geometrical structures and act as non-electrolytes in dimethylformamide (DMF) solvent. Using density functional theory (DFT) at the B3LYP level of theory and the 6-311G** basis set for the C, H, N, Cl, and O atoms and the LANL2DZ basis set for the Ni and Zn atoms. Natural bond orbital (NBO) analysis was used to compute and describe the natural charge population and precise electronic configuration. The small energy gap between HOMO and LUMO energies suggests that charge transfer occurs within Ni2+ and Zn2+ complexes. The first-order hyperpolarizability (β) of the complexes and the anisotropy of polarizability (α) values show promising optical properties. The electronic transitions of the prepared complexes were computed by time-dependent density functional theory (TD-DFT/PCM) with the B3LYP method using a 6-31G** basis set. The ethanol polarizable continuum model (PCM) was used to simulate the solvent effect. Utilizing a computer virtual screening technique through molecular docking, the anticipation of binding of 8-quinolinolazodye derivatives and their complexes with human CORONA virus protein (PDB ID: 5epw) was done. © 2022 John Wiley & Sons Ltd.

Cellulose Acetate-Based Electrospun Materials with a Variety of Biological Potentials: Antibacterial, Antifungal and Anticancer.

Novel eco-friendly fibrous materials with complex activities from cellulose acetate and cellulose acetate/polyethylene glycol (CA,PEG) containing 5-chloro-8-hydroxyquinoline as a model drug were obtained by electrospinning. Several methods, including scanning electron microscopy, X-ray diffraction analysis, ultraviolet-visible spectroscopy, water contact angle measurements, and mechanical tests, were utilized to characterize the obtained materials. The incorporation of PEG into the fibers facilitated the drug release. The amounts of the released drug from CA/5-Cl8Q and CA,PEG/5-Cl8Q were 78 ± 3.38% and 86 ± 3.02%, respectively (for 175 min). The antibacterial and antifungal activities of the obtained materials were studied. The measured zones of inhibition of CA/5-Cl8Q and CA,PEG/5-Cl8Q mats were 4.0 ± 0.18 and 4.5 ± 0.2 cm against S. aureus and around 4.0 ± 0.15 and 4.1 ± 0.22 cm against E. coli, respectively. The complete inhibition of the C. albicans growth was detected. The cytotoxicity of the obtained mats was tested toward HeLa cancer cells, SH-4 melanoma skin cells, and mouse BALB/c 3T3 fibroblasts as well. The CA/5-Cl8Q and CA,PEG/5-Cl8Q materials exhibited anticancer activity and low normal cell toxicity. Thus, the obtained fibrous materials can be suitable candidates for wound dressing applications and for application in local cancer treatment.