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1.
Carbohydr Polym ; 337: 122135, 2024 Aug 01.
Article En | MEDLINE | ID: mdl-38710549

The biggest obstacle to treating wound healing continues to be the production of simple, inexpensive wound dressings that satisfy the demands associated with full process of repair at the same time. Herein, a series of injectable composite hydrogels were successfully prepared by a one-pot method by utilizing the Schiff base reaction as well as hydrogen bonding forces between hydroxypropyl chitosan (HCS), ε-poly-l-lysine (EPL), and 2,3,4-trihydroxybenzaldehyde (TBA), and multiple cross-links formed by the reversible coordination between iron (III) and pyrogallol moieties. Notably, hydrogel exhibits excellent physicochemical properties, including injectability, self-healing, water retention, and adhesion, which enable to fill irregular wounds for a long period, providing a suitable moist environment for wound healing. Interestingly, the excellent hemostatic properties of the hydrogel can quickly stop bleeding and avoid the serious sequelae of massive blood loss in acute trauma. Moreover, the powerful antimicrobial and antioxidant properties also protect against bacterial infections and reduce inflammation at the wound site, thus promoting healing at all stages of the wound. The study of biohydrogel with multifunctional integration of wound treatment and smart medical treatment is clarified by this line of research.


Chitosan , Hemostatics , Hydrogels , Polylysine , Wound Healing , Wound Healing/drug effects , Hydrogels/chemistry , Hydrogels/pharmacology , Chitosan/chemistry , Chitosan/pharmacology , Chitosan/analogs & derivatives , Polylysine/chemistry , Polylysine/pharmacology , Animals , Hemostatics/chemistry , Hemostatics/pharmacology , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Mice , Staphylococcus aureus/drug effects , Escherichia coli/drug effects , Humans , Anti-Infective Agents/pharmacology , Anti-Infective Agents/chemistry , Schiff Bases/chemistry , Schiff Bases/pharmacology , Rats
2.
Int J Mol Sci ; 25(9)2024 May 03.
Article En | MEDLINE | ID: mdl-38732229

Oxidovanadium(V) complexes, [(+)VOL1-5] and [(-)VOL1-5], with chiral tetradentate Schiff bases, which are products of monocondensation of S(‒)-3-amino-1,2-propanediol or R(+)-3-amino-1,2-propanediol with salicylaldehyde derivatives, have been synthesized. Different spectroscopic methods, viz. 1H and 51V NMR, IR, UV-Vis, and circular dichroism, as well as elemental analysis, have been used for their detailed characterization. Furthermore, the epoxidation of styrene, cyclohexene, and two monoterpenes, S(‒)-limonene and (‒)-α-pinene, using two oxidants, aqueous 30% H2O2 or tert-butyl hydroperoxide (TBHP) in decane, has been studied with catalytic amounts of all complexes. Finally, biological cytotoxicity studies have also been performed with these oxidovanadium(V) compounds for comparison with cis-dioxidomolybdenum(VI) Schiff base complexes with the same chiral ligands, as well as to determine the cytoprotection against the oxidative damage caused by 30% H2O2 in the HT-22 hippocampal neuronal cells in the range of their 10-100 µM concentration.


Schiff Bases , Schiff Bases/chemistry , Schiff Bases/pharmacology , Schiff Bases/chemical synthesis , Catalysis , Stereoisomerism , Animals , Vanadium/chemistry , Coordination Complexes/chemistry , Coordination Complexes/pharmacology , Coordination Complexes/chemical synthesis , Oxidative Stress/drug effects , Mice , Humans
3.
Int J Biol Macromol ; 267(Pt 1): 131407, 2024 May.
Article En | MEDLINE | ID: mdl-38582463

Succinate dehydrogenase (SDH) is an important inner mitochondrial membrane-bound enzyme involved in redox reactions during the tricarboxylic acid cycle. Therefore, a series of novel chitosan derivatives were designed and synthesized as potential microbicides targeting SDH and precisely characterized by FTIR, 1H NMR and SEM. Their antifungal and antibacterial activities were evaluated against Botrytis cinerea, Fusarium graminearum, Staphylococcus aureus and Escherichia coli. The bioassays revealed that these chitosan derivatives exerted significant antifungal effects, with four of the compounds achieving 100 % inhibition of Fusarium graminearum merely at a concentration of 0.5 mg/mL. Additionally, CSGDCH showed 79.34 % inhibition of Botrytis cinerea at a concentration of 0.1 mg/mL. In vitro antibacterial tests revealed that CSGDCH and CSGDBH have excellent Staphylococcus aureus and Escherichia coli inhibition with MICs of 0.0156 mg/mL and 0.03125 mg/mL, respectively. Molecular docking studies have been carried out to explore the binding energy and binding mode of chitosan and chitosan derivatives with SDH. The analyses indicated that chitosan derivatives targeted the active site of the SDH protein more precisely, disrupting its normal function and ultimately repressing the growth of microbial cells. Furthermore, the chitosan derivatives were also evaluated biologically for antioxidation, and all of these compounds had a greater degree of reducing power, superoxide radical, hydroxyl radical and DPPH-radical scavenging activity than chitosan. This research has the potential for the development of agricultural antimicrobial agents.


Antioxidants , Chitosan , Enzyme Inhibitors , Molecular Docking Simulation , Schiff Bases , Succinate Dehydrogenase , Chitosan/chemistry , Chitosan/pharmacology , Succinate Dehydrogenase/antagonists & inhibitors , Succinate Dehydrogenase/metabolism , Succinate Dehydrogenase/chemistry , Schiff Bases/chemistry , Schiff Bases/pharmacology , Schiff Bases/chemical synthesis , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/chemical synthesis , Enzyme Inhibitors/pharmacology , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/chemical synthesis , Glycine/chemistry , Glycine/analogs & derivatives , Glycine/pharmacology , Anti-Infective Agents/pharmacology , Anti-Infective Agents/chemistry , Anti-Infective Agents/chemical synthesis , Staphylococcus aureus/drug effects , Microbial Sensitivity Tests , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/chemical synthesis , Escherichia coli/drug effects , Antifungal Agents/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/chemical synthesis , Fusarium/drug effects , Botrytis/drug effects , Chemistry Techniques, Synthetic
4.
Int J Mol Sci ; 25(8)2024 Apr 15.
Article En | MEDLINE | ID: mdl-38673948

A series of bench-stable Co(II) complexes containing hydrazone Schiff base ligands were evaluated in terms of their activity and selectivity in carbon-carbon multiple bond transfer hydrogenation. These cobalt complexes, especially a Co(II) precatalyst bearing pyridine-2-yl-N(Me)N=C-(1-methyl)imidazole-2-yl ligand, activated by LiHBEt3, were successfully used in the transfer hydrogenation of substituted styrenes and phenylacetylenes with ammonia borane as a hydrogen source. Key advantages of the reported catalytic system include mild reaction conditions, high selectivity and tolerance to functional groups of substrates.


Boranes , Cobalt , Schiff Bases , Hydrogenation , Cobalt/chemistry , Schiff Bases/chemistry , Catalysis , Boranes/chemistry , Coordination Complexes/chemistry , Alkynes/chemistry , Ammonia/chemistry , Molecular Structure
5.
Nat Commun ; 15(1): 3119, 2024 Apr 10.
Article En | MEDLINE | ID: mdl-38600129

Light-driven sodium pumps (NaRs) are unique ion-transporting microbial rhodopsins. The major group of NaRs is characterized by an NDQ motif and has two aspartic acid residues in the central region essential for sodium transport. Here we identify a subgroup of the NDQ rhodopsins bearing an additional glutamic acid residue in the close vicinity to the retinal Schiff base. We thoroughly characterize a member of this subgroup, namely the protein ErNaR from Erythrobacter sp. HL-111 and show that the additional glutamic acid results in almost complete loss of pH sensitivity for sodium-pumping activity, which is in contrast to previously studied NaRs. ErNaR is capable of transporting sodium efficiently even at acidic pH levels. X-ray crystallography and single particle cryo-electron microscopy reveal that the additional glutamic acid residue mediates the connection between the other two Schiff base counterions and strongly interacts with the aspartic acid of the characteristic NDQ motif. Hence, it reduces its pKa. Our findings shed light on a subgroup of NaRs and might serve as a basis for their rational optimization for optogenetics.


Schiff Bases , Sodium-Potassium-Exchanging ATPase , Sodium-Potassium-Exchanging ATPase/metabolism , Schiff Bases/chemistry , Aspartic Acid , Cryoelectron Microscopy , Glutamic Acid , Rhodopsins, Microbial/metabolism , Sodium/metabolism , Rhodopsin/chemistry
6.
Eur J Med Chem ; 270: 116363, 2024 Apr 15.
Article En | MEDLINE | ID: mdl-38593587

Overcoming multidrug resistance (MDR) is one of the major challenges in cancer therapy. In this respect, Schiff base-related compounds (bearing a R1R2CNR3 bond) gained high interest during the past decades. Schiff bases are considered privileged ligands for various reasons, including the easiness of their preparation and the possibility to form complexes with almost all transition metal ions. Schiff bases and their metal complexes exhibit many types of biological activities and are used for the treatment and diagnosis of various diseases. Until now, 13 Schiff bases have been investigated in clinical trials for cancer treatment and hypoxia imaging. This review represents the first collection of Schiff bases and their complexes which demonstrated MDR-reversal activity. The areas of drug resistance covered in this article involve: 1) Modulation of ABC transporter function, 2) Targeting lysosomal ABCB1 overexpression, 3) Circumvention of ABC transporter-mediated drug efflux by alternative routes of drug uptake, 4) Selective activity against MDR cancer models (collateral sensitivity), 5) Targeting GSH-detoxifying systems, 6) Overcoming apoptosis resistance by inducing necrosis and paraptosis, 7) Reactivation of mutated p53, 8) Restoration of sensitivity to DNA-damaging anticancer therapy, and 9) Overcoming drug resistance through modulation of the immune system. Through this approach, we would like to draw attention to Schiff bases and their metal complexes representing highly interesting anticancer drug candidates with the ability to overcome MDR.


Antineoplastic Agents , Coordination Complexes , Neoplasms , Coordination Complexes/pharmacology , Coordination Complexes/chemistry , Schiff Bases/pharmacology , Schiff Bases/chemistry , Drug Resistance, Multiple , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Neoplasms/drug therapy
7.
Int J Mol Sci ; 25(7)2024 Apr 04.
Article En | MEDLINE | ID: mdl-38612821

Antibiotic resistance is currently a global health emergency. Metallodrugs, especially metal coordination complexes, comprise a broad variety of candidates to combat antibacterial infections. In this work, we designed a new family of Schiff base zinc(II) complexes with iminopyridine as an organic ligand and different inorganic ligands: chloride, nitrate, and acetate. The antibacterial effect of the Zn(II) complexes was studied against planktonic bacterial cells of Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative) strains. The results showed a moderate biocide activity in both types of planktonic bacteria, which arises from the metal complexation to the Schiff base ligand. Importantly, we confirmed the crucial effect of the metal, with Zn(II) improving the activity of Cu(II) counterparts previously reported. On the other hand, the impact of the inorganic ligands was not significant for the antibacterial effect but was relevant for the complex solubility. Finally, as proof of concept of topical antibacterial formulation, we formulated an emulsion containing the most lipophilic Zn(II) complex and confirmed a sustained release for 24 h in a vertical cell diffusion assay. The promising activity of iminopyridine Zn(II) complexes is potentially worth exploring in more detailed studies.


Coordination Complexes , Zinc , Zinc/pharmacology , Ligands , Schiff Bases/pharmacology , Nitrates , Coordination Complexes/pharmacology , Anti-Bacterial Agents/pharmacology , Escherichia coli , Plankton
8.
Int J Mol Sci ; 25(8)2024 Apr 09.
Article En | MEDLINE | ID: mdl-38673744

Schiff bases (SBs) are important ligands in coordination chemistry due to their unique structural properties. Their ability to form complexes with metal ions has been exploited for the environmental detection of emerging water contaminants. In this work, we evaluated the complexation ability of three newly proposed SBs, 1-3, by complete conformational analysis, using a combination of Molecular Dynamics and Density Functional Theory studies, to understand their ability to coordinate toxic heavy metal (HMs) ions. From this study, it emerges that all the ligands present geometries that make them suitable to complex HMs through the N-imino moieties or, in the case of 3, with the support of the oxygen atoms of the ethylene diether chain. In particular, this ligand shows the most promising coordination behavior, particularly with Pb2+.


Coordination Complexes , Metals, Heavy , Molecular Dynamics Simulation , Schiff Bases , Schiff Bases/chemistry , Metals, Heavy/chemistry , Coordination Complexes/chemistry , Density Functional Theory , Ligands
9.
Luminescence ; 39(5): e4739, 2024 May.
Article En | MEDLINE | ID: mdl-38685743

Two new Schiff bases were synthesized from 1-(2,4-dihydroxyphenyl)ethanone and pyridine derivatives. Both compounds were characterized using infrared, UV-Vis., 1H NMR, 13C NMR and mass spectral studies. Density functional theory (DFT) calculations were performed for both the Schiff bases with 6-31G(d, p) as the basis set. Vibrational frequencies calculated using the theoretical method were in good agreement with the experimental values. Both the Schiff bases were highly fluorescent in nature. The cation-recognizing profile of the compounds was investigated in aqueous methanol medium. The Schiff base 4-(1-(pyridin-4-ylimino)ethyl)benzene-1,3-diol (PYEB) was found to interact with Fe(III) and Cu(II) ions, whereas the Schiff base 4,4'-((pyridine-2,3-diylbis(azanylylidene))bis(ethan-1-yl-1-ylidene))bis(benzene-1,3-diol) (PDEB) was found to detect Cu(II) ions. The mechanism of recognition was established as combined excited state intramolecular proton transfer (ESIPT)-chelation-enhanced fluorescence (CHEF) effect and chelation-enhanced quenching (CHEQ) process for the detection of Fe(III) and Cu(II) ions, respectively. The stability constant of the metal complexes formed during the sensing process was determined. The limit of detection for Fe(III) and Cu(II) ions with respect to Schiff base PYEB was found to be 1.64 × 10-6 and 2.16 × 10-7 M, respectively. With respect to Schiff base PDEB, the limit of detection for Cu(II) ion was found to be 4.54 × 10-4 M. The Cu(II) ion sensing property of the Schiff base PDEB was applied in bioimaging studies for the detection of HeLa cells.


Copper , Fluorescent Dyes , Schiff Bases , Schiff Bases/chemistry , Copper/chemistry , Copper/analysis , Fluorescent Dyes/chemistry , Fluorescent Dyes/chemical synthesis , Density Functional Theory , Spectrometry, Fluorescence , Molecular Structure , Ferric Compounds/chemistry , Ferric Compounds/analysis , Heterocyclic Compounds/chemistry , Heterocyclic Compounds/analysis , Humans , Ions/analysis
10.
Int J Mol Sci ; 25(8)2024 Apr 20.
Article En | MEDLINE | ID: mdl-38674119

The aim of this work is research dedicated to the search for new bactericidal systems for use in cosmetic formulations, dermocosmetics, or the production of wound dressings. Over the last two decades, chitosan, due to its special biological activity, has become a highly indispensable biopolymer with very wide application possibilities. Reports in the literature on the antibacterial effects of chitosan are very diverse, but our research has shown that they can be successfully improved through chemical modification. Therefore, in this study, results on the synthesis of new chitosan-based Schiff bases, dCsSB-SFD and dCsSB-PCA, are obtained using two aldehydes: sodium 4-formylbenzene-1,3-disulfonate (SFD) and 2-pyridine carboxaldehyde (PCA), respectively. Chitosan derivatives synthesized in this way demonstrate stronger antimicrobial activity. Carrying out the procedure of grafting chitosan with a caproyl chain allowed obtaining compatible blends of chitosan derivatives with κ-carrageenan, which are stable hydrogels with a high swelling coefficient. Furthermore, the covalently bounded poly(ε-caprolactone) (PCL) chain improved the solubility of obtained polymers in organic solvents. In this respect, the Schiff base-containing polymers obtained in this study, with special hydrogel and antimicrobial properties, are very promising materials for potential use as a controlled-release formulation of both hydrophilic and hydrophobic drugs in cosmetic products for skin health.


Anti-Bacterial Agents , Carrageenan , Chitosan , Schiff Bases , Chitosan/chemistry , Chitosan/analogs & derivatives , Chitosan/pharmacology , Carrageenan/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/chemical synthesis , Schiff Bases/chemistry , Hydrogels/chemistry , Microbial Sensitivity Tests , Solubility
11.
Molecules ; 29(8)2024 Apr 16.
Article En | MEDLINE | ID: mdl-38675623

Since the discovery of cisplatin in the 1960s, the search for metallo-drugs that are more efficient than platinum complexes with negligible side effects has attracted much interest. Among the other metals that have been examined for potential applications as anticancer agents is copper. The interest in copper was recently boosted by the discovery of cuproptosis, a recently evidenced form of cell death mediated by copper. However, copper is also known to induce the proliferation of cancer cells. In view of these contradictory results, there is a need to find the most suitable copper chelators, among which Schiff-based derivatives offer a wide range of possibilities. Gathering several metal complexes in a single, larger entity may provide enhanced properties. Among the nanometric objects suitable for such purpose are dendrimers, precisely engineered hyperbranched macromolecules, which are outstanding candidates for improving therapy and diagnosis. In this review article, we present an overview of the use of a particular Schiff base, namely pyridine-imine, linked to the surface of dendrimers, suitable for complexing copper, and the use of such dendrimer complexes in biology, in particular against cancers.


Antineoplastic Agents , Coordination Complexes , Copper , Dendrimers , Pyridines , Schiff Bases , Copper/chemistry , Dendrimers/chemistry , Humans , Pyridines/chemistry , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Coordination Complexes/chemistry , Coordination Complexes/pharmacology , Schiff Bases/chemistry , Imines/chemistry , Neoplasms/drug therapy , Animals , Chelating Agents/chemistry , Chelating Agents/pharmacology
12.
Acta Crystallogr C Struct Chem ; 80(Pt 4): 129-142, 2024 Apr 01.
Article En | MEDLINE | ID: mdl-38577890

This report presents a comprehensive investigation into the synthesis and characterization of Schiff base compounds derived from benzenesulfonamide. The synthesis process, involved the reaction between N-cycloamino-2-sulfanilamide and various substituted o-salicylaldehydes, resulted in a set of compounds that were subjected to rigorous characterization using advanced spectral techniques, including 1H NMR, 13C NMR and FT-IR spectroscopy, and single-crystal X-ray diffraction. Furthermore, an in-depth assessment of the synthesized compounds was conducted through Absorption, Distribution, Metabolism, Excretion and Toxicity (ADMET) analysis, in conjunction with docking studies, to elucidate their pharmacokinetic profiles and potential. Impressively, the ADMET analysis showcased encouraging drug-likeness properties of the newly synthesized Schiff bases. These computational findings were substantiated by molecular properties derived from density functional theory (DFT) calculations using the B3LYP/6-31G* method within the Jaguar Module of Schrödinger 2023-2 from Maestro (Schrodinger LLC, New York, USA). The exploration of frontier molecular orbitals (HOMO and LUMO) enabled the computation of global reactivity descriptors (GRDs), encompassing charge separation (Egap) and global softness (S). Notably, within this analysis, one Schiff base, namely, 4-bromo-2-{N-[2-(pyrrolidine-1-sulfonyl)phenyl]carboximidoyl}phenol, 20, emerged with the smallest charge separation (ΔEgap = 3.5780 eV), signifying heightened potential for biological properties. Conversely, 4-bromo-2-{N-[2-(piperidine-1-sulfonyl)phenyl]carboximidoyl}phenol, 17, exhibited the largest charge separation (ΔEgap = 4.9242 eV), implying a relatively lower propensity for biological activity. Moreover, the synthesized Schiff bases displayed remarkeable inhibition of tankyrase poly(ADP-ribose) polymerase enzymes, integral in colon cancer, surpassing the efficacy of a standard drug used for the same purpose. Additionally, their bioavailability scores aligned closely with established medications such as trifluridine and 5-fluorouracil. The exploration of molecular electrostatic potential through colour mapping delved into the electronic behaviour and reactivity tendencies intrinsic to this diverse range of molecules.


Colonic Neoplasms , Schiff Bases , Humans , Schiff Bases/chemistry , Models, Molecular , Molecular Conformation , Crystallography, X-Ray , Spectroscopy, Fourier Transform Infrared , Hydrogen Bonding , Phenols
13.
Int J Biol Macromol ; 267(Pt 2): 131429, 2024 May.
Article En | MEDLINE | ID: mdl-38583828

Herein, a novel chitosan Schiff base (CS-FGA) as a sustainable corrosion inhibitor has been successfully synthesized via a simple amidation reaction by using an imidazolium zwitterion and chitosan (CS). The corrosion inhibition property of CS-FGA for mild steel (MS) in a 1.0 M HCl solution was studied by various electrochemical tests and physical characterization methods. The findings indicate that the maximum inhibition efficiency of CS-FGA as a mixed-type inhibitor for MS in 1.0 M HCl solution with 400 mg L-1 reaches 97.6 %, much much higher than the CS and the recently reported chitosan-based inhibitors. Scanning electron microscopy (SEM), atomic force microscopy (AFM), and water contact angle (WCA) results reveal that the CS-FGA molecules firmly adsorb on the MS surface to form a protective layer. The adsorption of CS-FGA on the MS surface belongs to the Langmuir adsorption isotherm containing both the physisorption and chemisorption. According to the X-ray photoelectron spectroscopy (XPS) and UV-vis spectrum, FeN bonds presented on the MS surface further prove the chemisorption between CS-FGA and Fe to generate the stable protective layer. Additionally, theoretical calculations from quantum chemical calculation (DFT) and molecular simulations (MD) were performed to reveal the inhibition mechanism of CS-FGA.


Chitosan , Hydrochloric Acid , Steel , Chitosan/chemistry , Steel/chemistry , Corrosion , Hydrochloric Acid/chemistry , Adsorption , Schiff Bases/chemistry , Solutions , Photoelectron Spectroscopy , Surface Properties
14.
Int J Biol Macromol ; 267(Pt 2): 131635, 2024 May.
Article En | MEDLINE | ID: mdl-38641269

New quaternized salicylidene chitosan Schiff bases (QSCSBs) and their N-octyl derivatives (OQCs) have been synthesized and characterized, aiming to develop innovative antimicrobial and anti-biofilm agents. This research holds immense potential, as these compounds could be utilized as anti-biofouling additives in membrane technology in the future. The synthesis involved the modification of low molecular-weight-chitosan (LMC) through simultaneous Schiff base formation and quaternization processes to create QSCSBs. Subsequently, QSCSBs were catalytically reduced to form quaternized N-benzyl chitosan (QBCs) intermediates, which then underwent nucleophilic substitution reactions affording N-octyl quaternized chitosans (OQCs). Characterization techniques such as elemental, spectral, and microscopic analyses were used to confirm the successful synthesis of these materials. As membrane technology relies on surface charge, QSCSBs and OQCs with large zeta potentials could be used as positively charged additives. Moreover, SEM image revealed the regular distribution of pores and voids across the additives' surfaces raises intriguing questions about their implications for membrane performance. Meanwhile, the superior antibacterial and antibiofilm potential of these materials, particularly QSCSB2 and OQC2, indicate that the utilization of these compounds as anti-biofouling additives in membrane technology could significantly improve the performance and longevity of membranes used in various applications such as water treatment and desalination.


Anti-Infective Agents , Biofilms , Chitosan , Membranes, Artificial , Schiff Bases , Chitosan/chemistry , Chitosan/pharmacology , Chitosan/analogs & derivatives , Chitosan/chemical synthesis , Schiff Bases/chemistry , Schiff Bases/pharmacology , Schiff Bases/chemical synthesis , Biofilms/drug effects , Anti-Infective Agents/pharmacology , Anti-Infective Agents/chemistry , Anti-Infective Agents/chemical synthesis , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Microbial Sensitivity Tests
15.
Spectrochim Acta A Mol Biomol Spectrosc ; 315: 124265, 2024 Jul 05.
Article En | MEDLINE | ID: mdl-38626674

In recent years, extensive research has been directed towards understanding the interactions between various zinc complexes with DNA, specifically delving into their intercalation and binding behaviors. The binding of zinc complexes to DNA is particularly intriguing due to their distinctive intercalating capabilities. This study unveils a remarkable phenomenon observed with a specific Zn complex, ([B-Zn-N3], where B is a Schiff base ligand), during DNA intercalation investigations in the popular DMSO-Water binary solvent mixture. An unanticipated observation revealed time-dependent changes in the UV-visible absorption spectroscopic studies, coupled with the existence of an isosbestic point. This observation questions the stability of the intercalating agent itself during the intercalation process. The emergence of a decomposed product during the intercalation study has been confirmed through various analytical techniques, including CHN analysis, MALDI mass, XPS, Raman spectroscopy, and Powder XRD. The change in the chemical species on intercalation is further substantiated by theoretical studies, adding depth to our understanding of the intricate dynamics at play during DNA intercalation with the [B-Zn-N3] complex in the DMSO-Water system.


DNA , Dimethyl Sulfoxide , Intercalating Agents , Water , Dimethyl Sulfoxide/chemistry , Intercalating Agents/chemistry , DNA/chemistry , DNA/metabolism , Water/chemistry , Spectrum Analysis, Raman , Zinc/chemistry , Spectrophotometry, Ultraviolet , Coordination Complexes/chemistry , Coordination Complexes/metabolism , Schiff Bases/chemistry
16.
Chem Biodivers ; 21(5): e202301667, 2024 May.
Article En | MEDLINE | ID: mdl-38502834

In this paper, a new tridentate Schiff base ligand (L) with nitrogen donor atoms and its cadmium(II) complexes with the general formula of CdLX2 (X=Cl-, Br-, I-, SCN-, N3 -, NO3 -) have been synthesized and characterized by physical and spectral (FT/IR, UV-Vis, Mass, and 1H, 13C NMR spectroscopies) methods. Also nano-structured cadmium chloride and bromide complexes were synthesized by sonochemical method and then used to prepare nanostructured cadmium oxide confirmed by XRD and SEM techniques. Thermal behavior of the compounds was studied in the temperature range of 25 to 900 °C under N2 atmosphere at a heating rate of 20 °C/ min. Moreover, thermo-kinetic activation parameters of thermal decomposition steps were calculated according to the Coats-Redfern relationship. Antimicrobial activities of the synthesized compounds against two gram-positive and two gram-negative bacteria such as Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and two fungi of Candida albicans and Aspergillus niger were investigated by well diffusion method. SEM technique was used to monitor the morphological changes of the bacteria treated with the compounds. The 2,2-Diphenyl-1-picrylhydrazyl(DPPH) and the ferric reducing antioxidant power (FRAP) methods were used to evaluate the antioxidant ability of the ligand and its cadmium(II) complexes. In final, the cytotoxicity properties of the ligand and some cadmium(II) complexes against PC3 cancer cells were evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide) bioassay and nitric oxide (NO) level measurement. The morphological changes of prostate cancer (PC3) cells due to treatment with the ligand and its complexes confirmed their anticancer effectiveness.


Antineoplastic Agents , Antioxidants , Cadmium , Coordination Complexes , Microbial Sensitivity Tests , Antioxidants/pharmacology , Antioxidants/chemical synthesis , Antioxidants/chemistry , Humans , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Cadmium/chemistry , Cadmium/pharmacology , Coordination Complexes/pharmacology , Coordination Complexes/chemistry , Coordination Complexes/chemical synthesis , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Antifungal Agents/pharmacology , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry , Cell Line, Tumor , Drug Screening Assays, Antitumor , Gram-Positive Bacteria/drug effects , Cell Survival/drug effects , Gram-Negative Bacteria/drug effects , Molecular Structure , Schiff Bases/chemistry , Schiff Bases/pharmacology , Schiff Bases/chemical synthesis , Biphenyl Compounds/antagonists & inhibitors , Biphenyl Compounds/chemistry , Biphenyl Compounds/pharmacology , Candida albicans/drug effects , Cell Proliferation/drug effects , Fungi/drug effects , Structure-Activity Relationship , Picrates/antagonists & inhibitors , Anti-Infective Agents/pharmacology , Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/chemistry , Temperature
17.
Sci Rep ; 14(1): 6951, 2024 03 23.
Article En | MEDLINE | ID: mdl-38521876

A series of novel 1,2,3-triazole and chiral Schiff base hybrids 2-6 were synthesized by Schiff base condensation reaction from pre-prepared parent component of the hybrids (1,2,3-triazole 1) and series of primary chiral amines and their chemical structure were confirmed using NMR and FTIR spectroscopies, and CHN elemental analysis. Compounds 1-6 were evaluated for their anticancer activity against two cancer PC3 (prostate) and A375 (skin) and MRC-5 (healthy) cell lines by Almar Blue assay method. The compounds exhibited significant cytotoxicity against the tested cancer cell lines. Among the tested compounds 3 and 6 showed very good activity for the inhibition of the cancer cell lines and low toxicity for the healthy cell lines. All the compounds exhibited high binding affinity for Androgen receptor modulators (PDB ID: 5t8e) and Human MIA (PDB ID: 1i1j) inhibitors compared to the reference anticancer drug (cisplatin). Structure activity relationships (SARs) of the tested compounds is in good agreement with DFT and molecular docking studies. The compounds exhibited desirable physicochemical properties for drug likeness.


Antineoplastic Agents , Schiff Bases , Humans , Molecular Docking Simulation , Schiff Bases/pharmacology , Schiff Bases/chemistry , Triazoles/pharmacology , Triazoles/chemistry , Structure-Activity Relationship , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Molecular Structure
18.
Int J Mol Sci ; 25(6)2024 Mar 15.
Article En | MEDLINE | ID: mdl-38542315

Fluorinated imines (Schiff bases) and fluorinated hydrazones are of particular interest in medicinal chemistry due to their potential usefulness in treating opportunistic strains of bacteria that are resistant to commonly used antibacterial agents. The present review paper is focused on these fluorinated molecules revealing strong, moderate or weak in vitro antibacterial activities, which have been reported in the scientific papers during the last fifteen years. Fluorinated building blocks and reaction conditions used for the synthesis of imines and hydrazones are mentioned. The structural modifications, which have an influence on the antibacterial activity in all the reported classes of fluorinated small molecules, are highlighted, focusing mainly on the importance of specific substitutions. Advanced research techniques and innovations for the synthesis, design and development of fluorinated imines and hydrazones are also summarized.


Anti-Bacterial Agents , Hydrazones , Hydrazones/chemistry , Anti-Bacterial Agents/pharmacology , Imines/pharmacology , Imines/chemistry , Schiff Bases/chemistry , Bacteria
19.
J Mater Chem B ; 12(15): 3719-3740, 2024 Apr 17.
Article En | MEDLINE | ID: mdl-38529844

Elevated glucose levels, multiple pro-inflammatory cytokines and the generation of excessive reactive oxygen species (ROS) are pivotal characteristics within the microenvironments of chronic periodontitis with diabetes mellitus (CPDM). Control of inflammation and modulation of immune system are required in the initial phase of CPDM treatment, while late severe periodontitis requires a suitable scaffold to promote osteogenesis, rebuild periodontal tissue and reduce alveolar bone resorption. Herein, a whole-course-repair system is introduced by an injectable hydrogel using phenylboronic acid functionalized oxidized sodium alginate (OSA-PBA) and carboxymethyl chitosan (CMC). Epigallocatechin-3-gallate (EGCG) was loaded to simultaneously adjust the mechanical property of the OSA-PBA/CMC + EGCG hydrogel (OPCE). This hydrogel has distinctive adaptability, injectability, and ROS/glucose-triggered release of EGCG, making it an ideal drug delivery carrier. As expected, OPCE hydrogel shows favourable antioxidant and anti-inflammatory properties, along with a regulatory influence on the phenotypic transition of macrophages, providing a favourable immune microenvironment. Apart from that, it provides a favourable mechanical support for osteoblast/osteoclast differentiation regulation at the late proliferation stage of periodontal regeneration. The practical therapeutic effects of OPCE hydrogels were also confirmed when applied for treating periodontitis in diabetic rats. In summary, OPCE hydrogel may be a promising whole-course-repair system for the treatment of CPDM.


Catechin , Chronic Periodontitis , Diabetes Mellitus, Experimental , Drug Delivery Systems , Glucose , Reactive Oxygen Species , Glucose/metabolism , Reactive Oxygen Species/metabolism , Chronic Periodontitis/complications , Chronic Periodontitis/drug therapy , Diabetes Mellitus, Experimental/complications , Animals , Rats , Catechin/administration & dosage , Catechin/analogs & derivatives , Catechin/pharmacology , Catechin/therapeutic use , Rheology , Hydrogels , Antioxidants/metabolism , Macrophages/drug effects , Inflammation/drug therapy , Osteoclasts/cytology , Osteoblasts/cytology , Cell Differentiation , Bone Regeneration/drug effects , X-Ray Microtomography , Alveolar Bone Loss/drug therapy , Drug Delivery Systems/methods , Alginates , Schiff Bases , Male , Rats, Sprague-Dawley , RAW 264.7 Cells , Mice
20.
Luminescence ; 39(3): e4712, 2024 Mar.
Article En | MEDLINE | ID: mdl-38481369

In this study, a novel fluorescent chemosensor 1 based on chromone-3-carboxaldehyde Schiff base was synthesized and featured through nuclear magnetic resonance (NMR) and mass spectra. Spectroscopic investigation indicated that the fluorescent sensor showed high selectivity toward Zn2+ over other metal ions and that the detection limit of 1 could reach 10-7  M. These indicated that 1 acted as a highly selective and sensitive fluorescence chemosensor for Zn2+ .


Fluorescent Dyes , Schiff Bases , Spectrometry, Fluorescence/methods , Fluorescent Dyes/chemistry , Schiff Bases/chemistry , Chromones , Zinc
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