Azo Dye Ligand Research Articles

Synthesis, characterization, biological activity, and modelling protein docking of divalent, trivalent, and tetravalent metal ion complexes of new azo dye ligand (N,N,O) derived from benzimidazole

The ligand 2-[2′-(benzimidazole)azo]-4,6-dimethyl benzoic acid (BADMB) was employed to create coordination complexes with Pd(II), Co(III), and Pt(IV) ions. A variety of analytical methods were utilized to verify the structures of the synthesized chelates, including microanalysis, 1H NMR, 13C NMR, UV–Vis spectroscopy, FT-IR, mass spectrometry, magnetic susceptibility, molar conductivity, X-ray diffraction (XRD), and thermal analysis. The stoichiometry of the metal complexes was 1:1 [M:L] in the case of both Pd(II) and Pt(IV) complexes while that of the Co(III) complex was 1:2 [M:L]. The results of molar conductivity measurements confirmed that all of the complexes are electrolytes and that they fall within the range 15.74–40.11 Ω−1 cm2 mol−1. The findings indicated that the Co(III) and Pt(IV) complexes adopt an octahedral geometry, with the formulas [Co(BADMB)2]Cl·H2O and [Pt(BADMB)Cl3]·H2O, respectively. In contrast, the Pd(II) complex, represented by the general formula [Pd(BADMB)Cl]·H2O, has a square planar geometry. BADMB acts as a trident (N,N,O) ligand through two nitrogen atoms from the benzimidazole ring and an azo group and one oxygen atom of the carboxyl group. The antimicrobial activity of these compounds was evaluated against a variety of microorganisms, including Streptococcus, Staphylococcus aureus, Penicillium spp., and Aspergillus, as well as multidrug resistance. In addition, all compounds were active against Penicillium spp. fungi compared to the other microorganisms examined. Moreover, the cytotoxic effects of the BADMB, Pd(II), and Pt(IV) complexes were evaluated in a human hepatocellular carcinoma cell line (HepG2) and a normal cell line (WRL68). A molecular docking study was performed using MOE 2015 software and the PDBsum online server. The compounds showed a binding free energy greater than 5 kcal/mol and an RMSD value was present in the range of 1.41 to 2.01 Å, indicating their potential as ligands for further molecular studies with selected targets.

Novel Nanoparticle‐Sized Cu(II), Ru(III), and Th(IV) Chelates Derived From Quinaldine Azo Dye Ligand: DFT Studies, Molecular Docking, and Applications in Drug Development and Catalysis

ABSTRACTThree novel complexes of copper(II), ruthenium(III), and thorium(IV) ions with quinaldine azo dye ligand HL were synthesized in nanoscale. Applying mass spectroscopy, electronic, infrared, 1H NMR, elemental, and thermal investigations, their structures were examined. By using azo nitrogen and hydroxyl oxygen atoms to coordinate as a monobasic bidentate, it was found that the ligand displayed bicapped square antiprism geometry with thorium(IV) metal ion, square pyramidal arrangement in copper(II) complex and octahedral configuration in ruthenium(III) complex. In order to confirm the complexes' geometrical arrangement, theoretical investigations were carried out using DFT/B3LYP/6–311 + G(d,p)/LANLDZ. The dipole moment, geometrical configuration, energetic parameters, and HOMO–LUMO gap of energy have been calculated. The compounds were formed in nanometric forms, as indicated by the mean particle sizes obtained by applying TEM. Based on TEM images for the complexes of copper(II), ruthenium(III), and thorium(IV), their average particle sizes were 11.04, 3.89, and 1.52 nm, respectively. PANC‐1 and A‐549 cells were used in the tests to evaluate the compounds' anticancer activity against the vinblastine reference. The findings confirm the great cytotoxicity effect of the free ligand and its complexes against the investigated cell lines using different doses of the examined compounds. Ru(III) and Cu(II) complexes exhibited cytotoxic effectiveness greater than that of vinblastine. The azo ligand, HL, exhibited the strongest antibacterial activity that is superior to that of the conventional medicines themselves and greater than that of its metal complexes. The most physiologically active compound's ideal conformation was found using molecular docking research, and the manner in which the Ru(III) complex and the enzyme of Panc‐1 link together was determined. It interacts in three different modes with the target receptor (PANC‐1): hydrophobic force, electrostatic force, and H‐bond. In addition to increasing the candidate activity, these interactions can be used to design and predict new, effective compounds. The capacity of the ligand and its complexes to act as heterogeneous catalysts for the oxidation of methyl violet 2B was examined. The ruthenium(III) and thorium(IV) complexes generated the greatest catalytic efficiencies.

Synthesis, Characterization, DFT Calculations, and Pharmacological Activity of Azo Dye Ligand and Its Cu(II) Complex Comprising Nitrogen and Oxygen Donor Atoms

ABSTRACTCoupling the diazonium salt of sulfadiazine with dibenzoylmethane afforded the 4‐(2‐(1,3‐dioxo‐1,3‐diphenylpropan‐2‐ylidene)hydrazinyl)‐N‐(pyrimidin‐2‐yl)benzene sulfonamide ligand (HL). The ligand (HL) and its Cu(II) complex structure have been investigated via magnetic attraction testing, TGA, FTIR, UV–visible, XRD, and CHN analyses. The spectrum data indicate that the ligand demonstrates monobasic bidentate behavior via deprotonating opposite the oxygen atom of the carbonyl (CO) group and linking using the NH of the hydrazone group (NNH). Copper (II) complex present in octahedral structure. A number of TGA steps (Ea, A, ΔH*, ΔS*, and ΔG*) had their dynamical characteristics computed and described using the Coats–Redfern and Horowitz–Metzger formulas. Molecular studio programmer was utilized to perform density functional theory (DFT) calculations in order to investigate the ideal configuration of HL and its Cu(II) complex. The HL and its copper (II) complex exhibited antitumor effects against MCF‐7 and HepG‐2 cell lines. Furthermore, the width of the inhibition zone was employed to evaluate the in vitro antibacterial effect of HL and a specific complex towards Gram‐negative organisms Escherichia coli (E. coli) and Gram‐positive organisms Staphylococcus aureus. The ligand and its Cu(II) complex were examined using both the viscosity and spectrum of absorption of calf thymus DNA binding experiments.

Electrochemical, photocatalytic and biological investigation of carbaldehyde derived azo dye ligand and its Co(II), Ni(II), Cu(II) complexes

2-[(E)-(3-hydroxypyridin-2-yl)diazenyl]-1H-indole-3-carbaldehyde (HDC) a novel azo dye ligand and its Co(Ⅱ), Ni(Ⅱ) and Cu(Ⅱ) complexes have been prepared. The newly synthesized compounds were characterized by physiochemical techniques. The modified electrode, [Co(HDC)2Cl2]/GCE has been prepared by using the synthesized Co(Ⅱ) complex to check the electrocatalytic properties by cyclic Voltammetric (CV) studies. The biologically important molecule, folic acid present in the solution at different concentration has been detected by CV technique. The sensitivity of [Co(HDC)2Cl2]/GCE was 8.366 μAμM−1cm−2 and the limit of detection (LOD) 6.666 μM/L in the linear range 20–140 μM/L. The oxidation current of folic acid increased potentially with scan rate and the regression found was 0.9961, which indicates surface diffusion-controlled nature of process. The synthesized compounds were also screened for antimicrobial, antioxidant and anticancer activities. All the synthesized compounds gave promising results towards biological activities. The photodegradation of Methylene Blue dye was studied under visible light and in the presence of metal complexes to determine the catalytic efficiency of the synthesized metal complexes. The results indicated that the [Co(HDC)2Cl2] exhibited excellent results when compared to [Ni(HDC)2Cl2] and [Cu(HDC)2Cl2] complexes.

Nano-synthesis, characterization, theoretical, biological and catalytic studies of Mn(II), Cu(II), Cd(II), and Th(IV) complexes based on antipyrine azo dye ligand

The design and detailed characterization of the azo dye ligand obtained from the reaction of 4-aminoantipyrine diazonium salt with 3-hydroxybenzaldehyde (HL) and its novel metal chelates with Mn2+, Cu2+, Cd2+ and Th4+ ions have been presented. Utilizing modern spectroscopic and analytical techniques, these complexes were found to adopt an octahedral geometry, demonstrate inner sphere d2sp3 hybridization for Th(IV) complex and outer sphere sp3d2 hybridization for other complexes. Particle sizes calculated using the Debye-Scherrer equation on XRD patterns were 32.05 nm for Mn(II), 34.07 nm for Cu(II), 30.90 nm for Cd(II), and 22.05 nm for Th(IV). These substances' anticancer activity was assessed on human lung cancer cells (A-549) and pancreatic carcinoma cell lines (PANC-1). Cd(II) complex exhibited higher cytotoxicity against the A-549 cell line than the reference drug vinblastine sulfate (VinBLAStine Sulfate) which revealing its potential application as a new anticancer agent. Quantum chemical computations using the DMOL3 module's density functional theory (DFT) and molecular docking studies with the Schrödinger suite demonstrated significant inhibitory effects of the free organic compound and Cu(II) chelate on the FGFR1 protein, crucial for cell development and differentiation. Additionally, the study examined the catalytic activity of HL and its metal chelates in the oxidative degradation of methyl violet 2B dye in presence of H2O2. The order was followed by the pseudo-first-order rate constants: Th(IV) chelate (0.9556 min⁻¹) > HL (0.4911 min⁻¹) > Cu(II) chelate (0.5979 min⁻¹) > Mn(II) chelate (0.2645 min⁻¹) > Cd(II) chelate (0.2280 min⁻¹).

Synthesis of metal(II) acetate complexes with a heterocyclic azo dye ligand: Characterization, geometrical molecular structures, antioxidant, biological activities, DNA binding and molecular docking studies

A series of Cu(II), Co(II), Ni(II), Mn(II), and UO2(II) complexes have been prepared from the ligand 4-(2’,4’-dihydroxybenzaldehyde phenylazo)antipyrine (H2L). FT-IR spectra demonstrated that the ligand under investigation behaves as a bi-and tridentate centre ligand through the phenolic oxygen of aldehydic, azo nitrogen atoms and carbonyl oxygen of antipyrine and forms a stable five- and six-membered chelating ring. From the X-ray crystallographic analysis (XRD) patterns of the ligand and complexes showed the polycrystalline phases are indicated by the multiple diffraction peaks in the 1igand and its complex (5). The HOMO‒LUMO energy gaps (∆E) were used to create theoretical models for the structure and confirmation barriers in molecular systems for the ligand (H2L) and metal complexes. It was found that the Cu(II), Co(II), Ni(II), and Mn(II) complexes have lower values for HOMO‒LUMO energy gaps (∆E), indicating that they are more stable than the 1igand. The biological activities of ligand (H2L) and its metal complexes showed that ligand was stronger antimicrobial and antioxidant agent than its metal complexes. 50 µg/ml H2L caused inhibition zones ranged from 13 to 20 mm against the tested bacteria and 13 to 16 against fungi. In addition, the present study tested metal (II) acetate complexes with a heterocyclic azodye ligand for their application in the textile industry as antimicrobial dyed fabrics. All obtained results confirmed the possibility of using the prepared compounds in different industrial applications. The 1igand (H2L) and its metal complexes showed moderate to strong antimicrobial activities in agar well diffusion, MIC, and antioxidant tests. Ligand and its metal complexes revealed inhibition zones against all tested microbes ranged between 6 to 24 mm. The MIC values of ligand and its metal complexes were recorded at 20 to 30 μg/ml and 30 to 145 μg/ml, respectively. 50 µg/ml of 1igand and its metal complexes was enough to complete inhibit Gram negative E. coli moreover they could inhibit the multidrug resistant bacteria K. pneumoniae and Pseudomonas sp. By molecular docking study, it was found that the complex (1) showed the highest and better binding affinity (-8.38874 and -7.74442 kcal/mol) than other 1igand (H2L) and complexes (2–5) for the breast cancer (3HB5) protein central activity and the colon cancer (2HQ6) protein central activity.

Synthesis and characterizations of a novel trans-Pd(O,N)2 complex with an AZO-dye ligand: Crystal structure, theoretical studies and DNA binding interactions

The transition metal-azo dye complexes have attracted attention in both fundamental and applied research due to their electronic and structural properties, particularly due to their potential to yield new compounds with diverse biological activities and anticancer agents. A novel square planar-trans-Pd(O,N)2 was synthesized with a high yield utilizing a one-pot approach employing (E)-methyl 2-((2-hydroxynaphthalen-1-yl)diazenyl)benzoate as the AZO-dye ligand. In order to analyze their structure and understand their properties. The desired complex was characterized using FT-IR, UV–Vis, NMR, and CHN-EA techniques. Subsequently, theoretical modeling of the complex was performed using MEP/MAC/NPA methodologies. Two methodologies were employed to monitor the coordination process of AZO-ligand with Pd(II): UV–Vis absorption and FT-IR spectrum analysis. The TD-DFT and DFT/IR behaviors were simultaneously assessed to compare the experimental results with theoretical predictions. Furthermore, both SC-XRD and DFT analysis demonstrated that the deprotonated phenolic diazene form of the AZO-ligand attached to the Pd(II) center by utilizing one nitrogen atom of the AZO-ligand and the ionic oxygen of the phenol. The SC-XRD analysis verified the presence of a slightly distorted square-planar geometry around the PdII center in the neutral trans-Pd(O,N)2 complex. All of the oxygen atoms in the complex participated in non-classical C-H….O hydrogen bonding, leading to the formation of novel edge-fused rings R22(24) and R22(12) synthons. These synthons create a 3D-network with a linked parallel matrix. Interestingly, Hirshfeld surface analysis (HSA) stimulation revealed many hot sites on the complex surface, confirming the formation of strong non-classical [C-H....O] interactions. From the observed docking behavior with the DNA, it can be concluded that the trans-Pd(O,N)2 showed superior binding compared to the free AZO-ligand. The results of this work are a contribution to the study of this class of metal complexes and their physicochemical properties and offer promising perspectives for the realization of new works.

Design, synthesis, structural characterization, molecular docking, antibacterial, anticancer activities, and density functional theory calculations of novel MnII, CoII, NiII, and CuII complexes based on pyrazolone-sulfadiazine azo-dye ligand

This study was designed to prepare novel metal chelates obtained from 4-((3-methyl-5-oxo-1-phenyl-pyrazol-4-yl)diazenyl)-N-(pyrimidin-2-yl) benzenesulfon amide (MPSA). They are characterized through CHN-analysis, spectroscopic (1HNMR, FT-IR, UV–Vis), mass, and TG analysis. The FT-IR and UV–visible spectra were related to the computed results and showed good conformity. The mass spectra determined that the ligand's molecular weight and chelates matched well with the found m/z values. The optimization for the studied chelates indicated the formation of distorted octahedral geometry for the prepared chelates. The B3LYP/6–311G** level for the free ligand and the B3LYP/6–311G**-LANL2DZ functional level for the metal ions in chelates were used in density functional theory (DFT) calculations. The results showed that the DFT computations match those of the experimental ones. Using the B3LYP/6–31G(d,p) basis set, TD-DFT/PCM was applied to determine the electronic spectral transitions of the produced compounds. Also, B3LYP/6–31G(d,p) has been utilized to implement the vibrational wavenumbers, and the results are reliable with the innovative ones. The antimicrobial activities of the compounds were experimentally established against a subsection of G+ and G- bacteria. The anticancer activities of the ligand were examined against some cell lines. The MCF7 cell line had the highest activity and was subjected to the anticancer effect of the ligand and its chelates. The cytotoxicity on normal cells was estimated against normal HSF cell lines. The outcomes demonstrated that chelates enhanced their cytotoxic and anticancer properties. Molecular docking mechanisms were done to establish how the obtained substances attach to the breast cancer-targeted protein binding sites,

Novel metal chelates with antipyrine tridentate azo dye ligand for antimicrobial and antitumor applications: Synthesis, structure affirmation, DFT studies, and molecular docking simulation

Novel azo dye ligand [4‐([2,3‐dimethyl‐5‐oxo‐1‐phenyl‐2,5‐dihydro‐1H‐pyrazol‐4‐yl]diazenyl)‐3‐hydroxybenzaldehyde (HL)] and its Co(II), Ni(II), Ru(III), and Zr(IV) metal chelates, were produced and thoroughly described applying modern spectral and analytical approaches. The results showed that HL chelated in tridentate mode, leading to octahedral geometry toward the present metal ions where Co(II), Ni(II), and Zr(IV) complexes exhibit outer sphere hybridization, while the Ru(III) complex exhibits inner sphere hybridization. The calculated particle size values of the complexes reached 41.34, 46.41, 48.67, and 33.37 nm for Co(II), Ni(II), Ru(III), and Zr(IV) chelates, respectively applying the Debye–Scherrer equation on XRD patterns. When compared to its metal complexes, the ligand's antibacterial action against several bacteria demonstrates increased activity. Tests were conducted on A‐549 and PANC‐1 cells to evaluate the compounds' anticancer efficacy against the vinblastine standard. Co(II) nanosized complex exhibited cytotoxicity that was greater than that of the reference medication vinblastine sulfate against A‐549 cell line. It is promising to use the Co(II) complex to create novel anticancer medications. Quantum chemical calculations for ligand and its solid metal complexes were carried out utilizing the DFT of the DMOL3 module. Furthermore, the molecular docking studies were conducted on the A‐549 protein, associated with FGFR1, using the Schrödinger suite. The ligand and the Ru(III) complex exhibit the most potent inhibitory effects on the FGFR1 protein, a receptor tyrosine kinase integral to cellular growth and differentiation.

Synthesis, characterization and analytical study of new azo ligand driven from benzocaine and its metal complexes

The synthesis and spectrum of of a new azo ligand derived from acetylacetone and benzocaine (Ethyl p-aminobenzoate)). Spectral investigations such as 1H NMR,FT.IR, 13C-NMR and Mass spectra were performed to investigate the azo dye ligand's structure. Several physiochemical approaches, FT-IR, electronic spectra, molar conductivity, atom absorption, and magnetic susceptibility were used to identify new complexes with CO(II), and Zn(II) ions Complexes that are all 1:2 [M:L] were formed using the procedures described, and an tetrahedral geometry with sp3 hybridization. At several pH ranges (2–12), the electronic spectra of these azo dyes have been examined in terms of their acid–base properties, which included determining their isosbestic points and protonation and ionization constants. In the other study, azodye were used as an inductor for acid-base titration.

Synthesis, Analysis and Biological assessment of a Novel Coumarin AzoDye Ligand and Its 3d Metal Complexes for Photocatalytic investigationof MB dye

Synthesis, Analysis and Biological assessment of a Novel Coumarin AzoDye Ligand and Its 3d Metal Complexes for Photocatalytic investigationof MB dye

Barbituric acid‐derived azo dye metal complexes: Synthesis, characterization, DFT, and antimicrobial analysis

Two novel metal complexes, C1 and C2, were synthesized through the reaction of an azo dye ligand, obtained by coupling 4‐chloroaniline with 1,3‐dimethyl barbituric acid. The structure of the ligand was confirmed using Fourier‐transform infrared spectroscopy (FTIR) and Nuclear magnetic resonance (NMR). UV–Vis spectroscopy was employed to assess the ligand's sensing ability toward six different metal ions. Comprehensive characterization of the synthesized metal complexes was conducted using elemental analysis, X‐ray photoelectron spectroscopy (XPS), thermogravimetric analysis–difference thermogravimetry (TGA‐DTG), FTIR, UV–Vis spectroscopy, electron paramagnetic resonance (EPR) spectroscopy, and single‐crystal X‐ray diffraction (SC‐XRD). X‐ray analysis revealed octahedral coordination geometry with a 2:1 ligand‐to‐metal ratio and dimethylformamide (DMF) coordination with the metal atom in both complexes. Hirshfeld analysis and 2D fingerprint plots were employed to investigate supramolecular and intermolecular interactions within the crystal system. Density functional theory (DFT/B3LYP) calculations were utilized to compute energy gaps and other important theoretical features. Sensing experiments with tetrabutylammonium fluoride (TBAF) were conducted at a concentration of 1 × 10−5 M. Furthermore, the bioactivity of the synthesized metal complexes and ligand L was evaluated through molecular docking studies against Protein Data Bank (PDB IDs) 4XUY (Staphylococcus aureus) and 3BQW (Aspergillus niger). Also, antimicrobial activity was assessed using the agar well diffusion technique, revealing that complexes C1 and C2 exhibited enhanced antimicrobial activities against the tested organisms compared to the parent azo dye ligand. The computational and experimental bioactivity data are in good agreement with each other.

تحضير ، تشخيص دراسة التحلل الحراري فعالية مضادات الاكسدة لمعقدات العناصر الانتقالية مع ليكاند صبغة الازو

تم إجراء تفاعل ديازوتيزيشن بين 1- (6,4,2-ثلاثي هيدروكسي-فينيل) -إيثانون وأملاح ديازونيوم مما أدى إلى تكوين ليكاند 4- (3-أسيتيل -2،4،6-ثلاثي هيدروكسي-فينيل ازو) -N- (5-ميثيل-إيزوكسازول-3-يل) -بنزين سلفوناميد ، وهذا بدوره يتفاعل مع أيونات المعادن التالية (+V4، +Cr3، +Mn2 و +Cu2) مكونة معقدات مستقرة ثمانية السطوح لكل من الكروم والمنغنيز والنحاس و هرمي مربع القاعدة لـلفناديوم الرباعي .تم اكتشاف إنشاء مثل هذه المعقدات من خلال استخدام الوسائل الطيفية التي تنطوي على الأشعة فوق البنفسجية التي أثبتت الأشكال الهندسية التي تم الحصول عليها ، وأثبت IR تكوين مجموعة الآزو والتنسيق مع أيون المعدن من خلالها. أثبتت دراسات الانحلال الحراري (TGA & DSC) تنسيق بقايا الماء مع أيونات المعادن داخل مجال التناسق وكذلك ذرات الكلور. علاوة على ذلك ، التحليل الجزئي للعنصر و AAS الذي أعطى النتيجة المقابلة مع نتيجة العد النظري. (H &13C-NMR1) والكميات المغناطيسية يمكن أن تشير أيضًا إلى تكوين ليكاند H3L وحدوث التنسيق. تم حساب الثوابت الديناميكية الحرارية (H∆, S∆, G∆). سيتم استخدام طريقة الكسح الجذري DPPH لتقييم الأنشطة المضادة للأكسدة للمركبات التي أظهرت قدرتها المضادة للأكسدة على اخماد الجذور الحرة.

Synthesis, characterization, thermal, anticancer studies, and density functional theory for potentially active pyrimidine‐based complexes

This work aimed to create and characterize some new bioactive chelates of bis azodye ligand, 5‐((2‐hydroxy‐4,6‐dioxo‐1,4,5,6‐tetrahydropyrimidin‐5‐yl)diazenyl)naphthalen‐1‐yl)diazenyl) pyrimidine 2,4,6 (1H,3H,5H)‐trione. Except for the Sm(III) chelate, which exhibited a (3M:1L) molar ratio, all chelates had a (2M:1L) stoichiometry. According to Fourier transform infrared spectroscopy (FT‐IR), azo groups were not included in chelating with all ions except Sm(III), where just one azo group was coordinated. With the Ni(II) and Zn(II) ions, the ligand behaved as OON‐tridentate moiety; with the Co(II) and Cu(II) ions, it behaved as ON‐bidentate moiety. Co(II) and Cu(II) chelates had square planar structure, and Ni(II) and Zn(II) chelates had square pyramidal geometry. The chelates had greater thermal stability than the uncoordinated ligand due to the chelate's structure. [Sm3(H4L)(OH)7(NO3)2.H2O].4.5EtOH exhibited the maximum thermal stability, which may be due to the large number of solvent molecules and the high number of chelate rings. With the exception of the Sm(III) chelate, all of the examined chelates were more cytotoxic against MCF‐7 and Hep‐G2 cells than their parent ligand. With the exception of the Zn(II) chelate, which demonstrated activity on Hep‐G2 rather than MCF‐7, the effects of each metal chelate on the two cells were nearly equivalent. All of the studied chelates, especially Zn(II) and Co(II), were potent as antioxidants more than the native ligand. To support experimental findings, density functional theory (DFT) studies were performed via the CAM‐B3LYP/LanL2DZ method, and the geometry of the ligand and its chelates had been validated.

Analyzing the structure of the metal complexes of biologically active azo dye ligand

A novel azo dye ligand was created by diazotizing 4‐aminoantipyrine and then coupling it with 2‐aminophenol as part of a methodical investigation of physiologically active compounds, 4‐aminoantipyrine. The novel complexes containing Cr(III), Fe(III), Mn(II), Co(II), Ni(II), Zn(II), Cu(II), and Cd(II) were created from the target ligand (L). The structures of the ligand and metal complexes were verified by elemental analyses, thermogravimetric analysis–difference thermogravimetry (TGA‐DTG), conductivity measurements, infrared (IR), UV–Vis, 1H‐nuclear magnetic resonance (NMR), X‐ray diffraction (XRD), and mass spectrometry. Using the Gaussian 09 tool, the density functional theory (DFT)/B3LYP method was utilized to compute the energy gaps and other important theoretical features. Also, the newly synthesized azo dye ligand, in comparison with metal complexes, was screened for its antimicrobial activity. The crystal structures of Staphylococcus aureus and Bacillus subtilis as gram‐positive bacteria, Salmonella sp. and Escherichia coli as gram‐negative bacteria, and fungal (Aspergillus fumigatus and Candida albicans) species were compared with the produced azo dye and its metal complexes via molecular docking. Most of the complexes exhibited greater antimicrobial activities against these organisms than did the original azo dye ligand.

Synthesis, characterization, biological applications of novel coumarine azo-dye ligand and its transition metal complexes: Simultaneous electrochemical detection of paracetamol and uric acid

Coumarin is a well-known pharmacophore and structure with wide-ranging applications. It is a member of the heterocyclic family. Furthermore, metal complexes can improve the drug action and efficacy of organic therapeutic agents. Various physical and spectroscopic procedures are used to synthesize and characterize the novel azo dye ligand (HDM) and its transition metal complexes for their geometrical composition. The well diffusion method and DPPH technique were used to measure the antimicrobial potency and antioxidant levels, respectively. MTT analysis was performed to assess anticancer activity for Hela and P53 cell lines. CV and DPV were used to confirm the electro catalytic ability of [Co(HDM)2(H2O)2]/GCE (modified electrode) towards various concentrations of paracetamol and uric acid. The modified electrode performed well as a sensor with paracetamol and uric acid concentration of CV 10 to 80 µmol/L and 10 to 100 µmol/L; DPV 5 to 20 µmol/L and 5 to 20 µmol/L respectively and LOD values CV 3.333, 3.333 µmol/L; DPV 1.666, 1.666 µmol/L. This electrode has a sensitivity of CV 0.02287; DPV 0.0137 µAµM−1 for paracetamol and CV 7.558; DPV 0.01674 µAµM−1 for uric acid. The results showed that, when compared to bare glassy carbon electrode, the modified electrode had a good electro catalytic activities, high selectivity and sensitivity to the redox reaction of paracetamol and uric acid.

Synthesis, characterization and theoretical aspects of copper and zinc divalent ion complexes with azo dye derived from 4,5-diphenylimidazole

Azo dye ligand derived from 4,5-diphenyl imidazole and 4,4-diaminodiphenylmethane was synthesized by diazomium coupling reaction. In this reaction an amine (4,4-diaminodiphenylmethane was converted to the diazonium salt and coupled with 4,5-diphenyl imidazole. The bright coloured Cu(II) and Zn(II) complexes with this ligand were synthesized by refluxing the latest with both metals chloride salts. The prepared compounds were characterized by 1H-NMR, 13C-NMR, FTIR, UV-Visible, molar conductivity and atomic absorption. By the infrared data, the coordination between copper and zinc ions and the azo ligand achieved through the nitrogen of the azo group and one of the nitrogen atoms in the imidazole ring. By the molar conductivity test, the non- electrolytic nature of both complexes was also confirmed. The suggested structure for these complexes is octahedral. Using density functional theory (DFT) some theoretical data was obtained for the synthesized complexes. The obtained data include the highest occupied and the lowest unoccupied molecular orbitals energy (HOMO and LUMO), electron density, thermodynamic functions (ΔG°, ΔS°, ΔH°, ΔE°), ionization potential (IP), electron affinity (EA), electrophilicity(ὠ), electronegativity (En), chemical hardness (η) and dipole moment (μ). According to these studied parameters some properties of the two complexes were explained and discussed.
 KEY WORDS: Cu(II) and Zn(II) complexes, Azo ligand, 4,5-Diphenylimidazole, 4,4-Diaminodiphenylmethane, Theoretical study
 Bull. Chem. Soc. Ethiop. 2024, 38(2), 313-323. 
 DOI: https://dx.doi.org/10.4314/bcse.v38i2.4

Guanine Metal Complexes: Spectroscopic Studies, Dying Performance and as Indicator

Azo dyes are the most common and widely used dyes, accounting for more than half of each year's dyes. In this work, a complete description of a new innovative series of compounds with the elements [Ag (I), Zn (II)] generated from the guanine azo dye ligand (GAB) 8-[1-(3-carboxy) azo] guanine has been studied. The structural formula was studied using several physicochemical analyses and spectroscopic techniques (FT-IR spectra, UV-Vis). The FTIR spectrum of the ligand (GAB) was compared to the spectra of the metal ion complexes formed to determine its identity. Chelating caused some changes in the spectra of the complexes to appear to demonstrate that they could be linked to the ligand. The complexes have a tetrahedral geometry shape, the ligand functions as a bidentate ligand, and thermogravimetric analysis (TGA) is used to measure the thermal stability of compounds. The findings and equation presented by the analytical data seemed to be in good accord with the conclusions of the thermogravimetric investigation, which demonstrated that the disintegration of the ligand (GAB) and its complexes occur in multiple steps. The configuration that follows weakens thermal stability: GAB(35.52%)>[Ag(GAB)(H2O)2]NO3.2H2O(34.6%)>[Zn(GAB)Cl2].H2O(31.54%), and the complexes have tetrahedral geometry shape. Furthermore, elemental analysis, mole ratio, and the mole ratio of each complex (1:1) (M:L). The ligand was effective as an acid-base indicator when the pH changed; they exhibited a striking color change, similar to how the ligand (GAB) and its complexes can be used to dye wool textiles due to their wide range of colors. It investigated how well the ligand (GAB) and its complex worked as a wool dye. The ligand GAB and its metal complexes were used to color most of the protein filaments in wool fiber, which have a complex structure with amino and carboxyl groups and colors ranging from orange to green.

Synthesis and Structural Views on New Azo Ligand and Its Metal Complexes with Some of their Application

In this work, we presented a study of the structural formula for a new series of complexes with Ag(I), Cu(II), Zn(II), and Cd(II) derived from the guanine azo dye ligand 2-amino-8-((3-hydroxyphenyl)diazinyl)-1,7-dihydro-6H-purin-6-one (HAG), which is investigated using various physicochemical analyses, spectroscopic techniques (FT-IR, U.V-VIS, and 1H NMR), thermogravimetric analysis (TGA). In addition, elemental analyses, magnetic susceptibility, and molar conductance measurements were all stabilized. As well as the mole ratio, stability constant, and Gibbs free energy were studied for all complexes, where they showed high stability and spontaneous synthesis. The Cu(II) complex was suggested to have octahedral stereochemistry, while the Ag(I), Zn(II), and Cd(II) complexes were suggested to have tetrahedral stereochemistry. The ligand has been demonstrated to be a useful acid-base indicator, and it has been shown that the ligand (HAG) and its complexes exhibit high photostability and have various colors that can be used to dye wool materials.

Synthesis, Characterization, Thermal Analysis Study and Antioxidant Activity for Some Metal Ions Cr (III), Fe (III), Mn (II) and Pd(II) Complexes with Azo Dye Derived from p-methyl-2-hydroxybenzaldehyde

A new Azo Dye ligand HL was 4-((3-formyl-2-hydroxyphenyl)diazenyl)-N-(5-methylisoxazol-3-yl)benzenesulfonamide,this synthesized ligand was used for complexation with different metal ions like Cr(III), Fe(III), Mn(II) and Pd(II) by using a molar ratio of ligand: metalas 1:1. Resulted compounds were characterized by NMR (1H and 13C), UV–vis spectroscopy, TGA, DSC, FT‐IR, MS, elemental analysis, magnetic moment and molar conductivity studies. The results showed that the geometrical structural were octahedral geometries for the Cr(III), Mn(II) and Fe(III) complexes, square planer for Pd(II) complex. The antioxidant activities of the prepared compounds were assessed by using 1.1‐diphenyl‐2‐picrylhydrazyl as the free radical, and the results showed that the complex azo dye were found to possess potent antioxidant activity. The structure–activity relationship of the ligand and its complexes indicates that the presence of electron‐donating moieties, such as Cr(III), Mn(II) and Fe(III), in the chemical structure increases the antioxidant activity, whereas the Pd(II) complexes diminished the antioxidant activity, indicating the superior activity of the hydroxyl radical (OH·) over the superoxide radical.