Role of metal Cu(II) and Ag(I) on molecular structure of 4-amino-N-(2, 6-dimethoxypyrimidin-4-yl) benzenesulfonamide in presence of 3-methyl pyridine: Synthesis, spectral, crystallographic and DNA interaction studies

Abstract Mononuclear and dinuclear copper and silver complexes of bidentate sulfadimethoxine (sdmz), 4-Amino-N-(2,6-dimethoxypyrimidin-4-yl)benzenesulfonamide, ligand in presence of secondary ligand 3-methyl pyridine have been synthesized and characterized by X-ray diffraction and spectroscopic techniques. In crystal structure of mononuclear copper complex [{Cu(C12H12N4O4S).(C6H7N)}.(C6H7N)]; (complex 1), copper occupies special crystallographic position exhibiting a distorted octahedral geometry. A free solvent 3-methyl pyridine per asymmetric unit, completes the crystal structure of copper complex. Silver complex of bidentate sdmz ligand formulated as [Ag2(C12H12N4O4S)2(C6H7N)2]; (complex 2), crystallizes in centrosymmetric space group P21/c with two molecules per asymmetric unit. In the silver complex, silver located in a distorted tetrahedral coordination displaying argentophilic interactions with Ag-Ag separation distance of 2.8177(5) A in molecule A and 2.8227(5) A in molecule B. Secondary ligand plays a decisive role towards formulating coordination geometry as well as the molecular stability of both the complexes. Hirshfeld surface (HS) analysis reveals the quantitative contributions of different interactions on HS. Lipophilicity index (log P value) represents significant biological activity of the molecules, correlates well with the contribution of C H…π interaction. Both the complexes of sdmz ligand are screened for diverse biological activities to investigate the role of Cu(II) and Ag(I) metals on the molecular conformation of sdmz complexes. The interaction ability of both the metal complexes to DNA studied by absorption spectroscopy and viscosity measurement along with molecular docking study, conformed the intercalation mode of DNA binding with comparatively higher binding strength (Kb) for silver complex followed by copper complex and free sdmz ligand. The data of MIC against panel of gram positive and gram negative organisms confirm that both the metal complexes of sdmz possesses better inhibitory activities than that of sdmz ligand. Being less toxic, copper complex exhibits comparatively better response towards the panel of the gram positive and gram negative bacteria except B. subtilis. The observed differences in molecular structures and so on the biological activities of copper and silver complexes of sdmz-picoline ligand, point towards the impact of the respective metals.

• Publication year

  2020

• Venue

  Polyhedron

• Publication date

  2020-09-15

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1016/j.poly.2020.114696
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• DNA interaction, cytotoxicity and molecular structure of cobalt complex of 4‐amino‐N‐(6‐chloropyridazin‐3‐yl)benzene sulfonamide in the presence of secondary ligand pyridine

  2019cited by this paper
• Synthesis, spectroscopic characterization, crystal structure, interaction with DNA, CTAB as well as evaluation of biological potency, docking and Molecular Dynamics studies of N-(3,4,5-trimethoxybenzylidene)-2, 3-dimethylbenzenamine

  2019cited by this paper
• Synthesis and biological evaluation of biotin-conjugated anticancer thiosemicarbazones and their iron(III) and copper(II) complexes.

  2019cited by this paper
• Heteroleptic N,N-donor pyrazole based Pt(II) and Pd(II) complexes: DNA binding, molecular docking and cytotoxicity studies

  2019cited by this paper
• Crystal structure, Hirshfeld surface analysis, spectroscopic and biological studies on sulfamethazine and sulfaquinoxaline ternary complexes with 2,2′-biquinoline

  2018cited by this paper
• Biological Significance of Hetero-Scaffolds Based Gold(III) Complexes.

  2018cited by this paper
• Study on molecular structure, Spectral investigations, NBO, NLO, Hirshfeld surface analysis and Homo-Lumo energy of silver complex of 4-Amino-N-(2,6-dimethoxypyrimidin-4-yl)benzenesulfonamide

  2018cited by this paper
• Synthesis, physicochemical characterizations and in vitro biological evaluations of amide based Zn(II) carboxylates

  2018cited by this paper
• Novel cytotoxic oxovanadium(IV) complexes: Influence of pyrazole-incorporated heterocyclic scaffolds on their biological response

  2017cited by this paper
• Silver sulfadoxinate: Synthesis, structural and spectroscopic characterizations, and preliminary antibacterial assays in vitro

  2015cited by this paper
• Sulfamethazine copper(II) complexes as antimicrobial thermal stabilizers and co-stabilizers for rigid PVC: spectroscopic, thermal, and DFT studies

  2015cited by this paper
• A structural framework of biologically active coumarin derivatives: crystal structure and Hirshfeld surface analysis

  2014cited by this paper
• Anti-proliferative and anti-tumor activity of silver(I) compounds.

  2013cited by this paper
• A silver complex with tryptophan: Synthesis, structural characterization, DFT studies and antibacterial and antitumor assays in vitro

  2013cited by this paper
• Exploration of the medical periodic table: towards new targets.

  2013cited by this paper
• Synthesis and evaluation of gold(III) complexes as efficient DNA binders and cytotoxic agents.

  2013cited by this paper
• Prediction of log P: ALOGPS Application in Medicinal Chemistry Education

  2012cited by this paper
• The prevalence of metal-based drugs as therapeutic or diagnostic agents: beyond platinum.

  2012cited by this paper
• DNA interaction studies of a platinum (II) complex containing an antiviral drug, ribavirin: the effect of metal on DNA binding.

  2012cited by this paper
• Silver(I) and gold(I) complexes with penicillamine: Synthesis, spectroscopic characterization and biological studies

  2012cited by this paper
• Cu(II) and Fe(III) complexes of sulphadoxine mixed with pyramethamine: Synthesis, characterization, antimicrobial and toxicology study

  2012cited by this paper
• Chemical, spectroscopic characterization and antibacterial activities in vitro of a novel gold(I)–ibuprofen complex

  2011cited by this paper
• In vitro bacteriostatic and DNA interaction studies of drug-based mixed-ligand complexes of cobalt(II)

  2011cited by this paper
• DNA interaction, free radical scavenging and in-vitro antibacterial activity of drug-based copper(II) complexes

  2011cited by this paper
• Coordenação de metais a antibióticos como uma estratégia de combate à resistência bacteriana

  2011cited by this paper
• Pt(II) and Ag(I) complexes with acesulfame: crystal structure and a study of their antitumoral, antimicrobial and antiviral activities.

  2010cited by this paper
• Electrostatic potentials mapped on Hirshfeld surfaces provide direct insight into intermolecular interactions in crystals

  2008cited by this paper
• New Ni(II)-sulfonamide complexes: synthesis, structural characterization and antibacterial properties. X-ray diffraction of [Ni(sulfisoxazole)2(H2O)4].2H2O and [Ni(sulfapyridine)2].

  2008cited by this paper
• Solvent inclusion in the structural voids of form II carbamazepine: single-crystal X-ray diffraction, NMR spectroscopy and Hirshfeld surface analysis

  2007cited by this paper
• Effect of silver on burn wound infection control and healing: review of the literature.

  2007cited by this paper
• Copper complexes with heterocyclic sulfonamides: synthesis, spectroscopic characterization, microbiological and SOD-like activities: crystal structure of [Cu(sulfisoxazole)2(H2O)4] . 2H2O.

  2006cited by this paper
• Comparison of protective effects against reactive oxygen species of mononuclear and dinuclear Cu(II) complexes with N-substituted benzothiazolesulfonamides.

  2005cited by this paper
• Oxidative DNA cleavage mediated by a new copper (II) terpyridine complex: crystal structure and DNA binding studies.

  2005cited by this paper
• Synthesis, characterization, and antibacterial activity of three palladium(II) complexes of tetracyclines.

  2005cited by this paper
• Anomaly and correlation of killing in the therapeutic properties of silver (I) chelation with glutamic and tartaric acids.

  2004cited by this paper
• Strong protective action of Copper(II) N-substituted sulfonamide complexes against reactive oxygen species.

  2004cited by this paper
• Characterization of a Cu(II) complex of sulfadimethoxine.

  2003cited by this paper
• Development of novel copper(II) complexes of benzothiazole-N-sulfonamides as protective agents against superoxide anion. Crystal structures of [Cu(N–2-(4-methylbenzothiazole)benzenesulfonamidate)2(py)2] and [Cu(N–2-(6-nitrobenzothiazole)naphthalenesulfonamidate)2(py)2]

  2002cited by this paper
• Crystal and Molecular Structure of Sulfadimethoxine, Polymorph III

  2001cited by this paper
• Hirshfeld Surfaces: A New Tool for Visualising and Exploring Molecular Crystals

  1998cited by this paper
• Refinement of Twinned Structures with SHELXL97

  1998cited by this paper
• BYPASS: an effective method for the refinement of crystal structures containing disordered solvent regions

  1990cited by this paper
• The Characterization of the Silver Compounds of Some Sulfanilamide Derivatives

  1978cited by this paper
• Mechanism of Silver Sulfadiazine Action on Burn Wound Infections

  1974cited by this paper

• Improved antibacterial and anticancer activities of 4-amino-N-pyridin-2-ylbenzenesulfonamide via nickel coordination: Synthesis, Characterization, and Biological Evaluation

  2025cites this paper
• Identification of Imidazo[1,2-a]pyridines-pyrazole-pyran hybrids as Potent Glucose-6-phosphate Dehydrogenase (G6PD) Inhibitors: Synthesis, Molecular docking, DFT studies and ADME prediction

  2024cites this paper
• Visible light-driven photocatalysts, quantum chemical calculations, ADMET-SAR parameters, and DNA binding studies of nickel complex of sulfadiazine

  2023cites this paper
• DNA/BSA binding studies and in vitro anticancer and antibacterial studies of isoelectronic Cu(I)- and Ag(I)-pyridinyl Schiff base complexes incorporating triphenylphosphine as co-ligands

  2023cites this paper
• Ni2+ and Cu2+ complexes of N-(2,6-dichlorophenyl)-N-mesityl formamidine dithiocarbamate structural and functional properties as CYP3A4 potential substrates

  2023cites this paper
• 1-D MOF [Ag2(C10H10N3O3S)2(C4H8N)2]n: photocatalytic treatment, crystallographic evaluation, ADMET parameters, CT-DNA and anticancer activity

  2023influential citation
• Synthesis, Crystal Structure, Thermal, Spectroscopic and Dielectric Properties of Partial Substituted Hybrid Compound: (C6h5nh3)2[Cd1.44zn0.06cl5]

  2023cites this paper
• Structural investigation, quantum chemical calculation, energy framework analysis and MIC studies of silver and cobalt complexes of 4-amino-N-(4, 6-dimethyl-2 pyrimidinyl) benzenesulfonamide in presence of secondary ligand

  2023cites this paper
• Silver-Based 3D-Supramolecular Metal–Organic Framework: Crystallographic Evaluation, Antibiotic, Anticancer, and Visible-Light-Driven Photocatalytic Activity

  2023cites this paper
• Self-Assembly of Gold Nanoparticles Grafted with Amphiphilic Supramolecular Block Copolymers

  2022cites this paper
• Qualitative and quantitative contributions of intermolecular interactions of dinuclear Ag complexes of sulfathiazole and sulfadiazine: X-ray crystallographic, Hirshfeld surface analysis, DFT studies and biological activities

  2022cites this paper
• Lipophilicity, gas-phase optimized geometry, quantum chemical calculations, Hirshfeld surface analysis, energy frameworks, and molecular docking studies of novel (Z)-2-((3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one

  2021influential citation
• Synthesis, crystallographic investigation, DFT studies and Hirshfeld surface analysis of novel bromo hydrazine derivative: (E)-2-(2-bromo-4,5-dimethoxybenzilidene)-1-(4,5-dimethoxy-2-methylphenyl)-1-hydroxyhydrazine

  2021cites this paper
• Cytotoxicity Study

  2021cites this paper
• Molecular structure investigation, Hirshfeld surface analysis and DNA interaction of cadmium complex of 4-amino-N-(1,3-thiazol-2-yl)benzenesulfonamide monohydrate in the presence of the secondary ligand β-picoline

  2021cites this paper
• Coordination behavior of succinylsulfathiazole – Crystal structure of [Cu(SST).(Pyridine)3.H2O]n, DNA interaction and cytotoxic studies

  2021cites this paper
• Antifungal, phyto, cyto, genotoxic and lipophilic properties of three complexes of sulfadimethoxine (HSDM) with Ag(I). Synthesis and characterization of [Ag3SDM(SCN)2]·H2O and [Ag2(SDM)2o-phenanthroline]·H2O

  2020cites this paper
• Combined experimental and computational studies on molecular structure of nickel complex of 4-amino-N-(1, 3-thiazol-2-yl) benzenesulfonamide with coordinated pyridine

  2020cites this paper
• Coordination behavior of dinuclear silver complex of sulfamethoxazole with solvent molecule having static rotational disorder: Spectroscopic characterization, crystal structure, Hirshfeld surface and antimicrobial activity

  2020cites this paper
• Divalent zinc complex of succinylsulfathiazole: Synthesis, spectral, molecular structure, DNA interaction profile and Hirshfeld surface analysis

  2020cites this paper
• Gas-phase DFT studies, quantum chemical calculation and 3D energy framework analysis of novel copper complex of sulfadimethoxine in the presence of secondary ligand 3-methyl pyridine

  2020cites this paper