Investigation of disulfide-based Schiff base and its mono and binuclear Cu(II) complexes: Green synthesis, crystal structure analysis, Hirshfeld surface analysis, in-vitro biological assessment, DNA binding studies, and computational studies

IF 4 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Structure Pub Date : 2025-03-10 DOI:10.1016/j.molstruc.2025.141997

Thangjam Sanjurani, Sneha Paul, Diganta Kumar Bharali, Pranjit Barman

{"title":"Investigation of disulfide-based Schiff base and its mono and binuclear Cu(II) complexes: Green synthesis, crystal structure analysis, Hirshfeld surface analysis, in-vitro biological assessment, DNA binding studies, and computational studies","authors":"Thangjam Sanjurani, Sneha Paul, Diganta Kumar Bharali, Pranjit Barman","doi":"10.1016/j.molstruc.2025.141997","DOIUrl":null,"url":null,"abstract":"<div><div>A Schiff base, L (6,6′-((1E)-((disulfanediylbis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(2-methoxyphenol)), was synthesised via a heatless condensation of 2,2 diaminodiphenyl disulfide and o-vanillin. Its structure was confirmed by single crystal X-ray diffraction. Hirshfeld surface analysis highlighted significant intermolecular interactions among ligand molecules. Three Cu(II) complexes, [CuL(OAc)].OAc, [Cu2L(SO4)].H2O, and [Cu2L(NO3)], were synthesised using ultrasonic irradiation. Characterization of L and the metal complexes included elemental analysis, molar conductance, magnetic moments, FTIR, UV–Vis, EPR, mass spectrometry, and Job's Analysis. The molar conductance values of the complexes [CuL(OAc)].OAc, [Cu2L(SO4)], [Cu2L(NO3)].NO3 were respectively 25, 14 and 78 Ω−1 cm−1 mol−1, suggesting that [CuL(OAc)].OAc and [Cu2L(NO3)].NO3 are electrolytic in nature. The complexes exhibited paramagnetic behavior with a d⁹ electronic configuration, as indicated by their magnetic moment values ranging from 1.74 to 1.77 BM. Computational methods supported structural and stability assessments. Stability order was [CuL(OAc)].OAc < [Cu2L(NO3)].NO3 < [Cu2L(SO4)].H2O < L. DNA binding studies using UV–vis spectroscopy, fluorescence assays, and viscosity measurements confirmed intercalative binding, with intrinsic binding constants (Kb) and quenching constants (Ksv) values of 105 M−1. [Cu2L(NO3)].NO3 showed the highest antibacterial activity against gram-positive bacteria with a zone of inhibition up to 13 mm and the lowest MIC values. The antioxidant and anti-inflammatory properties of the complex were assessed through DPPH and egg albumin denaturation assays. The complex [Cu2L(NO3)].NO3 exhibited promising activity, with IC₅₀ values of 11.79 µg/mL for the antioxidant assay and 96.13 µg/mL for the anti-inflammatory study. Molecular docking studies on CT-DNA revealed strong binding affinities, with [Cu2L(NO3)].NO3 exhibiting the lowest binding energy of -8.36 kcal/mol. The synthesised compounds demonstrate significant potential for applications in medicinal chemistry and biological studies.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1335 ","pages":"Article 141997"},"PeriodicalIF":4.0000,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Molecular Structure","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0022286025006829","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}

引用次数: 0

Abstract

A Schiff base, L (6,6′-((1E)-((disulfanediylbis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(2-methoxyphenol)), was synthesised via a heatless condensation of 2,2 diaminodiphenyl disulfide and o-vanillin. Its structure was confirmed by single crystal X-ray diffraction. Hirshfeld surface analysis highlighted significant intermolecular interactions among ligand molecules. Three Cu(II) complexes, [CuL(OAc)].OAc, [Cu₂L(SO₄)].H₂O, and [Cu₂L(NO₃)], were synthesised using ultrasonic irradiation. Characterization of L and the metal complexes included elemental analysis, molar conductance, magnetic moments, FTIR, UV–Vis, EPR, mass spectrometry, and Job's Analysis. The molar conductance values of the complexes [CuL(OAc)].OAc, [Cu₂L(SO₄)], [Cu₂L(NO₃)].NO₃ were respectively 25, 14 and 78 Ω⁻¹ cm⁻¹ mol⁻¹, suggesting that [CuL(OAc)].OAc and [Cu₂L(NO₃)].NO₃ are electrolytic in nature. The complexes exhibited paramagnetic behavior with a d⁹ electronic configuration, as indicated by their magnetic moment values ranging from 1.74 to 1.77 BM. Computational methods supported structural and stability assessments. Stability order was [CuL(OAc)].OAc < [Cu₂L(NO₃)].NO₃ < [Cu₂L(SO₄)].H₂O < L. DNA binding studies using UV–vis spectroscopy, fluorescence assays, and viscosity measurements confirmed intercalative binding, with intrinsic binding constants (K_b) and quenching constants (K_sv) values of 10⁵ M⁻¹. [Cu₂L(NO₃)].NO₃ showed the highest antibacterial activity against gram-positive bacteria with a zone of inhibition up to 13 mm and the lowest MIC values. The antioxidant and anti-inflammatory properties of the complex were assessed through DPPH and egg albumin denaturation assays. The complex [Cu₂L(NO₃)].NO₃ exhibited promising activity, with IC₅₀ values of 11.79 µg/mL for the antioxidant assay and 96.13 µg/mL for the anti-inflammatory study. Molecular docking studies on CT-DNA revealed strong binding affinities, with [Cu₂L(NO₃)].NO₃ exhibiting the lowest binding energy of -8.36 kcal/mol. The synthesised compounds demonstrate significant potential for applications in medicinal chemistry and biological studies.

Abstract Image

查看原文本刊更多论文

求助全文

约1分钟内获得全文求助全文

来源期刊

Journal of Molecular Structure 化学-物理化学

CiteScore

7.10

自引率

15.80%

发文量

2384

审稿时长

45 days

期刊介绍： The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including: • Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.) • Chemical intermediates • Molecules in excited states • Biological molecules • Polymers. The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example: • Infrared spectroscopy (mid, far, near) • Raman spectroscopy and non-linear Raman methods (CARS, etc.) • Electronic absorption spectroscopy • Optical rotatory dispersion and circular dichroism • Fluorescence and phosphorescence techniques • Electron spectroscopies (PES, XPS), EXAFS, etc. • Microwave spectroscopy • Electron diffraction • NMR and ESR spectroscopies • Mössbauer spectroscopy • X-ray crystallography • Charge Density Analyses • Computational Studies (supplementing experimental methods) We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.