Experimental and theoretical studies on new organotin(IV) complexes with oxygen donor ligand: DNA binding, molecular docking and antimicrobial activity

Khan, Rabbia; Rani, Sonia; Tariq, Muhammad; Rasool, Faiz; Hussain, Ajaz; Mahmood, Khalid; Asif, Hafiz Muhammad; Usman, Muhammad; Sirajuddin, Muhammad

doi:10.1007/s12039-023-02207-9

J Chem Sci

2023

DOI: 10.1007/s12039-023-02207-9

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Experimental and theoretical studies on new organotin(IV) complexes with oxygen donor ligand: DNA binding, molecular docking and antimicrobial activity

Rabbia Khan,

Sonia Rani,

Muhammad Tariq

et al.

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2024

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Cited by 6 publications

References 40 publications

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Exploring Antiplasmodial, Antimicrobial, Antioxidant, and Docking Profile: Conjugating Organotin Moiety With Hydrazones for Enhanced Efficacy

Boora,

Devi,

Kumar

2024

Applied Organom Chemis

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In the 21st century, pathogenic deformities contribute significantly to global morbidity and mortality. Our research investigates the antimalarial, antimicrobial, and antioxidant activities of newly synthesized hydrazones and their organotin (IV) complexes, derived from 2‐benzoyl‐1H‐indene‐1,3(2H)‐dione and 2‐phenoxypropanehydrazide/2‐(2,4‐dichlorophenoxy)propanehydrazide. Structural confirmation was achieved through multinuclear nuclear magnetic resonance (NMR), UV–Vis, IR, HRMS, thermogravimetric analysis (TGA), and scanning electron microscopy (SEM)‐energy‐dispersive X‐ray analysis (EDAX), revealing tridentate coordination of ligands to the tin metal via imine nitrogen and two enolic oxygens, forming a pentacoordinated geometry. The SEM analysis revealed that hydrazone ligand (1) exhibits a rectangular bar‐like microstructure, whereas its complex (5) shows a rugged surface with distinct territorial patches. Compounds (5) [Bu2SnL1] and (6) [Ph2SnL1] stood out with significant bioactivity, with antimalarial IC50 values ranging from 0.54 ± 0.07 to 0.67 ± 0.06 μM and antioxidant IC50 values from 4.39 ± 0.02 to 4.67 ± 0.01 μM. Additionally, compounds (6) [Ph2SnL1] and (10) [Ph2SnL4] exhibited the highest antimicrobial activity, with MIC values ranging from 0.0045 to 0.0042 μmol/mL, respectively, comparable to standard drugs. Complementing the experimental data, in silico molecular docking studies were performed on the most effective ligand (1) [H2L1] and its phenyl complex (6) [Ph2SnL1] with Plasmodium falciparum lactate dehydrogenase, revealing binding energies of −6.0 and −6.9 kcal/mol, respectively, and corroborating the experimental findings. Further, comprehensive absorption, distribution, metabolism, excretion, and toxicity (ADMET) evaluations were performed on each compound to gauge their suitability as drug candidates and potential for toxicity.

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Exploring Antiplasmodial, Antimicrobial, Antioxidant, and Docking Profile: Conjugating Organotin Moiety With Hydrazones for Enhanced Efficacy

Boora,

Devi,

Kumar

2024

Applied Organom Chemis

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Comprehensive Investigation of Organotin(IV) Complexes Derived From a Novel Schiff Base: Synthesis, Characterization, Antioxidant, ADME Profiling, and In Vitro Biological Evaluation

Abbas,

Zahid,

Parveen

et al. 2024

Applied Organom Chemis

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Six organotin(IV) complexes (1–6) were synthesized, following the general formulas as R2Sn(L)Cl and R3Sn(L), have been reported. In these complexes, L represents a Schiff base prepared by the reaction of phenylhydrazine with 5‐bromo‐2‐hydroxybenzaldehyde, and R = Me, n‐Bu, Ph. Various analytical techniques were employed to characterize and determine the structure of the newly synthesized compounds. The techniques, including the elemental analysis, molar conductivity measurements, UV–visible, FT‐IR, NMR spectroscopy, and mass spectrometry. Spectroscopic analysis suggested that the ligand (4‐bromo‐2‐[(2‐phenylhydrazinylidene)meth‐yl]phenol) (HL) coordinates with the tin (Sn) metal through its phenolic oxygen (O) and azomethine nitrogen (N) atoms. Molar conductivity measurements indicated that all the synthesized compounds are nonelectrolytes. The percent CHN analysis data also corroborates the spectroscopic results. UV–Vis spectra revealed the mode of transitions of electrons due to the π–π* transitions, n–π* transitions, and transitions involving charge transfer from the ligand to the metal, which occurred in recently developed ligand and organotin (IV) complexes. The emergence of additional bands in the FT‐IR spectra of complexes (1–6), attributed to ν(Sn–O) and ν(Sn–N), which were absent in the precursor, offers further proof for the synthesis of these complexes. NMR spectral studies give information about the nature and number of all protons having the same or different chemical environment in the structure of all the compounds being reported in this study. The potential to be used as bioactive compounds in the future was assessed by performing the biological activities (antimicrobial and antioxidant) of these synthesized compounds and the DPPH free radical method for the antioxidant potential of these compounds. Based on these assessments, it can be concluded that the ligand's efficiency improves upon complexation, primarily due to the type and quantity of alkyl groups attached to the [Sn] metal atom. ADME and studies were conducted to forecast the biological effectiveness of the ligand and its metal complexes. Among these, the ligand and complexes 1 and 4 are prioritized for docking with Aspergillus flavus, Bacillus subtilis, and Escherichia coli. The complexes 1 and 4 were found biologically more effective towards different microbes. The Antioxidant activity of the test complexes follows this trend: Methyltin(IV) complexes exhibit the lowest activity, whereas butyltin(IV) and phenyl(IV) complexes exhibit higher levels of activity, with phenyltin(IV) showing the most significant activity.

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From synthesis to bioactivity: Characterization, crystallography, antimalarial and antimicrobial activities of hydrazone-derived organotin(IV) complexes

Boora,

Devi,

Lal

et al. 2024

Inorganica Chimica Acta

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Experimental and theoretical studies on new organotin(IV) complexes with oxygen donor ligand: DNA binding, molecular docking and antimicrobial activity

Cited by 6 publications

References 40 publications

Exploring Antiplasmodial, Antimicrobial, Antioxidant, and Docking Profile: Conjugating Organotin Moiety With Hydrazones for Enhanced Efficacy

Exploring Antiplasmodial, Antimicrobial, Antioxidant, and Docking Profile: Conjugating Organotin Moiety With Hydrazones for Enhanced Efficacy

Comprehensive Investigation of Organotin(IV) Complexes Derived From a Novel Schiff Base: Synthesis, Characterization, Antioxidant, ADME Profiling, and In Vitro Biological Evaluation

From synthesis to bioactivity: Characterization, crystallography, antimalarial and antimicrobial activities of hydrazone-derived organotin(IV) complexes

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