Structural studies of diethyltin(IV) derivatives and their biological aspects as potential antitumor agents against <i>Agrobacterium tumefacien cells</i>

Hussain, Mukhtiar; Zia-ur-Rehman, .; Hanif, Muhammad; Altaf, Muhammad; Aziz-Ur-Rehman, -; Ali, Saqib; Cavell, Kingsley J.

doi:10.1002/aoc.1777

Cited by 20 publications

(4 citation statements)

References 25 publications

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“…The data is given in Tables 10 and 11 . It was found that the organotin(IV) complexes possessed significantly higher activity towards the tested organisms than the free ligands as reported earlier [ 12 , 14 , 35 ]. The coordination of the ligand with chlorodi- or triorganotin(IV) moieties has appreciably enhanced the activities of the product complexes.…”

Section: Resultssupporting

confidence: 80%

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Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic Acid

Hussain¹,

Ali

Shahzadi

et al. 2014

Bioinorganic Chemistry and Applications

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Organotin (IV) carboxylates with the general formulae R2Sn(Cl)L [R = Me (1), n-Bu (2), Ph (3)] and R3SnL [R = Me (4), Ph (5)] have been synthesized by the reaction of 4-piperidinecarboxylic acid (HL) with KOH and R2SnCl2 (R = Me, n-Bu, Ph)/R3SnCl (R = Me, Ph) in methanol under stirring conditions. The metal ligand binding site, structure, and stability of complexes have been verified by FT-IR, (1H, 13C) NMR, EI-MS technique, and semiempirical study. The FT-IR data indicate the bidentate chelating mode of the carboxylate ligand which is also confirmed by semiempirical study. In solution state, five and four coordinated geometry around tin was confirmed by NMR spectroscopy. The EI-MS data agreed well with the molecular structure of the complexes. Thermodynamic parameters and molecular descriptors were calculated by using semiempirical PM3 method. HOMO-LUMO calculations show that chlorodiorganotin complexes are more susceptible to nucleophilic attack as compared to triorganotin complexes. Computed negative heat of formation indicates that complexes 1–4 are thermodynamically stable. The organotin(IV) carboxylates displayed powerful antimicrobial activities against various strains of bacteria and fungi and their minimal inhibitory concentration were also evaluated. The complexes exhibited comparatively higher hemolytic activity as compared to free ligand.

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Section: Resultssupporting

confidence: 80%

“…On the other hand, organotin(IV) compounds have been tested for their in vitro activity against a large variety of tumor cell lines [ 14 ] and have been found to be as effective as or better than traditional heavy metal anticancer drugs such as cisplatin.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic Acid

Hussain¹,

Ali

Shahzadi

et al. 2014

Bioinorganic Chemistry and Applications

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“…The synthesis and characterization of organotin(IV) complexes of Schiff base ligands have always attracted the attention of inorganic chemists and is well established in the literature [10][11][12][13][14]. Organotin(IV) complexes have been extensively studied due to their beneficial biological activities as well as their wide industrial and agricultural applications [15][16][17][18][19][20][21]. de Sousa et al have reported organotin(IV) derivatives of 2hydroxyacetophenone-N(4)-phenylthiosemicarbazone and found that the Sn(IV) atom adopts a strongly distorted trigonal bipyramidal configuration [22].…”

Section: Introductionmentioning

confidence: 99%

Organotin(IV) complexes of 2-hydroxyacetophenone-N(4)-cyclohexylthiosemicarbazone (H2dact): Synthesis, spectral characterization, crystal structure and biological studies

Affan

Salam

Ahmad

et al. 2012

Inorganica Chimica Acta

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Sn NMR spectral studies. The molecular structure of complex (5) has also been determined by single-crystal X-ray diffraction. The crystal structure of complex (5) showed that the ligand is doubly deprotonated at the oxygen and sulfur atoms and is coordinated to the tin(IV) atom through thiolate-S, azomethine-N and phenoxide-O atoms. X-ray diffraction studies indicated that complex (5) is a monomer and the central tin(IV) atom is five coordinated in a distorted trigonal bipyramidal geometry. The cytotoxicity of the ligand (1) as well as its organotin(IV) complexes (2-5) was studied against Artemia salina. The in vitro antibacterial activities of these compounds were also evaluated. The screening results have shown that the organotin(IV) complexes (2-5) have better antibacterial activity than the free ligand. Furthermore, it has been shown that diphenyltin(IV) derivative (5) exhibits significantly better activity than the monoorganotin(IV) derivatives (2-4).

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“…The biological activity of organotin compounds is greatly influenced by the structure of the molecule, molecular mass and conceivably by the nuclearity. The role of a ligand is also quite significant in transportation of organotin moiety to the site of action …”

Section: Decomposition Kineticsmentioning

confidence: 99%

Synthesis, characterization, thermal, computational and biological activity studies of new potential bioactive diorganotin (IV) nitrosubstitutedhydroxamates‐A comparative study

Choudhary

Bhatt

Dash

et al. 2020

Applied Organom Chemis

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The new diorganotin (IV) complexes of composition [Me2SnCl(3,5‐(NO2)2C6H2(OH)CONHO)] (I) and [n‐Bu2SnCl(3,5‐(NO2)2C6H2(OH)CONHO)] (II) have been synthesized by the reactions of Me2SnCl2 and n‐Bu2SnCl2 with potassium 3,5‐dinitrosalicylhydroxamate [3,5‐(NO2)2C6H2(OH)CONHOK]‐ a ligand of biological significance bearing –NO2 and –OH substituents presumed to yield complexes with efficient bioactivity. The complexes have been characterized by elemental analyses, IR, 1H, 13C and 119Sn NMR and mass spectrometry in order to study the ligational behavior and probale geometry around tin as the ligand might show different bonding modes and geometry in complexes. The geometries of (I) and (II) have been computed using B3LYP/6–31 + G(d,p) set by DFT method and the vibrational frequencies, 1H and 13C NMR spectra compared with the experimental data. A comparison of computed bond lengths (C=O, C‐N, and N‐O) of (I) and (II) with that of free ligand, the Sn‐O bond lengths, bond angles coupled with 119Sn NMR and IR spectral data have suggested coordination through carbonyl and hydroxamic oxygens (O, O coordination) displaying five‐coordinate distorted trigonal‐bipyramidal geometry around tin. The thermal behavior of (I) and (II) has been studied by thermogravimetric techniques (TGA, DTG, DTA) and various kinetic parameters have been calculated. The electrochemical behavior of ligand, (I) and (II) studied by cyclic voltammetric technique has shown ligand centered redection. The HOMO‐LUMO energies and orbitals, global reactivity descriptors, various thermodynamic parameters and dipole moment (μ) have been computed to determin the molecular properties of complexes. The in vitro antimicrobial activity assay against bacteria and fungi by MIC method has indicated higher potency of (I) than (II). The in vitro cytotoxicity on human muscle rhabdomyosarcoma (RD) by MTT method and the antioxidant potential by DPPH free radical scavenging showed higher inhibitory effect of complexes than ligand.

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Structural studies of diethyltin(IV) derivatives and their biological aspects as potential antitumor agents against Agrobacterium tumefacien cells

Cited by 20 publications

References 25 publications

Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic Acid

Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic Acid

Organotin(IV) complexes of 2-hydroxyacetophenone-N(4)-cyclohexylthiosemicarbazone (H2dact): Synthesis, spectral characterization, crystal structure and biological studies

Synthesis, characterization, thermal, computational and biological activity studies of new potential bioactive diorganotin (IV) nitrosubstitutedhydroxamates‐A comparative study

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