Synthesis and structural characterization of monomeric and polymeric supramolecular organotin(IV) 4-chlorophenylethanoates

Muhammad, Niaz; Rehman, Zia ur; Shujah, Shaukat; Ali, Saqib; Shah, Afzal; Meetsma, Auke

doi:10.1080/00958972.2014.898755

Cited by 14 publications

(5 citation statements)

References 29 publications

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“…The 13 C-NMR spectra of complexes revealed six signals in the predicted locations for the magnetically non-equivalent carbons of the carboxylate ligand. By comparing the signals of the produced complexes to those of comparable reported tin carboxylate complexes, the carbons of the tin bound alkyl groups were allocated ( Muhammad et al, 2014 ). Four coordinated tetrahedral tin centres have been verified in complexes 3 and 4 using 1 J ( 119 Sn, 13 C) coupling constant values of 343 and 394 Hz, respectively ( Muhammad et al, 2014 ).…”

Section: Resultsmentioning

confidence: 99%

“…By comparing the signals of the produced complexes to those of comparable reported tin carboxylate complexes, the carbons of the tin bound alkyl groups were allocated ( Muhammad et al, 2014 ). Four coordinated tetrahedral tin centres have been verified in complexes 3 and 4 using 1 J ( 119 Sn, 13 C) coupling constant values of 343 and 394 Hz, respectively ( Muhammad et al, 2014 ). In the carbon NMR spectra of all produced compounds, no additional peak was identified.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Characterization, Biological Activity and Molecular Docking Studies of Novel Organotin(IV) Carboxylates

et al. 2022

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Four new carboxylates complexes with general formula R2SnL2 and R3SnL, where R = n-butyl (1, 3), methyl (2, 4) and L = 4-Chlorophenoxyacetate, were synthesized in significant yields. FT-IR analysis revealed a chelating (1 and 2) and a bridging bidentate (3 and 4) coordination modes for the carboxylate ligand in solid state which was further confirmed by the single crystal X-ray analysis of complex 4. The NMR data (1H, 13C and 119Sn) revealed a higher coordination number around the tin center in R2SnL2 (1 and 2) compared to R3SnL (3 and 4). A close matching was observed between the experimental and calculated structures (obtained at B3LYP/6-31G* + LANL2DZ basis set). Quantum chemical analysis indicates that the carboxylate moiety has the major contribution in the formation of filled and unfilled orbitals as well as in ligand to ligand intramolecular charge transfer during the electronic transitions. The cytotoxicity data of the screened compounds evaluated against lung cancer cell line (A549) and normal lung fibroblast cell line (MRC-5) revealed that 1, 3 and 4 have shown dose dependent cytotoxic effects while HL and 2 have shown steady and low cytotoxic activities. The antibacterial activity of complexes 1–4 is higher than that of HL. Molecular docking study showed an intercalation binding mode for complex 3 with DNA (docking score = −3.6005) involving four polar interactions. Complex 3 docking with tubulin (PDB ID 1SA0) with colchicine as a target protein resulted in three polar interactions (docking score −5.2957). Further, the docking analysis of the HL and 1–4 has shown an adequate interactions with the coronavirus SARS-CoV-2 spike protein, nucleocapsid protein and human angiotensin converting enzyme (ACE2).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, Biological Activity and Molecular Docking Studies of Novel Organotin(IV) Carboxylates

et al. 2022

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“…The final difference Fourier map was essentially featureless with a few peaks of max. 1.27 (10) e/Å 3 within 1.0 Å from Sn position, but were neglected/rejected, being artefacts. No other significant peaks having chemical meaning above the general background were observed in the final difference Fourier syntheses.…”

Section: X-ray Crystallographic Studiesmentioning

confidence: 99%

“…Organotin(IV) compounds have been recognized for their therapeutic potential in biocompatible strategy for cancer treatment [1], antimicrobial activities [2], photocatalytic applications [3] as precursors for tin oxide in gas sensors [4,5], manufacture of organic light emitting diodes [6] and ability to generate well-organized supramolecular architecture through strong metal ligand coordinate bonds and weak cooperative forces like hydrogen bonds and π-π interactions [7][8][9][10]. Through careful synthesis control, metal or ligand directed self-assembly can be consciously designed into a synthetic framework with interesting properties and useful applications in various fields like molecular recognition, chiroptical switching devices and gas storage materials.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular homobimetallic bis-diorganotin(IV) complexes of ditopic oxygen nitrogen donor ligand: synthesis, spectroscopic characterization, crystal structure and biological screening

et al. 2017

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Six new homobimetallic bis-diorganotin(IV) complexes: [Mehave been synthesized and structurally characterized by means of elemental analysis, mass spectroscopy, FT-IR, NMR ( 1 H, 13 C{ 1 H}, 119 Sn) and single-crystal X-ray diffraction. Spectroscopic studies indicate coordination of the ligand to the diorganotin(IV) moieties via iminolic oxygen, nitrogen and phenolic oxygen atoms generating pentacoordinated tin centers. Single-crystal X-ray analysis of (1) revealed homobimetallic nature of complex with dimethyltin moieties oriented in trans-conformation. The ligand is nonplanar with each Sn atom in a distorted square pyramidal coordination geometry. Packing diagrams suggest the essential role of C-H … N and C-H … O interactions in generating supramolecular assembly. The ligand and complexes were screened for in vitro antimicrobial activity and cytotoxicity. Compound (4) exhibits highest cytotoxicity.

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“…[11][12][13][14][15][16] In recent years organotin(IV) complexes are of great interest due to their potential applications in biology, medicine, catalysis, and materials science. [17][18][19][20] Many in vitro studies have shown that some organotin(IV) compounds demonstrate better anticancer potential as drugs in comparison to cisplatin. 21,22 Additionally, a more recent study on SBA-15 mesoporous nanomaterial loaded with 6-(triphenylstannyl)hexan-1-ol exhibits a non-aggressive manner of action, greatly efficient toward tumor cells.…”

Section: Introductionmentioning

confidence: 99%

In vitro anticancer evaluation of novel triphenyltin(IV) compounds with some N-acetyl-S-naphthoquinonylcysteine derivatives

et al. 2019

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Triphenyltin(IV) compounds with naphthoquinone derivatives containing N-acetylcysteine, N-acetyl-S-(3,4-dihydro-3,4-dioxo-1-naphthyl)cysteine (1,2-NQC), 1, and N-acetyl-S-(1,4-dihydro-1,4-dioxo-2-naphthyl)cysteine (1,4-NQC), 2, were synthesized and characterized by elemental microanalysis, IR, multinuclear (1 H, 13 C, 119 Sn) NMR spectroscopy as well as HR-ESI mass spectrometry. With the aim of in vitro anticancer activity determination of ligand precursors and novel synthesized organotin(IV) compounds against human cervix adenocarcinoma (HeLa), human colon carcinoma (HT-29) and melanoma carcinoma cell line (B16F10), MTT colorimetric assay method was applied. The results indicate that synthesized compounds exhibited remarkable antiproliferative activity toward all tested cell lines with IC 50 in the range from 0.17 to 0.87 µM. Complex 1 showed the greatest activity against HT-29 cells, with IC 50 value of 0.21±0.01 µM, 119 times better than cisplatin, while complex 2 demonstrated the highest activity toward HeLa cells, IC 50 = 0.17±0.01 µM, which is ~26 times better than cisplatin.

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Synthesis and structural characterization of monomeric and polymeric supramolecular organotin(IV) 4-chlorophenylethanoates

Cited by 14 publications

References 29 publications

Synthesis, Characterization, Biological Activity and Molecular Docking Studies of Novel Organotin(IV) Carboxylates

Synthesis, Characterization, Biological Activity and Molecular Docking Studies of Novel Organotin(IV) Carboxylates

Supramolecular homobimetallic bis-diorganotin(IV) complexes of ditopic oxygen nitrogen donor ligand: synthesis, spectroscopic characterization, crystal structure and biological screening

In vitro anticancer evaluation of novel triphenyltin(IV) compounds with some N-acetyl-S-naphthoquinonylcysteine derivatives

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