Synthesis, structural characterization and antimicrobial activities of triorganotin(IV)azo-carboxylates derived from ortho/para-amino benzoic acids and β-naphthol

Debnath, Paresh; Das, Ankit; Singh, Keisham Surjit; Yama, Tage; Singh, Shivom; Butcher, Ray J.; Sieroń, Lesław; Maniukiewicz, Waldemar

doi:10.1016/j.ica.2019.119172

Cited by 20 publications

(11 citation statements)

References 44 publications

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“…Organotin(IV) carboxylates are found be the most promising alternatives, as these have shown higher apoptosis inducing character compared to the platinum complexes, both in vivo and in vitro ( Indumathy et al, 2007 ; Butt et al, 2019 ). In addition to the anticancer potential, organotin(IV) carboxylates also possess significant antibacterial, antifungal, insecticidal, anti-tuberculosis and antidiabetic activities ( Kovala-Demertzi et al, 2009 ; Tzimopoulos et al, 2010 ; Tariq et al, 2013 ; Sirajuddin et al, 2014a ; Sirajuddin et al, 2014b ; Shah et al, 2015 ; Tariq et al, 2016 ; Debnath et al, 2019 ; Sirajuddin et al, 2021 ).…”

Section: Introductionmentioning

confidence: 99%

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: Introductionmentioning

confidence: 99%

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

et al. 2022

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“…Therefore, the discovery and development of new and potent a-glucosidase inhibitors have gained immense attention in pharmaceutical chemistry [8][9][10] . In this regard, a new derivative from a series of sulphonamide containing diarylpentadienones was found to be a promising inhibitor of a-glucosidase (IC 50 5.69 ± 0.5 mM) with the competitive mode of inhibition 11 , some new benzamide derivatives of thiourea (IC 50 range 20.44 À 333.41 mM) were evaluated as good candidates for targeting a-glucosidase enzyme 12 . The literature also suggested that the derivatives of triazole thiones were found to be effective inhibitors of a-glucosidase (IC 50 value 36.11 lg/mL) 13 .…”

Section: Introductionmentioning

confidence: 99%

“…Ravi and colleagues studied the anti-mycobacterial and DNA cleaving efficiency of 2-aminothiazole incorporated azo derivatives 4 , the most active derivative found to be intervened with the active amino acids of Mycobacterium tuberculosis . Debnath et al evaluated the antimicrobial efficacy of triorganotin(IV) azo-carboxylates 5 against the bacterium ( S. aureus ) and the fungus ( F. oxysporum ) with significant antimicrobial properties compared to the standard antibiotics. Similarly, Ispir and colleagues examined the anti-oxidant and anti-proliferative potential of azo-azomethine ligands and their metal complexes with Zn(II), Co(II) and Cu(II) 6 .…”

Section: Introductionmentioning

confidence: 99%

Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies

Tahir

Shahzad

Tabassum

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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In the present study, a series of azo derivatives (TR-1 to TR-9) have been synthesised via the diazo-coupling approach between substituted aromatic amines with phenol or naphthol derivatives. The compounds were evaluated for their therapeutic applications against alpha-glucosidase (anti-diabetic) and pathogenic bacterial strains E. coli (gram-negative), S. aureus (gram-positive), S. aureus (gram-positive) drug-resistant strain, P. aeruginosa (gram-negative), P. aeruginosa (gram-negative) drug-resistant strain and P. vulgaris (gram-negative). The IC 50 (mg/mL) of TR-1 was found to be most effective (15.70 ± 1.3 mg/mL) compared to the reference drug acarbose (21.59 ± 1.5 mg/mL), hence, it was further selected for the kinetic studies in order to illustrate the mechanism of inhibition. The enzyme inhibitory kinetics and mode of binding for the most active inhibitor (TR-1) was performed which showed that the compound is a noncompetitive inhibitor and effectively inhibits the target enzyme by binding to its binuclear active site reversibly.

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“…A prominent element in anti-bacterial research is tin, usually present as an organometallic species, and a comprehensive review of the potential of these compounds as anti-bacterial agents has appeared [33]. In recent years, a broad range of synthetic organotin compounds have been investigated it his context including those of dithiocarbamates [34], hydroxamates [35], thiosemicarbazones [36] and, especially, carboxylates [37,38], sometimes derived from organic anti-bacterial agents, such as Ciprofloxacin [39]. The carboxylates chosen in the present study are derived from the symmetric cage compound adamantane, which is, as mentioned above, lipophilic in nature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural and in vitro biological evaluation of diamondoid-decorated lipophilic organotin(IV) derivatives

Baul

Manne

Duthie

et al. 2021

Journal of Organometallic Chemistry

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A series of diamondoid-decorated organotin(IV) derivatives of composition Me3Sn(L 1 ) (1), Ph3Sn(L 1 ) (2), {[Me2Sn(L 1 )]2O}2 (3), [BzSn(O)(L 1 )]6 (4), Me3Sn(L 2 )OH2 ( 5), [Ph3Sn(L 2 )]n (6), Bu2Sn(L 2 )2 (7), Bz2Sn(L 2 )2OH2 ( 8) and [BzSn(O)(L 2 )]6 (9) were prepared by reacting appropriate organotin(IV) precursors with either acid forms of the pro-ligands adamantane-1carboxylic acid (HL 1 ) and 2-(adamantan-1-yl)acetic acid (HL 2 ) or their sodium salts.Compounds 1-9 were characterised by spectroscopic techniques, including 119 Sn NMR in non-coordinating solvent for assessment of the solution-state structures. The molecular and crystal structures of 2-8 were established by X-ray crystallography. The packing is largely dictated by hydrophobic interactions with the exception in the crystals of 6, where Sn … O secondary bonding is apparent, and in each of 5 and 8 where O-H … O hydrogen bonding is present leading to a two-dimensional array and zig-zag chains, respectively. The organotin compounds were evaluated for their anti-bacterial activity against 15 human bacterial pathogens. Based on disc diffusion and minimum inhibitory concentration assays, the two triphenyltin species, 2 and 6, and di-n-butyl species, 7, are effective against both Grampositive and Gram-negative bacteria, including methicillin resistant Staphylococcus aureus (MTCC 381123) and Shigella flexneri (ATCC 12022), a causative agent for shigellosis. Time-kill assays showed that 2 and 6 had both time-and concentration-dependent antibacterial effects against susceptible bacteria. Cell viability assays showed that 2 and 6 were moderately toxic to a normal cell line, that is, human embryonic kidney 293T (HEK293T).

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Synthesis, structural characterization and antimicrobial activities of triorganotin(IV)azo-carboxylates derived from ortho/para-amino benzoic acids and β-naphthol

Cited by 20 publications

References 44 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

Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies

Synthesis, structural and in vitro biological evaluation of diamondoid-decorated lipophilic organotin(IV) derivatives

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