New di‐ and triorganotin(IV) carboxylates derived from a Schiff base: synthesis, characterization and <i>in vitro</i> antimicrobial activities

Six novel organotin (IV) complexes, [(Me 3 Sn) 2 (H 2 O) 2 L] (1), [(R 3 Sn) 2 L] n (R = Me 2, R = n-Bu 3), [(Ph 3 Sn) 2 L] (4), [Me 2 SnL] n (5), [(Me 2 Sn) 2 L(μ 3 -O)] n (6) have been designed and synthesized by the reactions of 4,4′-oxybisbenzoic acid (H 2 L) and triorganotin (IV) chloride or oxide. All the complexes have been characterized by elemental analysis, FT-IR, NMR, ESI-Mass, PXRD and X-ray crystallography.The single crystal diffraction reveals that complexes 1 and 4 represent dinuclear tin monomers. Complexes 2 and 3 display 2D network structure and 2D corrugated framework respectively, which both contain tetranuclear 36-membered macrocycles. Furthermore, 2D structures are linked into a 3D supramolecular structures through intermolecular C-H···π interactions. Complex 5 shows 1D infinite helical chain and further constructs 3D ladder supramolecular architecture through additional Sn···O and C-H···O intermolecular interactions. Complex 6 displays 1D infinite polymeric chain containing 28-membered macrocyclic ring. Preliminarily in vitro cytostatic activity studies on cervical carcinoma cell lines (HeLa) and hepatocellular carcinoma cell lines (HepG-2) by MTT assay for some complexes reveal that complexes 3 and 4 exhibit high cytostatic activity. Further, complexes 3 and 4 were selected to investigate interactions of bovine serum albumin (BSA) by fluorescence quenching spectra and synchronous fluorescence spectra, which indicates that the complexes could quench the intrinsic fluorescence of BSA in a static quenching process.

Section: Resultssupporting

confidence: 84%

Novel organotin (IV) complexes derived from 4,4′‐oxybisbenzoic acid: synthesis, structure, in vitro cytostatic activity and binding interaction with BSA

Wang

Zhang

et al. 2019

“…In the last few decades, the of interdisciplinary organometallic field has witnessed a significant growth in the chemistry of organotin(IV) compounds owing to their accessible structural design, and broad range of industrial and biological applications specifically as potential non‐platinum metal‐based antitumour/anticancer agents . In recent years, organotin(IV) complexes with O/N donor systems such as Schiff bases derived from amino acids, amino alcohols, hydrazones and so forth have been extensively studied owing to their interesting structural possibilities, broad range of industrial applications and wide spectrum of biological activities . For instance, a few di‐ and tri‐ n ‐butyltin(IV) complexes of 2‐{[5‐(2‐nitrophenyl)furan‐2‐yl]methyleneamino}benzoic acid have been reported to exhibit greater biocidal activity as compared to methyltin(IV) analogues and reference drug nystatin; specifically, tri‐ n ‐butyltin complex exhibited highest activity against Aspergillus parasiticus and Candida albicans with very low minimum inhibitory concentration (MIC) values of 1.19 and 6.56 μg mol −1 .…”

Section: Introductionmentioning

confidence: 99%

“…In recent years, organotin(IV) complexes with O/N donor systems such as Schiff bases derived from amino acids, amino alcohols, hydrazones and so forth have been extensively studied owing to their interesting structural possibilities, broad range of industrial applications and wide spectrum of biological activities . For instance, a few di‐ and tri‐ n ‐butyltin(IV) complexes of 2‐{[5‐(2‐nitrophenyl)furan‐2‐yl]methyleneamino}benzoic acid have been reported to exhibit greater biocidal activity as compared to methyltin(IV) analogues and reference drug nystatin; specifically, tri‐ n ‐butyltin complex exhibited highest activity against Aspergillus parasiticus and Candida albicans with very low minimum inhibitory concentration (MIC) values of 1.19 and 6.56 μg mol −1 . Similarly, a few diphenyltin(IV) complexes of Schiff bases of the type Ph 2 SnL 1–3 (L 1 : N ‐phenacyl‐5‐bromosalicylideneimine; L 2 : N ‐phenacyl‐3,5‐dichlorosalicylideneimine; L 3 : N ‐phenacyl‐4‐methoxysalicylideneimine) were reported to exhibit mild antifungal activity against some fungi .…”

Section: Introductionmentioning

confidence: 99%

“…[26][27][28][29][30][31] For instance, a few di-and tri-n-butyltin(IV) complexes of 2-{[5-(2-nitrophenyl) furan-2-yl]methyleneamino}benzoic acid have been reported to exhibit greater biocidal activity as compared to methyltin(IV) analogues and reference drug nystatin; specifically, tri-n-butyltin complex exhibited highest activity against Aspergillus parasiticus and Candida albicans with very low minimum inhibitory concentration (MIC) values of 1.19 and 6.56 μg mol −1 . [30] Similarly, a few diphenyltin(IV) complexes of Schiff bases of the type Ph 2 SnL 1-3 (L 1 : N-phenacyl-5-bromosalicylideneimine; L 2 :…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

New diorganotin(IV) complexes of Schiff base derived from 4‐amino‐3‐hydrazino‐5‐mercapto‐4H‐1,2,4‐triazole: Synthesis, structural characterization, density functional theory studies, atoms‐in‐molecules analysis and antifungal activity

Joshi

Kumari

Singh

et al. 2019

New diorganotin(IV) complexes of a Schiff base (HL) having general formula R2Sn(L)Cl (where L is the monoanion of HL and R = n‐Bu or Ph) have been synthesized and characterized using elemental analysis, infrared, NMR (1H, 13C, 119Sn) and UV–visible spectroscopies and mass spectrometry. These investigations suggest that in these 1:1 monomeric derivatives the Schiff base ligand acts in a monoanionic bidentate manner coordinating through the Ophenolic and Nazomethine, with proposed distorted trigonal bipyramidal geometry around tin with Ophenolic and two organic groups in the equatorial plane and the Nazomethine and the third organic group in axial positions. The proposed structures have been validated by density functional theory (DFT)‐based quantum chemical calculations at the B3LYP/6‐31G(d,p)/Def2‐SVP (Sn) level of theory. The simulated UV–visible spectrum was obtained with the time‐dependent DFT method in the gas phase and in the solvent field with the integral equation formalism–polarizable continuum model. A comparative analysis of the experimental vibrational frequencies and simulated harmonic frequencies indicates a good correlation between them. An insight into the intramolecular bonding and interactions among bonds in organotin(IV) complexes of HL was obtained by means of natural bond orbital analysis. The topological and energetic properties of the electron density distribution for the tin–ligand interaction in R2Sn(L)Cl have been theoretically calculated at the bonds around the central tin atom in terms of atoms‐in‐molecules theory. The R2Sn(L)Cl complexes were screened for their in vitro antifungal activity against chosen fungal strains.

“…Besides preparing new organotin derivatives and investigating their biocidal activity against some microorganisms, we have been interested in the pharmacological mechanisms of such complexes. We have recently reported the synthesis, spectroscopic and X‐ray structural characterization of organotin(IV) valproate complexes and discrete diorganotin(IV) coordination entities bearing the 4‐phenylbutanoate anion, Ph(CH 2 ) 3 CO 2 − ( − OPh b ), namely [{(Me 2 SnOPh b ) 2 O} 2 ], [Bu 2 Sn(OPh b ) 2 ] and [{PhSn(O)OPh b } 6 ] .…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic and X‐ray structural characterization of new polymeric organotin(IV) carboxylates and their in vitro antifungal activities: Part II

Rocha

Morais

Rodrigues

et al. 2016

Funding informationCNPq, CAPES and FAPEMIG The reactions of R 3 SnCl (R = Me, Bu or Ph) with sodium 4-phenylbutyrate, Na(OPh b ), in EtOH yielded three polymeric triorganotin carboxylates, namely [R 3 Sn(OPh b )] n (R = Me (1), Bu (2) or Ph (3)). All complexes were spectroscopically characterized using Fourier transform infrared, 119 Sn Mössbauer, 1 H NMR, 13 C{ 1 H} NMR and 119 Sn{ 1 H} NMR spectral techniques. In addition, the crystal structures of 1 and 3 were determined using single-crystal X-ray diffraction. Their polymeric structures are sustained by bridging carboxylates which connect two five-coordinate Sn(IV) centres. Each metallic cation displays a distorted trigonal bipyramidal coordination geometry (Addison's parameters ranging from 0.84 in 1 to 0.77-0.91 in 3), with the oxygen atoms occupying the apical positions and the organic groups at the equatorial corners. The one-dimensional zigzag chains of 1 propagate along the b-axis, whereas 3 displays wave-like double polymeric chains along the b-axis. For both 1 and 3, parallel one-dimensional polymeric chains are interconnected by C─H⋅⋅⋅π interactions. The antifungal activity of 1-3 was screened against Candida albicans (ATCC 18804), C. tropicalis (ATCC 750), C. glabrata (ATCC 90030), C. parapsilosis (ATCC 22019), C. lusitaniae (CBS 6936) and C. dubliniensis (clinical isolate 28). The antifungal activity of 3 was noteworthy since it was not only more active than 1 and 2, but also more active than the control drugs (nystatin and fluconazole nitrate) in some cases.