o-Vanillin derived Schiff Bases and their Organotin(IV) Compounds: Synthesis, structural characterisation, in-Silico studies and cytotoxicity

Published on Feb 15, 2019in International Journal of Molecular Sciences4.183
· DOI :10.3390/ijms20040854
Enis Nadia Md Yusof3
Estimated H-index: 3
Muhammad A. M. Latif1
Estimated H-index: 1
+ 6 AuthorsThahira Begum S. A. Ravoof9
Estimated H-index: 9
Six new organotin(IV) compounds of Schiff bases derived from S-R-dithiocarbazate [R = benzyl (B), 2- or 4-methylbenzyl (2M and 4M, respectively)] condensed with 2-hydroxy-3-methoxybenzaldehyde (oVa) were synthesised and characterised by elemental analysis, various spectroscopic techniques including infrared, UV-vis, multinuclear (1H, 13C, 119Sn) NMR and mass spectrometry, and single crystal X-ray diffraction. The organotin(IV) compounds were synthesised from the reaction of Ph2SnCl2 or Me2SnCl2 with the Schiff bases (S2MoVaH/S4MoVaH/SBoVaH) to form a total of six new organotin(IV) compounds that had a general formula of [R2Sn(L)] (where L = Schiff base; R = Ph or Me). The molecular geometries of Me2Sn(S2MoVa), Me2Sn(S4MoVa) and Me2Sn(SBoVa) were established by X-ray crystallography and verified using density functional theory calculations. Interestingly, each experimental structure contained two independent but chemically similar molecules in the crystallographic asymmetric unit. The coordination geometry for each molecule was defined by thiolate-sulphur, phenoxide-oxygen and imine-nitrogen atoms derived from a dinegative, tridentate dithiocarbazate ligand with the remaining positions occupied by the methyl-carbon atoms of the organo groups. In each case, the resulting five-coordinate C2NOS geometry was almost exactly intermediate between ideal trigonal-bipyramidal and square-pyramidal geometries. The cytotoxic activities of the Schiff bases and organotin(IV) compounds were investigated against EJ-28 and RT-112 (bladder), HT29 (colon), U87 and SJ-G2 (glioblastoma), MCF-7 (breast) A2780 (ovarian), H460 (lung), A431 (skin), DU145 (prostate), BE2-C (neuroblastoma) and MIA (pancreatic) cancer cell lines and one normal breast cell line (MCF-10A). Diphenyltin(IV) compounds exhibited greater potency than either the Schiff bases or the respective dimethyltin(IV) compounds. Mechanistic studies on the action of these compounds against bladder cancer cells revealed that they induced the production of reactive oxygen species (ROS). The bladder cancer cells were apoptotic after 24 h post-treatment with the diphenyltin(IV) compounds. The interactions of the organotin(IV) compounds with calf thymus DNA (CT-DNA) were experimentally explored using UV-vis absorption spectroscopy. This study revealed that the organotin(IV) compounds have strong DNA binding affinity, verified via molecular docking simulations, which suggests that these organotin(IV) compounds interact with DNA via groove-binding interactions.
Figures & Tables
  • References (94)
  • Citations (3)
📖 Papers frequently viewed together
39 Citations
15 Citations
28 Citations
78% of Scinapse members use related papers. After signing in, all features are FREE.
#1Özlem Mıhçıokur (Erciyes University)H-Index: 2
#2Talat Özpozan (Erciyes University)H-Index: 9
Abstract Oxindole and its derivatives have wide applications in different industries such as in synthetic & natural fibers, dyes for hair and plastic materials in addition to their biological importance. In the present study, one of the oxindole derivatives, N-(2-diethylaminoethyl)-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide (Sunitinib), which is used as an anti-cancer drug, was investigated in terms of structural, vibrational spectroscopic and theoret...
10 CitationsSource
#1Shadia A. Elsayed (Damietta University)H-Index: 9
#2Aya M. Noufal (Damietta University)H-Index: 1
Last. Ahmed M. El-Hendawy (Damietta University)H-Index: 14
view all 3 authors...
Abstract New complexes containing vanadium(IV), Mo(VI)/(IV) and Ru(II) derived from Schiff base of pyridoxal and S-benzyldithiocarbazate (H 2 pysb) or p -toluidine (Hpytol) have been prepared. The structures of the described compounds were elucidated by elemental analyses, spectroscopic techniques (IR, 1 H NMR, UV–Vis and EPR) magnetism, molar conductivity and thermal analysis measurements. Their redox behaviors were also studied by cyclic voltammetry. The ligand H 2 pysb showed coordination to ...
11 CitationsSource
#1Dušan P. Malenov (University of Belgrade)H-Index: 5
#2Goran V. Janjić (University of Belgrade)H-Index: 13
Last. Snežana D. Zarić (University of Belgrade)H-Index: 26
view all 5 authors...
Abstract Analysis of crystal structure data deposited in the Cambridge Structural Database (CSD) has shown that aromatic rings tend to stack with square planar transition metal complexes when they contain chelate rings. In these interactions, the orientation between chelate and aryl ring is a parallel-displaced orientation, like stacking interactions between aromatic molecules. In fused systems containing chelate and aryl rings, the aryl rings prefer to stack with the chelate rather than with ot...
35 CitationsSource
#1Kai Liu (Liaocheng University)H-Index: 2
#2Hun Yan (Liaocheng University)H-Index: 1
Last. Min Hong (Liaocheng University)H-Index: 15
view all 6 authors...
Abstract Four new organotin(IV) complexes Me 2 SnL 1 , Ph 2 SnL 1 , Me 2 SnL 2 and Ph 2 SnL 2 (H 2 L 1 = 5-chlorosalicylaldehyde isonicotinoyl hydrazone and H 2 L 2 = 2-hydroxy-4-methoxybenzaldehyde isonicotinoyl hydrazone) have been synthesized and characterized by elemental analyses, FT-IR, NMR ( 1 H, 13 C and 119 Sn) and single crystal X-ray diffraction techniques. The crystal structure analysis shows that complexes 1 and 2 are trinuclear compounds, of which the enolic hydrazone Schiff base l...
24 CitationsSource
Abstract An overview of supramolecular assembly sustained by intermolecular contacts pertinent to the coordination chemistry community is presented. Herein, the supramolecular architectures sustained by secondary bonding, encompassing tetrel, pnictogen and chalcogen bonding, interactions occurring between metal centres, metal⋯hydrogen, metal⋯π, main group element(lone pair)⋯π, and finally, those involving chelate rings sustained by formal bonding or by hydrogen bonding are described. Whenever po...
67 CitationsSource
#1Kathleen E. Prosser (SFU: Simon Fraser University)H-Index: 6
#2Stephanie W. Chang (SFU: Simon Fraser University)H-Index: 3
Last. Charles J. Walsby (SFU: Simon Fraser University)H-Index: 19
view all 5 authors...
Abstract The Cu(II) complex CuCl 2 (pbzH), pbzH = 2-(2-pyridyl)benzimidazole, and derivatives modified at the non-coordinated nitrogen of the benzimidazole fragment, have been studied as anticancer agents. These compounds show promising cytotoxicity against A549 adenocarcinomic alveolar basal epithelial cells with IC 50 values in the range of 5–10 μM. Importantly, this activity is higher than either CuCl 2 ·2H 2 O or the individual ligands, demonstrating that ligand coordination to the Cu(II) ce...
30 CitationsSource
#1Rajesh Malhotra (Guru Jambheshwar University of Science and Technology)H-Index: 6
#2Ankit Ravesh (Guru Jambheshwar University of Science and Technology)H-Index: 1
Last. Vikramjeet Singh (Guru Jambheshwar University of Science and Technology)H-Index: 2
view all 3 authors...
ABSTRACTOrganotin complexes of type R2SnClL [where L = Schiff base obtained by the condensation of 2-(4-Bromo/Chloro-benzyloxy)-3-methoxy-benzaldehyde and nicotinic/isonicotinic hydrazides; R = Me, Et, Bu, and Ph] have been synthesized and characterized by elemental analysis, molar conductance, infrared and NMR (1H, 13C, and 119Sn) spectral analyses. The ligands and their organotin complexes have been evaluated for antimicrobial activity and the QSAR studies indicated that antimicrobial activity...
3 CitationsSource
#1Wajid Rehman (HU: Hazara University)H-Index: 15
#2Rehana Yasmeen (Gomal University)H-Index: 2
Last. Khurshid Ayub (CUI: COMSATS Institute of Information Technology)H-Index: 23
view all 8 authors...
Abstract The search for an alternative to platinum anticancer agents is a major motivation for continuing investigations concerning the antitumor properties of other transition metal-based compounds. Keeping this in view, synthesis, antitumor and antimicrobial activity of diorganotin (IV) complexes was studied. A novel series of diorganotin (IV) complexes of the Schiff base ligand derived from 7-methoxy-2-hydroxy-1-naphthaldehyde, 1,2-phenylenediamine, Salicylaldehyde were synthesized. Physical ...
7 CitationsSource
#1Cristina González-García (UAM: Autonomous University of Madrid)H-Index: 2
#2Alejandro Mata (UAM: Autonomous University of Madrid)H-Index: 1
Last. Elena López-Torres (UAM: Autonomous University of Madrid)H-Index: 14
view all 5 authors...
Abstract Four novel ligands derived from 2,3-butanedione have been synthesized, two dissymmetric thiosemicarbazone/3-hydroxy-2-naphthohydrazone ligands, H 2 L 1 (bearing 4-isopropyl-3-thiosemicarbazone) and H 2 L 2 (containing 4-cyclohexyl-3-thiosemicarbazone) and the symmetric H 2 L 3 , diacetyl bis(3-hydroxy-2-naphthohydrazone), and H 2 L 4 , diacetyl bis(4-cyclohexyl-3-thiosemicarbazone). Their reactivity with SnR 2 Cl 2 (R = methyl, n -butyl and phenyl) was explored and the resulting complex...
9 CitationsSource
#1Min Hong (Liaocheng University)H-Index: 15
#2Guoliang Chang (Liaocheng University)H-Index: 6
Last. Meiju Niu (Liaocheng University)H-Index: 13
view all 4 authors...
Five new mono- or di-organotin(IV) complexes, Me2SnL (1), Ph2SnL (2), n-Bu2SnL (3), n-Oct2SnL (4) and n-BuSnCl(H2O)L·CH3CH2OH (5), where H2L is 2-hydroxy-N′-[(2-hydroxy-3-methoxyphenyl)methylidene]-benzohydrazone, were synthesized and characterized by elemental analysis and spectroscopic techniques (IR and 1H, 13C, 119Sn NMR). The crystal structures of all compounds were established by X-ray diffraction, showing the hydrazone Schiff base ligand bound to the tin atom as ONO tridentate chelate. In...
33 CitationsSource
Cited By3
#1Enis Nadia Md Yusof (University of Newcastle)H-Index: 3
#2Muhammad Alif Mohammad Latif (UPM: Universiti Putra Malaysia)H-Index: 6
Last. Thahira Begum S. A. Ravoof (UPM: Universiti Putra Malaysia)H-Index: 9
view all 8 authors...
Abstract Six new tin(IV) compounds derived from tridentate dinegatively charged ONS dithiocarbazate Schiff bases derived from 2-hydroxy-3-methoxybenzaldehyde (H2L1, H2L2 and H2L3) and 2,3-dihydroxybenzaldehyde (H2L4, H2L5 and H2L6) (where H2Ln = di-acids of Schiff base) are reported. The compounds were characterised by elemental analysis, FT-IR and multinuclear NMR (1H, 13C and 119Sn) spectroscopy. The crystal structures of tin(IV) [S-4-methybenzyl-β-N-(2-hydroxy-3-methoxybenzylmethylene)dithioc...
A series of tridentate ONS Schiff bases were synthesised via condensation by reacting 2,3-dihydroxybenzaldehyde with S-2-methylbenzyldithiocarbazate (S2MBDTC) (1), S-4-methylbenzyldithiocarbazate (S4MBDTC) (2) and S-benzyldithiocarbazate (SBDTC) (3) in an equimolar ratio (10 mmol). The Schiff bases were then reacted with diphenyltin(IV) and dimethyltin(IV) dichloride in an equimolar ratio (1 mmol) yielding six new organotin(IV) compounds (4–9). All the compounds were successfully characterised b...
#1Badri Z. Momeni (KNTU: K.N.Toosi University of Technology)H-Index: 9
#2Nastaran Fathi (KNTU: K.N.Toosi University of Technology)H-Index: 2
Last. Jan Janczak (PAN: Polish Academy of Sciences)H-Index: 27
view all 4 authors...
#1Cássia de Q. O. Cavalcante (UnB: University of Brasília)H-Index: 1
#2Daniel da Silva Arcanjo (UnB: University of Brasília)
Last. Claudia C. Gatto (UnB: University of Brasília)H-Index: 14
view all 5 authors...
The current work reports the synthesis and investigation by physical-chemistry and spectroscopic methods of three dithiocarbazates (2-acetylpyridine-S-allyl-dithiocarbazate – HL1; 2-acetylpyridine-S-p-bromobenzyl-dithiocarbazate – HL2; and 2-acetylpyridine-S-p-nitrobenzyl-dithiocarbazate – HL3) and six novel metal complexes derived from these Schiff-bases. Four crystal structures of the complexes are reported. The single crystal X-ray study showed two binuclear zinc(II) complexes with symmetrica...
1 CitationsSource
The title NiII complex, Ni(L)(LH2) (1), where LH2 is S-2-methybenzyl-β-N-(2-hydroxy-3-methoxybenzylmethylene) dithiocarbazate, was isolated from the reaction of Ni(acetate)2·4H2O and two molar equivalents of LH2. The complex was characterized by elemental analysis, spectroscopy (IR and UV) as well as by a single-crystal X-ray structure determination. The nickel(II) center is coordinated within a cis-NOS2 donor set that defines a square planar geometry. Three donor atoms, i.e., N, O, and S, are p...