Piperidine Dithiocarbamate Research Articles

Synthesis, spectroscopic characterization and anticancer potential studies of organoruthenium(II) arene dithiocarbamate complexes

Four organoruthenium(II) arene dithiocarbamate complexes: RuCl(piperidine dithiocarbamate)(p-cymene), C1; RuCl(1-phenylpiperazine dithiocarbamate)(p-cymene), C2, RuCl(ethylphenyl dithiocarbamate)(p-cymene), C3; RuCl(4-benzylpiperidine dithiocarbamate)(p-cymene), C4 were synthesized and characterized by elemental analysis, UV-Vis, FTIR, NMR and mass spectroscopic techniques. Spectroscopic data indicate that the complexes are four coordinate tetrahedral geometry consisting of one dithiocarbamato anion, p-cymene and a chlorido ligand around the ruthenium(II) ion. The dithiocarbamato anions coordinate the ruthenium(II) ions isobidentately. The cytotoxic effects of the compounds were assessed against human cervical cancer (HeLa) and human lung fibroblast (MRC5-SV2) cell lines using the 3-(4,5-dimethylthiazol-2-yl)−2,5-diphenyl tetrazolium bromide (MTT) assay. Only two compounds, C1 and C3 showed potent cytotoxicity after 48 h treatment. C1 was the most potent, with IC50 values of 6.7 ± 2.3 µM and 8.1 ± 0.8 µM against the HeLa and MRC5-SV2 cells, respectively, while C3 had IC50 values of 11.5 ± 3.1 µM and 10.3 ± 1.3 µM, respectively. Remarkably, compared to cisplatin (used as the reference anticancer drug), C1 was twice more potent against HeLa cells and more than five times more potent against MRC5-SV2 cells, while C3 was nearly equipotent with cisplatin against HeLa cells but five times more potent against MRC5-SV2 cells. These two compounds exhibited good potential as anticancer agents, thus warranting further studies.

Response to oxidative stress generation in Rhodotorula glutinis and Candida tropicalis by thallium dithiocarbamate complexes

Sodium diethyldithiocarbamate trihydrate (NaEt2dtc·3H2O) and sodium piperidine dithiocarbamate monohydrate (NaPidtc·H2O) reacted with thallium(I) carbonate to produce the complexes [Tl2(Et2dtc)2] C1 and [Tl2(Pidtc)2] C2. X-ray crystallographic analysis of the complexes elucidated their triclinic P-1 and monoclinic P21/n space groups, respectively, in addition to chelation via SS atoms from the uninegative ligands. Further, this analysis revealed the complexes' assembly as one-dimensional polymers of dimeric building blocks. The complexes (50 µg/ml) caused greater growth inhibitions in two pathogenic yeasts comparing with the ligand salts and cycloheximide. The ligand salts, respectively, inhibited R. glutinis with 15.02 and 15.14 % and C. tropicalis with 11.09 and 11.45 %, while cycloheximide, C1 and C2 offered inhibitions with 26.16, 38.9 and 46.4 % in R. glutinis and 13.4, 29.8 and 38.9 % in C. tropicalis, respectively. Further, the thallium complexes significantly affected the yeasts' soluble proteins {cycloheximide, C1 and C2 afforded 7.06 ± 0.05, 6.11 ± 0.08 and 5.43 ± 0.05 mg/g fresh weight (for R. glutinis) and 7.67 ± 0.15, 7.26 ± 0.06 and 6.025 ± 0.14 mg/g fresh weight (for C. tropicalis)} and total antioxidants {cycloheximide, C1 and C2 afforded 10.15 ± 0.21, 11.27 ± 0.16 and 14.97 ± 1.3 mg/g protein (for R. glutinis) and 19.4 ± 0.65, 16.0 ± 0.24 and 17.19 ± 0.55 mg/g protein (for C. tropicalis)} in addition to the catalase and peroxidase enzyme activities.

Synthesis of photoluminescent europium dithiocarbamate complexes with dimethyl phenanthroline and bipyridyl co-ligands

This paper reports the synthesis of photoluminescent europium diphenylamine and piperidine dithiocarbamate complexes compound containing co-ligands 2,9 dimethyl-1,10 phenanthroline and bipyridyl. Nuclear magnetic resonance analysis result indicated that the complex compound of europium diphenylamine dithiocarbamate-2,9 dimethyl-1,10 phenanthroline [(dpa-dtc)2--Eu-(Dmphen)] has an Eu metal to bind to 2 diphenylamine dithiocarbamate ligands in bidentate structure. Meanwhile, the piperidine dithiocarbamate-2,2 bipyridyl [(pip-dtc)-Eu-(Bipy)] indicates the structure to have 1 Bipy co-ligand and 1 piperidine dithiocarbamate ligand which is monodentate bonded to the Eu metal. The photoluminescence analysis results showed that the [(dpa-dtc)2-Eu-(Dmphen)] and [(pip-dtc)-Eu-(Bipy)] complexes exhibited a photoluminescent in the region of red-orange, which is associated with the electronic transition of 5D0 → 7F2. Europium dithiocarbamate complex compounds have the potential to be applied as an active material for display and others electronics devices applications.

Facile synthesis of PbS, Bi2S3 and Bi-doped PbS nanoparticles from metal piperidine dithiocarbamates complexes

Single source precursors are advantageous starting materials to the syntheses of nanomaterials. In this study, lead and bismuth piperidine dithiocarbamate complexes have been synthesized and used as efficient precursors for synthesizing PbS and Bi2S3 nanoparticles using hot injection techniques. The bismuth piperidine dithiocarbamate complex was then used as a dopant to form Bi-doped PbS nanoparticles. Alloys are functional materials for present day applications. In the energy sector, they allow for band gap engineering and size dependent quantum confinement effects. The p-XRD pattern of the PbS was indexed to a cubic rocksalt structure, whereas the Bi2S3 was indexed to an orthorhombic structure. The morphological studies using the TEM revealed the formation of cubes and rods for the PbS and Bi2S3, respectively. An interplay of these structures was observed for the alloy depending on the mole fraction of Bi doping in the injected precursor solution. The optical band gaps were blue-shifted to 0.72 and 1.94 eV for PbS and Bi2S3, respectively. The Bi-doped PbS nanoparticles displayed optical band gaps in between the binary materials.

Antimicrobial properties of metal piperidine dithiocarbamate complexes against Staphylococcus aureus and Candida albicans

In this study, a series of metal piperidine dithiocarbamate complexes (M = Zn, Cu, Co, Fe, Ni, Bi and Ag) were synthesized and characterized using microelemental, 1HNMR, mass spectrometry and FT-IR analyses. Antimicrobial properties of the complexes were tested against Staphylococcus aureus and Candida albicans in a 96-well plate, using the broth dilution assay. The antimicrobial activity of the complexes was in the order Zn>Co>Cu>Ag=Bi=Ni>Fe against Staphylococcus aureus and Co> Zn >Fe>Ag=Bi=Cu=Ni against Candida albicans. The results indicate that the complexes were effective against the microorganisms at high concentrations.

Antimicrobial, computational, and molecular docking studies of Zn (II) and Pd (II) complexes derived from piperidine dithiocarbamate

Mixed ligand complexes of Zn (II) and Pd (II) have been prepared from piperidine dithiocarbamate (PipDT) and amine ligand {2,2′‐bipyridine (Bipy), 1,10‐phenanthroline (Phen), and 3‐aminopyridine (3Apy)} to afford complexes of the type [M(κ1‐PipDT)(κ2‐Bipy)] {MIIZn, Pd} (1,4), [M(κ1‐PipDT)(κ2‐Phen)] (2,5), and [M(κ1‐PipDT)(κ1‐3Apy)2] (3,6). The reaction of equivalent molar of sodium benzisothiazolinate (Nabit) or sodium saccharinate (Nasac) with cis‐[PdCl2(PPh3)2], followed by addition, sodium piperidine dithiocarbamate (NaPipDT) afforded complexes of the type trans‐[Pd(κ1‐PipDT)(κ1‐N‐bit)(PPh3)2] (7) and trans‐[Pd(κ1‐PipDT)(κ1‐N‐sac)(PPh3)2] (8). The obtained complexes were characterized by elemental analysis and spectroscopic techniques. The PipDT− was bonded as monodentate fashion via sulfur atom, whereas the diamine ligands were coordinated as bidentate chelating, while the 3Apy ligand bonded as monodentate mode through the nitrogen of heterocyclic ring. In complexes (7) and (8), the bit− and sac− ligand coordinated as monodentate through the nitrogen atom of heterocyclic ring. The antimicrobial activity of the complexes was tested. All the complexes showed moderate to good activity compared with standard antimicrobial. Moreover, the calculations of the density functional theory (DFT) were performed to estimate the thermal parameters, dipole moment, polarizability, and molecular electrostatic potential of the present complexes; in addition, Mulliken atomic charges of the complexes, total electron density (TED), electrostatic surface potential (ESP), lethal concentration (LC50), and docking studies as well as the descriptors of chemical reactivity were studied.

Labelled micelles for the delivery of cytotoxic Cu(II) and Ru(III) compounds in the treatment of aggressive orphan cancers: Design and biological in vitro data

A recent study on our metal-dithiocarbamato complexes pointed out the antiproliferative properties and the druglikeness of some new patented derivatives. In this work, the best compounds have been encapsulated in micellar nanocarriers, being also carbohydrate-functionalized on their hydrophilic surface to investigate the possibility of a cancer-selective delivery. In particular, the nonionic block copolymer Pluronic® F127 (PF127) has been chemically modified with sugars and the derivatives characterized by means of NMR spectroscopy and FT-IR spectrophotometry. Then, the two selected complexes (β-[Ru2(PipeDTC)5]Cl (PipeDTC = piperidine dithiocarbamate) and [Cu(ProOMeDTC)2] (ProOMeDTC = L-proline methyl ester dithiocarbamate)), have been loaded into the hydrophobic core of PF127 micelles and cancer-targeting counterparts. These nanoformulations have been studied for their dimensions (DLS, TEM) and stability, and tested for their cytotoxicity against aggressive human cancer cell lines. The in vitro results were paralleled with mechanistic studies through Confocal Laser Scanning Microscopy and xCELLigence analysis.

Optical and structural characterization of copper sulphide nanoparticles from copper(II) piperidine dithiocarbamate

We report the preparation of copper sulphide nanoparticles from copper(II) piperidine dithiocarbamate. Powder XRD patterns confirmed covellite copper sulphide (CuS) for nanoparticles obtained at 120 °C while nanoparticles prepared at 180 and 220 °C exist in digenite copper sulphide (Cu9S5) crystalline phases. TEM micrographs showed CuS obtained at 120 °C have mixture of hexagonal, triangular, and spherical shapes with no agglomeration with crystallite sizes in the range 4.9–51.4 nm. Copper sulphide obtained at 180 °C have particle sizes in the range 31.3–44.0 nm while agglomerated particles were obtained at 220 °C with particle sizes of 74.4–125.4 nm. The results confirmed that the particle sizes of the as-prepared copper sulphide nanoparticles are temperature dependent. Optical studies of the copper sulphide nanoparticles indicates the absorption band edges are blue shifted due to decreased crystallite sizes of the nanoparticles compared to bulk copper sulphide.

Synthesis, Characterization, Spectral Studies and Antimicrobial Study on Mixed Ligand Complexes of Chloro-arsenic(III) Derived from β-Ketiminates & Piperidine Dithiocarbamate Ligand Moity

A series of Chloro-arsenic(III) complexes with N, O donor β-ketiminate ligand (L1) and S, S donor piperidine dithiocarbamate ligand (L2) have been synthesized by the reactions of AsCl3 with both ligands in equimolar ratio by stirring at room temperature in benzene solution. All these synthesized compounds have been characterized by Elemental Analysis, IR, (1H and 13C) NMR Spectral and ESI-Mass Studies. Both Ligands and their corresponding Chloro-arsenic (III) complexes have been screened for antimicrobial activity against the various bacterial (E. Coli, B. Subtalis and P. Aeruginosa) and fungal (T. Resei, P. Funiculosum and Fusarium) strains and results obtained .

Nickel Complexes Bearing SNN and SS Donor Atom Ligands: Synthesis, Structural Characterization and Biological activity

Based on a tridentate thiosemicarbazone ligand {HL = 4‐(2,4‐dimethylphenyl)‐1‐((pyridin‐2‐yl)methylene)thiosemicarbazide}, the nickel complexes [NiCl(L)] 1, [Ni(L)(diEtdtc)(H2O)] 2 and [Ni(L)(pipdtc)(H2O)] 3 were prepared {NadiEtdtc = sodium diethyldithiocarbamate and Napipdtc = sodium piperidine dithiocarbamate} and their structures were elucidated according to their elemental analyses, solution conductivities, magnetic moments and spectroscopic (IR and electronic) data. X‐ray single crystal studies have confirmed the structure of 1 as a square planar complex in which each nickel atom is linked to three (two nitrogen and one sulfur) atoms from the thiosemicarbazone ligand and a chlorine atom to ensure the complex neutrality. Moreover, the asymmetric unit cell of the complex was found to consist of two independent complex molecules of slightly different conformations (A&B). The complexes, especially the binary one, displayed high bactericidal activities that, in several instances, were comparable to or higher than those of the chloramphenicol standard.

Synthesis and characterization of antimony (III) heteroleptic derivatives having oxygen, nitrogen and sulfur containing organic moieties with their antibacterial and antioxidant activities

Six antimony(III) heteroleptic derivatives of the type [(R)(R′)C = NO]2[where R= –C6H5, R′= –CH3 (A); R= –C6H4CH3, R′= –CH3 (B); R= –C6H4Cl, R′= –CH3 (C); R= –C6H4Br, R′= –CH3 (D); R= –C6H4OH, R′= –H (E); R(R′)C = (F)] have been synthesized by the reactions of antimony trichloride with the sodium salt of substituted oximes and piperidine dithiocarbamate in 1:2:1 stoichiometry. These heteroleptic derivatives have been characterized by physico-chemical and elemental analyses (C, H, N, S and Sb). The tentative structures have been proposed on the basis of IR, 1H and 13C NMR spectral and LC-mass spectrometry. The oxime moiety behaves as a unidentate ligand whereas the dithiocarbamate moiety behaves in mono functional anisobidentate manner. Distorted trigonal bipyramidal geometry around antimony metal has been proposed for these derivatives. Powder XRD study revealed that derivative (A) has nano range particle size, which supports the crystalline nature of the derivative. These newly synthesized heteroleptic antimony(III) derivatives have been examined against the B. Subtilis (gram positive) and E. coli (gram negative) bacteria for antibacterial potential and two derivatives [(C6H5)(CH3)C = NO]2Sb[S2C] (A) and [(C6H4CH3)(CH3)C = NO]2Sb[S2C ] (B) were examined for their antioxidant activity. Structural-activity relationship for antibacterial potential amongst the six derivatives (A-F) was also explored.

Synthesis of (Bi1-x Sb x )2S3 solid solutions via thermal decomposition of bismuth and antimony piperidinedithiocarbamates.

The synthesis of the complete range of (Bi1−xSbx)2S3 solid solutions, where 0 ≤ x ≤ 1, by the variation of the mole ratio of bismuth and antimony piperidine dithiocarbamate complexes is reported. There was a near linear expansion of a and c lattice parameters as the mole ratio of the antimony precursor was increased. The composition of the particles directionally followed the amount of precursor ratio used. When the composition of particles was compared to cell parameters, a slight deviation from Vegard's law was observed with a corresponding contraction of the b parameter and an approximately 3.5% reduction of the lattice volume. The nanorods obtained showed aspect ratios that depend on the composition of the material. The Bi and Sb rich materials had high aspect ratios of 16.58 and 16.58 respectively with a minimum aspect ratio of 2.58 observed for x = 0.50.

Developing a nontoxic and biocompatible polymeric self-assembly by using RAFT methodology for biomedical application

The amphiphilic block copolymer poly(N-vinylpyrrolidone)-b-poly(N-vinylcarbazole) (PVP-b-PVK) was synthesized by reversible-deactivation radical polymerization (RDRP)using reversible addition-fragmentation chain transfer (RAFT) methodology by new chain transfer agent (CTA) i.e. benzyl piperidine dithiocarbamate (BPDC). The pseudo-first-order kinetics and linear evolution of the molar mass with N-vinylpyrrolidone (NVP) conversion were obtained with the molar mass dispersity (Ð) 1.30–1.41 in toluene. 1H NMR spectrum indicates the presence of chain-end functional groups on homopolymer and block copolymer. The above block copolymer get self-assembled and form micelles in the aqueous medium, the size of micelles is characterized by 1H NMR, transmission electron micrographs (TEM) and dynamic laser light scattering (DLS) analyses, and critical micelles concentration (CMC) was determined by UV–vis spectroscopy. Trypan blue exclusion and MTT assay were done to ensure the cytotoxic effect of PVP-b-PVK on different types of normal cells (thymocytes, splenocytes and macrophage), and no cytotoxic effect was shown by block copolymer on cells, while observed biocompatibility with cells was 200 mg/mL. Further, the beads of block copolymer releases (65%) highly water-soluble levofloxacin drug up to 8 h in a controlled manner at pH 7.4 (37 ± 0.2 °C), while loading of levofloxacin drug was 62% (w/w).

Synthesis and antibacterial evaluation of new sulfanyltetrazole derivatives bearing piperidine dithiocarbamate moiety

ABSTRACTA series of new alkyl or aryl sulfanyltetrazole derivatives containing dithiocarbamate moiety (5a–6e) were synthesized. The structures of the compounds were characterized by IR, 1H NMR, 13C NMR spectra, and elemental analysis data. The present study examines the antibacterial potential of novel synthetic sulfanyltetrazole compounds against clinically important gram-positive and -negative strains. The results of screening showed that attachment of dithiocarbamate to sulfanyltetrazole derivatives results in enhancement of antibacterial activity. The compound 6d showed the best activity among the tested compounds. Also, the less polar 2,5-disubstituted sulfanyltetrazole regioisomers showed an increased antibacterial activity compared with the corresponding more polar regioisomers.

Synthesis, Characterization of some Transition metal complexes of Piperidine dithiocarbamate and ethylenediamine

Synthesis, Characterization of some Transition metal complexes of Piperidine dithiocarbamate and ethylenediamine

Syntheses, characterization, antibacterial activity and molecular modelling of phenylantimony(III) heteroleptic derivatives containing substituted oximes and piperidine dithiocarbamate

Six new heteroleptic phenylantimony(III) derivatives containing substituted oximes and dithiocarbamate moieties of the type (where R = ─C6H5, X = ─CH3 (2a); R = ─C6H4CH3, X = ─CH3 (2b); R = ─C6H4Cl, X = ─CH3 (2c); R = ─C6H4Br, X = ─CH3 (2d); R = ─C6H4OH, X = ─H (2e); R(X)C = (2f)) have been synthesized by the reactions of phenylantimony(III) dichloride with the sodium salt of substituted oximes and dithiocarbamate moiety in unimolar ratio with stirring in dichloromethane. All these newly synthesized derivatives have been characterized using physicochemical and elemental analyses. Structures have been proposed on the basis of infrared, 1H NMR, 13C NMR and LC–MS spectral studies and molecular modelling. In these derivatives the oxime behaves in an unidentate manner whereas dithiocarbamate behaves in a monofunctional anisobidentate manner. Pseudo‐trigonal bipyramidal (ψ‐TBP) geometry around the antimony metal centre is proposed for these phenylantimony(III) heteroleptic derivatives. The geometry of a representative complex has been optimized through molecular modelling. These newly synthesized derivatives were screened against Bacillus subtilis (Gram‐positive) and Escherichia coli (Gram‐negative) bacteria to evaluate their antibacterial potential. The structure–activity relationship for antibacterial activity among the four derivatives 2a, 2c, 2e and 2f is discussed.

Synthesis and characterization of CdS nanocrystallites and OMWCNT-supported cadmium sulfide composite and their photocatalytic activity under visible light irradiation

CdS nanocrystallites and CdS- oxidized multiwalled carbon nanotubes (OMWCNT) composite were prepared by the solvothermal decomposition of a single-source molecular precursor, [Cd(pip.dtc)2] (pip.dtc = piperidine dithiocarbamate) in the presence of ethylene glycol. The as prepared CdS nanocrystallites and CdS-OMWCNT composite were characterized by powder X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX), transmission electron microscopy (TEM), UV-vis and Raman spectroscopy. Peak broadening in the XRD shows the formation of nanocrystalline CdS. TEM images of CdS nanocrystallites revealed the nearly spherical shape morphology of the particles, whereas, TEM images of composite showed the deposition of CdS nanocrystallites on the OMWCNT. EDX measurements matches with a 1:1 stoichiometry of Cd and S in CdS nanocrystallites, whereas, that of the composite showed the presence of Cd and S along with C. The vibrational properties of CdS nanocrystallites and their composite with OMWCNT were studied by Raman spectroscopy. Furthermore, the photocatalytic activity studies for the degradation of methylene blue under visible light irradiation using these materials were carried out. The surface area calculated using BET surface analyzer for CdS-OMWCNT composite (148.31 m2/g) was found to be more compared to bare CdS nanocrystallites (56.78 m2/g). The CdS-OMWCNT composite exhibited very good photocatalytic activity for the degradation of methylene blue under visible light irradiation which has been attributed to the increased surface area and synergistic effect in the composite compared to bare CdS nanocrystallites.

Synthesis of hierarchical PbS nanostructures capped with castor oil

We report the synthesis of castor oil capped hierarchical PbS nanostructures using piperidine dithiocarbamate of lead(II) complex as a single source precursor. The anisotropic structures of PbS were obtained at reaction temperatures of 190, 230, 270 and 300°C. The optical properties of the PbS nanostructures show evidence of quantum confinement.

Synthesis, crystal structures, luminescence properties and catalytic application of lanthanide(III) piperidine dithiocarbamate complexes

A series of lanthanide(III) piperidine dithiocarbamate complexes [Ln(Pip-Dtc)3(Phen)] [where Ln=La(III), Ce(III), Pr(III), Nd(III), Sm(III), Gd(III), Tb(III), Dy(III), Er(III); Pip-Dtc=piperidine dithiocarbamate and Phen=1,10-phenanthroline] has been synthesized and structurally characterized by analytical and various spectral techniques such as FT-IR, UV–Vis and 1H NMR. The molecular structure of [Pr(Pip-Dtc)3(Phen)], [Nd(Pip-Dtc)3(Phen)] and [Sm(Pip-Dtc)3(Phen)] complexes were determined by single crystal X-ray diffraction studies. The binding of the Pip-Dtc to the metal center involves two sulfur atoms and Phen through two nitrogen atoms. The metal center is octa-coordinated by three Pip-Dtc and one Phen ligands. The coordination geometry around Ln(III) ion is distorted dodecahedron. The photoluminescence properties of Sm(III), Pr(III), Tb(III), Dy(III) complexes indicated that the emission intensity depend on the nature of the metal ion, ligand and polarity of the medium. These complexes exhibited good to excellent catalytic activity in trimethylsilyl cyanation of benzaldehyde.

Fabrication of copper nanoparticles decorated multiwalled carbon nanotubes as a high performance electrochemical sensor for the detection of neotame.

A highly sensitive and novel electrochemical sensor for the detection of neotame using differential pulse voltammetry with a modified glassy carbon electrode is presented. The method was further customized by the fabrication of the electrode surface with copper nanoparticles-ammonium piperidine dithiocarbamate-mutiwalled carbon nanotubes assimilated with β-cyclodextrin. The multiwalled carbon nanotubes assimilated with β-cyclodextrin/glassy carbon electrode exhibited catalytic activity towards the oxidation of neotame at a potential of 1.3 V at pH 3.0. The transmission electron microscopy, thermogravimetric analysis, frontier transform infrared spectroscopy and cyclic voltammetry were employed to characterize the electrochemical sensor. The sensitivity and detection limits of the electrode increased two-fold in contrast to the β-CD-MWCNTs/GCE sensor. The developed method was successfully applied for the determination of neotame in food samples, with results similar to those achieved by our modified capillary electrophoresis method with a 96% confidence level.