- Synthesis of (Bi1-xSbx)2S3 solid solutions via thermal decomposition of bismuth and antimony piperidinedithiocarbamates
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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.
- Kun, Walter N.,McNaughter, Paul D.,Nyamen, Linda D.,Spencer, Ben F.,O'Brien, Paul,Ndifon, Peter T.,Revaprasadu, Neerish
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- Heterocyclic Bismuth(III) Dithiocarbamato Complexes as Single-Source Precursors for the Synthesis of Anisotropic Bi2S3Nanoparticles
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New complexes catena-(μ2-nitrato-O,O′)bis(piperidinedithiocarbamato)bismuth(III) (1) and tetrakis(μ-nitrato)tetrakis[bis(tetrahydroquinolinedithiocarbamato)bismuth(III)] (2) were synthesised and characterised by elemental analysis, FTIR spectroscopy and thermogravimetric analysis. The single-crystal X-ray structures of 1 and 2 were determined. The coordination numbers of the BiIIIion are 8 for 1 and ≥6 for 2 when the experimental electron density for the nominal 6s2lone pair of electrons is included. Both complexes were used as single-source precursors for the synthesis of dodecylamine-, hexadecylamine-, oleylamine and tri-n-octylphosphine oxide-capped Bi2S3nanoparticles at different temperatures. UV/Vis spectra showed a blueshift in the absorbance band edge characteristic of a quantum size effect. High-quality, crystalline, long and short Bi2S3nanorods were obtained depending on the thermolysis temperature, which was varied from 190 to 270 °C. A general trend of increasing particle breadth with increasing reaction temperature and increasing length of the carbon chain of the amine (capping agent) was observed. Powder XRD patterns revealed the orthorhombic crystal structure of Bi2S3.
- Kun, Walter N.,Mlowe, Sixberth,Nyamen, Linda D.,Ndifon, Peter T.,Malik, Mohammad A.,Munro, Orde Q.,Revaprasadu, Neerish
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- Functionalised trimethyltetrathiafulvalene (TriMe-TTF) derivatives via reactions of trimethyltetrathiafulvalenyllithium with electrophiles: X-ray crystal structures of benzoyl-TriMe-TTF and benzoylthio-TriMe-TTF
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A high yielding synthesis of trimethyltetrathiafulvalene is reported and a range of functionalised derivatives have been prepared via reactions of trimethyltetrathiafulvalenyllithium with electrophiles.
- Moore,Bryce,Batsanov,Cole,Howard
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- Heterocyclo-substituted sulfa drugs: Part XI. Novel biologically active N-(piperidino-, morpholino-, piperazino-) dithiocarbamyl-azo dyes and their chelates
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A Series of novel azo-sulfa drugs of piperidino-, morpholino-, mono-, and bis-piperazino-N-dithiocarbamyl-azo dyes (Ia-h - IV a-h) are synthesiezed via a reaction of 4-[(4′-heterocyclo-substituted) suflamoyl and/or sulfonyl] benzenediazonium salts with N-piperidino-, N-morpholino-, mono-, and bis- N-piperazino- dithiocarbamate sodium salts in acid medium to afford the corresponding azo dye legands. Interaction of these ligands with metal salts: iron(III), copper(II) and mercuric(II) chlorides in ethanolic solution afforded the corresponding metal chelates (I′a-h - ′IVa-h), (I″a-h - ″IVa-h) and (I?a-h - ≈IVa-h). Ligands and their metal chelates are characterized by microanalysis, IR, UV-Vis H-NMR spectroscopy and are screened in vitro for their antimicrobial activities. Chelation of ligands induces a remarkable increase in their antimicrobial activity.
- Awad, Ibrahim M.A.
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- The syntheses and structures of Zn(II) heterocyclic piperidine and tetrahydroquinoline dithiocarbamates and their use as single source precursors for ZnS nanoparticles
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We report the synthesis and single X-ray structures of bis(dipiperidinyldithio-carbamato)zinc(II) and bis(ditetrahydroquinolinyldithiocarbamato)zinc(II) complexes. The complexes were thermolysed in hexadecylamine (HDA) and tri-n-octylphosphine oxide (TOPO) at different reaction temperatures to produce HDA and TOPO capped ZnS nanoparticles. The microstructure and morphology of the as-prepared ZnS nanoparticles were characterized using X-ray diffraction (XRD), transmission electron microscopy (TEM) and high transmission electron microscopy (HRTEM). Predominantly close to spherical shaped particles were observed in the TEM images of all samples. The optical properties of the particles studied by UV-Vis and photoluminescence (PL) spectroscopy showed evidence of quantum confinement.
- Nyamen, Linda D.,Nejo, Adeola A.,Pullabhotla, Viswanadha S.R.,Ndifon, Peter T.,Malik, Mohammad Azad,Akhtar, Javeed,O'Brien, Paul,Revaprasadu, Neerish
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- Dithiocarbamates combined with copper for revitalizing meropenem efficacy against NDM-1-producing Carbapenem-resistant Enterobacteriaceae
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The worldwide prevalence of NDM-1-producing Gram-negative pathogens has drastically undermined the clinical efficacy of carbapenems, prompting a need to devise an effective strategy to preserve their clinical value. Here we constructed a focused compound library of dithiocarbamates and systematically evaluated their potential synergistic antibacterial activities combined with copper. SA09-Cu exhibited excellent inhibition against a series of clinical NDM-1-producing carbapenem-resistant Enterobacteriaceae (CRE) in restoring meropenem effect, and slowed down the development of carbapenem resistance. Enzymatic kinetic and isothermal titration calorimetry studies demonstrated that SA09-Cu was a noncompetitive NDM-1 inhibitor. The electron paramagnetic resonance (EPR) and X-ray photoelectron spectroscopy (XPS) revealed a novel inhibition mechanism, which is that SA09-Cu could convert NDM-1 into an inactive state by oxidizing the Zn(II)-thiolate site of the enzyme. Importantly, SA09-Cu showed a unique redox tuning ability, and avoided to be reduced by intracellular thiols of bacteria. In vivo experiments indicated that SA09 combined with CuGlu could effectively potentiate MER's effect against NDM-1-producing E. coli (EC23) in the murine infection model. This study provides a highly promising scaffold in developing novel inhibitors to combat NDM-1-producing CREs.
- Chen, Cheng,Yang, Ke-Wu,Zhai, Le,Ding, Huan-Huan,Chigan, Jia-Zhu
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supporting information
(2021/11/20)
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- Synthesis, Characterization, and Molecular Docking Study of Some Novel Imidazole Derivatives as Potential Antifungal Agents
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The azole pharmacophore is still regarded as a viable lead structure for the synthesis of more effective antifungal agents. In this study, two novel series of imidazole derivatives containing dithiocarbamate (5a–5g) and (benz)azolethiol (6a–6n) side chains that are structurally related to the famous antifungal azole pharmacophore were synthesized, and the structures of them were characterized by spectral (IR, 1H NMR, 13C NMR, and MS spectra) analyses. The synthesized compounds were screened in vitro antifungal activity against pathogenic strains fungi. Theoretical ADME (absorption, distribution, metabolism, and excretion) predictions were calculated for final compounds. A molecular docking study of the most active compound with target “lanosterol 14α-demethylase” (CYP51) was performed to unravel the mode of antifungal action. Compound 5e, which features imidazole and 4-methoxybenzyl piperazine scaffolds, showed the most promising antifungal activity with an MIC50 value of 0.78?μg/mL against C. krusei. Effect of the compound 5e against ergosterol biosynthesis was observed by LC–MS–MS method, which is based on quantification of ergosterol level in C.?krusei.
- I??k, Ay?en,Acar ?evik, Ulviye,Sa?l?k, Begüm Nurpelin,?zkay, Yusuf
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p. 142 - 152
(2019/01/04)
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- Novel imidazole derivatives as antifungal agents: Synthesis, biological evaluation, ADME prediction and molecular docking studies
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A series of 2-(substituteddithiocarbamoyl)-N-[4-((1H-imidazol-1-yl)methyl)phenyl]acetamide derivatives was designed and synthesized to combat the increasing incidence of drug-resistant fungal infections. All synthesized compounds were characterized by IR, 1H-NMR, 13C-NMR, and HRMS spectra and elemental analyses. Antifungal activity tests were performed against four different fungal strains. Molecular docking studies were performed to investigate the mode of action towards the fungal lanosterol 14α-demethylase, a cytochrome P450-dependent enzyme. ADME studies were carried out and a connection between activities and physicochemical properties of the target compounds was determined. Most of the final compounds exhibited significant activity against Candida albicans and Candida krusei with MIC50 value 12.5 μg/mL. The results of in vitro anti-Candida activity, a docking study and ADME prediction revealed that the newly synthesized compounds have potential anti-Candida activity and evidenced the most active derivative, 5b (2-Pyrrolidinthiocarbonylthio-N-[4-((1H-imidazol-1-yl)methyl)phenyl]acetamide), which can be further optimized as a lead compound.
- Alt?nda?, Firuze Diyar,Sa?l?k, Begüm Nurpelin,Acar ?evik, Ulviye,I??kda?, ?lhan,?zkay, Yusuf,Karaca Gen?er, Hülya
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p. 887 - 894
(2019/02/03)
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- Design, Synthesis, Molecular Docking, and Cholinesterase Inhibitory Potential of Phthalimide-Dithiocarbamate Hybrids as New Agents for Treatment of Alzheimer's Disease
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A novel series of phthalimide-dithiocarbamate hybrids was synthesized and evaluated for in vitro inhibitory potentials against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The anti-cholinesterase results indicated that among the synthesized compounds, the compounds 7g and 7h showed the most potent anti-AChE and anti-BuChE activities, respectively. Molecular docking and dynamic studies of the compounds 7g and 7h, respectively, in the active site of AChE and BuChE revealed that these compounds as well interacted with studied cholinesterases. These compounds also possessed drug-like properties and were able to cross the BBB.
- Asadi, Mehdi,Ebrahimi, Mostafa,Mohammadi-Khanaposhtani, Maryam,Azizian, Homa,Sepehri, Saghi,Nadri, Hamid,Biglar, Mahmood,Amanlou, Massoud,Larijani, Bagher,Mirzazadeh, Roghieh,Edraki, Najmeh,Mahdavi, Mohammad
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- Dithiocarbamates: Efficient metallo-β-lactamase inhibitors with good antibacterial activity when combined with meropenem
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The activity of β-lactam antibiotics is compromised by metallo-β-lactamases (MBLs). Herein, a series of dithiocarbamate derivatives were designed and synthesized. Their antibacterial activities were tested in combination with meropenem (MEM) against several MBL (NDM and IMP type)-producing clinical isolates. Clinical isolates harboring NDM-1 and IMP-4 became susceptible to MEM when it was combined with dithiocarbamate compounds 4a, 4b or 4f synthesized in this work. Compounds 4a and 4b increased the effectiveness of MEM by up to 2560 times against strains. In vitro bactericidal dynamics tests showed that bacteria died within 24 h when they were treated with compound 4f + MEM. Compounds 4a, 4b and 4f were non-hemolytic and exhibited low toxicity toward HeLa cells in vitro. These data show that compounds containing dithiocarbamate functional group may be helpful in the development of MBL inhibitors.
- Wang, Ming-Ming,Chu, Wen-Chao,Yang, Yi,Yang, Qian-Qian,Qin, Shang-Shang,Zhang, En
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supporting information
p. 3436 - 3440
(2018/09/29)
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- Substituted carbamothioic amine-1-carbothioic thioanhydrides as novel trichomonicidal fungicides: Design, synthesis, and biology
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Sexually transmitted diseases like trichomoniasis along with opportunistic fungal infections like candidiasis are major global health burden in female reproductive health. In this context a novel non-nitroimidazole class of substituted carbamothioic amine-1-carbothioic thioanhydride series was designed, synthesized, evaluated for trichomonacidal and fungicidal activities, and was found to be more active than the standard drug Metronidazole (MTZ). Compounds were trichomonicidal in the MIC ranges of 4.77–294.1 μM and 32.46–735.20 μM against MTZ-susceptible and -resistant strains, respectively. Further, compounds inhibited the growth of at least two out of ten fungal strains tested at MIC of 7.50–240.38 μM. The most active compound (20) of this series was 3.8 and 9.5 fold more active than the MTZ against the two Trichomonas strains tested. Compound 20 also significantly inhibited the sulfhydryl groups present over Trichomonas vaginalis and was found to be more active than the MTZ in vivo. Further, a docking analysis carried out with cysteine proteases supported their thiol inhibiting ability and preliminary pharmacokinetic study has shown good distribution and systemic clearance.
- Mandalapu, Dhanaraju,Kushwaha, Bhavana,Gupta, Sonal,Krishna, Shagun,Srivastava, Nidhi,Shukla, Mahendra,Singh, Pratiksha,Chauhan, Bhavana S.,Goyani, Ravi,Maikhuri, Jagdamba P.,Sashidhara, Koneni V.,Kumar, Brijesh,Tripathi, Renu,Shukla, Praveen K.,Siddiqi, Mohammad I.,Lal, Jawahar,Gupta, Gopal,Sharma, Vishnu L.
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p. 632 - 645
(2017/12/08)
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- Synthesis and biological evaluation of new cholinesterase inhibitors for Alzheimer's disease
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Alzheimer's disease (AD) is a neurodegenerative disorder mostly influencing the elderly, and causes death due to dementia. The main pathogenic feature connected with the progression of this multifactorial disease is the weakening of the cholinergic system in the brain. Cholinesterase (ChE) inhibitors are recognized as one of the choices in the treatment of AD. The inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) were approved as a therapeutic strategy to reduce the symptoms of AD and prevent its progression. The capacity of BChE is not completely known yet; rather, it is accepted to assume a part in a few disorders such as AD. Thus, BChE inhibitors may have a greater role for the treatment of AD in the future. In the present study, 2-(9-acridinylamino)-2-oxoethyl piperazine/piperidine/morpholinecarbodithioate derivatives were synthesized in order to investigate anticholinesterase activity. Eight derivatives demonstrated a specific and promising action against BChE. Furthermore, compound 4n showed inhibitory activity against both enzymes. It was found that the active compounds were well tolerated in the cytotoxicity test. Possible interactions between the lead compound, 4n, and the BChE enzyme were determined through a docking study. The findings obtained within this paper will contribute to the development of new and effective synthetic anti-Alzheimer compounds, and will ideally encourage future screening against AD.
- Hussein, Weiam,Sa?lik, Begüm Nurpelin,Levent, Serkan,Korkut, Bü?ra,Ilgin, Sinem,?zkay, Yusuf,Kaplancikli, Zafer Asim
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- Synthesis and evaluation of new benzodioxole-based dithiocarbamate derivatives as potential anticancer agents and hCA-I and hCA-II inhibitors
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In the current work, new benzodioxole-based dithiocarbamate derivatives were synthesized via the reaction of N-(1,3-benzodioxol-5-ylmethyl)-2-chloroacetamide with appropriate sodium salts of N,N-disubstituted dithiocarbamic acids. These derivatives were evaluated for their cytotoxic effects on A549 human lung adenocarcinoma and C6 rat glioma cell lines. N-(1,3-Benzodioxol-5-ylmethyl)-2-[4-(4-nitrophenyl)-1-piperazinylthiocarbamoylthio]acetamide (10) can be identified as the most promising anticancer agent against C6 cell line due to its notable inhibitory effect on C6 cells with an IC50value of 23.33 ± 7.63 μg/mL when compared with cisplatin (IC50= 19.00 ± 5.29 μg/mL). On the other hand, compound 10 did not show any significant cytotoxic activity against A549 cell line. The compounds were also tested for their in vitro inhibitory effects on hCA-I and hCA-II. Generally, the tested compounds were more effective on CAs than acetazolamide, the reference agent. Among these compounds, N-(1,3-benzodioxol-5-ylmethyl)-2-[(morpholinyl)thiocarbamoylthio]acetamide (3) and N-(1,3-benzodioxol-5-ylmethyl)-2-[(thiomorpholinyl)thiocarbamoylthio]acetamide (4) were found to be the most effective compounds on hCA-I with IC50values of 0.346 nM and 0.288 nM, and hCA-II with IC50values of 0.287 nM and 0.338 nM, respectively.
- Alt?ntop, Mehlika Dilek,Sever, Belgin,Akal?n ?ift?i, Gül?en,Kucukoglu, Kaan,?zdemir, Ahmet,Soleimani, Seyedeh Sara,Nadaroglu, Hayrunnisa,Kaplanc?kl?, Zafer As?m
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p. 190 - 196
(2016/12/02)
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- Design, synthesis and pharmacological analysis of 5-[4′-(substituted-methyl)[1,1′-biphenyl]-2-yl]-1H-tetrazoles
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In the present paper 5-[4′-({4-[(4-aryloxy)methyl]-1H-1,2,3-triazol-1-yl}methyl)[1,1′-biphenyl]-2-yl]-1H-tetrazoles (5a–g) and [2′-(1H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl-substituted-1-carbodithioates (11h–q) have been designed and synthesized. These compounds were subjected to docking (against AT1 receptor protein enzyme in complex with Lisinopril), in vitro angiotensin converting enzyme inhibition, anti-proliferative, anti-inflammatory screening (through egg albumin denaturation inhibition and red blood cell membrane stabilization assay) and finally anti-fungal activity analyses. Some of the compounds have shown significant pharmacological properties.
- Kamble, Atulkumar,Kamble, Ravindra,Dodamani, Suneel,Jalalpure, Sunil,Rasal, Vijaykumar,Kumbar, Mahadev,Joshi, Shrinivas,Dixit, Sheshagiri
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p. 444 - 457
(2017/04/13)
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- Role of disulfide linkage in action of bis(dialkylaminethiocarbonyl)disulfides as potent double-Edged microbicidal spermicide: Design, synthesis and biology
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Trichomoniasis and candidiasis are amongst the most common morbidity-causing reproductive tract infections, generally treated by Metronidazole and Fluconazole respectively. Poor vaginal efficacy, drug-resistance and non-spermicidal nature limit their use as topical microbicidal contraceptives. Bis(dialkylaminethiocarbonyl)disulfides (4-38) were designed as dually active, non-surfactant molecules capable of eliminating Trichomonas vaginalis and Candida strains as well as irreversibly immobilizing 100% human sperm instantly, at doses non-cytotoxic to human cervical epithelial cells and vaginal microflora in vitro. Compounds 12, 16, 17 were fifty times more active than nonoxynol-9, OTC vaginal spermicide, and compounds 12 and 17 have shown remarkable in vivo activity in rabbit model. Most promising compound 17 has shown promise for further development as a double-edged vaginal microbicide due to their improved activity and safety along with notable in vivo trichomonicidal activity. Role of disulfide group was established by loss of spermicidal activity on chemical modifications (39-56). These disulfides might be targeting thiol groups present over cell membrane of human sperm and Trichomonas as shown by fluorescence labeling of free thiols.
- Lal, Nand,Jangir, Santosh,Bala, Veenu,Mandalapu, Dhanaraju,Sarswat, Amit,Kumar, Lalit,Jain, Ashish,Kumar, Lokesh,Kushwaha, Bhavana,Pandey, Atindra K.,Krishna, Shagun,Rawat, Tara,Shukla, Praveen K.,Maikhuri, Jagdamba P.,Siddiqi, Mohammad I.,Gupta, Gopal,Sharma, Vishnu L.
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p. 275 - 290
(2016/04/26)
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- Aerosol assisted chemical vapor deposition (AACVD) of CdS thin films from heterocyclic cadmium(II) complexes
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Abstract Cadmium dithiocarbamato complexes of piperidine (1) and tetrahydroquinoline (2) were synthesized and characterized by elemental analysis, FT-IR spectroscopy, NMR and TGA analyses. The X-ray single crystal structure of bis(piperidinedithiocarbamato)cadmium(II) complex (1) was determined. The synthesized compounds were used as single source precursors to deposit CdS films on glass substrates at 350, 400 and 450 °C using the aerosol assisted chemical vapor deposition (AACVD) method. The surface morphology and the size of the CdS films were determined by AFM and SEM analyses; the crystalline phases by p-XRD analyses and the elemental composition by EDX measurements. The particle sizes were found to be in the range between 50-110 nm and 100-220 nm for complex (1) and (2), respectively. The electronic properties of the CdS films were analyzed by UV-Vis and Raman spectroscopic methods. Results revealed that the morphology, size and composition of the films are influenced by the deposition temperature.
- Mlowe, Sixberth,Nyamen, Linda D.,Ndifon, Peter T.,Malik, M. Azad,Raftery, James,O'Brien, Paul,Revaprasadu, Neerish
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p. 181 - 187
(2015/06/22)
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- Synthesis, crystal structures, luminescence properties and catalytic application of lanthanide(III) piperidine dithiocarbamate complexes
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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.
- Pitchaimani, Ponnuchamy,Lo, Kong Mun,Elango, Kuppanagounder P.
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- Synthesis of multi-podal CdS nanostructures using heterocyclic dithiocarbamato complexes as precursors
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Bis(dipiperidinyldithiocarbamato)cadmium(II) (1) and bis(ditetrahydroquinolinyldithio-carbamato)cadmium(II) (2) were used as precursors for the synthesis of oleylamine (OA), decylamine (DA) and dodecylamine (DDA) capped CdS nanoparticles. The optical properties of these particles have been studied. The absorption spectra for the amine capped CdS particles are blue shifted in relation to the bulk material. The corresponding photoluminescence spectra show a narrow band edge emission. High quality crystalline CdS particles of different shapes, ranging from short nanorods and elongated nanorods (rods, bipods, tripods and tetrapods) to nanocubes were obtained when the reaction temperature was varied between 180 and 270 C. A decrease in the length of the rods and bipodal nanoparticles was observed with an increase in the length of the chain of the amine (capping agent) used. The p-XRD patterns revealed the hexagonal phase of CdS to be dominant in all the samples. Infra-red studies suggest that the mode of bonding of the amines (oleylamine, decylamine and dodecylamine) on the CdS nanoparticle surfaces is through electron donation from the nitrogen atoms.
- Nyamen, Linda D.,Revaprasadu, Neerish,Pullabhotla, Rajasekhar V.S.R.,Nejo, Adeola A.,Ndifon, Peter T.,Malik, Mohammad Azad,O'Brien, Paul
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- Synthesis, characterization and cytotoxicity of the Au(III) complexes with cyclic amine-based dithiocarbamate ligands
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Seven new Au(III) complexes ([(PipDTC)AuCl2] (1), [(MoDTC)AuCl2] (2), [(BzoPizDTC)AuCl2] (3), [(TsPizDTC)AuCl2] (4), [(PizDTC)Au2Cl4] (5), [(MePizDTC)Au2Cl5] (6) and [(EtPizDTC)Au 2Cl5] (7)) with cyclic amine-based dithiocarbamate have been synthesized, characterized and evaluated in vitro. The results indicate that these complexes exert selective cytotoxic effects against HL-60, BGC-823, Bel-7402 and KB cells lines. Complex 1 shows 11-, 5- and 1-folds higher cytotoxicity than cisplatin against KB, BGC-823 and Bel-7402 cell lines. Complex 2 exhibits higher cytotoxicity than cisplatin against BGC-823 and Bel-7402 cell lines. Complexes 3 and 4 display higher cytotoxicity than cisplatin against BGC-823 cell line. The nature of cyclic amine and the number of metal centers have important effects on cytotoxicity of these Au(III) complexes.
- Shi, Yanan,Chu, Wenhao,Wang, Yuechai,Wang, Shuxiang,Du, Jianlong,Zhang, Jinchao,Li, Shenghui,Zhou, Guoqiang,Qin, Xinying,Zhang, Chenliang
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p. 178 - 181
(2013/07/04)
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- Synthesis and biological evaluation of a series of dithiocarbamates as new cholinesterase inhibitors
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In the present paper, a novel series of dithiocarbamates was synthesized via the treatment of 4-(trifluoromethyl)benzyl chloride with appropriate sodium salts of N,N-disubstituted dithiocarbamic acids. The chemical structures of the compounds were elucidated by 1H NMR, mass spectral data, and elemental analyses. Each derivative was evaluated for its ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) using a modification of Ellman's spectrophotometric method. The most potent AChE inhibitor was found as compound 2g (IC50 = 0.53 ± 0.001 μM) followed by compounds 2f (IC50 = 0.74 ± 0.001 μM) and 2j (IC50 = 0.89 ± 0.002 μM) when compared with donepezil (IC50 = 0.048 ± 0.001 μM). Compounds 2f and 2g were more effective than donepezil (IC50 = 7.88 ± 0.52 μM) on BuChE inhibition. Compounds 2f and 2g exhibited the inhibitory effect on BuChE with IC50 values of 1.39 ± 0.041 and 3.64 ± 0.072 μM, respectively.
- Altintop, Mehlika D.,Gurkan-Alp, A. Selen,Oezkay, Yusuf,Kaplancbox, Zafer A.
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p. 571 - 576
(2013/09/02)
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- Synthesis of anisotropic PbS nanoparticles using heterocyclic dithiocarbamate complexes
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We report the synthesis of lead piperidine and lead tetrahydroquinoline dithiocarbamate (DTC) complexes and their use as single source precursors for the preparation of anisotropic PbS nanoparticles. The complexes were thermolysed in coordinating solvents such hexadecylamime (HDA), tri-n-octylphosphine oxide (TOPO), oleylamine (OA) and decylamine (DA) at various reaction temperatures. The variation of the reaction conditions and precursors produced PbS particles with shapes ranging from spheres to cubes and rods. The size of the particles is generally larger than those synthesized by conventional precursor routes. The electron microscopy and X-ray diffraction data confirm the particles to be very crystalline with the dominant cubic rock salt phase present in all samples. The Royal Society of Chemistry 2012.
- Nyamen, Linda D.,Rajasekhar Pullabhotla,Nejo, Adeola A.,Ndifon, Peter T.,Warner, Jamie H.,Revaprasadu, Neerish
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experimental part
p. 8297 - 8302
(2012/07/28)
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- Polynuclear complexes of gold(III) of the composition ([Au(S 2CNR2)2][AuCl4]) n (R = C4H9, R2 = (CH2)5): Synthesis, supramolecular structures, and thermal behavior
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The interaction of binuclear cadmium dialkyldithiocarbamates [Cd 2(S2CNR2)4] with solutions of AuCl3 in 2M HCl gives polynuclear gold(III) complexes ([Au(S 2CNR2)2][AuCl4]) n, where R = C4H9 (I) and R2 = (CH2) 5 (II). The structures of the synthesized compounds solved by X-ray diffraction analysis are char-acterized by a complicated organization at the supramolecular level. The structures are based on polymer chains (I) and layers (II) involving isomeric cations [Au(S2CNR2) 2]+ and anions [AuCl4]-. The thermal behavior of the synthesized complexes is studied by simultaneous thermal analysis including thermogravimetry and differential scanning calorimetry. The final product of the thermal transformations of the studied complexes is shown to be reduced metallic gold.
- Ivanov,Zinkin,Gerasimenko,Sergienko
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experimental part
p. 452 - 459
(2011/09/20)
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- Biological in vitro and in vivo studies of a series of new asymmetrical cationic [99mTc(N)(DTC-Ln)(PNP)]+ Complex (DTC-Ln = alicyclic dithiocarbamate and PNP = Diphosphinoamine)
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99mTc(N)-DBODC5 is a cationic mixed compound under clinical investigation as potential myocardial imaging agent. In spite of this, analogously to the other cationic 99mTc-agents, presents a relatively low first-pass extraction. Thus, modification of 99mTc(N)-DBODC(5) direct to increase its first-pass extraction keeping unaltered the favorable imaging properties would be desirable. This work describes the synthesis and biological evaluation of a series of novel cationic 99mTc-nitrido complexes, of general formula [99mTcN(DTC-Ln)(PNP)]+ (DTC-Ln= alicyclic dithiocarbamates; PNP = diphosphinoamine), as potential radiotracers for myocardial perfusion imaging. The synthesis of cationic 99mTc-(N)-complexes were accomplished in two steps. Biodistribution studies were performed in rats and compared with the distribution profiles of 99mTc(N)-DBODC5 and 99mTc-Sestamibi. The metabolisms of the most promising compounds were evaluated by HPLC methods. Biological studies revealed that most of the complexes have a high initial and persistent heart uptake with rapid clearance from nontarget tissues. Among tested compounds, 2 and 12 showed improved heart uptake with respect to the gold standard 99mTc-complexes with favorable heart-to-liver and slightly lower heart-to-lung ratios. Chromatographic profiles of 99mTc(N)- radioactivity extracted from tissues and fluids were coincident with the native compound evidencing remarkable in vivo stability of these agents. This study shows that the incorporation of alicyclic dithiocarbamate in the [ 99mTc(N)(PNP)]+ building block yields to a significant increase of the heart uptake at early injection point suggesting that the first-pass extraction fraction of these novel complexes may be increased with respect to the other cationic 99mTc-agents keeping almost unaltered the favorable target/nontarget ratios.
- Bolzati, Cristina,Cavazza-Ceccato, Mario,Agostini, Stefania,Refosco, Fiorenzo,Yamamichi, Yoshihiro,Tokunaga, Shinji,Carta, Davide,Salvarese, Nicola,Bernardini, Daniele,Bandoli, Giuliano
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experimental part
p. 928 - 939
(2011/02/22)
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- Exploring the structural requirements for inhibition of the ubiquitin E3 ligase breast cancer associated protein 2 (BCA2) as a treatment for breast cancer
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The zinc-ejecting aldehyde dehydrogenase (ALDH) inhibitory drug disulfiram (DSF) was found to be a breast cancer-associated protein 2 (BCA2) inhibitor with potent antitumor activity. We herein describe our work in the synthesis and evaluation of new series of zinc-affinic molecules to explore the structural requirements for selective BCA2-inhibitory antitumor activity. An N(C - S)S - S motif was found to be required, based on selective activity in BCA2-expressing breast cancer cell lines and against recombinant BCA2 protein. Notably, the DSF analogs (3a and 3c) and dithio(peroxo)thioate compounds (5d and 5f) were found to have potent activity (submicromolar IC50) in BCA2 positive MCF-7 and T47D cells but were inactive (IC50 > 10 μM) in BCA2 negative MDA-MB-231 breast cancer cells and the normal breast epithelial cell line MCF10A. Testing in the isogenic BCA2 +ve MDA-MB-231/ER cell line restored antitumor activity for compounds that were inactive in the BCA2 -ve MDA-MB-231 cell line. In contrast, structurally related dithiocarbamates and benzisothiazolones (lacking the disulfide bond) were all inactive. Compounds 5d and 5f were additionally found to lack ALDH-inhibitory activity, suggestive of selective E3 ligase-inhibitory activity and worthy of further development.
- Brahemi, Ghali,Kona, Fathima R.,Fiasella, Annalisa,Buac, Daniela,Soukupová, Jitka,Brancale, Andrea,Burger, Angelika M.,Westwell, Andrew D.
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experimental part
p. 2757 - 2765
(2010/08/20)
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- Technetium or rhenium complexes, radiopharmaceutical products comprising them
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The invention relates to a technetium or rhenium complex of formula (I): [in-line-formulae][M (R1CS3)2L]??(I) [/in-line-formulae] in which M is Tc or Re, R1 represents an alkyl, cycloalkyl, aralkyl or aryl group which is unsubstituted or substituted by one or more substituents chosen from halogen atoms, the hydroxyl group, alkyl groups and alkoxy groups, and L is a dithiolate ligand, with the exception of the ligand of formula R2CS2 in which R2 is identical to R1. The dithiolate ligand is preferably a dithiocarbamate. The invention also relates to a radiopharmaceutical product comprising a complex of formula (I) with M representing 99Tc, 186Re or 188Re.
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- Synthesis of some 1-[(N,N-disubstituted thiocarbamoylthio)acetyl]-3-(2- thienyl)-5-aryl-2-pyrazoline derivatives and investigation of their antibacterial and antifungal activities
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Fourteen new 1-[(N,N-disubstituted thiocarbamoylthio)acetyl]-3-(2-thienyl)- 5-aryl-2-pyrazoline derivatives (7a-n) were synthesised by reacting 1-(chloroacetyl)-3-(2-thienyl)-5-aryl-2-pyrazolines (5a-g) and appropriate sodium salts of N,N-disubstituted dithiocarbamoic acids (6a, b). The structures of the synthesised compounds were confirmed by elemental analyses, UV, IR, 1H-NMR and FAB+-MS spectral data. Their antibacterial activities against Proteus vulgaris (NRRL B-123), Escherichia coli (NRRL B-3704), Aeromonas hydrophila (Ankara University, Faculty of Veterinary Sciences), Salmonella typhimurium (NRRL B-4420), Streptococcus feacalis (NRRL B-14617), Micrococcus luteus (NRLL B-4375) were investigated and in this investigation, a significant level of activity was illustrated. Antifungal activities of the compounds against Candida albicans and Candida globrata (isolates obtained from Osmangazi Uni. Fac. of Medicine) were found to be inactive. Compounds 7c-n were also evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system and BACTEC 12B medium. The preliminary results indicated that all of the tested compounds were inactive against the test organism.
- Turan-Zitouni, Gulhan,Oezdemir, Ahmet,Gueven, Kiymet
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- Studies on organomercury(II) complexes with piperidine and 2-aminopyridine dithiocarbamates
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The complexes of organomercury (II) chloride [RHgCl, where R=C 6H5 (phenyl), p-Cl C6H4 (p-chlorophenyl), p-Br C6H4 (p-bromophenyl), o-, p-HOC6H4, (o-, p-hydroxyphenyl) with piperidine dithiocarbamate (L1) and 2-aminopyridine dithiocarbamate (L 2) have been synthesized and characterised by IR, UV and 1H NMR spectral studies. Conductance measurement reveals that the compounds are non electrolytes. Thermogravimetric (TG) and differential thermal analysis (DTA) curves and their variations have been correlated with some structural parameters of the complexes. Activity of all the complexes vs. E. Coli, Z. mobilis bacterial strains and activity vs. A.niger, Cerveleria fungal strians have been studied and the general order of activity has been deduced.
- Sharma, Rama,Kaushik
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p. 769 - 772
(2007/10/03)
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- Synthesis, characterization and evaluation of biological activity of palladium (II) and platinum (II) complexes with dithiocarbamic acids and their derivatives as ligands
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We report the preparation and characterization of new complexes of palladium (II) and platinum (II) with some heterocyclic containing dithiocarbamate ligands, such as piperidine-, morpholine-, and thiomorpholine-dithiocarbamate, their methyl esters and the corresponding thiouramdisulphides. These compounds have been studied through spectroscopic techniques, IR spectra, and electronic spectra, thermogravimetric and conductivity measurements. Thermal decomposition of the complexes takes place through a multi-step process involving pyrolysis of the organic moiety that leads to palladium oxide and platinum sponge respectively. All the complexes have been tested for cytostatic activity on KB cells and the most effective compounds also against L1210 and P388 cells.
- Marcheselli,Preti,Tagliazucchi,Cherchi,Sindellari,Furlani,Papaioannou,Scarcia
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p. 347 - 352
(2007/10/02)
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- Reduction Potentials of Thiuram Disulfide/Dithiocarbamate Couples in Acetone/Water
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Reduction potentials relative to the saturated calomel electrode, Eo, of a series of thiuram disulfide/dithiocarbamate couples have been measured in 30percent v/v water in acetone and at μ 0.2 mol l-1 (NaNO3) by a combination of potentiometric measurements and equilibrium constant determinations for thiolate/disulfide interchange reactions.Eo values lie in the range -250 to -340 mV which place dithiocarbamates as intermediate between thiophenolate (Eo -540 mV) and ethylxanthate (Eo -206 mV) in reducing properties.The significant effect on Eo of varying the substituents on the nitrogen in the dithiocarbamates correlates with the substituent effects on the acid dissociation constants of the parent dithiocarbamic acid and with trends in the half-wave potentials for metal-based oxidation and reduction of transition metal dithiocarbamate complexes.
- Nichols, Peter J.,Grant, Michael W.
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p. 2455 - 2463
(2007/10/02)
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- REACTION OF DITHIOCARBAMIC ACID SALTS WITH 4-SUBSTITUTED 2-THIOLENE- AND 3,4-DISUBSTITUTED THIOLANE 1,1-DIOXIDES. STRUCTURAL STUDIES OF N-PHENYLTHIOLANOTHIAZOLIDINE-2-THIONE 5,5-DIOXIDE
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The reaction of monoalkyl(aryl)dithiocarbamic acid salts with 4-substituted 2-thiolene and 3,4-disubstituted thiolane 1,1-dioxides gave N-alkyl(aryl)thiolanothiazolidine-2-thione 5,5-dioxides, the structure of which was proved by X-ray diffraction studies. 1,1-Dioxothiol-3-en-3-yl esters were obtained with salts of dialkyl(heteryl)dithiocarbamic acids.
- Bezmenova, T. E.,Khaskin, G. I.,Slutskii, V. I.,Dul'nev, P. G.,Zakharov, L. N.,et al.
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p. 668 - 672
(2007/10/02)
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- INVESTIGATIONS OF CHROMIUM(III), MAGANESE(III), TIN(II) AND LEAD(II) DITHIOCARBAMATE COMPLEXES
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Piperidine-, morpholine-4-, N-methylpiperazine-4- and thiomorpholine-4-carbodithioate complexes of chromium(III), manganese(III), tin(II) and lead(II) are prepared and characterized by chemical analyses, spectroscopic methods (I.R. and electronic spectra), magnetic susceptibilities, conductivity measurements and mass spectra.The complexes are of the type M(R2dtc)n, where n is the oxidation number of the metal ion.Where possible a tentative stereochemistry of the complexes is discussed on the basis of the results obtained.In all the complexes the dithiocarbamate ligands show bidentate behaviour.
- Preti, Carlo,Tosi, Giuseppe,Zannini, Paolo
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p. 283 - 292
(2007/10/02)
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- 2-(2-Methyl-5-nitro-1-imidazolyl)ethyl cycloaminocarbodithioates
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2-(2-Methyl-5-nitro-1-imidazolyl)ethyl esters of cycloaminocarbodithioates are herein described. These compounds are anti-protozoal and anti-fungal agents. The compounds are prepared in 2 steps. The reaction of the appropriate cycloamine with carbon disulfide in aqueous base forms the aminocarbodithioate salt and the final products are formed by the reaction of this salt with 1-(2-chloroethyl)-2-methyl-5-nitroimidazole.
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