All of the chemicals used throughout experiments (Ni(NO3)2, CoCl2∙6H2O, CuSO4∙5H2O, FeCl3∙6H2O, pyridoxal, thiosemicarbazide, Bovine Serum Albumin (BSA)), and the solvents (ethanol, DMSO) were obtained from Merck as p.a. purity chemicals. The ultra-pure water was used for the spectrofluorometric measurements (Milli-Q® EQ 7000 ultrapure water system). Fetal bovine serum (FBS) and culture mediums RPMI-1640 and Dulbecco’s Modified Eagle Medium (DMEM) were purchased from Capricorn Scientific GmbH (Hessen, Germany). Penicillin Streptomycin solution was purchased from Biological Industries (Cromwell, CT, USA). Trypsin, phosphate-buffered saline (PBS), and dimethyl sulfoxide (DMSO) were purchased from Sigma (St. Louis, MO, USA). 3-(4,5 dimethythiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) was purchased from AppliChem (Maryland Heights, MO, USA). Paraformaldehyde (PFA) was purchased from Serva (Heidelberg, Germany). Crystal violet (CV) was purchased from Biowest (Riverside, MO, USA).
Thiosemicarbazide
Manufactured by Merck Group
Sourced in Germany, United States, Poland
Thiosemicarbazide is a chemical compound that serves as a reagent for various analytical and research applications in laboratory settings. It is a white, crystalline solid that is soluble in water and organic solvents. Thiosemicarbazide is commonly used in analytical chemistry, biochemistry, and materials science, but a detailed description of its core function without interpretation or extrapolation cannot be provided while maintaining an unbiased and factual approach.
Automatically generated - may contain errors
Lab products found in correlation
Hydrochloric acid (hcl), by Merck Group (4 mentions)
Phosphoric acid, by Merck Group (3 mentions)
Isoniazid, by Merck Group (3 mentions)
Dimethyl sulfoxide (dmso), by Merck Group (2 mentions)
Bovine serum albumin (bsa), by Merck Group (2 mentions)
Methanol, by Merck Group (2 mentions)
Dichloromethane, by Merck Group (2 mentions)
Piperidine, by Merck Group (2 mentions)
Chloroform, by Merck Group (2 mentions)
Ethanol, by Merck Group (2 mentions)
Potassium hydroxide, by Merck Group (2 mentions)
Ammonium iron 3 sulfate dodecahydrate, by Merck Group (2 mentions)
Sodium hydroxide (naoh), by Merck Group (2 mentions)
Diacetyl monoxime, by Merck Group (2 mentions)
Sulfuric acid, by Merck Group (2 mentions)
Iron 3 chloride, by Merck Group (2 mentions)
4 chloroacetophenone, by Merck Group (2 mentions)
4 methylacetophenone, by Merck Group (2 mentions)
4 methoxyacetophenone, by Merck Group (2 mentions)
Hesperetin, by Merck Group (2 mentions)
31 protocols using thiosemicarbazide
1
Cytotoxicity Evaluation of Metal Complexes
2
Synthesis of Thiosemicarbazide and Peptide Compounds
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For the synthesis of TSCs, all solvents were of commercial quality and purchased from a local supplier (Avantor). Thiosemicarbazide (catalogue nr T33405); racemic ketoprofen (catalogue nr K1751); 4-acetylbenzoic acid (catalogue nr 177458); 4-formylbenzoic acid (catalogue nr 124915); and p-toluenesulfonic acid monohydrate (catalogue nr T35920) were purchased from Merck (Darmstadt, Germany).
For peptide synthesis, all Fmoc-protected amino acids Fmoc-Phe-OH, Fmoc-Tyr(tBu)-OH, and Fmoc-Trp(Boc)-OH were purchased from Iris Biotech GmbH (Marktredwitz, Germany). Peptide synthesis grade N,N′-Dimethylformamide (DMF) and acetonitrile (ACN) were purchased from Carlo Erba (Milano, Italy). Dichloromethane (DCM), trifluoroacetic acid (TFA), triisopropylsilane (TIS), methanol (MeOH), piperidine, N,N′-Diisopropylethylamine (DIPEA), N-Methylmorpholine (NMM), 1,2-Ethanedithiol (EDT), and acetic anhydride were purchased from Sigma-Aldrich (Milano, Italy). Fmoc-Tyr(tBu)-Wang resin (100–200 mesh, loading: 0.70 mmol/g) was purchased from Novabiochem (Merck, Darmstadt, Germany).
For peptide synthesis, all Fmoc-protected amino acids Fmoc-Phe-OH, Fmoc-Tyr(tBu)-OH, and Fmoc-Trp(Boc)-OH were purchased from Iris Biotech GmbH (Marktredwitz, Germany). Peptide synthesis grade N,N′-Dimethylformamide (DMF) and acetonitrile (ACN) were purchased from Carlo Erba (Milano, Italy). Dichloromethane (DCM), trifluoroacetic acid (TFA), triisopropylsilane (TIS), methanol (MeOH), piperidine, N,N′-Diisopropylethylamine (DIPEA), N-Methylmorpholine (NMM), 1,2-Ethanedithiol (EDT), and acetic anhydride were purchased from Sigma-Aldrich (Milano, Italy). Fmoc-Tyr(tBu)-Wang resin (100–200 mesh, loading: 0.70 mmol/g) was purchased from Novabiochem (Merck, Darmstadt, Germany).
3
Optimization and Characterization of Novel Compounds
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Ethyl acetoacetate, DPPH, ABTS, deuterated dimethyl sulfoxide, and salicylaldehyde and its hydroxylated derivatives were purchased from Alfa Aesar (Kandel, Germany). Absolute ethanol, piperidine, deuterated chloroform, thiosemicarbazide, and acetic acid were purchased from Merck (Milan, Italy). Reagents were used as received without further purification.
NMR spectra were acquired with a Bruker Advance III HD 600 spectrometer (Rheinstetten, Germany) at room temperature with tetramethylsilane (TMS) as the internal standard in DMSO-d6 or CDCl3. ESI mass spectra were recorded with a triple quadrupole QqQ Varian 310-MS mass spectrometer (Palo Alto, CA, USA) using previously optimized parameters [5 (link)]. High-resolution ESI mass spectra were acquired on a Thermofisher ORBITRAP-ELITE (Waltham, MA, USA). Melting points were measured on a Kofler Hot Stage (Rochford, UK) and are uncorrected.
NMR spectra were acquired with a Bruker Advance III HD 600 spectrometer (Rheinstetten, Germany) at room temperature with tetramethylsilane (TMS) as the internal standard in DMSO-d6 or CDCl3. ESI mass spectra were recorded with a triple quadrupole QqQ Varian 310-MS mass spectrometer (Palo Alto, CA, USA) using previously optimized parameters [5 (link)]. High-resolution ESI mass spectra were acquired on a Thermofisher ORBITRAP-ELITE (Waltham, MA, USA). Melting points were measured on a Kofler Hot Stage (Rochford, UK) and are uncorrected.
4
Synthesis of Ethyl 2-[2-(2-nitrobenzylidene)hydrazinyl]thiazole-4-carboxylate
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Ethyl 2-[2-(2-nitrobenzylidene)hydrazinyl]thiazole-4-carboxylate (1) was synthesized by the reaction of 1-(2-nitrobenzylidene)Thiosemicarbazide and ethyl bromopyruvate (Scheme 1 ). The pure reagent grade chemicals were purchased and used as such. Thiosemicarbazide, 4-nitrobenzaldehyde and ethyl bromopyruvate were purchased form Merck Germany. Pre-coated Silica 60 HF254 Aluminum sheets (Merck, Germany) were used to monitor the reaction with thin layer chromatography (TLC). The melting point determination, functional group identification, NMR chemicals shifts and single crystal analysis were carried out as reported elsewhere [25 ]. Dimethyl sulfoxide-deuterated (DMSO-d6) was used to record the proton and carbon NMR (nuclear magnetic resonance), using 300 and 75 MHz frequency, respectively. High resolution mass spectrometry (HRMS) was carried out on Bruker Micro TOF-ESI (time of flight-electrospray ionization) spectrometer, positive targeted mode.![]()
Synthesis of ethyl 2-[2-(2-nitrobenzylidene)hydrazinyl]thiazole-4-carboxylate
5
Synthesis and Characterization of Novel Heterocyclic Compounds
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Thiosemicarbazide, ethyl cyanoacetate, and
malononitrile were purchased from Merck, Germany, and acetophenone
from Prolabo, Paris. p-Chloroacetophenone and p-bromoacetophenone were purchased from Fluka, and p-methylacetophenone from Riedel-de Haen ag. Ethyl acetoacetate
was purchased from Aldrich and benzoylacetone from Sigma. Acetylacetone
and glacial acetic acid were purchased from El-Goumahouria. Sodium
chloride (NaCl), sodium sulfate (Na2SO4), sodium
fluoride (NaCl), lead chloride (PbCl2), cadmium chloride
(CdCl2), dithizone, chloroform (CHCl3), potassium
cyanide (KCN), and hydroxylamine hydrochloride (NH2Cl·H2O) were purchased from Sigma-Aldrich, Germany. All solutions
were prepared with Milli-Q water and filtered using a 0.22 μm
Nylon membrane filter.
malononitrile were purchased from Merck, Germany, and acetophenone
from Prolabo, Paris. p-Chloroacetophenone and p-bromoacetophenone were purchased from Fluka, and p-methylacetophenone from Riedel-de Haen ag. Ethyl acetoacetate
was purchased from Aldrich and benzoylacetone from Sigma. Acetylacetone
and glacial acetic acid were purchased from El-Goumahouria. Sodium
chloride (NaCl), sodium sulfate (Na2SO4), sodium
fluoride (NaCl), lead chloride (PbCl2), cadmium chloride
(CdCl2), dithizone, chloroform (CHCl3), potassium
cyanide (KCN), and hydroxylamine hydrochloride (NH2Cl·H2O) were purchased from Sigma-Aldrich, Germany. All solutions
were prepared with Milli-Q water and filtered using a 0.22 μm
Nylon membrane filter.
6
Synthesis and Characterization of Novel Benzaldehyde Compounds
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4-hydroxybenzaldehyde(Aldrich Chemical Co. Ltd-Steinheim, Germany), 1,6-dibromohexane (Sigma Aldrich Inc, St.Louis USA), ethylenediamine (E-Merck, Germany), 1,3-propylenediamine (Fluka, switzerland), 4,4-diaminophenyl ether (Tokyo Chemical Industry Ltd, Tokyo, Japan), 2,6-diaminopyridine (Sigma-Aldrich, Germany), thiosemicarbazide (E.Merck, Darmstadt, Germany), N-N-dimethylformamide (DMF) (BDH AnalaR, England), dimethyl sulfoxide (DMSO) (BDH AnalaR, England), anhydrous sodium carbonate (Sigma-Aldrich, Germany), ethanol (Merck, Germany), toluene (Fluka Chemie, Switzerland), potassium hydroxide (E-Merck, Germany) and hydrochloric acid (Merck, Germany) were used. Freshly prepared double distilled water was used throughout the study.
7
Nickel(II) Nitrate Thiosemicarbazone Synthesis
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All materials were of reagent grade and were used without further purification. Nickel(II) nitrate hexahydrate [Ni(NO 3 ) 2 •6H 2 O], thiosemicarbazide (Sigma Aldrich), and p-anisaldehyde (Sigma-Aldrich) were used as received.
8
Synthesis and Characterization of Bioactive Compounds
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All melting points were measured on an Electrothermal 9100 series digital melting point apparatus (Shimadzu, Japan). Microanalytical data were obtained with a Vario Elementar apparatus (Shimadzu). Elemental analyses of all compounds were within ± 0.4 % of the theoretical values. Physicochemical data are given in Table I. The IR spectra (KBr) were recorded on a Perkin Elmer 1650 spectrometer (USA). 1 H NMR spectra were recorded on a JEOL EX-300 and a JEOL ECA-500 (Japan). Chemical shift s were expressed in ppm relative to SiMe 4 as internal standard and DMSO-d 6 as solvent. Mass spectra were recorded on a 70 ev EI Ms-QP 1000 EX (Shimadzu). Spectral data are given in Tables II andIII. Thin layer chromatography (chloroform/methanol, 8:2) indicated the formation of pure compounds. Compounds ethyl-3-(2-carbamothioyl-hydrazinylidene) butanoate (1) (link) and arylidene malononitriles (2a,b) were obtained using the procedures reported elsewhere (17, 18) . Ethyl acetoacetate, thiosemicarbazide, 1-bromo-2,3,5-tri-O-acetyl-α-D-ribo-/or xylo and arabinofuranose, 2,3,4,6-tetra-O-acetyl-α-D-gluco-and galacto pyranosyl bromide were purchased from Sigma-Aldrich (USA). Ofl oxacine, miconazole and doxorubicin disks were supplied by the Pasteur Laboratory (Giza, Egypt).
9
Synthesis and Characterization of HM Compound
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Hexane (95%), thiosemicarbazide (98%) was purchased from Sigma-Aldrich (St. Louis, MO, USA). HM was prepared in the Medicinal and Process Chemistry Division of Central Drug Research Institute, Lucknow, Uttar Pradesh, India. Milli-Q pure water was obtained from a Millipore Elix water purification system (Millipore India Pvt. Ltd., New Delhi, India). high-performance liquid chromatography (HPLC) grade methanol and acetonitrile (ACN) were purchased from Merck Ltd., (Mumbai, India). IR spectra was recorded using potassium bromide (KBr) discs, on a PerkinElmer Spectrum RX1 infrared (IR) spectrophotometer. 1H and 13C nuclear magnetic resonance (NMR) spectra were recorded in dimethyl sulfoxide (DMSO) on Bruker DRX-300 (400 MHz) and JEOL AL300 Fourier transform (FT)-NMR (400 MHz) systems; chemical shift (d) is reported in ppm using tetramethyl silane as an internal reference. Mass spectra were recorded on Agilent 6520 mass spectrometer. Elemental analysis was performed on Elementar's Vario EL III micro-analyzer.
10
Purification and Characterization of Peptidylarginine Deiminases
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Dithiothreitol
(DTT), 4-(2-hydroxyethyl)-1-piperazineethanesulfonic
acid (HEPES), ammonium iron(III) sulfate dodecahydrate, tris(2-carboxyethyl)phosphine
(TCEP), and thiosemicarbazide were acquired from Sigma–Aldrich.
Diacetylmonooxime (DAMO), N-α-benzoyl-l -arginine ethyl ester (BAEE), and N-α-benzoyl-l -arginine amide (BAA) were obtained from Acros. Detailed synthetic
procedures are described in theSupporting Information . PAD1, -2, -3, and -4 were purified analogously to previously described
methods.35 (link),57 (link)
(DTT), 4-(2-hydroxyethyl)-1-piperazineethanesulfonic
acid (HEPES), ammonium iron(III) sulfate dodecahydrate, tris(2-carboxyethyl)phosphine
(TCEP), and thiosemicarbazide were acquired from Sigma–Aldrich.
Diacetylmonooxime (DAMO), N-α-benzoyl-
procedures are described in the
methods.35 (link),57 (link)
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