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Chloroacetaldehyde

Manufactured by Merck Group
Sourced in France, United States

Chloroacetaldehyde is a chemical compound used as a laboratory reagent. It is a colorless liquid with a pungent odor. Chloroacetaldehyde is primarily utilized in chemical synthesis and analysis processes, though its specific applications may vary.

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9 protocols using chloroacetaldehyde

1

Quantitative Analysis of Chlorinated Compounds

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Trichloroethene (≥ 99.5%), tetrachloroethene (≥ 99.5%), formic acid (98%), chloroacetic acid (99%), dichloroacetic acid (99.2%), formaldehyde, trichloroacetic acid (≥ 99%), oxalic acid (≥ 99%), glyoxylic acid (98%), chloroacetaldehyde, acetonitrile of HPLC grade (≥ 99.9%), perchloric acid (70%) all prepared from Sigma Aldrich, sulphuric acid (VWR, 95%) and chloroform (Aldrich, 99.8%) were used. All solutions were prepared using ultrapure water (resistivity 18.2 MΩ cm).
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2

Methylation profiling of human tissues

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Chloroacetaldehyde (~55 wt. % in H2O) was purchased from Sigma-Aldrich. PBS tablets were from Gibco. Oligodeoxynucleotides (i.e.,5’-TCA GTC GGA TAA GCA AAG AGA-3’ and 5’-TCA GTC GGA TAA GCA AAG AGA-3’ (“C” stands for 5mC) were customer ordered from Sigma-Aldrich (both were of HPLC purified grade). The de-identified tissue samples were provided by Dr. Xinchun Zhou, whose protocol for sample collection was approved by Institutional Reviewed Board at University of Mississippi Medical Center (#2011–0079).
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3

Characterizing Enzymatic Assays in E. coli

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Isopropyl-β-D-1-thiogalactopyranoside (IPTG) was purchased from Bio Basic Inc. (Ontario, Canada). Tetrabuthylammoniumhydrogensulfate (TBAS) was purchased from Waters Corp (Milford, MA). Adenosyne 5’-triphosphate, o-nitrophenyl-β-galactoside, 4-amino-antipyrine, N-ethyl-N-(3-sulfopropyl) m-anisidine, chloroacetaldehyde, glycerol 3-phosphate oxidase from Aerococcus viridans, horseradish peroxidase, glycerol kinase from Cellulomonas sp., and β-galactosidase from E. coli were purchased from Sigma-Aldrich (St Louis, MO). Restriction enzymes were purchased from New England Biolabs (Ipswich, MA).
All E. coli strains and oligonucleotides are described in Supplementary Tables 1 and 2, respectively. Unless stated otherwise, all strains were derived from the prototrophic E. coli K-12 strain NCM372236 (link). For details on reagents and strain construction, see “Strain construction” below.
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4

Characterizing Enzymatic Assays in E. coli

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Isopropyl-β-D-1-thiogalactopyranoside (IPTG) was purchased from Bio Basic Inc. (Ontario, Canada). Tetrabuthylammoniumhydrogensulfate (TBAS) was purchased from Waters Corp (Milford, MA). Adenosyne 5’-triphosphate, o-nitrophenyl-β-galactoside, 4-amino-antipyrine, N-ethyl-N-(3-sulfopropyl) m-anisidine, chloroacetaldehyde, glycerol 3-phosphate oxidase from Aerococcus viridans, horseradish peroxidase, glycerol kinase from Cellulomonas sp., and β-galactosidase from E. coli were purchased from Sigma-Aldrich (St Louis, MO). Restriction enzymes were purchased from New England Biolabs (Ipswich, MA).
All E. coli strains and oligonucleotides are described in Supplementary Tables 1 and 2, respectively. Unless stated otherwise, all strains were derived from the prototrophic E. coli K-12 strain NCM372236 (link). For details on reagents and strain construction, see “Strain construction” below.
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5

Photochemical Damage Analysis Reagents

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Methanol (MeOH) >99.9 % purity (CHROMASOLV grade) was purchased from Sigma-Aldrich and LC-MS grade acetonitrile (ACN) from Carlo Erba. Triethylammonium acetate (TEAA, 1 M in water), tris(hydroxymethyl)aminomethane (Tris), ethylene diamine tetraacetic acid (EDTA), sucrose, Triton-X100, sodium dodecyl sulfate (SDS), chloroacetaldehyde and 1,N 6 -etheno-2'-deoxyadenosine (dAdo) were from Sigma (Saint-Quentin-Fallavier, France). Reagents and solvents for synthesis
(5'-dimethoxytrityl-3'-phosphoramidite-thymidine, dimethoxytrityl chloride, acetic anhydride, acetic acid, pyridine, ethyl-S-triazol, iodine, ammonium hydroxide) were of the highest purity available and purchased form Aldrich (Saint-Quentin-Fallavier, France). ( 13 C10, 98% 15 N2, 96-98%)-thymidine was from Cambridge Isotope Laboratories. [ 15 N5]-dAdo was synthetized as previously reported (35) . Thymidylyl-(3'-5')-thymidine (TpT) was prepared by phosphodiester synthesis and all photoproducts of dinucleoside monophosphates were obtained as previously reported (23) .
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6

TDF Degradation Protocol for Mono-ester Intermediate

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TDF was provided by the NIH AIDS Research and Reference Reagent Program (Germantown, MD). TFV was obtained from Watson International (Kunshan City, China). Dimethylsulfoxide (DMSO) and tetrabutylammonium sulfate were obtained from Acros-Organics (Geel, Belgium). Acetic acid was obtained from Chem-lab (Zedelgem, Belgium). Acetonitrile was purchased from Fisher Scientific (Leicestershire, UK). Monobasic potassium phosphate monohydrate (KH2PO4.H2O), bis-4nitrophenylphosphate, chloroacetaldehyde and pancreatin from porcine pancreas (powder, suitable for cell culture, 4× USP specifications) were obtained from Sigma-Aldrich (St. Louis, MO). Methanol and sodium acetate were purchased from VWR International (Leuven, Belgium). Water was purified with a Maxima system (Elga Ltd., High Wycombe Bucks, UK). All stock solutions were prepared in dimethyl sulfoxide. The mono-ester intermediate of TDF was obtained by degradation of TDF at neutral pH: a 100µM solution of TDF was made in a phosphate buffer (pH 7); following chemical degradation during 7h at 60°C, an equal amount of 1M HCl was added to the solution; quantitative transformation into the intermediate without formation of TFV was confirmed.
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7

Cytotoxicity of Chemotherapy Agents

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Chemicals were of analytic grade and obtained from Sigma-Aldrich (St Louis, USA).
Cyclophosphamide (monohydrate salt), ifosfamide, acrolein, chloroacetaldehyde, resazurin salt, 2′,7′-dichlorofluorescein diacetate (DCF-DA) and salts for Krebs-bicarbonate solution were purchased from Sigma-Aldrich (St Louis, USA). This is a post-peer-review, pre-copyedit version of an article published in Archives of Toxicology.
The final authenticated version is available online at: http://dx.doi.org/10.1007/s00204-019-02589-1.
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8

Citalopram Pharmacological Analysis Protocol

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Citalopram was obtained from Fako-Actavis Company (Istanbul, Turkey) and was prepared in distilled water (80 mg/mL). Urethane, α-chloralose, DPCPX, CSC, adenosine, dilazep dihydrochloride, indomethacin, EHNA, NBTI, EDTA, G- EDTA, trichloroacetic acid, potassium hydroxide, zinc sulfate, and barium hydroxide were obtained from Sigma Chemical (St. Louis, MO, USA). DMSO and chloroacetaldehyde were obtained from Aldrich Chemical. Urethane and α-chloralose were prepared as 300 mg/mL and 40 mg/mL stock solutions in distilled water, respectively. Sodium cromoglycate was prepared at a concentration of 12 mg/mL in distilled water. DPCPX was prepared as 4 mg/mL stock solution in DMSO. CSC was prepared as 6 mg/mL stock solution in DMSO. EHNA was prepared at a concentration of 10 mg/mL in DMSO. NBTI was prepared as 1 mg/mL stock solution in DMSO.
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9

Synthesis and Characterization of Modified Nucleic Acids

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Poly(dT), poly(dA), ATP, and Tween-20 were obtained from Sigma-Aldrich (St. Louis, MO, USA). HsRad51 was purified according to a previously described procedure [49 (link)]. Poly(dεA) was synthesized by chemical modification of poly(dA) using chloroacetaldehyde (Aldrich), according to a previous method [50 (link)]. The degree of modification was approximately 93%, determined by spectroscopy using the formula provided by Ledneva et al. [51 (link)]. Concentrations were determined based on UV absorption, utilizing the following extinction coefficients: ε263nm = 8520 M−1 cm−1 for Poly(dT), ε257nm = 3800 M−1 cm−1 for poly(dεA), and ε260nm = 15,400 M−1 cm−1 for ATP.
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