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15 protocols using trifluoroacetic acid

1

Blueberry Leaf Extract Preparation

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BLEx was prepared as a hot water extract by Bizen Chemical Co. Ltd (Okayama, Japan). Briefly, blueberry leaf powder was extracted in 16 parts of hot water (95–100 ° C) for 30 min twice. Then, the extract was filtered and heat sterilized. Finally, the extract was dried with a spray dryer, producing a powder. Ethanol was purchased from the Wako Pure Chemical Industries (Osaka, Japan). The oxidized form of β-nicotinamide adenine dinucleotide hydrate (NADH), 4-methylpyrazole, 2,4-dinitrophenylhydrazine, and trifluoroacetic acid (TFA) were purchased from the Tokyo Chemical Industry (Tokyo, Japan).
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2

Peptide Synthesis Reagents and Materials

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The tyrosine pre-loaded resin and fluorenylmethoxycarbonyl (Fmoc)-protected amino acids used in peptide synthesis were purchased from GL Biochem. N,N′-diisopropylcarbodiimide (DIC) and trifluoroAcetic acid (TFA) were purchased from Tokyo Chemical Industry (TCI). Acetic acid, α-cyano-4-hydroxycinnamic acid (CHCA), deuterium oxide (D2O), fluorescein isothiocyanate (FITC), piperidine, potassium fluoride (KF), triisopropylsilane (TIPS), sodium chloride (NaCl), sodium bromide (NaBr) and sodium sulfate (Na2SO4) were purchased from Sigma-Aldrich. Acetonitrile (ACN), dichloromethane and N,N-dimethylformamide were purchased from Thermo Fisher Scientific.
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3

Chestnut Rose Fruit Bioactive Compounds

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Fresh seedless chestnut rose (R. sterilis) fruits were collected in October 2021 on the farmland of Zhenning, Anshun, located in Guizhou Province, China (26°2′49.42″ N, 105°41′59.45″ E, 1247.6 m above sea level). Standard monosaccharides, 3-Phenylphenol, trifluoroacetic acid (TFA), 1,10-Phenanthroline, 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azinobis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS), and 3-(2-Pyridyl)-5,6-diphenyl-1,2,4-triazine-p,p′-disulfonic acid monosodium salt hydrate were purchased from TOKYO Chemical Industry Co., Ltd. (Tokyo, Japan). Sodium hydroxide was purchased from Thermo Fisher Co., Waltham, MA, USA. The pullulan polysaccharide calibration kit was purchased from Agilent Co., Santa Clara, CA, USA. α-Glucosidase, p-nitrophenyl-α-d-glucopyranoside (PNPG), and serum albumin (BSA) were obtained from Yuanye Bio-technology (Shanghai, China). All additional solvents and chemical reagents were acquired locally and were of either HPLC or analytical quality.
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4

Mycotoxin Assay Reagent Preparation

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AF reagents (AFB1, AFB2, AFG1, AFG2 mixture solution, 25 µg mL−1) for mycotoxin assay, AITC, ethanol, methanol, glucose, and hexane were purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan). MITC, BITC, and trifluoroacetic acid were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). PEITC was purchased from Acros Organics (Geel, Belgium). Acetonitrile and sucrose were purchased from NACALAI TESQUE, Inc. (Kyoto, Japan). Potato dextrose broth, yeast extract, and agar were purchased from BD Biosciences (Franklin Lakes, NJ, USA). Ethyl acetate was purchased from KISHIDA CHEMICAL Co., Ltd. (Osaka, Japan).
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5

Radiosynthesis of 211At-MABG for Cancer Therapy

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The radionuclide 211At was produced by irradiation of a Bi target (New Metals and Chemicals, Essex, UK) with an external vertical beam and an NIRS AVF-930 cyclotron (Sumitomo Heavy Industries, Tokyo, Japan) with recovery through dry distillation, as described previously [20] (link). The 211At-MABG was radiosynthesized under no-carrier-added conditions through radiohalogenation of meta-trimethylsilylbenzylguanidine (ABX Advanced Biochemical Compounds, Radeberg, Germany) with N-chlorosuccinimide (Tokyo Chemical Industries, Tokyo, Japan) in trifluoroacetic acid (Tokyo Chemical Industries, Tokyo, Japan), as described previously [11] (link). Unpurified 211At-MABG was trapped on a tC18 cartridge (Sep-Pak light; Waters, Milford, MA), washed with 1 ml of pure water (Fujifilm Wako Pure Chemical), and then eluted as the final product with 2 ml of 5% EtOH. The radiochemical yield was 57.8% ± 7.6% (decay-uncorrected), and the radiochemical purity was greater than 98.8%.
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6

Synthesis of DOTA-based Molecular Probe

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4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM), ethylenediamine, Tri-tert-butyl 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetate (triBoc-DOTA), and trifluoroacetic acid were purchased from the Tokyo Chemical Industry Co, Ltd (Japan), All organic solvents used for the synthesis and coassembly were of analytical grade.
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7

Synthesis and Characterization of Antifungal Peptides

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N,N′-Diisopropylcarbodiimide (DIC), 3,6-dioxa-1,8-octane-dithiol (DODT), trifluoroacetic acid (TFA), and triisopropylsilane (TIS) were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma Pure), 9-fluorrenylmethoxycarbonyl (Fmoc) amino acids, and Rink Amide ProTide Resin were obtained from CEM Co. (Matthews, NC, USA). All other materials were of analytical grade and used as received. Propidium iodide (PI), Dulbecco’s modified Eagle medium (DMEM), Roswell Park Memorial Institute (RPMI)-1640, GlutaMax, fetal bovine serum (BSA), antibiotics (penicillin/streptomycin), and FAM were purchased from Thermo Fisher Scientific (Waltham, MA, USA). C. albicans CCARM 14007, which was first isolated in 1999, and was found to be resistant to amphotericin B, flucytisine, and fluconazole, was purchased from the Culture Collection of Antimicrobial-resistant Microbes (CCARM), in South Korea.
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8

Synthesis and Characterization of Phospholipid Derivative

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Dipalmitoyl-sn-glycero-3-phosphoethanolamine, CDCl3, trifluoroacetic acid, trityl bromide, and sodium methoxide were obtained from Tokyo Chemical Industry (Tokyo, Japan), CD3OD is obtained from Cambridge Isotope Laboratories, Inc.,. All other reagents of synthetic grade and LC-MS grade (methanol) were purchased from Wako Pure Chemical Corporation (Tokyo, Japan). TLC was performed on Merck pre-coated plates (20 cm × 20 cm; layer thickness, 0.25 mm; Silica Gel 60F254); the spots were visualized by spraying Ninhydrin in ethanol or 5% H2SO4 in methanol when applicable. Silica Gel N60 (spherical type, particle size 40-50 μm; Kanto Chemical Industry) was used for column chromatographic purification. Proton and carbon NMR was recorded with 400 MHz JNM-ECX400P (JEOL, Japan; 1 H: 400 MHz, 13 C: 100 MHz); multiplicities are given as singlet (s), broad (br), doublet (d), double doublets (dd), triple doublets (td), triplet (t), quintet (q), or multiplet (m). Chemical shifts are given in ppm. 1 H NMR spectra were processed by ACD/NMR processor software (Advanced Chemistry Development, inc.). High-resolution electrospray ionization mass spectra (HR-ESI-MS) was recorded by Linear trap quadrupole (LTQ) Orbitrap XL (Thermo Fisher scientific). Lowresolution electrospray ionization mass spectra (LR-ESI-MS) was recorded by LXQ (Thermo Fisher scientific).
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9

Solvation Behavior Characterization Protocol

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Choline chloride (98.0%) and urea (99.0-100.5%) were obtained from Algry Quimica S. L. and Sigma-Aldrich, respectively. The pH of the solvents was adjusted with 0.1 M sodium hydroxide from FF Chemicals. Softwood Kraft pulp fibers used in the swelling experiments were obtained from Metsa ¨Fibre, Finland.
Deionized water was used throughout the experiments. Probes used in solvatochromic measurements were 4-nitroaniline (Z99%) (NA) from Sigma-Aldrich, N,N-diethyl-4-nitroaniline (98%) (DENA) from Apollo Scientific Ltd, and Nile Red from Tokio Chemical Industry Co. The reference solvents were dimethyl sulfoxide (499.0%) from GC Chemicals and cyclohexane (99%) from RCI Labscan. Probes used in solvatomagnetic measurements were 4-fluoroanisole (Z97.0%, GC Chemicals), 4fluorophenol (499.0%, Tokyo Chemical Industry Co.), and pyridine-N-oxide (95%, Sigma-Aldrich). Deuterated chloroform with 0.03% tetramethylsilane (99.80% D, Eurisotop) and trifluoroacetic acid (499.0%, Tokyo Chemical Industry Co.) were used as internal standards. The chemical structure of the compounds used to produce solvent systems as well as used probes in solvatochromic and solvatomagnetic experiments are presented in Fig. S1 (ESI †).
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10

Fabrication of Polymeric Delivery Systems

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Poly (lactic acid) (PLA) was purchased from Ultimaker (Geldermalsen, Netherlands), and transparent LSR9–9508-30 silicone elastomer mix from Polymer Systems Technology (High Wycombe, UK). Gantrez® S-97, a copolymer of methyl vinyl ether and maleic acid (1,500,000 Da) and poly (vinylpyrrolidone) (PVP) (58,000 Da) were a kind donation from Ashland (Kidderminster, UK). Poly (vinyl alcohol) 9000–10,000 Da (PVA 10 K), Poly (vinyl alcohol) 31,000–50,000 Da (PVA 50 K), poly (ethylene glycol) (PEG) 10,000 Da, anhydrous sodium carbonate (Na2CO3), anhydrous monobasic potassium phosphate, propylene glycol monomethyl ether acetate, isopropyl alcohol, trichloro(1H,1H,2H,2H-perfluorooctyl)silane and ibuprofen sodium (IBU Na) were obtained from Sigma-Aldrich (St. Louis, USA). Micronised cabotegravir sodium (CAB Na) was kindly supplied by ViiV Healthcare (Research Triangle (North Carolina), USA). Cryogel® SG/3 (gelatine) was acquired from PB Gelatins GmbH (Nienburg/Weser, Germany), Pearlitol 50 C (mannitol) from Roquette (Lestrem, France), phosphoric acid 85% from Amresco Inc. (Ohio, USA) and acetonitrile ≥99.9% from Honeywell Research Chemicals (Bucharest, Romania). Trifluoroacetic acid was purchased from Tokyo Chemical Industry (Tokyo, Japan). All other chemicals used were of analytical reagent grade.
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