MPC was purchased from Sigma-Aldrich Japan Co., LLC. (Tokyo, Japan). BMA, pentaerythritol, and triethylamine were purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan), while 2-Bromoisobutyryl bromide was obtained from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Ethylene bis(2-bromobutyrate), 2,2′-bipyridyl, copper(II) bromide, and l -ascorbic acid were purchased from Sigma-Aldrich Japan Co., LLC. (Tokyo, Japan). HeLa cells were obtained from the RIKEN Cell Bank (Saitama, Japan). RPMI-1640, Dulbecco’s modified Eagle medium (DMEM), fetal bovine serum (FBS), and phosphate-buffered saline (PBS) were purchased from Thermo Fisher Scientific, Inc. (Waltham, MA, USA). Cell counting kit-8 (CCK8) was purchased from Dojindo Laboratories Co., Ltd. (Kumamoto, Japan), LDH-Cytotoxic Test Wako from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan), Spectra/Por dialysis membrane from Spectrum Chemical Mfg. Corp. (New Brunswick, NJ, USA), and Methacryloxyethyl thiocarbamoyl rhodamine B from Polysciences Inc. (Warrington, PA, USA). The other solvents and reagents were of extra-pure grade and used without further purification.
Triethylamine
Manufactured by Fujifilm
Sourced in Japan
Triethylamine is a colorless liquid chemical compound commonly used in laboratory settings. It serves as a base and is often employed as a catalyst or reagent in various chemical reactions and processes. The core function of triethylamine is to facilitate and enable specific chemical transformations within a controlled laboratory environment.
Automatically generated - may contain errors
Lab products found in correlation
Methanol, by Fujifilm (6 mentions)
Acetonitrile, by Fujifilm (6 mentions)
Chloroform, by Fujifilm (4 mentions)
Hydrochloric acid (hcl), by Fujifilm (4 mentions)
Formic acid, by Fujifilm (3 mentions)
Dimethyl sulfoxide (dmso), by Fujifilm (3 mentions)
Fetal bovine serum (fbs), by Thermo Fisher Scientific (3 mentions)
N hexane, by Fujifilm (2 mentions)
2 propanol, by Fujifilm (2 mentions)
Toluene, by Fujifilm (2 mentions)
Diethyl ether, by Fujifilm (2 mentions)
Acetone, by Fujifilm (2 mentions)
N n dimethylformamide (dmf), by Fujifilm (2 mentions)
Ethanol, by Fujifilm (2 mentions)
Dichloromethane, by Nacalai Tesque (2 mentions)
Acryloyl chloride, by Fujifilm (2 mentions)
Stearoyl chloride, by Tokyo Chemical Industry (2 mentions)
Citric acid, by Fujifilm (2 mentions)
Pentaerythritol, by Fujifilm (1 mentions)
Methacryloxyethyl thiocarbamoyl rhodamine b, by Polysciences (1 mentions)
25 protocols using triethylamine
1
Synthesis of Fluorescent Polymeric Nanoparticles
2
Quantification of Anti-Influenza Drugs
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OS (purity 99%) and ZAN (purity 99%) were purchased from LKT Laboratories (St. Paul, MN, USA). LAN (purity 98%) was purchased from Toronto Research Chemicals Inc. (Toronto, Ontario, Canada). OC (purity 99%) was purchased from Acanthus Research Inc. (Mississauga, Ontario, Canada). PER (purity 99%) was provided by Shionogi & Co., Ltd. (Osaka, Japan) and purchased from ChemScene, LLC. (Monmouth Junction, NJ, USA). The chemical structures and physicochemical properties of these anti-influenza drugs [22 (link),28 (link)–37 ] are shown in Table 1 . It is noted in similarities of chemical and physicochemical properties of ZAN and LAN. LC-MS-grade solvents (methanol, acetone, and acetonitrile), formic acid, hydrochloric acid, ascorbic acid, and triethylamine were purchased from Wako Pure Chemical Industries, Ltd. (Osaka, Japan). Individual standard stock solutions of OS, OC, ZAN, PER, and LAN at 1 mg/100 mL were prepared in methanol and stored at –30°C.
3
Quantification of Anserine and Related Compounds
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Anserine (Figure 1 ), carnosine, L-histidine, 1-methyL-histidine, β-alanine, phenylephrine, acetonitrile, trifluoroacetic acid, trichloroacetic acid, aminoadipic acid, triethylamine and phenyl isothiocyanate were purchased from Fujifilm Wako Pure Chemical (Osaka, Japan). Hydrophilic nylon syringe filters (0.45 μm) were purchased from Hamach Scientific (Xi’an, China). Anserine, carnosine, L-histidine, 1-methyL-histidine and β-alanine were dissolved in distilled water and filtered before used. Marine Active® was provided by Yaizu Suisankagaku Industry (Shizuoka, Japan) and stored at 4 °C. Marine Active® contains 38% anserine, 26.2% L-histidine, 3.4% carnosine and 32.4% others.
4
Analysis of Oxysterol Biomarkers in Serum
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The standards of 4β-OHC and 4β-OHC-D7 (4β-hydroxycholesterol-25, 26, 26, 26, 27, 27, 27-D7, isotopically labelled internal standard of 4β-OHC) were purchased from Avanti Polar Lipids, Inc (Alabama) and 4α-OHC standard from Toronto Research Chemicals (Ontario, Canada). The standards of 7α-OHC, 7β-OHC, 22(R)-OHC, 22(S)-OHC, 24(S)-OHC, 25-OHC, and 27-OHC, isomers of 4β-OHC and 4α-OHC, were purchased from Sigma-Aldrich (St. Louis). Human serum albumin (HSA) was purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan). Other reagents (2-methyl-6-nitrobenzoic anhydride, 4-dimethylamino-pyridine, and picolinic acid) were purchased from Tokyo Chemical Industry Co, Ltd (Tokyo, Japan). Other solvents (water, methanol, 2-propanol, acetonitrile, n-hexane, formic acid, pyridine, triethylamine, and 28% sodium methoxide methanol solution) were of the highest analytical quality and were purchased from FUJIFILM Wako Pure Chemical Corporation.
5
Synthesis and Characterization of Thermoresponsive Hydrogels
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NIPAAm
was purchased from
KJ Chemicals (Tokyo, Japan) and was purified by recrystallization
from toluene and n-hexane. PEG (Mn: 10 kDa), oxalyl chloride, and chloroform-d were purchased from Sigma-Aldrich (St Louis, MO) and were used without
further purification. DDMAT was purchased from Trylead Chemical Technology
(Hangzhou, China). NAS, 2,2′-azobis(2,4-dimethylvaleronitrile)
(V-65), 2,2′-azobis(isobutyronitrile) (AIBN), dichloromethane
(super dehydrated), acetone, toluene, n-hexane, ethanol,
1,4-dioxane, diethyl ether, DEEA, triethylamine, N,N-dimethylformamide, hydrochloric acid, sodium
carbonate, acetic acid, and sodium acetate trihydrate were purchased
from Wako Pure Chemical (Osaka, Japan) and were used without purification.
PAA (Mn: 150 kDa, 40 wt % solution) was
kindly provided by Nittobo Medical (Tokyo, Japan).
was purchased from
KJ Chemicals (Tokyo, Japan) and was purified by recrystallization
from toluene and n-hexane. PEG (Mn: 10 kDa), oxalyl chloride, and chloroform-d were purchased from Sigma-Aldrich (St Louis, MO) and were used without
further purification. DDMAT was purchased from Trylead Chemical Technology
(Hangzhou, China). NAS, 2,2′-azobis(2,4-dimethylvaleronitrile)
(V-65), 2,2′-azobis(isobutyronitrile) (AIBN), dichloromethane
(super dehydrated), acetone, toluene, n-hexane, ethanol,
1,4-dioxane, diethyl ether, DEEA, triethylamine, N,N-dimethylformamide, hydrochloric acid, sodium
carbonate, acetic acid, and sodium acetate trihydrate were purchased
from Wako Pure Chemical (Osaka, Japan) and were used without purification.
PAA (Mn: 150 kDa, 40 wt % solution) was
kindly provided by Nittobo Medical (Tokyo, Japan).
6
Synthesis of Compound 63 via Methylene Chloride
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Example 4
[Step 4-1]
To 175 parts of methylene chloride, 3.0 parts of the compound of the formula [57-2] were added, and the mixture was stirred. Subsequently, 1.3 parts of propionyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise thereto at room temperature, then 1.4 parts of triethylamine (Wako Pure Chemical Industries, Ltd.) were added dropwise thereto at the same temperature as above, and the mixture was stirred for 1 hour. After the completion of the reaction, the reaction mixture was washed with a 10% aqueous HCl solution and a saturated aqueous solution of sodium bicarbonate in this order, and methylene chloride was distilled off under reduced pressure. The residue was washed with ethyl acetate and water in this order and dried in vacuum to obtain compound 63 described in Table 1 as a white solid (2.5 parts).
MS(ESI): [M−H]−: cal.: 282.1, found: 282.1.
7
Synthesis and Characterization of PEG-HDI Polyurethanes
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Hexamethylene diisocyanate (HDI), di-n-butyltin dilaurate (DBTDL), and tri(ethylene glycol) (TEG) were purchased from Tokyo Chemical Industry Co., Japan. Poly(ethylene glycol) (PEG) (Mn = 1,000 g mol−1) was purchased from Kanto Chemical Co., Inc., Japan. Triethylamine and all organic solvents were purchased from Wako Pure Chemical Industries, Ltd., Japan. Triethanolamine (TEA) was purchased from Sigma-Aldrich, USA. HDI was vacuum distilled and stored under N2 atmosphere at 5°C before use. 1,4-Dioxane was distilled and stored under Ar atmosphere before use. Other chemicals were used as received. Bis(2-hydroxyethyl) diselenide (DSe) [53 ] and 2,6-bis(hydroxymethyl)-1-methylpyridin-1-ium iodide (iPDM) [57 ] were prepared according to the literature procedures.
8
Bioconjugation Reagents for Protein Modification
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1,4-Butanediamine, di-tert-butyl di-carbonate, chloroform, dichloromethane, triethylamine, sodium hydroxide, ethanol, diethyl ether, sodium chloride, N,N-dimethylformamide (DMF), hydrochloric acid, dimethyl sulfoxide (DMSO), and N-(2-Aminoethyl)maleimide trifluoroacetate salt were purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan) and used as received. Cinnamoyl chloride was purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan) and used as received. Succinimidyl-tetra-PEG (pentaerythritol tetra (succinimidyloxyglutaryl) polyoxyethylene), maleimide-tetra-PEG (N-(2-aminoethyl)maleimide trifluoroacetate salt, and Pentaerythritol tetra {[3-(3-maleimido-1-oxopropyl)amino]propyl} polyoxyethylene) were purchased from NOF Corporation (Tokyo, Japan) and used as received. All aqueous solutions were prepared with ultrapure water (Milli-Q, 18.2 MΩ·cm). Other solvents and reagents of analytical grade were obtained from commercial sources and were used without further purification.
9
Synthesis of SMA-Based Thiol Conjugates
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Example 23
To 300 mg of SMA-maleic acid copolymer powders (1.3 mmole equivalents as maleic anhydride) was added 15 ml of dimethylformamide (DMF) to dissolve the powders. Then 505.3 mg (6.6 mmol) of 2-aminoethanethiol (Wako Pure Chemical Industries, Osaka) was added. After stirring for 2 to 3 minutes with a magnetic stirrer, 500 μl of triethylamine (Wako Pure Chemical Industries, Oosaka) was added and stirred for another 24 hours at room temperature with a magnetic stirrer. After the reaction for 24 hours, the clouded liquid was filtered under reduced pressure (glass filter No. 5C) and concentrated in a rotary evaporator. Precipitates were generated by diluting with distilled water. The crude product was dialyzed with a dialysis membrane with a MW cut-off at 1000 Da [Spectrum Laboratories] 2 to 3 times. The filtrates and the precipitates were separated by decantation, and then the precipitates were lyophilized to obtain white powders (about 248.1 mg). The yield was about 80% based on the original SMA conjugate. Table 1 shows the result of elemental analyses.
10
Synthesis of Aromatic Diamines for Polymeric Materials
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4-Aminocinnamic acid, pentafluoropropionic anhydride, triphenyl phosphite, 4,4′-diaminodiphenyl ether, 4,4′-diaminodiphenylmethane, 2,2-bis(4-aminophenyl)hexafluoropropane, 4,4′-diaminobenzophenone, and 4,4′-diaminodiphenyl sulfone were purchased from Tokyo Chemical Industry Co., LTD, Tokyo, Japan. Trifluoroacetic anhydride, triethylamine, and N,N-dimethylacetamide were purchased from FUJIFILM Wako Pure Chemical Corporation. Dichloromethane, methanol, ethanol, pyridine, N,N-dimethylformamide (DMF), and N-methyl-2-pyrrolidone (NMP) were purchased from Kanto Chemical Co., Inc, Tokyo, Japan. All chemicals were directly used as purchased. 4,4′-Diamino-α-truxillic acid and 4,4′-diamino-α-truxillic acid dimethyl ester were synthesized based on previous research [4 (link),5 (link),10 (link)].
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