Chemicals. Acetone (HPLC grade, Caledon), hexane (HPLC grade, Caledon), xylene (reagent grade, 98.5%, EMD), deuterated chloroform (CDCl3, 99.8%, Cambridge Isotope Laboratories, Inc.), tetrahydrofuran (THF, HPLC grade, Caledon), dodecane (anhydrous, 99%, Sigma-Aldrich), ethyl ether (anhydrous, 99% Sigma-Aldrich), ethyl acetate (HPLC, 99.7% Sigma-Aldrich), and 2-dodecanone (GC grade, 97%, Sigma-Aldrich) were used as received. The chemicals hexamethylenediamine (HMDA, 98%), diethylenetriamine (DETA, 99%), triethylenetetramine (TETA, 97%), tetraethylenepentamine (TEPA, technical grade), pentaethylenehexamine (PEHA, technical grade), dibutylamine (DBA, 99.5%), octylamine (99%), N-methylsuccinimide (N-MSI, 99%), butylamine (BUA, 99%), diethylamine (DEA, 99.5%), triethylamine (TEA, 99.5%), ethylene carbonate (EC, 98%), magnesium sulfate anhydrous (97%), and activated charcoal (100 mesh) were purchased from Sigma-Aldrich and were employed without further purification. Polyisobutylene succinic anhydride (PIBSA) was supplied by Imperial Oil. The chemical composition of this sample was characterized by NMR, GPC, and FTIR analysis and found to contain on average one SA unit per 52 ± 2 isobutylene monomers. Assuming one SA moiety per chain, this PIBSA sample would have an Mn of 3,012 g.mol equivalent to a total acid number (TAN) of 37.2 mg of KOH per gram of PIBSA.
Dibutylamine
Manufactured by Merck Group
Sourced in Italy, United States
Dibutylamine is a chemical compound used in various laboratory applications. It is a colorless liquid with a distinct amine-like odor. Dibutylamine is commonly utilized as a reagent, solvent, and intermediate in organic synthesis and pharmaceutical manufacturing processes.
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Lab products found in correlation
Ammonium chloride, by Merck Group (4 mentions)
Calcium acetate, by Merck Group (3 mentions)
Sodium dihydrogen phosphate monohydrate, by Merck Group (3 mentions)
Sodium hydrogen phosphate dihydrate, by Merck Group (3 mentions)
Sodium nitrite, by Merck Group (3 mentions)
Sodium nitrate, by Merck Group (3 mentions)
Sodium azide, by Merck Group (3 mentions)
Sodium tetraborate, by Merck Group (3 mentions)
Deuterium oxide, by Eurisotop (3 mentions)
Hydrochloric acid (hcl), by Merck Group (3 mentions)
Ammonium acetate, by Merck Group (3 mentions)
Methanol, by Merck Group (3 mentions)
Diethylamine, by Merck Group (2 mentions)
1 8 diazabicyclo 5.4.0 undec 7 ene dbu, by Merck Group (2 mentions)
Sodium acetate, by Merck Group (2 mentions)
Acetic acid, by Merck Group (2 mentions)
Chloroform, by Merck Group (2 mentions)
Sodium acetate and naoh, by Merck Group (2 mentions)
Amberlite ir45, by Carlo Erba (2 mentions)
Deuterated ethylenediaminetetraacetic acid edta d16, by Cambridge Isotopes (2 mentions)
19 protocols using dibutylamine
1
Characterization of Polyisobutylene Succinic Anhydride
2
Synthesis and Characterization of Bioactive Compounds
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Phthalimide (PM), 3-Ethoxy-4-methoxyphenol (EMP), o-cyanobenzoic acid (CBA), dibutylamine (DBA), bis-2 (ethylhexyl) phthalate (BEP), indole (IND), hexahydro-3-(2-methylpropyl)-pyrrolopyrazine-1,4-dione (HMPP), and salicylic acid (SA) were purchased from Sigma-Aldrich Korea (Seoul, Korea) and dissolved in dimethylsulfoxide (DMSO). Phosphate-buffered saline (PBS, pH 7.4) was prepared with 100 mM phosphoric acid and 0.7% sodium chloride. Anticoagulant buffer (ACB, pH 4.5) was prepared to contain 186 mM NaCl, 17 mM Na2EDTA, and 41 mM citric acid. A transfection reagent (Metafectene Pro) was purchased from Biontex (Plannegg, Germany).
3
Synthesis of C10M-B Diethylphosphonate
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To a solution of dibutylamine (Sigma Aldrich, 0.32 g, 2.5 mmol) in dimethylformamide (8 ml) was added sodium iodide (0.03 g, 0.25 mmol), potassium carbonate (1 g, 7.5 mmol), and diethyl‐(3‐bromopropyl)‐phosphonate (Sigma Aldrich, 1.42 g, 5.5 mmol) at 0°C. Reaction mixture was heated to 100°C for 14 h. The progress of the reaction was monitored by thin layer chromatography. Reaction mixture was cooled to 0°C and quenched with water (15 ml) and extracted with ethyl acetate (15 ml × 2). Combined organic layer was washed with brine (20 ml), dried over sodium sulfate, and concentrated under vacuum. The residue was separated by silica gel chromatography to provide C10M‐B diethyl‐(3‐(dibutylamino)propyl)‐phosphonate (215 mg, 0.7 mmol) in 28% yield.
4
HPLC Quantification of DOPAC and HVA in CSF
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3,4-dihydroxyphenylacetic acid (DOPAC) and 4-hydroxy-3-methoxyphenylacetic acid (HVA) were measured in CSF samples based on previously reported methods (9 (link), 39 (link)). Prior to the analysis, the samples were thawed and centrifuged at 15000 rpm for 15 min. The supernatant was transferred and diluted 1/2 with 0.5 M acetic acid (Fisher Scientific, United Kingdom). The samples were injected automatically on a reversed-phase liquid chromatography system (autosampler ASI-100 and HPLC pump P680 A HPG/2, Dionex, Amsterdam, The Netherlands) with electrochemical detection (potential = + 700 mV) (Amperometric Detector LC-4C, BAS, Indiana, United States). The separation was achieved using a narrowbore C18 column (XBridge, 3.5 μm 2.1x150mm, Waters, Milford, United States). The mobile phase buffer contained 0.1 M sodium acetate (Carl Roth GmbH + Co, Karlsruhe, Germany), 20 mM citric acid (Sigma Aldrich, Saint Louis, United States), 1 mM sodium octane sulfonic acid (Carl Roth GmbH + Co), 1 mM dibutylamine (Sigma Aldrich), and 0.1 mM Na2EDTA adjusted to pH 3.7 (mobile phase composition: 97 buffer/3 methanol [v/v]). The sample concentration was expressed as ng monoamine/100 μL.
5
Characterization of Ion Pairing Agents
6
Quantifying Duodenal 5-HT via HPLC
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Duodenal 5-HT was measured using HPLC with electrochemical detection. One milligram of duodenal tissue was dissolved in 0.1 mol/L of analytical grade perchloric acid (HCLO4,), treated with an ultrasonic cell crusher, and centrifuged at a speed of 16992 g for 10 min at 4°C. Twenty microlitres of supernatant was obtained and injected into an HPLC system (2695, Waters Alliance, USA) fitted with an Atlantis C18 column (2.1×150 mm, 3 μm, Waters Alliance) and electrochemical detector (2465, Waters Alliance). The mobile phase consisted of 50 mM citric acid (C6H8O7, analytical grade), sodium acetate (C2H3O2Na, analytical grade), buffer solution (pH 3.5, 1.8 mM dibutylamine, 0.3 mM Na2EDTA, Sigma), and methanol (CH3OH, HPLC grade) (96:4, v/v). The column temperature was set to 35°C, detection voltage +0.75V, and flow rate 0.35 mL/min. The HPLC method met requirements with elution of 5-HT after 19.3 min. Resolution far exceeded 1.5, confirming that 5-HT could be measured precisely without interference from other endogenous substances.
7
Self-Lubricating Polymer Coating
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Diethylamine, dibutylamine, dihexylamine, carbon disulfide, and silver nitrate (99.8%) were purchased from Sigma-Aldrich Trading Company Limited (Shanghai, China). Polyamic acid with a solid content of 38.0% was obtained from Beijing Sino-rich Technology Company Limited (Beijing, China). The mixed solvent of N,N-dimethylformamide and N-methylpyrrolidone (volume ratio 1:1) was used as the co-dispersion medium of the paint. All chemicals were directly used as-received. AISI-1045 steel block (19.00 mm × 12.00 mm × 12.00 mm, Rockwellhardness (HRC) 28–32, E = 210 GPa) was used as the substrate, and AISI-52100 bearing steel ball (Φ 6 mm, HRC 58–61, E = 208 GPa, Ra = 0.02 μm) was used as the counterpart.
8
Comparative Analysis of Heparin Samples
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Seven danaparoid API batches (CAT271-277), one heparin sodium USP and one Nadroparin calcium samples were provided by Aspen Oss B.V., Oss, Netherlands. Heparin lyases I (EC 4.2.2.7), II and III (EC 4.2.2.8) were purchased from Grampian Enzymes, Aberdeen, UK. Chondroitin ABC lyase from Proteus vulgaris (EC 4.2.2.4), ammonium acetate (≥98%), sodium azide (≥99.0%), sodium nitrate (≥99.0%), sodium dihydrogen phosphate monohydrate (>98%), sodium hydrogen phosphate dihydrate (≥99.0%), trimethylsilyl-3-propionic acid (TSP 98% D), dibutylamine (≥99.5%), acetic acid (glacial, 99.9%), acetonitrile (LC-MS grade), methanol (LC-MS grade), ammonium chloride (≥99.5%), sodium nitrite (>95%), sodium tetraborate (≥98%), hydrochloric acid (≥37%) were purchased from Sigma Aldrich (Milan, Italy); calcium acetate (≥97%) from BDH; sodium acetate (≥99%) and NaOH (≥99%) from Merck (Kenilworth, NJ, USA); Amberlite IR 120 H+ and 0.1 M NaOH from Fluka Analytical (Milan, Italy).
Ethanol (96%) was purchased from Girelli Alcool (Milan, Italy); ethylenediaminetetraacetic acid (EDTA D16, 98%) from Cambridge Isotope Laboratories (Tewksbury, MA, USA) and deuterium oxide (≥99.9%) from Euriso-top (Saint-Aubin, France). Deionized water (conductivity less than 0.15 µS) was prepared with an osmosis inverse system (Culligan, Milan, Italy).
Ethanol (96%) was purchased from Girelli Alcool (Milan, Italy); ethylenediaminetetraacetic acid (EDTA D16, 98%) from Cambridge Isotope Laboratories (Tewksbury, MA, USA) and deuterium oxide (≥99.9%) from Euriso-top (Saint-Aubin, France). Deionized water (conductivity less than 0.15 µS) was prepared with an osmosis inverse system (Culligan, Milan, Italy).
9
Synthesis and Characterization of N,N-dibutylundecenoylamide
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The following chemicals were obtained from Sigma-Aldrich (St. Louis, MI, USA): undecenoic acid (98%), dibutylamine (99.5%), thionyl chloride (97%), chloroform (99%), and dichloromethane (99.8%). Suspension polyvinyl chloride KSF-70 was purchased from Karpatnaftochim (Ukraine).
The commercially available poly(3-hydroxybutyrate), the ENMAT Y1000 brand (Tianan Biologic Material Co., Ningbo, China), a semi-crystalline thermoplastic polymer with a density of ρ = 1.25 g/cm3 and a melting temperature Tm = 170–176 °C was used as a biodegradable component of thin films and welded joints. The raw PHB polymer was dissolved in chloroform, precipitated in hexane, and dried in a vacuum at a temperature of 40 °C [5 (link),14 (link)]. N,N-dibutylundecenoylamide (Table 1 ) was synthesized and purified as previously described [20 (link),21 ], and their purity was confirmed using 1H NMR spectroscopy.
1H NMR (400 MHz, CDCl3) δ: 0.93 (t, 6H, CH3), 1.3 (m, 14H, (CH2)5, -NCH2CH2CH2), 1.49 (m, 4H, NCH2CH2), 1.63 (m, 2H, -CH2CH2CO-), 2.03 (m, 2H, -CH2=CH-CH2-), 2.28 (t, 2H, -CH2CO-), 3.2 (t, 2H, NCH2), 3.3 (t, 2H, NCH2), 4.94 (m, 2H, -CH2=CH-), 5.82 (m, 1H, -CH2=CH-).
The commercially available poly(3-hydroxybutyrate), the ENMAT Y1000 brand (Tianan Biologic Material Co., Ningbo, China), a semi-crystalline thermoplastic polymer with a density of ρ = 1.25 g/cm3 and a melting temperature Tm = 170–176 °C was used as a biodegradable component of thin films and welded joints. The raw PHB polymer was dissolved in chloroform, precipitated in hexane, and dried in a vacuum at a temperature of 40 °C [5 (link),14 (link)]. N,N-dibutylundecenoylamide (
1H NMR (400 MHz, CDCl3) δ: 0.93 (t, 6H, CH3), 1.3 (m, 14H, (CH2)5, -NCH2CH2CH2), 1.49 (m, 4H, NCH2CH2), 1.63 (m, 2H, -CH2CH2CO-), 2.03 (m, 2H, -CH2=CH-CH2-), 2.28 (t, 2H, -CH2CO-), 3.2 (t, 2H, NCH2), 3.3 (t, 2H, NCH2), 4.94 (m, 2H, -CH2=CH-), 5.82 (m, 1H, -CH2=CH-).
10
Quantitative Heparan Sulfate Analysis
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Purification of HS from BMDCs was carried out using HS preparation methods as previously described [18] (link). Cells were harvested from 10-day GM-CSF based DC differentiation cultures of marrow from the femurs of Ndst1f/f CD11cCre+ versus Cre− control mice as described for BMDC Primary Cell Preparations, above. Briefly, following glycan de-polymerization with heparin lyases overnight, disaccharide analysis was carried out using quantitative liquid chromatography/mass spectrometry (LC/MS) [19] (link): After drying samples down, aniline labeling of disaccharide reducing ends was carried out (in 15 μl of 1 M NaCNBH3 and [12C6]aniline freshly prepared in dimethyl sulfoxide/acetic acid (7:3, v/v) for 16 h at 37 °C) with products dried down. Using a C18 reversed phase column (0.21 × 15 cm; Thermo), derivatized disaccharides were separated with ion pairing agent (dibutylamine, Sigma) [20] (link), and eluted ions of interest were monitored in negative ion mode on a mass spectrometer (LTQ Orbitrap, Thermo-Finnigan; capillary temp 150 °C; spray voltage 4.0 kV). Extracted ion current data were analyzed with Qual Browser software (Thermo-Finnigan). Quantitative composition analysis of disaccharides was performed by comparison with known amounts of differentially labeled standard [13C6]aniline added to the sample before LC/MS.
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