All capsules were analysed for their API content by UV-Vis-HPLC using a Shimadzu LC-20A prominence (Shimadzu, Duisburg, Germany) equipped with a UV-Vis detector. Spironolactone assays were carried out referring to Sandall et al. (2006) [26 (link)]. A Nucleosil® 100—5 C18 125 × 4 mm, 5 µm (Macherey-Nagel GmbH and Co. KG, Düren, Germany) was used with mobile phase A and B consisting of water and MeOH (Sigma-Aldrich, Steinheim, Germany) respectively. The flow was isocratic with a ratio of 60:40 (v/v) (A/B) at a flow rate of 0.8 mL min−1. The oven temperature was kept at 40 °C and 10 µL were injected. Spironolactone was detected at a wavelength of 254 nm. Referring to a method of Dukova et al. (2015) [27 (link)], baclofen was quantified using a Nucleodur® 100-5 C18 Gravity 125 × 4 mm, 5 µm (Macherey-Nagel GmbH and Co. KG, Düren, Germany). Mobile phase A and B consisted of water with a pH adjusted to 9 with triethylamine (VWR International S.A.S, Fontenay-sous-Bois, France) and acetonitrile, respectively. An isocratic flow with a ratio of 90:10 (v/v) (A/B) was chosen at a flow rate of 1.0 mL/min. Baclofen was detected at 220 nm and the injection volume was 10 µL. All 30 capsules of each batch were analysed.
Triethylamine
Manufactured by Avantor
Sourced in United States, Poland
Triethylamine is a colorless, volatile, and flammable liquid. It is a common organic compound used as a solvent, a catalyst, and a reagent in various chemical reactions and processes.
Automatically generated - may contain errors
Lab products found in correlation
Methanol, by Avantor (3 mentions)
Acetonitrile, by Merck Group (2 mentions)
Formic acid, by Merck Group (2 mentions)
Hydrochloric acid (hcl), by Avantor (2 mentions)
Chloroform, by Avantor (2 mentions)
Prominence lc 20a, by Shimadzu (1 mentions)
Spermidine, by Merck Group (1 mentions)
Dichloromethane, by Avantor (1 mentions)
Anhydrous dimethylformamide, by Thermo Fisher Scientific (1 mentions)
Ethyl trifluoroacetate, by Merck Group (1 mentions)
Aqueous ammonia, by Merck Group (1 mentions)
Ninhydrin, by Merck Group (1 mentions)
Acrylonitrile, by Merck Group (1 mentions)
Di tert butyl dicarbonate, by Merck Group (1 mentions)
Sodium sulfate na2so4, by Merck Group (1 mentions)
Chloroform, by Thermo Fisher Scientific (1 mentions)
Succinic anhydride, by Merck Group (1 mentions)
1 12 diaminododecane, by Merck Group (1 mentions)
Aqueous ammonia, by Avantor (1 mentions)
Anhydrous pyridine, by Thermo Fisher Scientific (1 mentions)
11 protocols using triethylamine
1
API Quantification of Spironolactone and Baclofen in Capsules
2
Synthesis and Purification of Polyamines
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D2O, CD3OD, and
CDCl3 were purchased from Goss Scientific
(UK). Aqueous ammonia (32%), dichloromethane (DCM), dimethylformamide
(DMF), ethanol (EtOH), ethyl acetate, methanol (MeOH), and triethylamine
(TEA) were purchased from VWR (UK). Anhydrous pyridine, anhydrous
dimethylformamide (DMF), and chloroform were purchased from Fisher
Scientific (UK). Acrylonitrile, 1,12-diaminododecane, di-tert-butyl dicarbonate [(Boc)2O], ethyl trifluoroacetate,
ninhydrin, norspermine (thermine), Raney-Nickel, spermidine, spermine,
sodium hydroxide (NaOH), succinic anhydride, N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate
(HBTu), trifluoroacetic acid (TFA), potassium bromide (KBr), and sodium
sulfate (Na2SO4) were purchased from Sigma-Aldrich
(UK).
Column chromatography was performed over silica gel 60–120
mesh (purchased from Sigma-Aldrich, UK) using different ratios of
MeOH, EtOH, ethyl acetate, DCM, and Aqueous ammonia (32%) as eluents.
Thin-layer chromatography (TLC) was performed over silica gel using
aluminum-backed sheets coated with Kieselgel 60 F254 purchased
from Merck (UK). ninhydrin TLC spray reagent was used for detecting
amine functional groups [ninhydrin (0.2 g) in 100 mL EtOH].
CDCl3 were purchased from Goss Scientific
(UK). Aqueous ammonia (32%), dichloromethane (DCM), dimethylformamide
(DMF), ethanol (EtOH), ethyl acetate, methanol (MeOH), and triethylamine
(TEA) were purchased from VWR (UK). Anhydrous pyridine, anhydrous
dimethylformamide (DMF), and chloroform were purchased from Fisher
Scientific (UK). Acrylonitrile, 1,12-diaminododecane, di-tert-butyl dicarbonate [(Boc)2O], ethyl trifluoroacetate,
ninhydrin, norspermine (thermine), Raney-Nickel, spermidine, spermine,
sodium hydroxide (NaOH), succinic anhydride, N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate
(HBTu), trifluoroacetic acid (TFA), potassium bromide (KBr), and sodium
sulfate (Na2SO4) were purchased from Sigma-Aldrich
(UK).
Column chromatography was performed over silica gel 60–120
mesh (purchased from Sigma-Aldrich, UK) using different ratios of
MeOH, EtOH, ethyl acetate, DCM, and Aqueous ammonia (32%) as eluents.
Thin-layer chromatography (TLC) was performed over silica gel using
aluminum-backed sheets coated with Kieselgel 60 F254 purchased
from Merck (UK). ninhydrin TLC spray reagent was used for detecting
amine functional groups [ninhydrin (0.2 g) in 100 mL EtOH].
3
Fabrication of Omniphobic-Omniphilic Patterned Surfaces
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An activated glass slide was modified by inserting into modification mixture (0.8 mL triethylamine (VWR), 50 mg of 4-dimethylaminopyridine (Merck), 0.2 mL chloro(dimethyl)vinyl silane (Sigma-Aldrich) in 49 mL dichloromethane) for 2 min under stirring at room temperature. The slide surface was patterned by first applying 300 µL of a 20% v/v solution of 1H, 1H, 2H, 2H-perfluorodecanethiol (Sigma-Aldrich) in acetone onto the modified surface and carried out a thiol-ene photoclick reaction by irradiating the slide through a photomask (Rose Fotomasken) with 260 nm UV light (OAI model 30) at 4 mW cm−2 intensity for 1 min to create omniphobic borders. Round omniphilic spots with a diameter of 2.83 mm were formed by applying 200 µL of a 10 wt% cysteamine hydrochloride (Alfa Aesar) solution in 1:2 water:ethanol onto the patterned surface and irradiating the slide with 260 nm, UV light (OAI model 30) at 4 mW cm−2 intensity for 1 min.
4
Moxifloxacin-based Antimicrobial Ocular Formulation
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MOX (>99% purity) was purchased from LC Labs (Woburn, MA). Formalin, PAM, sodium oleate, sodium laurate, and sodium chloride were purchased from Sigma (St. Louis, MO). High‐performance liquid chromatography (HPLC)‐grade acetonitrile, sodium dihydrogen phosphate, and triethylamine were obtained from VWR International (Radnor, PA). Vigamox® (0.5% moxifloxacin eye drops, Alcon Laboratories Inc., Fort Worth, TX) was obtained from the Johns Hopkins Pharmacy. Zirconium oxide beads (0.5 mm in diameter) were purchased from Next Advance (Averill Park, NY). Sterile cell strainers (100 μm) were purchased from Fisher Scientific (Hampton, NH). Pluronic F127 (Poloxamer 407) was obtained as free samples from BASF Corporation (Tarrytown, NY). Tryptic soy agar, tryptic soy broth, sterile cotton‐tipped applicator, sterile disposable petri plates, and sterile phosphate‐buffered saline (PBS) and 20‐G needles were purchased from Thermo Fisher Scientific (Walthum, MA). Staphylococcus aureus (ATCC 25923) was obtained from ATCC (Manassas, VA). Proparacaine eye drops were obtained from Bausch and Lomb Inc. (Tampa, FL).
5
Synthesis of Polyurethane Nanoparticles
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Three types of PU NPs were prepared, abbreviated as PU1, PU2, and PU3. They differed in the soft segment (oligodiol) composition. PU1 used 100 wt% poly(ε-caprolactone) diol (PCL diol, Mn 2,000 g/mol; Sigma-Aldrich, St Louis, MO, USA) as the soft segment. PU2 used 80 wt% PCL diol and 20 wt% polyethylene butylene adipate diol (PEBA diol, Mn 2,000 g/mol; Yong Shun Chemical Corp, Taipei, Taiwan, Republic of China). PU3 used 40 wt% PCL diol and 60 wt% PEBA diol as the soft segment (Figure 1A ). PU NPs were synthesized according to the procedures described previously.25 Briefly, prepolymerization was carried out by adding oligodiols, isophorone diisocyanate (IPDI, Evonik Degussa GmbH, Essen, Germany), and the catalyst tin(II)2-ethylhexanoate (T-9, Alfa Aesar) at 75°C for 3 h under nitrogen environment with mechanical stirring at 180 rpm. After this, 2,2-bis(hydroxymethyl)propionic acid (Sigma-Aldrich) and methyl ethyl ketone (MEK) (Avantor Performance Materials, Pennsylvania, PA, USA) were added and made to react for 1 h. The temperature was cooled down to 45°C and triethylamine (Avantor Performance Materials) was added. After 30 min, water was added rapidly with vigorous (1,200 rpm) stirring for 2–3 min. Ethylenediamine (Tedia, Fairfield, OH, USA) diluted in water was added and made to react for chain extension. Residual MEK and triethylamine were removed by vacuum distillation.
6
Extraction and Separation of MGN Compounds
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The reagents for extraction and chromatographic separation of MGN, namely methanol, methyl-t-butyl ether, hydrochloric acid and triethylamine were of reagent grade and were purchased from Avantor Performance Materials (Gliwice, Poland). HPLC analysis was performed using the chromatography grade acetonitrile, acetic acid (Merck, Darmstadt, Germany) and double-distilled water (Millipore, Temecula, CA, USA), whereas the mass spectrometry analysis of the isolate required the spectrometric purity water, acetonitrile, and formic acid, which were also delivered by Merck.
7
Alkaloids Extraction and Separation
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The reagents, such as methanol, chloroform, hydrochloric acid and triethylamine, used for the extraction and chromatographic separation of alkaloids, were of analytical grade and were purchased from Avantor Performance Materials (Gliwice, Poland). Spectroscopic grade solvents used for the HPLC-MS analyses—acetonitrile, water and formic acid were manufactured by Merck (Darmstadt, Germany). All cell culture reagents, standards of berberine (13 ), coptisine (11 ), jatrorrhizine (10 ) and palmatine (12 ) (purity exceeding 95%) were obtained from Sigma-Aldrich (St. Louis, MO, USA).
8
Synthesis and Characterization of Oxime Derivatives
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Hydroxylamine hydrochloride, potassium hydroxide (85 %), potassium iodide, magnesium sulfate, anhydrous ethanol, dimethylsulfoxide (DMSO), chloroform, ethyl acetate, n‐hexane, triethylamine (Avantor, Poland), organic reagents, 1‐(2‐thienyl)ethan‐1‐one (>99 %), n‐butyl chloride (>99 %), 1‐(chloromethyl)naphthalene (>97 %), 2‐chloro‐N,N‐dimethylethylamine hydrochloride (99 %), 3‐chloro‐N,N‐dimethylpropylamine hydrochloride (>96 %), 4‐(2‐chloroethyl)morpholine hydrochloride (99 %), chloroacetic acid (99 %), cyclohexanone oxime (97 %), acetone oxime (98 %) (Sigma–Aldrich), and acetophenone oxime (98 %) (Alfa‐Aesar) were commercially available. The 1‐(2‐thienyl)ethan‐1‐one oxime was synthesized following the procedures described in the literature.30 All NMR spectra were recorded on a Bruker Avance III 400 MHz or 700 MHz spectrometer, using CDCl3 as the solvent, with TMS as an internal standard. Mass spectra were recorded on a Shimadzu LC‐MS 8030 spectrometer (triple quadrupole). HRMS spectra were recorded on QTOF (Impact HD, Bruker) spectrometer. Melting points were determined by using DigiMelt MPA161 digital melting point apparatus and were uncorrected. The reaction times were analyzed by TLC analysis. For non‐absorbing compounds under a UV lamp (254 nm), TLC (vanillin, ethanol, sulfuric acid) was used.
9
Synthesis and Characterization of Polyurethane-Based Materials
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5,5-dimethylhydantoin (DMH), 4-vinylbenzyl chloride, copper(I) bromide, [2-(Methacryloyloxy) ethyl] dimethyl-(3-sulfopropyl) ammonium hydroxide (SBMA), poly (ethyl glycol) methacrylate (PEGMA, Mn = 360 Da), and ethyl-2-bromoisobutyrate (EBIB) were purchased from Sigma-Aldrich (Sigma-Aldrich, St. Louis, MO, USA). 2-bromoisobutyryl bromide (BIBB), 2-(Dimethylamino) pyridine, 2-2’-bipyridine (bpy), and 2-hydroxyethyl methacrylate (HEMA) were purchased from Alfa Aesar (Lancashire, UK). Triethylamine and ethanol were purchased from J.T. Baker (Allentown, PA, USA). Methanol, dichloromethane, and toluene were from MACRON (Allentown, PA, USA). N,N-dimethylformamide (DMF) was acquired from Duksan (Ansan, Korea). All the above chemicals were purchased at the highest purity grade. The thermoplastic ester-based polyurethane pellet (TPU, Estane, S385A) was purchased from Lubrizol Advanced Materials, (Inc., Wickliffe, OH, USA).
10
Liposomal Ciprofloxacin Formulation Characterization
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CFI, a liposomal ciprofloxacin formulation comprised of 50 mg/mL ciprofloxacin in a pH 6.0 histidine-buffered aqueous formulation, was manufactured by Northern Lipids Incorporated (Burnaby, BC, Canada). (The ciprofloxacin concentrations are expressed in terms of ciprofloxacin hydrochloride.) The following materials were utilized: sodium chloride (Amresco, Solon, OH), sucrose (Sigma-Aldrich, St. Louis, MO), HEPES, free acid (Avantor, Center Valley, PA), polysorbate 20 (VWR Int., West Chester, NJ), HPLC grade methanol (Fisher Scientific, Fair Lawn, NJ), triethylamine (TEA, JT Baker, USA), Donor Adult Bovine Serum (HyClone, Logan, Utah), and Nanosep centrifugal filtration devices, 10K and 30K molecular weight (Pall Corporation, Ann Arbor, MI). Deionized water was used for all studies.
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