Synthesis of OPF was performed as previously described.29 , 32 , 33 (link) Briefly, anhydrous dichloromethane (EMD, Billerica, MA) was obtained through refluxing in the presence of calcium hydride (Sigma Aldrich, St. Louis, MO) followed by distillation. Anhydrous PEG (Mn = 9.3 ± 0.1 kDa, Mw = 13.1 ± 0.1 kDa, n =3) (Sigma Aldrich, St. Louis, MO) was generated through distillation in toluene (Fisher Scientific, Waltham, MA) and then added to the anhydrous dichloromethane. Triethylamine (Sigma Aldrich, St. Louis, MO) and fumaryl chloride (Acros, Geel, Belgium) were added to this PEG solution drop wise and the reaction was incubated for 2 days. Purification was then performed and characterization of the product was performed through analysis with gel permeation chromatography using PEG standards and 1H NMR to verify correct structure and fumarate PEG ratios as previously described.29 , 32 , 33 (link) The OPF used in this work has a Mn of 19.8± 0.3 kDa and a Mw of 89.9 ± 3.9 kDa (n = 3).
Anhydrous dichloromethane
Manufactured by Thermo Fisher Scientific
Sourced in United Kingdom, United States
Anhydrous dichloromethane is a colorless, volatile organic compound with the chemical formula CH2Cl2. It is commonly used as a solvent in various laboratory applications.
Automatically generated - may contain errors
Lab products found in correlation
Triethylamine, by Merck Group (2 mentions)
Anhydrous n n dimethylformamide, by Thermo Fisher Scientific (2 mentions)
Calcium hydride, by Merck Group (1 mentions)
Toluene, by Thermo Fisher Scientific (1 mentions)
Ethyl acetate, by Thermo Fisher Scientific (1 mentions)
Bovine serum albumin (bsa), by Merck Group (1 mentions)
Dimethyl sulfoxide (dmso), by Thermo Fisher Scientific (1 mentions)
Ethyl ether, by Thermo Fisher Scientific (1 mentions)
Anhydrous dimethylformamide, by Thermo Fisher Scientific (1 mentions)
Chloroform, by Thermo Fisher Scientific (1 mentions)
Dowex 50wx8 200 400 h, by Thermo Fisher Scientific (1 mentions)
Hplc grade acetonitrile, by Thermo Fisher Scientific (1 mentions)
Sodium bicarbonate, by Merck Group (1 mentions)
Sodium chloride (nacl), by Merck Group (1 mentions)
Anhydrous sodium sulfate, by Merck Group (1 mentions)
Anhydrous pyridine, by Merck Group (1 mentions)
Thiophenol, by Merck Group (1 mentions)
Oxalyl chloride, by Merck Group (1 mentions)
Morpholine, by Merck Group (1 mentions)
Anhydrous aluminum chloride, by Merck Group (1 mentions)
5 protocols using anhydrous dichloromethane
1
Synthesis and Characterization of OPF
2
Synthesis and Characterization of PLGA Nanoparticles
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PLGA copolymers with lactic: glycolic acid ratios of 1:1 (MW: 29–38 kDa) were purchased from Evonik (Darmstadt, Germany). PVA samples: 98% hydrolysed (MW: 13–23 kDa), 99+ % hydrolysed (MW: 146–186 kDa), 99+ % hydrolysed (MW: 89–98 kDa), bovine serum albumin (~66kDa) and QuantiPro Bicinchoninic Assay (BCA) kit were obtained from Sigma-Aldrich (Poole, Dorset, UK). Anhydrous dichloromethane (≥ 99.8% with 50–150 ppm amylene as stabiliser) and ethyl acetate (≥ 99.5%) were purchased from Fisher Scientific (Loughborough, Leicester, UK).
3
PEG-Hyaluronic Acid Hydrogel Synthesis
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The 4 kDa poly(ethylene glycol) (PEG) was purchased from Fluka (Buchs, Switzerland). Sodium hyaluronate (1.5 MDa) was purchased from Lifecore Biomedical (Chaska, MN, USA). Dexamethasone (DX), chloroacetyl chloride, 1,1′-carbonyldiimidazole (CDI), sodium acrylate, triethylamine (TEA), 4-methoxyphenol, anhydrous sodium sulfate, sodium bicarbonate, and sodium chloride were purchased from Sigma-Aldrich (Milwaukee, WI, USA). Dowex 50WX8 200-400 (H) was purchased from Alfa Aeser (Ward Hill, MA, USA). Anhydrous dichloromethane, anhydrous dimethylformamide, HPLC-grade acetonitrile, chloroform, ethyl ether, and dimethyl sulfoxide (DMSO) were purchased from Fisher Chemical (Fair Lawn, NJ, USA). The 2-hydroxy-1-[4-(hydroxyethoxy) phenol]-2-methyl-1-propanone (Irgacure 2959, I-2959) was donated by BASF (Florham Park, NJ, USA).
4
Characterization of Indole Derivatives
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Example 3
General information: 1H NMR spectra were recorded on a Bruker Avance III600 instrument, in deuterated solvents and were referenced to TMS (6 scale). Flash chromatography was performed on Merck silica gel 60 (0.040-0.063 mm). Analytical thin layer chromatography (TLC) was carried out on precoated (0.25 mm) Merck silica gel F-254 plates. Mass spectra were recorded with a LTQ Orbitrap Discovery instrument, possessing an Ionmax ionization source. 3-Acetoxyindole, 5-bromoindole, 6-chloroindole, 5-cyanoindole, methyl indole-5-carboxylate, methyl indole-6-carboxylate, 5-methylindole, iodine, potassium iodide, thiophenol, oxalyl chloride, anhydrous aluminum chloride, hydroxylamine hydrochloride, anhydrous pyridine, triethylamine, 1,2-dibromoethane, piperazine and morpholine were purchased from Sigma-Aldrich. Anhydrous dichloromethane and anhydrous N,N-dimethylformamide were purchased from Acros organics.
5
Synthesis of Organic Compounds
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Example 2
2-Bromotoluene was purchased from Oakwood Products. Urea, bromoethane, 2-bromopropane, tetrabutylammonium hexafluorophosphate, tris(4-bromophenyl)aminium hexachloroantimonate, anhydrous toluene, and anhydrous p-dioxane were purchased from Sigma Aldrich. Phenothiazine, sodium hydride (60% dispersion in mineral oil), bis(dibenzylideneacetone)palladium(0), sodium tert-butoxide, sulfur, iodine, o-dichlorobenzene (ODCB), anhydrous dichloromethane (DCM), anhydrous tetrahydrofuran, anhydrous N,N-dimethylformamide (DMF), and magnesium sulfate were obtained from Acros Organics. Tri-tert-butylphosphonium tetrafluoroborate was obtained from Oxchem. Silica gel and neutral alumina used for column chromatography were purchased from Silicycle and Sorbent Technologies, respectively. Ethyl acetate, hexanes, and diethyl ether were purchased from VWR. Solvents used for NMR spectroscopy were obtained from Cambridge Isotope Laboratories.
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