4,5-Diazofluoren-9-one (DAFO) was synthesized in our laboratory following the synthetic route described in the literature [38 (link)] and modified by us [39 (link)]. The detailed synthesis of DAFO is described in the S1 Section in the Supporting Information . The 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA, 99% of purity) was supplied by TCI Europe (Zwijndrecht, Belgium), and it was purified by sublimation at 220 °C under high vacuum prior to use. The 2,2′-bis(4-aminophenyl)hexafluoropropane (6FpDA, 99% of purity) and 2,4,6-trimethyl-m-phenylenediamine (TMPD, 96% of purity) were purchased from Cymit Química (Barcelona, Spain) and Sigma-Aldrich (St. Louis, MO, USA), respectively, and purified by sublimation at 220 °C and 110 °C before use. Matrimid 5218 was kindly gifted by Huntsman. Chlorotrimethyl silane (CTMS, >98% of purity) and N,N-dimethylaminopyridine (DMAP, ≥99% of purity) were purchased from TCI. Anhydrous dimethylacetamide (DMAc, 99.8% of purity), anhydrous pyridine (Py, 99.5% of purity), acetic anhydride (97% of purity), and 1,3,5-triphenylbenzene (135TPB, >99% of purity) were purchased from Alpha Aesar (Haverhill, MA, USA). The trifluoromethanesulfonic acid (TFSA, 99% of purity) was purchased from Fluorochem (Glossop, UK).
Acetic anhydride
Manufactured by Thermo Fisher Scientific
Sourced in United States, Belgium, Poland, Germany, United Kingdom
Acetic anhydride is a chemical compound used in various laboratory applications. It serves as a reagent for the acetylation of organic compounds, a process that introduces an acetyl group (-COCH3) into a molecule. This can be used for the modification of organic structures and the preparation of various derivatives. Acetic anhydride is a clear, colorless liquid with a pungent odor.
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Lab products found in correlation
Methylene chloride, by Thermo Fisher Scientific (8 mentions)
Acetonitrile, by Thermo Fisher Scientific (7 mentions)
Sulfuric acid, by Thermo Fisher Scientific (7 mentions)
Toluene, by Thermo Fisher Scientific (7 mentions)
Dimethylformamide, by Thermo Fisher Scientific (6 mentions)
Acetone, by Thermo Fisher Scientific (5 mentions)
1 methyl 2 pyrrolidinone, by Merck Group (5 mentions)
Triethylene glycol, by Merck Group (5 mentions)
1 6 dibromohexane, by Merck Group (5 mentions)
Sodium hydroxide (naoh), by Thermo Fisher Scientific (5 mentions)
Potassium carbonate, by Thermo Fisher Scientific (4 mentions)
Hexane, by Thermo Fisher Scientific (4 mentions)
Acetic acid, by Thermo Fisher Scientific (4 mentions)
Deuterated chloroform, by Cambridge Isotopes (4 mentions)
4 p fluorobenzonitrile, by Apollo Scientific (4 mentions)
Pentane, by Thermo Fisher Scientific (4 mentions)
Hydrochloric acid (hcl), by Thermo Fisher Scientific (3 mentions)
Chloroform, by Thermo Fisher Scientific (3 mentions)
Petroleum ether, by Thermo Fisher Scientific (3 mentions)
Ethyl ether, by Thermo Fisher Scientific (3 mentions)
37 protocols using acetic anhydride
1
Synthesis and Purification of 4,5-Diazofluoren-9-one
2
Synthesis of L-α-Glycerophosphocholine
3
Synthesis of Naphthalene Derivatives
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2,3-Dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 4-bromoaniline, potassium carbonate, and formamidine were received from Acros. Acetic anhydride, HCl, and triflic acid were ordered from Alfa Aesar. Dioxane, chloroform, n-butanol and o-dichlorobenzene, acetic acid, DMF, THF, and acetone were obtained from J. T. Baker (Phillipsburg, NJ, USA). Raw chemical materials and solvents were purchased from commercial resources and then used as they were.
4
Annexin V Hemolysis Assay
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Piperidine and acetic anhydride were supplied by Alfa Aesar (Haverhill, MA). Caspofungin was supplied by AM Beed (Arlington Heights, IL). Sodium hydroxide was supplied by Avantor (Philipsburg, NJ). Yeast peptone dextrose media was supplied by Beckton Dickinson (Franklin Lakes, NJ). Formic acid and Sabouraud dextrose agar were supplied by Merck (Kenilworth NJ). Wang resin and fluorenylmethoxycarbonly (Fmoc) protected amino acids were supplied by Novabiochem (Burlington, MA). O-(1H-6-Chlorobenzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HCTU) was supplied by Peptides International (Louisville, KY). Bio-Rad Assay Reagents were supplied by Bio-Rad (Richmond, CA). Sulfuric Acid was supplied by Pharmco (Brookfield CT). Alexafluor350 and Alexafluor350-labeled Annexin V were supplied by Thermo Fisher Scientific (Waltham, MA). Dimethyl formaldehyde (DMF), Dimethyl sulfoxide (DMSO) and Acetonitrile (ACN) were supplied by VWR (Radnor, PA). Human red blood cells (RBCs) were supplied by Interstate Blood Bank (Philadelphia, PA). All other materials and reagents were supplied by Sigma-Aldrich (St. Louis, MO).
5
Preparation and Characterization of Zirconium Alkoxide Compounds
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Zirconium(IV) propoxide (Zr(OnPr)4, 70 % in 1‐propanol) and zirconium (IV) chloride (ZCL, 99.9 %) were purchased from Sigma–Aldrich. Anhydrous benzyl alcohol (BnOH, 99.8 %), diisopropylether (DIPE, 99 %) and acetophenone (AcPh, 99 %) were also purchased from Sigma–Aldrich. Acetic anhydride (Ac2O, 99 %), ethanol (EtOH, 99.5 %) and anhydrous acetone (ACE, 99.8 %) were purchased from ACROS Organics. 2‐pentanone (MPK, 99.5 %) was purchased from Alfa Aesar. Zirconium(IV) propoxide (Zr(OnPr)4, 70 % in 1‐propanol) was treated before use for 15 h under primary vacuum at 120 °C to remove 1‐propanol and obtain pure Zr(OnPr)4 (ZNP). Complete removal of 1‐propanol was checked by FTIR spectrometry, by the absence of the OH stretching band from the alcohol (Figure S1). The water content of all oxygen donors was measured by Karl Fischer titration and, if necessary, they were dried over molecular sieves to ensure adequate drying (<10 ppm H2O for Ac2O, DIPE; <20 ppm for ACE, MPK, AcPh; <50 ppm H2O for EtOH, BnOH). Toluene (Sigma‐Aldrich, 99.7 %) and dichloromethane (Sigma–Aldrich, 99.8 %) were dried over a PureSolve MD5 solvent purification system (H2O <10 ppm, controlled with by Karl Fischer titration).
6
Coriander Seed Oil Extraction
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The vegetable oil of C. sativum fruits was isolated via twin-screw extrusion at LCA via a previously reported procedure (Uitterhaegen et al. 2015 (link)). Trimethylsulfonium hydroxide (TMSH), t-butyl methyl ether (TBME), hydrochloric acid (HCl), hexane, sodium citrate tribasic dihydrate, ammonium chloride (NH4Cl), potassium phosphate monobasic (KH2PO4), potassium phosphate dibasic (K2HPO4), magnesium sulfate heptahydrate (MgSO4∙7H2O), calcium chloride dihydrate (CaCl2∙2H2O), sodium, 4-dimethylaminopyridine (DMAP), Sudan III and diethyl ether were purchased from Sigma-Aldrich (Belgium). Yeast extract was purchased from Difco (Belgium). Sodium hydroxide (NaOH), dry methanol, acetic anhydride and sodium triacetoxyborohydride [NaBH(OAc)3] were purchased from Acros Organics (Belgium). Magnesium sulfate (MgSO4) and sodium bicarbonate (NaHCO3) were purchased from Fisher Scientific (Belgium). Ethyl acetate and tetrahydrofuran (THF) were purchased from Chem-Lab (Belgium). Glucose monohydrate was purchased from Cargill (Belgium). Sodium chloride (NaCl) was purchased from Colruyt (Belgium).
7
Glioma Cell Culture and Characterization
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Ferrous chloride tetrahydrate (FeCl2 · 4H2O >99%), ammonia (28% to 30% NH3 in aqueous solution), triethylamine, acetic anhydride, and dimethyl sulfoxide (DMSO) were purchased from Sinopharm Chemical Reagent Co., Ltd (Shanghai, China). The APTS and acetic anhydride were from Acros Organics (Geel, Belgium). C6 glioma cells (a rat C6 glioma cell line) were purchased from the Institute of Biochemistry and Cell Biology at the Chinese Academy of Sciences (Shanghai, China). RPMI 1640 medium, fetal bovine serum (FBS), penicillin, and streptomycin were purchased from Hangzhou Jinuo Biomedical Technology (Hangzhou, China). The MTT was acquired from Shanghai Sangon Biological Engineering Technology and Services Co., Ltd (Shanghai, China). The water that was used in all of the experiments was purified using a Milli-Q Plus 185 water purification system (Millipore, Bedford, MA, USA) with a resistivity that was higher than 18.2 MΩ cm.
8
Synthesis of (+)-Catechin Ester Derivatives
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(+)-Catechin and butyric anhydride with 98% purity and 4-dimethylamino pyridine with 99% purity were purchased from Sigma Aldrich (St. Louis, MO, USA). Acetic anhydride with 99% purity was purchased from Acros (Morris Plains, NJ, USA). Silica gel (P60, 40–63 µm, 60 Å) was purchased from SiliCycle (Quebec, QC, Canada), and Silica Gel 60 F254 Coated Aluminum-Backed TLC (thin layer chromatography) sheets were purchased from EMD Millipore (Billerica, MA, USA).
9
Betulin Disuccinate-based Nanoformulations
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Betulin disuccinate (obtained in the laboratory according to the procedure described in the article [26 (link)]), acetic anhydride (POCh S.A., Gliwice, Poland), sebacic acid (ACROS Organics, Geel, Belgium), rifampicin (Biosynth Carbosynth, Berkshire, UK), poly(vinyl alcohol) (Mw = 88,000 g/mol, 88% hydrolyzed) (ACROS Organics, Geel, Belgium), and methylene chloride (Chempur, Piekary Śl., Poland) were used as supplied.
10
Betulin Disuccinate Synthesis and Evaluation
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Betulin disuccinate (obtained in the laboratory according to the procedure described in the article [7] ), acetic anhydride (POCh S.A.), sebacic acid (ACROS Organics), dimethyl sulfoxide (DMSO) (Chempur), trichloroacetic acid (Chempur), acetic acid (Chempur), Tris buffer, sulforhodamine, poly(vinyl alcohol) (Mw = 88,000 g/mol, 88% hydrolyzed) (ACROS Organics), methylene chloride (Chempur) were used as supplied.
KB, HeLa and Hep-G2 cells were obtained from the European Collection of Cell Culture (ECACC) supplied by Sigma Aldrich. A-549, U-87 and HDF cells were purchased from the American Type Culture Collection (ATCC) through LGC Standards (Lomianki). KB, Hep-G2 and U-87 cells were cultured in EMEM medium while HeLa cells were grown in RPMI 1640 medium, A-549 cells in F-12K medium and HDF cells in Fibroblasts Growth Medium. Each medium was supplemented with 10% fetal bovine serum, 1% L-glutamine and 1% penicillin/streptomycin solution. All cultures were maintained at 37 °C in a humidified atmosphere containing 5% CO2.
KB, HeLa and Hep-G2 cells were obtained from the European Collection of Cell Culture (ECACC) supplied by Sigma Aldrich. A-549, U-87 and HDF cells were purchased from the American Type Culture Collection (ATCC) through LGC Standards (Lomianki). KB, Hep-G2 and U-87 cells were cultured in EMEM medium while HeLa cells were grown in RPMI 1640 medium, A-549 cells in F-12K medium and HDF cells in Fibroblasts Growth Medium. Each medium was supplemented with 10% fetal bovine serum, 1% L-glutamine and 1% penicillin/streptomycin solution. All cultures were maintained at 37 °C in a humidified atmosphere containing 5% CO2.
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