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6 protocols using deuterated dmso

1

Synthesis and Characterization of Ibuprofen Derivatives

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All used in this research reagents were commercially available materials and were used without further purification. (R,S)-Ibuprofen (>98%) was provided from Am-Beed (Arlington Heights, IL, USA). Thionyl chloride (99.5%) was obtained from Acros Organics (Geel, Belgium). l-Histidine (≥99%) and l-phenylalanine (>98.5%) were purchased from Carl Roth (Karlsruhe, Germany). l-Tyrosine, acetonitrile (≥99.9%) for HPLC gradient grade, deuterated DMSO (99.9%), 2-ethylhexyl acrylate (2-EHA) (98%), isobornyl methacrylate (IBOMA) (>99%), azobis(isobutyronitrile) (AIBN) (99%), and n-octanol (≥99%) were provided by Sigma-Aldrich (Steinheim am Albuch, Germany). l-Tryptophan was provided by Tokyo Chemical Industry Co., Ltd (TCI, Tokyo, Japan). Propanol (PrOH), ammonium hydroxide solution 25% (NH3·H2O), anhydrous sodium sulfate, n-hexane, methylene chloride, and diethyl ether were high-purity obtained from Chempur (Gliwice, Poland). 4-Acryloyloxy benzophenone (ABP) was obtained from POLY-CHEM BmbH (Bitterfeld-Wolfen, Germany). Acrylic acid (AA) (>98%), ethanol (EtOH), chloroform, toluene, and ethyl acetate were of analytical grade purchased from StanLab (Lublin, Poland). Deuterated chloroform (CDCl3) (99.8%) (+0.03% TMSCl) was purchased from Eurisotop (Cheshire, England).
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2

Preparation and Characterization of Vanillin-Benzyl Amine Derivatives

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Ready for dyeing (RFD) bleached cotton fabric (40 × 40/132 × 72 twill weave) of 100 g/cm2 (GSM) and PET (plain weave) fabric of 100 g/cm2 (GSM) having no optical brightening agent added into them were purchased from a local market in New Delhi. Vanillin, benzyl amine, 2,2-diphenyl-1-picrylhydrazyl (DPPH), sodium borohydride, methanol, and ethanol were purchased from Central Drug House (CDH) and used in the study without further purification. Analytical grade TLC Silica gel 60 F254 plate and extra pure Agar–Agar were purchased from Merck and Luria broth was purchased from Himedia, respectively which were used in the antibacterial study. CDCl3, Deuterated DMSO and KBr of analytical grade were purchased from Sigma Aldrich and used for NMR and FTIR sample preparation, respectively.
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3

Comprehensive Chemical Synthesis Protocol

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Urea (CH4N2O, Proquimsa, Coahuila, Mexico), phosphorus pentoxide (P2O5, Sigma-Aldrich, St. Louis, MO, USA), zinc powder (Chemical Dynamics, Florida, USA), ethanol (C2H6O, Sigma-Aldrich, St. Louis, MO, USA), methanol (CH4O, Sigma-Aldrich, St. Louis, MO, USA), acetone (C3H6O, Sigma-Aldrich, St. Louis, MO, USA), Toluene (C7H8, Sigma-Aldrich, St. Louis, MO, USA), Hexane (Sigma-Aldrich, St. Louis, MO, USA), Phosphoric Acid (H3PO4, Fermont, Nuevo León, Mexico), Ammonium Hydroxide 30% (NH4OH, Fermont, Nuevo León, Mexico), Hydrochloric Acid 30% (HCl, Fermont, Nuevo León, Mexico), porcine hematin (Sigma-Aldrich, St. Louis, MO, USA), aniline (Sigma-Aldrich, St. Louis, MO, USA), sodium carbonate (Na2CO3, Sigma-Aldrich, St. Louis, MO, USA), sodium bicarbonate (NaHCO3, Sigma-Aldrich St. Louis, MO, USA), p-toluene sulfonic acid (TSA, Sigma-Aldrich, St. Louis, MO, USA), hydrogen peroxide (H2O2, Sigma-Aldrich, St. Louis, MO, USA), Dimethyl sulfoxide (DMSO, Sigma-Aldrich, St. Louis, MO, USA), N-Methyl-2-pyrrolidone (NMP, Sigma-Aldrich, St. Louis, MO, USA), deuterated sulfuric acid (D2SO4, Sigma-Aldrich, St. Louis, MO, USA), deuterated DMSO (Sigma-Aldrich, St. Louis, MO, USA), deuterated acetone (Sigma-Aldrich, St. Louis, MO, USA) and deuterated water (D2O, Sigma-Aldrich, St. Louis, MO, USA).
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4

1H NMR Characterization of Bioactive Compounds

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1H NMR spectra were recorded using a Bruker Avance III 400 MHz spectrometer. 1–2 mg of each sample was dissolved in 0.5 mL of deuterated solvent. Dopamine hydrochloride, nitrodopamine, and the NDPM ligand were dissolved in deuterated DMSO (99.9 atom % D, Sigma Aldrich). NHS-palmitate ester was dissolved in 0.5 mL of deuterated chloroform (99.8 atom % D, Sigma Aldrich).
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5

Synthesis and Characterization of Polymer Hydrogels

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Lauryl acrylate (LA) and hydroxyethyl methacrylate (HEMA) were purchased from WPA Chemicals, Shanghai, China. 2-Hydroxyethyl acrylate (HEA), 2,2-azobis (2-methylpropionitrile, azobisisobutyronitrile/AIBN), gelatin powder (300B, porcine skin), stearyl acrylate (SA), and maleic anhydride (MA) were received from Glentham Life Sciences Ltd., Corsham, UK. Tetrahydrofuran (THF), diethyl ether, and dichloromethane were received from VWR Chemicals, BDH, Radnor, PA, USA. Deionized water was obtained from Quality Operations Laboratory (UVAS). NaOH (sodium hydroxide) and aniline (aminobenzene) was obtained from Merck (Darmstadt, Germany). Absolute ethanol (96% v/v), n-hexane, acetone, thymol blue, deuteroform (CDCl3), deuterated DMSO, and triethanolamine (TEOA) was received from Sigma-Aldrich (Burlington, MA, USA). Phosphate-buffered saline (PBS) tablets were received from Bio World (Bio-Plus Chemicals, Kuala Lumpur, Malaysia).
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6

Preparative HPLC and LC-MS Analysis

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HPLC grade acetonitrile (ACN) and methanol (MeOH) (Chromasolve®, for preparative HPLC), LC-MS grade ACN (Chromasolve®, for LC-MS analysis) and reagent-grade formic acid (≥98%)
were purchased from Sigma-Aldrich (Steinheim, Germany). Ultra-pure water was prepared using a Millipore Milli-Q purification system (Bedford, MA, USA). Deuterated DMSO and methanol were purchased from Sigma-Aldrich (Steinheim, Germany
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