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5 protocols using triethylamine

1

Synthesis and Functionalization of Silica Nanoparticles

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N-Cetyltrimethylammonium bromide (CTAB), tetraethyl orthosilicate (TEOS), sodium hydroxide (NaOH), 3-aminopropyltriethoxysilane (APTES), pyruvic acid (PA), N-hydroxysuccinimide (NHS), 1-ethyl-3-(3-(dimethylamino) propyl) carbodiimide hydrochloride (EDC), (2-thienylmethyl)hydrazine hydrochloride, (5,6-dimethylthieno[2,3-d]pyrimidin-4-yl)hydrazine, trifluoroacetic acid (TFA), triethylamine (TEA), ethanol, 2-propanol from Carl Roth (Carl Roth GmbH & Co. KG, Karlsruhe, Germany), dichloro(p-cymene)ruthenium(II) dimer, phosphate buffered saline (PBS), toluene and crystal violet (CV) were purchased from Sigma-Aldrich (Merck KGaA, Darmstadt, Germany). Dulbecco’s Modified Eagle Medium (DMEM) was purchased from Biowest (Riverside, CA, USA). For in vitro experiments nutrition medium RPMI 1640, FCS (fetal calb serum), penicillin/streptomycin and phosphate buffer saline (PBS) were obtained from Capricorn scientific GmbH (Ebsdorfergrund, Germany), glutamine and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) from GE healthcare (Chicago, IL, USA) and Biomol GmbH (Hamburg, Germany), respectively.
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2

Sensitive Vitamin D Metabolite Quantification

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Standards of 3β-25(OH)D3 and 1,25(OH)2D3 were purchased from Cayman Chemical (Ann Arbor, MI, USA); vitamin D3 and (24R)-24,25(OH)2D3 from Toronto Research Chemicals (Toronto, ON, Canada); 3α-25(OH)D3, 4-phenyl-1,2,4-triazoline-3,5-dione, 2-fluoro-1-methylpyridinium-p-toluenesulfonate, isonicotinoyl chloride hydrochloride (95%), nicotinoyl chloride hydrochloride (97%), acetic anhydride (≥ 99%), pyridine (anhydrous, 99.8%), acetonitrile (anhydrous, 99.8%), and 4-dimethylaminopyridine (99%) from Sigma-Aldrich (Steinheim, Germany); acetic acid and triethylamine (≥ 99.5%) from Carl Roth (Karlsruhe, Germany); 4-[2-(6,7-dimethoxy-4-methyl-3-oxo-3,4-dihydroquinoxalinyl)ethyl]-1,2,4-triazoline-3,5-dione from Enzo Life Sciences (NY, USA); 2-nitrosopyridine from MedChemExpress (Monmouth Junction, NJ, USA); Amplifex Diene Reagent Kit from Sciex (Darmstadt, Germany); and 3β-25(ΟΗ)D3-[26,26,26,27,27,27-d6] monohydrate from IsoSciences (Ambler, PA, USA). UHPLC-MS-grade acetonitrile and methanol were obtained from Chemsolute (Th. Geyer, Renningen, Germany) and formic acid (97%) from Alfa Aesar (Karlsruhe, Germany). Organic-free water was generated by a Millipore (Bedford, MA, USA) Direct-Q8 purification system. Human vitamin D3-free serum (VD-DDC Mass Spect Gold® serum) was purchased from Sigma-Aldrich.
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3

Synthesis and Characterization of Glucuronic Acid Derivative

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D-(+)-glucuronic acid γ-lactone, pyridine, methyl-(p-hydroxymethyl) benzoate, triethylamine (TEA), acetic acid, dichloromethane (DCM), acetonitrile (ACN), methanol (MeOH), heptane, ethyl acetate, toluene, tetrahydrofuran (THF), N, N-dimethylformamide (DMF) were ordered from Carl Roth. Tert-butyldimethylsilyl chloride (TBDMSCl), diphenyl phosphoryl azide (DPPA), lithium methoxide solution (LiOMe), 4-nitrophenyl chloroformate (Cl-COOPhNO2) were ordered from Sigma. Doxorubicin hydrochloride salt (DOX·HCl) was ordered from Biomol.
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4

Synthesis of N-n-propylacrylamide via Schotten-Baumann

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N-n-propylacrylamide (NNPAM) was synthesized by a Schotten-Baumann reaction following the protocol described by Hirano et al.50 (link). A solution of 0.5 mol of acryloyl chloride (Alfa Aesar, Ward Hill, U.S.A) in 200 ml dichloromethane (HiPerSolv, VWR, Center Valley, U.S.A.) was added dropwise over 3 hours to a mechanically stirred and ice-bath cooled solution of 0.6 mol of n-propylamine (purum, Sigma-Aldrich, St-Louis, U.S.A.) and 0.5 mol of triethylamine (for synthesis, Carl Roth GmbH & Co. KG, Karlsruhe, Germany) in 200 ml dichloromethane. The mixture was kept stirring at room temperature for 24 hours and filtrated with a Büchner funnel afterwards. The filtrate was washed with 10% sodium hydrogen carbonate and dried over sodium sulfate. The solvent was removed by rotary evaporation and the final product obtained after vacuum distillation (115 °C, 10 mbar) with a yield of 30–40%.
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5

Functionalized Cellulose Nanoparticles Synthesis

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Microcrystalline cellulose (MCC, Avicel PH-101), 4-cyano-4-(phenylcarbonothioylthio)pentatonic acid (CPPA, > 97%), 2,2′-azobis (2-methylpropionitrile) (AIBN, 98%), rhodamine B isothiocyanate (RBITC, mixed isomers, BioReagent), poly(ethylene glycol) methyl ether methacrylate (OEGMA, M n ≈ 475 g mol -1 , 98%), 2hydroxyethyl methacrylate (HEMA, >97%), N,N-dimethylformamide (DMF, analytical grade) were purchased from Merck, Germany. Anhydrous DMSO (≥99.8%) and triethylamine (TEA, ≥99.5%) were provided by Carl Roth, Germany. OEGMA and HEMA were purified by passing through a basic alumina column.
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