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4 protocols using 4 dimethylaminopyridine dmap

1

Lipid-based Nanoparticle Synthesis

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All reagents used in this study were of analytical grade. Deionized water was prepared using an Elix water purification system (Millipore Co. Ltd, Molsheim, France). Dipalmitoylphosphatidylcholine (DPPC), 1,2-dipalmitoyl-3-trimethylammonium-propane chloride salt (TAP) and 1,2-dipalmitoyl-sn-glycero-3-phosphate sodium salt (PA) were obtained from Avanti Polar Lipids (Alabaster, AL, USA). Phosphate buffered saline (PBS) was purchased from Thermo Fisher Scientific (Yokohama, Japan). Acetone, chloroform, toluene, sodium sulphate anhydrous, sodium borohydride, rhodamine B, sodium tetrachloroaurate(III) dihydrate, 4-dimethylaminopyridine (DMAP) and tetraoctylammonium bromide were purchased from Wako Pure Chemical Industries (Osaka, Japan). Ethanol was purchased from Sigma-Aldrich (St Louis, MO, USA). Sulphuric acid, hydrochloric acid, aqueous ammonia and 30% hydrogen peroxide were obtained from Kanto Chemical (Tokyo, Japan). Polystyrene beads (diameter, 1.0 µm) were purchased from Funakoshi (Tokyo, Japan).
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2

Curcumin-PEG Conjugate Synthesis and Evaluation

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Curcumin was purchased from Tokyo Chemical Industry (Tokyo, Japan). Poly(ethylene glycol) methyl ether (MePEG750, Mw: 750 Da), poly(ethylene glycol)-diol (PEG1500, Mw: 1500 Da) and 4-arm branched poly(ethylene glycol) (4-arm PEG, Mw: 10,000 Da) were purchased from Sigma-Aldrich Japan (Tokyo, Japan). 4-Dimethylaminopyridine (DMAP) and N,N′-carbonyldiimidazole (CDI), dehydrated tetrahydrofuran (THF), dehydrated dichloromethane, diethyl ether, dimethyl sulfoxide (DMSO), methanol, deuterated chloroform (containing TMS), and deuterated water were purchased from Wako Pure Chemical Industries (Osaka, Japan). Dialysis membrane Spectra/Por 7 (MWCO: 3500) was purchased from Spectrum Laboratories. HepG2 human hepatocellular liver carcinoma cell and PC-3 human prostate cancer cell were purchased from the American Type Culture Collection (ATCC). 3-(4,5-dimethylthial-2-yl)-2,5-diphenyltetrazalium bromide (MTT) and Hoechst 33342 were purchased from Dojindo (Kumamoto, Japan).
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3

Hydroxypropyl Cellulose Polymer Modification

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Hydroxypropyl cellulose (HPC) was purchased from Tokyo Chemical Industry Co., Ltd. (TCI) and the molecular parameters are as follows: number- and weight-average molecular weights, 9.9 × 104 and 1.5 × 104 respectively; degree of substitution, DS = 1.4 and MS = 3.9,28 (link) where DS and MS denote an average number of substituted hydroxyl group and that of introduced hydroxypropyl group, respectively. Methyl acrylate (MA), methyl methacrylate (MMA), ethyl acrylate (EA), ethyl methacrylate (EMA), isopropyl methacrylate (iPMA), and 4-acryloylmorpholine (ACMO) were obtained from TCI and used after passing through a column packed with activated alumina (Wako Pure Chemical Industries, Ltd. (Wako)). Dehydrated pyridine (Wako), propionic anhydride (TCI), 4-dimethylaminopyridine (DMAP) (Wako), 2-hydroxy-2-methylpropiophenone (HMPPh) (Sigma Aldrich Co. LCC.) were used without further purification.
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4

Synthesis of Glycopolymer Probes for Lectin Binding

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Materials. Triethylamine (TEA, 99%), trimethylolethane (98%), 1-ethyl-3-(3-dimethyl aminopropyl)carbodiimide hydrochloride (EDC•HCl, 98%), 4-methoxyphenol (99%), acryloyl chloride (95%), propargyl alcohol (98%), lithium bromide (LiBr, 99%) and N,Ndimethylacrylamide (DMA, 99%) were purchased from Tokyo Chemical Industry (Tokyo, Japan). 4-Dimethylaminopyridine (DMAP, 99%), 2,2'-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride (AIPD, 98%) and formic acid (99%) were purchased from Wako Pure Chemical Industries (Osaka, Japan). Diethylether (Et2O), N,N-dimethylformamide (DMF), copper(II) sulfate (CuSO4, 97.5%), and sodium L-ascorbate (98%) were purchased from Kanto Chemical (Tokyo, Japan). Acetonitrile (MeCN) and fetuin from fetal bovine serum were purchased from Sigma Aldrich (St. Louis, USA). Blood cell suspension from a chicken was purchased from Nippon Bio-test Laboratory Inc (Saitama, Japan). 2-{[(Butylsulfanyl)carbonothioyl]sulfanyl}propanoic acid (BTPA), 36 6'-sialyllactose azide (6'-SALac azide), 37 and trifunctional RAFT agent 35 were prepared according to previous papers. Commercial monomers including the radical inhibitor were purified by passing through an alumina column prior to use.
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