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5 protocols using 4 dimethylaminopyridine

1

Synthesis of PLGA-PEG Copolymer

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Triethylamine and dichloromethane were dried with calcium hydride before use as described previously (26 (link)). Carboxylate-functionalized copolymer PLGA-PEG was synthesized by the conjugation of PLGA-COOH and NH2-PEG-COOH. Briefly, 200 mg PLGA-COOH, 2.9 mg 1-(3-Dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (Sigma-Aldrich; Merck KGaA), 1.8 mg N-Hydroxysuccinimide (NHS; Sinopharm Chemical Reagent Co., Ltd.) and 1 mg 4-dimethylaminopyridine (Sino-pharm Chemical Reagent Co., Ltd.) were dissolved in 10 ml dichloromethane, and stirred for 24 h at room temperature to convert PLGA-COOH to PLGA-NHS. Then, 34 mg NH2-PEG-COOH and 8.6 µl triethylamine were added into the solution. After further stirring for 8 h at room temperature, dichloromethane was removed through the use of a rotary evaporator and 5 ml N,N-Dimethylformamide (Sino-pharm Chemical Reagent Co., Ltd.) was added to dissolve PLGA-PEG. Then, the solution was added to a dialysis bag (width, 44 mm; MW cut-off, 8,000-14,000); unreacted PEG and other small molecules were removed by dialyzing for 3 days, and then PLGA-PEG was freeze-dried for 24-48 h.
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2

Synthesis of Silver Nanoparticles

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Folic acid, 2-Hydroxy-1-ethanethiol, and dimethyl sulfoxide (DMSO) were purchased from Tianjin Guangcheng Chemical Reagent Co., Ltd. (Tianjin, China); ethanol, ethyl acetate, sodium hydroxide, oleylamine (OA), isooctane, ascorbic acid, bis (2-ethylhexyl) sulfosuccinate sodium (AOT, 98.0%), and dithiothreitol (DTT) were obtained from Macklin reagents Co., Ltd. (Shanghai, China); and sodium borohydride, Polyvinylpyrrolidone (PVP), silver nitrate, 4-dimethylaminopyridine (DMAP), Dicyclohexylcarbodiimide (DCC), and ammonia water were purchased from Sinopharm Chemical Reagent Co., Ltd. (Tianjin, China). All reagents were analytically pure and were used as received.
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3

Synthesis of Functionalized Polymers

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Toluene, 4-methylbenzenesulfonic acid, 4-dimethylaminopyridine, pyridine, and dichloromethane were purchased from Sinopharm Chemical Reagent Co., Ltd (Beijing, China). SBS (Mw∼153 000–185 000, 70 wt % PB block), 2-Mercaptoethanol, and succinic anhydride were purchased from Sigma-Aldrich. 9-anthracenemethanol was purchased from Alfa Aesar. All the reagents were used as received.
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4

Synthesis and Characterization of Cellulose Nanocrystals-TPE Conjugates

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Cellulose nanocrystals were purchased from Shanghai ScienceK Ltd, China, which were synthesized by sulphuric acid hydrolysis of microcrystal cellulose. 4-(1,2,2-Triphenylvinyl)benzoicacid (TPE-COOH) was purchased from Xi'an Qiyue Biotechnology Co. Ltd, China. Epichlorohydrin, sodium hydroxide (NaOH), ammonium hydroxide (NH3·H2O), dimethyl sulfoxide (DMSO), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC), 4-dimethylaminopyridine (DMAP), as well as NaCl, MgCl2·6H2O, CaCl2, ZnCl2, Pb(NO3)2, HgCl2, FeSO4·7H2O, FeCl3·6H2O, CuSO4·5H2O, CoCl2·6H2O, BaCl2·2H2O, AlCl3, CdCl2 and MnSO4 were purchased from Sinopharm Chemical Reagent Co. Ltd, China. All reagents were analytical grade and received directly without any further purification. The deionized water was used to prepare all aqueous solutions.
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5

Pluronic P123-Chitosan Nanoparticle Synthesis

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Pluronic P123 (PEO20-PPO70-PEO20, ~5800 kDa) was obtained from Sigma Aldrich. Chitosan oligosaccharide (1162 kDa, deacetylation degree: >90%) was provided by Shandong Weikang Biomedical Technology. N, N′-disuccinimidyl carbonate, 4-dimethylaminopyridine, acetonitrile, and ethanol were obtained from Sinopharm Chemical Reagent. Paclitaxel (98%) and 4′, 6-diamidino-2-phenylindole (DAPI) were obtained from Dalian Meilun Biotechnology. Dipalmitoyl phosphatidylcholine (DPPC) was purchased from A.V.T. Pharmaceutical.
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