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6 protocols using dichloromethane

1

Hydrophobically Treated Microfluidic Synthesis

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Glycinamide hydrochloride and serine methyl ester hydrochloride were purchased from Watanabe Chemical Industry Co, Ltd. (Hiroshima, Japan). Acryloyl chloride, hydrochloric acid (12 M), potassium carbonate, sodium hydroxide, diethyl ether, methanol, ethanol, tetramethylsilane (TMS), ammonium persulfate (APS), sodium trimethylsilyl propane sulfonate (DSS), N,N-diisopropylethylamine (DIPEA), dichloromethane (DCM), and anhydrous sodium sulfate (Na2SO4) were purchased from Nacalai Tesque, Inc. (Kyoto, Japan). Deuterium oxide (D2O), 25% glutaraldehyde solution, and Wako Gel® FC-40 were purchased from FUJIFILM Wako Pure Chemical, Co. (Osaka, Japan). Deuterated dimethyl sulfoxide (DMSO-d6) was purchased from Cambridge Isotope Laboratories, Inc. (Tewksbury, MA, USA). Polyethylene glycol diacrylate (PEGDA) was purchased from Tokyo Chemical Industry Co. (Tokyo, Japan) and dialysis membrane (MWCO: 25,000 Da) from Funakoshi Co. (Tokyo, Japan). The glass plates (76 mm × 52 mm) were obtained from Matsunami Glass Industry Co., Ltd. (Osaka, Japan). glass plates were hydrophobically treated with Siliconize L-25 (Fuji Systems Co., Tokyo, Japan) before use. Silicone rubber plates (1 mm) were obtained from As One Co. (Osaka, Japan). All the reagents were used without further purification.
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2

Functionalized Lipid Nanoparticle Synthesis

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α-N-Hydroxysuccinimidyl-ω-Boc protected-amino-PEG (NHS-PEG-NH2-Boc, Mw: 5000), 1,2-dimyristoyl-sn-glycerol-3-phosphatidylethanolamine (DMPE), 1,2-dipalmitoyl-sn-glycerol-3-phosphatidylethanolamine (DPPE), and 1,2-distearoyl-sn-glycerol-3-phosphatidylethanolamine (DSPE) were purchased from NOF Corporation (Tokyo, Japan). Dichloromethane, chloroform, toluene, diethyl ether, and n-butyl amine were obtained from Nacalai Tesque (Kyoto, Japan). Methoxyl-PEG-succinimidyl propionate (MeO-PEG-NHS, Mw 5000) was purchased from Nektar Therapeutics (San Carlos, CA, USA). L-α-Phosphatidylcholine from egg yolk (EggPC) and bovine serum albumin (BSA) were purchased from Sigma-Aldrich Co. (St Louis, MO, USA). Fluorescein isothiocyanate (FITC) was obtained from Dojindo Laboratories (Kumamoto, Japan). Phosphate-buffered saline (PBS) was obtained from Nissui Pharmaceutical, Co., Ltd (Tokyo, Japan). 1-Hexadecanethiol was purchased from Tokyo Chemical Industry Co., Ltd (Tokyo, Japan). Trifluoroacetic acid (TFA) and phospholipid C-test wako were purchased from Wako Pure Chemical Industries, Ltd (Osaka, Japan). Octadecyl triethoxysilane was supplied from Shin-Etsu Chemical Co., Ltd (Tokyo, Japan). L-α-Palmitoyl-NBD dodecanoyl phosphatidylethanolamine was purchased from Avanti Polar Lipids, Inc. (Alabaster, AL, USA).
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3

Synthesis and Purification of Dyes 2a and 2b

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Acetone, methanol, and ethyl acetate were purchased from Kanto Chemical Industry Co., Inc. Tetrahydrofuran (THF; stabilizers not included), dimethyl sulfoxide, chloroform, triethylamine, aniline, and tetrabutylammonium chloride were purchased from FUJIFILM Wako Pure Chemical Co. n-Hexylamine, diethylamine, tetrabutylammonium fluoride, and tetrabutylammonium acetate were purchased from TCI Co., Ltd. Tetrabutylammonium bromide was purchased from Sigma-Aldrich. Tetrabutylammonium perchlorate and dichloromethane were purchased from Nacalai Tesque Inc. Dyes 2a and 2b were synthesized by our method.40 (link)
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4

Synthesis of Metal-Organic Complexes

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Zinc sulfate heptahydrate (ZnSO4·7H2O), lithium hydroxide monohydride (LiOH·H2O), and polyethylene glycol 400 (PEG-400) were obtained from Wako Pure Chemicals Co. (Osaka, Japan); 3-Hydroxy-2-methyl-4(H)-pyran-4-one (maltol) was from Tokyo Chemical Industry Co. (Tokyo, Japan). Lawesson’s reagent, (±)-adrenaline hydrochloride, and bovine serum albumin (BSA: fraction V) were obtained from Sigma Aldrich Inc. (St. Louis, MO, USA). Dry toluene and dichloromethane were obtained from Nacalai Tesque Inc. (Kyoto, Japan). Acetone was obtained from JUNSEI Chemical Co., Ltd. (Kyoto, Japan). Dimethyl sulfoxide was obtained from Kishida Chemical Co. (Osaka, Japan).
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5

Synthesis of Nitro-Substituted Compounds

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3-Nitroaniline and stearoyl chloride were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Calcium chloride, dichloromethane, diethyl ester, magnesium sulfate, and sodium chloride were purchased from Nacalai Tesque, Inc. (Kyoto, Japan). (+)-Camphor, chloroform, and triethylamine were purchased from Fujifilm Wako Pure Chemical Corp. (Osaka, Japan). 4-Nitro-1,3-phenylenediamine was purchased from Combi-Blocks (San Diego, CA, USA).
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6

Comprehensive Analytical Reagent Procurement

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Acetone, diethylether, magnesium sulfate, sodium hydroxide, dichloromethane, chlorobenzene, toluene, ethyl acetate, methanol, ethylbenzene, butylbenzene, hexylbenzene, phenyloctane, tetrahydrofuran (THF), chloroform, n-hexane were purchased from Nacalai Tesque (Kyoto, Japan), methyl pentafluorobenzoate (MPFB), diethyl amine, 3-aminopropyltrimethoxysilane (APTMS), d-( +)-trehalose dihydrate from Tokyo Chemical Industry (Tokyo, Japan), sodium azide, N-hydroxysuccinimide (NHS), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDAC), d-( +)-glucose, maltose monohydrate, sucrose from Wako Pure Chemical Industries (Osaka, Japan), C60-fullerene (C60), C70-fullerene (C70), dextran (Mw = 1,000) (glucose homopolymer) from Sigma-Aldrich Japan (Tokyo, Japan), 2-AB Dextran Calibration Ladder (2-AB labeled glucose homopolymer) from Waters (USA), respectively. Deionized water was obtained by a Milli-Q Direct-Q 3UV system (Merck Millipore, Tokyo, Japan). Silica monolithic capillaries (ULTRON HF-SIL, ULTRON HF-ODS) were purchased from Shinwa Chemical Industries Ltd. (Kyoto, Japan). Porous graphite carbon column (PGC column) was purchased from Thermo Fischer Scientific USA).
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