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2 protocols using potassium hydroxide

1

Synthesis and Characterization of N-Alkyl-N,N-2-Dihydroxyethyl-N-Methylammonium Bromide Compounds

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Methanol, acetonitrile, acetone, isopropanol, and dimethyl sulfoxide (DMSO), toluene, diethyl ether, and potassium hydroxide were of analytical grade and purchased from Energy Chemical Co., Ltd. (Shanghai, China). The above agents were used without further distillation. Dichloroacetic acid (CAS no. 79-43-6), 1-bromododecane (CAS no. 143-15-7), 1-bromotetradecane (CAS no. 112-71-0), 1-bromohexadecane (CAS no. 112-82-3) and hydroxylalkylamines were purchased from Energy Chemicals (Shanghai, China). Glyphosate isopropylamine salt (purity 62%, aqueous solution) was obtained from Lier Chemical Co., Ltd (Sichuan, China). N-Alkyl-N,N-2-dihydroxyethyl-N-methylammonium bromide (CnDHAB, n = 12, 14 and 16) were synthesized according to reported procedures described in the literature.45 Methyl sulfoxide-d6 with a deuteration degree of 99.8% for NMR spectra was obtained from J & K Scientific Co., Ltd. (Beijing, China).
The 1H, 13C NMR spectra were recorded with a Bruker 400 spectrometer (Bruker, Germany) at 400 and 100 MHz, respectively. Chemical shifts (δ) are reported relative to the residual solvent resonances of methyl sulfoxide-d6.
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2

Synthesis and Characterization of Photosensitizers

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Human serum albumin (HSA, ≥ 98%), Bovine serum albumin (BSA, ≥ 98%), β-Lactoglobulin from bovine blood (β-LG, ≥ 90%), L-Cysteine (Cys, ≥ 98%), IR-780 ( ≥ 98%), and anhydrous dimethyl sulfoxide (DMSO, ≥ 99%) were purchased from Sigma-Aldrich. ICG (modified) for human injection was purchased from Dandong Yichuang Pharmaceutical Co. Ltd. IR-808 ( ≥ 95%) was purchased from Beijing Zhongying Biotechnology Co., Ltd. Cyanine5 NHS ester (Cy5, ≥ 99%) was purchased from Aladdin (Shanghai, China). Recombinant human albumin domain I (DI, ≥ 95%), recombinant human albumin domain II (DII, ≥ 95%), and recombinant human albumin domain III (DIII, ≥ 95%) were purchased from Albumin Therapeutics LLC. Benzo[cd]indol-2(1H)-one, phosphorus pentasulfide, pyridine, sodium hydroxide (NaOH), methyl iodide, acetone, methanol, 2,2-dimethyl-1,3-dioxane-4,6-dione, ethanol, triethylamine, ethyl iodide, N,N-Dimethylformamide (DMF), potassium carbonate, concentrated hydrochloric acid (HCl), potassium iodide, acetic acid, acetic anhydride, 1-iodopropane, 1,4-butylenesulfone, potassium hydroxide, N-methylpyrrolidone(NMP), 2,6-di-tert-butyl-4-methyl pyridine (DTBMP), toluene, 1-butanol, and ethyl 6-bromohexanoate were purchased from Energy Chemical.
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