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5 protocols using pyridine

1

Synthesis of Heterocyclic Compounds

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n-Butyllithium, phosphinic
acid, potassium carbonate, pyridine, o-phenylendiamine, o-dichlorobenzene, cuprous iodide, trifluoroacetic anhydride,
18-crown-6, carbazole, phenothiazine, diisopropylethylamine, sodium t-butoxide, and tribenzylidene acetone dipalladium (II)
were purchased from Energy Chemical. Tetrahydrofuran, dichloromethane,
petroleum ether, methanol, and ethyl acetate were purchased from Sinopharm
Chemical Reagent Co., Ltd. Chemicals were used without further purification
unless otherwise noted. Anhydrous solvents were distilled from commercial
sources with sodium/benzopheneone or calcium hydride.
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2

Synthesis and Characterization of Organic Compounds

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Methanol (99.5%), hydrochloric acid (HCl 36–38%) and sulfuric acid (H2SO4 95–98%) were purchased from Chengdu Chron Chemicals Company (Chengdu, China). o-phenylenediamine (o-PDA) (98%), tert-butyl hydroperoxide (TBHP) (70%), 3-chloroperbenzoic acid (85%), butylamine (99%), aniline (99.5%), pyridine (99%), pyrrole (99.9%), indole (99%), quinoline (99%), imidazole (98%), spermidine (99%), lysine (98.5%), tetracycline (98%), purine (98%), and N, N-Diisopropylethylamine (98%) and 8-Diazabicyclo [5.4.0] undec-7-ene (99%) were purchased from Energy Chemical Company (Shanghai, China). All the reagents were used as received without further purification, unless otherwise noted. The deionized water used in all experiments was made from a Master Touch-S laboratory ultrapure water machine (Master Touch, Shanghai, China).
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3

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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4

Synthesis and Purification of HATU Reagent

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1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (C10H15OF6N6P, HATU, 99.5%), AlCl3·6H2O (98%), diisopropylamine (98%), benzyltriethylammonium chloride (99%), 1-benzylimidazole (98%), toluene (99.5%), ethanol (99.7%), acetonitrile (99%), N,N-dimethylformamide (DMF, 99.5%) and pyridine (99.5%) were purchased from Energy Chemical, Vetec™, Alfa Aesar, Shanghai Dahe Chemical and Tansoole Company. All reagents were of analytical or reagent grades and used without further purification. Deionized water (18.2 MΩ cm) was obtained from a F’DEER water purification system.
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5

Enzymatic Synthesis of Fatty Acid Esters

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Raffinose (99.0%), t-BuOH (anhydrous), pyridine (anhydrous), N, N-dimethylformamide (DMF), benzene, Span 20, Span 40, Span 60, Span 80, Tween 20 and Tween 80 were purchased from the Energy Chemical Co., Ltd (Shanghai, China). Vinyl hexanoate (>99.0%), vinyl n-octanoate (>99.0%), vinyl decanoate (>99.0%), vinyl laurate (>99.0%), vinyl myristate (>99.0%), vinyl palmitate (>96.0%) and vinyl stearate (>95.0%) were purchased from the Tokyo Chemical Industry Co. Ltd. (Tokyo, Japan). Novo Nordisk (Bagsvaerd, Denmark) provided lipozyme TLIM while the Mitsubishi-Chemical Foods Corporation was the source of the sucrose esters P-1570 and P-1670. Pure olive oil, on the other hand, was purchased from a local food store.
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