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5 protocols using 4 dimethylaminopyridine dmap

1

Synthesis and Antimicrobial Evaluation

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4-Formylbenzoic acid (97%), 3-aminopropyltrimethoxysilane (Aps, 97%) and anhydrous tetrahydrofuran (THF, 99.5%) were purchased from J&K Scientific. 4-Dimethylaminopyridine (DMAP, 99%) and N, N’-dicyclohexylcarbodiimide (DCC, 99%) were purchased from Tokyo Chemical Industry (TCI). L-borneol (97%) and D-borneol (97%) were purchased from Sigma-Aldrich. Malt extract agar, tryptone soy agar (TSA) and trypticase soy broth (TSB) were purchased from Aladdin. The BacLight live/dead kit (Molecular Probes) was purchased from Thermo Fisher Scientific. Other reagents were purchased from Sinopharm Chemical Reagent Co., Ltd, China. E. coli (ATCC 25922), S. aureus (ATCC 25923), P. aeruginosa (CICC 10351), S. epidermidis (CICC 1043), M. racemosus (CICC 3161), A. niger (CICC 41254) and C. albicans (CICC 32380) were obtained from the China Center of Industrial Culture Collection.
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2

Multifunctional PEG-PCL Nanocarrier

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SN38 and rapamycin were purchased from MedChemExpress (Cat# HY-13704; Cat# HY-10219, MCE, USA). Poly (ethylene glycol)-block-poly (ε-caprolactone) (PEG-b-PCL) was customized by Daigang Biomaterial Co., Ltd (Jinan, China). Triethylene glycol monomethyl ether (Cat# T0709), stannous octoate (Sn(Oct)2) (Cat# T3149), ε-caprolactone (Cat# C0702), 1,3-diisopropylcarbodiimide (DISC) (Cat# D0254), and 4-dimethylamino pyridine (DMAP) (Cat# D1450) were purchased from Tokyo Chemical Industry (TCI, Japan). Near-infrared fluorescent probe Cyanine5.5 (Cy5.5) amine was purchased from Lumiprobe (Cat# 270C0, Maryland, USA).
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3

Steroid Metabolite Quantification Protocol

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F, DHEA, Δ5-diol, E2, and fusaric acid (FA) were from Sigma-Aldrich (St. Louis, MO, USA). 7α-OH-DHEA and 3βAdiol were from Steraloids (Newport, RI, USA). F-d4 was from C/D/N Isotopes Inc. (Quebec, Canada). DHEA-13C3 was synthesized at Tohoku Pharmaceutical University (Miyagi, Japan). Δ5-diol-d4 and 7α-OH-DHEA-d2 were synthesized at ASKA Pharma Medical Co. Ltd. (Kanagawa, Japan). E2-13C4 was from Hayashi Pure Chemical Ind. Ltd. (Osaka, Japan). 4-dimethylaminopyridine (DMAP), 2-methyl-6-nitrobenzoic anhydride (MNBA), and picolinic acid (PA) were from Tokyo Chemical Industry (Tokyo, Japan). Triethylamine (TEA), O-ethylhydroxyl-ammonium chloride, pentafluoropyridine, and 1 M sodium hydroxide solutions were from Wako Pure Chemical Industries (Osaka, Japan). OASIS MAX cartridge (60 mg, 3 mL) was from Waters Corporation (Milford, MA, USA). InertSep SI cartridge (500 mg, 3 mL) was from GL Science (Tokyo, Japan). All other reagents and solvents were of analytical grade.
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4

Synthesis and Characterization of Functional Polymers

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MPC, diisopropylethylamine, N,N′-diisopropylcarbodiimide (DIC),
pyrene, and DMAEMA were purchased from Sigma-Aldrich, 2,2′-azobis(2-methylpropionitrile)
(AIBN), 1-bromobutane (C4), 1-bromododecane (C12), allyl alcohol,
1-bromooctadecane (C18), and BMA were bought from Alfa-Aesar. Isobutyltrichlorosilane
(iBTS), 4-hydroxybenzophenone, and 4-dimethylaminopyridine (DMAP)
were purchased from Tokyo Chemical Industry. Acryloyl chloride was
purchased from Beantown. 4-VBP42 (link) and 4-benzoylbenzoic
acid48 (link) were synthesized according to previous
reports.
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5

Solid-Phase Peptide Synthesis Reagents

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9-Fluorenylmethyloxycarbonyl
(Fmoc) amino acids were purchased from Merck Ltd. (Darmstadt, Germany).
Fmoc-NH-SAL-MBHA resin (100–200 mesh), N,N-diisopropylethylamine (DIPEA), trifluoroacetic acid (TFA),
and (1-cyano-2-ethoxy-2-oxoethylidenaminooxy) dimethylaminomorpholinocarbenium
hexafluorophosphate (COMU) were purchased from Watanabe Chemical Industries
Ltd. (Hiroshima, Japan). 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyl
uronium hexafluorophosphate (HBTU) and 1-hydroxybenzotriazole (HOBt)
were purchased from Kokusan Chemical Co., Ltd. (Tokyo, Japan). 1-Ethyl-3-(3-dimethylaminopropyl)
carbodiimide monohydrochloride (WSCD) was purchased from Peptide Institute,
Inc. (Osaka, Japan). Nitrilotriacetic acid (NTA), nitrilotriacetic
acid disodium salt, 4-dimethylaminopyridine (DMAP), and triisopropylsilane
(TIS) were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo,
Japan). N,N-diethyldithiocarbamate
(Na-DDTC) for quantification of copper ion was purchased from Nacalai
Tesque Co. Ltd (Kyoto, Japan). Water for experiment was purified by
Milli-Q Integral 3 (Merck Millipore, Darmstadt, Germany). Other solvents
and reagents were also obtained from commercial suppliers and used
without further purification.
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