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3 protocols using palladium on carbon pd c

1

Synthesis of N3-dxDAP Dendrons

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The synthesis of the dendrons N3-dxDAP, where x represents the number of peripheral DAP units, is outlined in Scheme 2; Scheme 3, and the synthesis of thymine cross-linkers is outlined in Scheme 4. Compounds (1)-(5) were synthesized according to previously reported procedures [47 (link),48 (link),49 (link)]. Polyethylenglycol monomethyl ether (PEG2k–OH) was purchased from Sigma Aldrich (Sigma Aldrich Gmbh, Steinheim, Germany) and used as received (according to certificate of analysis, batch 1257344: Mn = 1678 g mol−1, Ð = 1.21; according to MALDI-TOF mass spectrometry: Mn = 1948.0 g mol−1 corresponding to the more intense m/z peak) (Figure S1). Palladium on carbon (Pd/C) (10 wt% loading, matrix-activated carbon support) catalyst was purchased from Sigma Aldrich. Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA) was purchased from ACROS Organics (Thermo Fisher Scientific, Geel, Belgium). The azide-functionalized Merrifield’s resin was prepared from Merrifield’s resin cross-linked with 1% divinylbenzene (200–400 mesh) (0.8–1.3 mmol g−1) (TCI Europe N.V., Zwijndrecht, Belgium) according to the literature procedure [50 (link)]. Other reagents were purchased from Sigma Aldrich and used as received. Fourier Transformed Infrared Spectroscopy (FTIR) and 1H NMR spectra are collected at the Supporting Information (Figures S2–S35).
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2

Synthesis and Characterization of Radiolabeled Compounds

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SMZ (>98%) was provided by China Institute of Veterinary Drug Control (Beijing, China). Palladium on Carbon (Pd/C) was obtained from Sigma-Aldrich (Shanghai, China). Reagents such as H2O2(30%), sodium chloride (Nacl) and anhydrous sodium sulfate (Na2SO4) were purchased from Sinopharm Chemical Reagent Co., LTD. (Shanghai, China). Solvable (tissue solubilizing fluid), and Ultima Gold scintillation fluid were obtained from PerkinElmer Life and Analytical Sciences (Groningen, The Netherlands; Waltham, MA, USA, respectively). Stop Flow AD scintillation liquid was purchased from AIM Research Co. (Hockessin, DE, USA). Water was purified by using a Milli-Q system (Bedford, MA, USA). All reagents and other chemicals are analytical grade or higher purity.
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3

Synthesis of Adapalene-loaded Polymeric Micelles

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Methoxy polyethylene glycol (MPEG; number average molecular weight Mn ​= ​750 ​g/mol), 1.0 ​M HCl in diethyl ether, 10 ​wt% palladium on carbon (Pd/C), 4-nitrophenyl chloroformate, triethylamine, 1,4-diaminobutane, adapalene, glycerin, caprylic/capric triglyceride oil (CCT oil), tetraglycol, and Tween 80 were purchased from Sigma-Aldrich (St. Louis, MO, USA). ε-Caprolactone (CL, TCI, Tokyo, Japan) was sequentially distilled from CaCl2 and CaH2 under nitrogen before use. Chloroform-D and acetone-D were purchased from Cambridge Isotope Laboratories, Inc. (MA, USA). Toluene, dichloromethane, n-hexane, ethyl ether, anhydrous tetrahydrofuran (THF), ethyl acetate (EA), celite, acetone, HCl (35.0%–37.0% in deionized water), magnesium sulfate (MgSO4), and xylene were purchased from Samchun (Gyeonggi, Korea). Ethanol was purchased from Burdick & Jackson (MI, USA). Steareth-21, composed of polyethylene glycol ethers of stearic acid (PEG-100 stearate), was purchased from Clariant (Houston, TX). Divinyl dimethicone and silica silylate were obtained from Dow Corning (Seneffe, Belgium). Deionized water (DW) was prepared with an Ultra-Pure System (Romax, Hanam, Korea). Chloroform was purchased from J.T. Baker (Phillipsburg, NJ, USA).
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