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5 protocols using sulfur trioxide pyridine complex

1

In Vitro Licochalcone A Metabolism

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Licochalcone A (E-97%, Z-3% by NMR, Electronic Supplemental Material S1) and β-nicotinamide adenine dinucleotide phosphate, reduced sodium salt (NADPH), uridine 5’-diphosphoglucuronic acid triammonium salt (UDPGA), sulfatase, β-glucuronidase, sulfur trioxide-pyridine complex, and glutathione (GSH) were purchased from Sigma-Aldrich (St. Louis, MO). Pooled human liver microsomes (20 mg/mL, 150 men and women donors), cDNA-expressed human cytochrome P450 1A2, CYP2A6, CYP2B6, CYP2C8, CYP2C9, CYP2C18, CYP2C19, CYP2D6, CYP2E1, and CYP3A4 (0.5 nmol of P450 in 0.5 mL) and cDNA-expressed recombinant human UGTs including UGT1A1, UGT1A3, UGT1A4, UGT1A6, UGT1A7, UGT1A8, UGT1A9, UGT1A10, UGT2B4, UGT2B7, UGT2B15, and UGT2B17 (5 mg protein/mL), were purchased from Corning Life Sciences (Tewksbury, MA). HPLC-grade solvents were purchased from Thermo Fisher (Pittsburgh, PA). Cryopreserved human hepatocytes (50 donors pooled) and manufacturer-specified cell culture media were purchased from Thermo Fisher (Waltham, MA).
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2

Quantitative Analysis of Deterenol Acetate

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Iodomethane (purum), potassium carbonate (p.a.), IPNS (Deterenol acetate), 3‐chloroperbenzoic acid (<77%), acetone, lithium aluminium hydride (powder, 95%), potassium carbonate (>99%), sulfur trioxide pyridine complex (97%), and octopamine hydrochloride (analytical standard) were obtained from Sigma‐Aldrich (Deisendorf, Germany), acetonitrile, formic acid, and ammonium acetate (all analytical grade) were purchased from Merck (Darmstadt, Germany), and solid‐phase extraction cartridges (OASIS HLB, 3 mL, 60 mg sorbent) were obtained from Waters (Eschborn, Germany). The internal standard IPNS‐d7 (deterenol‐d7) was provided by LGC Standards GmbH (Wesel, Germany).
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3

Synthesis and Purification of Sulfated Polymers

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Glycidol (96%) and ε-caprolactone (99%) were purchased from Acros Organics, (Morris Plains, NJ, USA) and were distilled prior to their use. Tin (II)-2-ethylhexanoate (Sn(Oct)2) and sulfur trioxide pyridine complex were purchased from Sigma-Aldrich (Hamburg, Germany). Tofacitinib citrate was purchased from Medchemexpress (Monmouth Junction, NJ, USA). Sunitinib was purchased from Selleckchem (Houston, TX, USA). A PD-10 SephadexTM G-25 Desalting Column was purchased from GE Healthcare (Stockholm, Sweden). For the purification of the polymer before sulfation, tangential flow filtration (TFF) was used with a 30 kDa molecular weight cut-off (MWCO) regenerated cellulose cassette (Merck, Darmstadt, Germany) in a cassette holder (Sartorius, Göttingen, Germany). A peristaltic pump (Gibson, Nashville, TN, USA) was used to circulate the solution into the system. Benzoylated cellulose dialysis membrane (Sigma-Aldrich, Hamburg, Germany, MWCO = 2 kDa) was used to purify the sulfated polymer.
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4

Chitosan-Curdlan Adjuvant for Vaccine Delivery

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Chitosan (molecular weight [MW] 100 kDa, .90% degree of deacetylation) was obtained from Haidebei Marine Bioengineering (Jinan, China). Curdlan (MW 100 kDa) was supplied by Zhongke Biotechnology (Weifang, China). Ova, glycidyl trimethylammonium chloride (GTMAC), and a sulfur trioxide–pyridine complex were purchased from Sigma-Aldrich (St Louis, MO, USA). Alhydrogel adjuvant 2% (aluminum hydroxide gel) was obtained from InvivoGen (San Diego, CA, USA). MTT and fluorescein isothiocyanate (FITC) were obtained from Solarbio Bioscience and Technology (Shanghai, China). Neutral red was supplied by Sangon (Shanghai, China). Goat antimouse HRP-conjugated IgG, IgG1, IgG2a, and IgA were purchased from Abcam (Cambridge, UK). IFNγ and IL4 enzyme-linked immunosorbent assay (ELISA) kits were supplied by Bio-Swamp (Wuhan, China). Antimouse FITC-CD3, APC-CD4, FITC-CD4, PE-CD8a, PE-CD69, PE-F4/80, PE-CD11c, FITC-CD40, FITC-CD86, and FITC–major histocompatibility complex (MHC)-II were purchased from Thermo Fisher Scientific (Waltham, MA, USA). All other chemicals used were of analytical grade.
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5

Hyaluronic Acid-based Thermoresponsive Hydrogel

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Hyaluronic acid sodium salt with weight-average molecular weight of ∼1100 ​kDa was supplied from Kewpie (Tokyo, Japan) in a form of dry powder. 1-ethyl-3-(3-dimethyl aminopropyl) carbodiimide hydrochloride (EDC), N,N-dimethylformamide (DMF), sulfur trioxide-DMF complex, and sulfur trioxide pyridine complex were purchased from Sigma-Aldrich (St. Louis, MO, USA). N-hydroxysuccinimide (NHS) and N-isopropylacrylamide (NIPAAm) were supplied by Acros Organics (Geel, Belgium). Before use, NIPAAm was purified by recrystallization from n-hexane. 2,2′-azobisisobutyronitrile (AIBN) was obtained from Otsuka Chemical (Tokyo, Japan). 2-aminoethanethiol hydrochloride (AESH) was purchased from Tokyo Chemical Industry (Tokyo, Japan). Phosphate-buffered saline (PBS, pH 7.4) was obtained from Biochrom (Berlin, Germany). Eagle's Minimum Essential Medium (MEM) was provided by Gibco-BRL (Grand Island, NY, USA). Fetal bovine serum (FBS) was acquired from Biological Industries (Kibbutz Beit Haemek, Israel). All the other chemicals were of reagent grade and used as received.
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