γ cyclodextrin

γ-Cyclodextrin (γ-CD), succinic anhydride (SA), dimethylsulfoxide (DMSO), N,N’-dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP), 3-(diethylamino)propylamine (DEAP), hydroxysuccinimide (NHS), triethylamine (TEA), sodium tetraborate, adipic acid dihydrazide (ADH), N-phenylacetic acid (PA), methanol (MeOH), triiron dodecacarbonyl (FeCO), acetonitrile (HPLC grade), deionized water (HPLC grade), sodium azide, tween 80, hemoglobin (Hb), sodium dithionite, 4′,6-diamidino-2-phenylindole dihydrochloride (DAPI), and formaldehyde were purchased from Sigma-Aldrich (St. Louis, MO, USA). Sodium hyaluronate (HA, M_w = 4.8 kDa) was purchased from Lifecore Biomedical Inc. (Chaska, MN, USA). Paclitaxel (PTX) was purchased from Samyang Biopharm (Seoul, Republic of Korea). RPMI-1640, fetal bovine serum (FBS), penicillin, streptomycin, trypsin, and ethylene diamine tetra-acetic acid (EDTA) were purchased from Welgene Inc. (Seoul, Republic of Korea). Chlorin e6 (Ce6) was purchased from Frontier Scientific Inc. (Logan, UT, USA). Wheat Germ Agglutinin Alexa Fluor^® 488 conjugate (WGA-Alexa Fluor^® 488) was purchased from Life Technologies (Carlsbad, CA, USA). Cell Counting Kit-8 (CCK-8) was purchased from Dojindo Molecular Technologies Inc. (Rockville, MD, USA).

γ-cyclodextrin (>90% purity), Methanol (HPLC-grade, >99.9% purity), and curcumin (from Curcuma longa (turmeric), powder, >65% purity) were purchased from Sigma-Aldrich (Steinheim, Germany). Potassium hydroxide (pellets, ACS reagent, >85% purity) was purchased from Fisher Scientific (Loughborough, UK). Absolute ethanol (HPLC-grade, >99.8%) was purchased from VWR Chemicals (Paris, France). Pure deionised water (with a resistivity of not less than 18.4 MΩ cm) was used in all experiments from a Milli-Q IQ 7000 system (Merck Millipore, Darmstadt, Germany).

The thermophilic fungus T. leycettanus JCM12802 was purchased from the Japan Collection of Microorganisms RIKEN BioResource Center (Tsukuba, Japan) and was maintained at 4 ℃ on a potato dextrose agar plate. Soluble starch, amylose, glycogen, α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin were purchased from Sigma-Aldrich. All other chemicals were of analytical grade and commercially available.

ScaleS0 [20% (w/v) sorbitol, 5% (w/v) glycerol, 1 mM methyl-β-cyclodextrin (Sigma-Aldrich Inc., St. Louis, MO, United States), 1 mM γ-cyclodextrin (Sigma-Aldrich Inc., St. Louis, MO, United States), 1% (w/v) N-acetyl-L-hydroxyproline (Sigma-Aldrich Inc., St. Louis, MO, United States), 3% (v/v) DMSO (Sigma-Aldrich Inc., St. Louis, MO, United States) in 0.1 M PBS], ScaleS1 [20% (w/v) sorbitol, 5% (w/v) glycerol, 4 M urea, and 0.2% (w/v) Triton X-100 in dH₂O], ScaleS2 [27% (w/v) sorbitol, 2.7 M urea, 0.1% (w/v) Triton X-100, and 8.3% (v/v) DMSO in dH₂O], ScaleS3 [36.4% (w/v) sorbitol, 2.7 M urea, and 9.1% (v/v) DMSO in dH₂O], ScaleS4 [40% (w/v) sorbitol, 10% (w/v) glycerol, 4 M urea, 0.2% (w/v) Triton X-100, and 20% (v/v) DMSO in dH₂O] was prepared. After fixation in 4% PFA, samples were sequentially incubated in ScaleS0, ScaleS1, ScaleS2, and ScaleS3 at 37°C for each 3 h. Then samples were washed with 0.1 M PBS at 4°C for 30 min. After that, sample were incubated for 3 h at 37°C with ScaleS4.

Oleanolic acid (OA, purity of 97%) was supplied by Natac Biotech SL (Alcorcón, Madrid, Spain). Poloxamer 188, Poloxamer 407, β-Cyclodextrin sulphated sodium salt, Heptakis (2,3,6-tri-O-methyl)-β-Cyclodextrin (TRIMEB), γ-Cyclodextrin, sodium dodecyl sulfate (SDS), and HPLC-grade solvents were obtained from Sigma Aldrich (Saint Louis, MO, USA) with the support of Sigma Aldrich Italia (Milan, Italy). Soluplus^® was provided by BASF (Ludwigshafen, Germany) with the support of BASF Italia, BTC Chemical Distribution Unit (Cesano Maderno, Monza e Brianza, Italy). PEG 4000 was purchased from Merck (Milano, Italy) and PEG 6000 from Galeno (Comeana, Prato, Italy). Distilled water was obtained from a Simplicity^®UV Water Purification System, Merck Millipore (Darmstadt, Germany).

Butamben (BTB) (butyl-4-aminobenzoate), cholesterol (CH), l-α-phosphatidylcholine from egg yolk (PC), α-Cyclodextrin (αCD), γ-Cyclodextrin (γCD), stearylamine (SA) and sodium cholate (SC) were from Sigma-Aldrich (Milan, Italy). β-Cyclodextrin (βCD) and hydroxypropyl-β-Cyclodextrin (HPβCD), with an average substitution degree per anhydroglucose unit of 0.6), were kindly provided by Roquette (Lille, France). Hydroxypropyl-α-Cyclodextrin (HPαCD) (MS 0.6) and randomly methylated β-Cyclodextrin (RAMEB), (MS 1.8) were donated by Wacker Chemie GmbH (München, Germany). Sulfobutylether-β-Cyclodextrin (SBEβCD) (Captisol) was given as a kind gift from CyDex Inc. (Dallas, TX, USA). Carbopol^® 940 (polyacrylic acid) was kindly provided by Noveon, Inc. (Cleveland, OH, USA). All other chemicals were of analytical reagent quality.