Sodium chloride (nacl)

2,2-diphenyl-1-picrylhydrazyl (DPPH), 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), ibuprofen, lidocaine hydrochloride, and caffeine were purchased from Sigma Aldrich (Poznań, Poland); disodium phosphate and potassium dihydrogen phosphate from Merck, Darmstadt (Germany); Biobase, beeswax were purchased from Mazidła.com (Poznań, Poland); grape seed oil was purchased from Monini (Spoleto, Italy); sodium acetate anhydrous, potassium persulfate, potassium acetate, xylene, 99.5% acetic acid, aluminium chloride, 36% hydrochloric acid, sodium chloride, potassium chloride, sodium sulphate anhydrous as well as propylene glycol, ethanol, and methanol were from Chempur (Piekary Śląskie, Poland), whereas acetonitrile for HPLC from J.T. Baker, (Landsmeer, The Netherlands). All reagents were of analytical grade.

The synthesis of N-(2-hydroxybenzyl)phenylalanine (PhAlaSal) has been described in [14] (link). Solutions of cobalt(II) nitrate hexahydrate and cobalt(II) perchlorate hexahydrate (Sigma-Aldrich, Saint Louis, USA) were titrated with EDTA disodium salt in the presence of murexide. Solutions of carbonate-free 0.1 M and 1.0 M NaOH, methanol and water (HPLC-grade) were purchased from J.T. Baker. The acid solutions from Sigma–Aldrich were standardized alkalimetrically and determined by the Gran method [38] (link). Potassium nitrate(V) (J.T. Baker) and sodium perchlorate monohydrate (Sigma-Aldrich) solutions were used to adjust the ionic medium. Tris-HCl (Sigma-Aldrich), sodium chloride (Chempur, Piekary Śląskie, Poland) and argon of high purity (Linde, Dublin, Irlandia) were used.

Racemic (E)-5-ethylidene-4-phenyldihydrofuran-2-one (2a), (E)-5-ethylidene-4-(4′ methylphenyl)dihydrofuran-2-one (2b), (E)-5-ethylidene-4-(4′-methoxyphenyl)dihydrofuran-2-one (2c) and (E)-4-(benzo[d][1,′3′]dioxol-5′-yl)-5-ethylidenedihydrofuran-2-one (2d) were synthesized previously by our research team from corresponding aromatic aldehydes [33 (link),34 (link)]. (+)-cis-(4S,5S,6R)-5-(1-Iodoethyl)-4-(4′-methylphenyl)dihydrofuran-2-one (1) was synthesized earlier from (+)-(2R,3E)-4-(4′-methylphenyl)but-3-en-2-ol [35 (link)]. 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, purity ≥ 98%) was purchased form Merck. Sodium chloride, anhydrous magnesium sulphate, hydrochloric acid (35–37%) and organic solvents used for the synthesis and extraction were purchased form Chempur. The chemicals used for the preparation of a growing media were purchased from BTL.

The captan standard was purchased from Dr. Ehrenstorfer (Augsburg, Germany). All reagents were of sufficiently high purity for GC analysis. Acetonitrile, acetone, and petroleum ether were purchased from Honeywell Specialty Chemicals Seelze GmbH (Seelze, Germany). Anhydrous magnesium sulphate, sodium chloride, and tri-sodium citrate dihydrate were from Chempur (Piekary Slaskie, Poland). Sodium citrate dibasic sesquihydrate was purchased from Sigma-Aldrich (Steinheim, Germany). As for the sorbents, PSA was purchased from Supelco (Bellefonte, PA, USA), Al₂O₃, ZrO₂, SiO₂ were from POCH (Gliwice, Poland) and Florisil^® was from Sigma-Aldrich (St. Louis, MO, USA).

1,2-Dimyristoyl-sn-glycero-3-phosphocholine (DMPC), N-(carbonyl-methoxypolyethylenglycol-2000)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine, and Na-salt (DSPE-PEG 2000) were purchased from Lipoid, Ludwigshafen, Germany. Baicalein was purchased from Haoxuan Biotech, Xi’an, China. Chloroform, methanol, and tert-butanol were purchased from Stanlab, Lublin, Poland. Sodium chloride, dimethylsulfoxide (DMSO), and ethylenediaminetetraacetic acid (EDTA) were purchased from ChemPur, Piekary Śląskie, Poland. Sepharose 4B CL, thiazolyl blue tetrazolium bromide, 2-(4-amidinophenyl)-6-indolecarbamidine dihydrochloride, and 4′,6-diamidino-2-phenylindole dihydrochloride (DAPI) were purchased from Merck, Darmstadt Germany. The DiL stain (1,1ʹ-dioctadecyl-3,3,3’,3’-tetramethylindocarbocyanine perchlorate) was purchased from Thermo Fisher, Waltham, USA. The RPMI-1640 and MEM-Alpha cell culture media were purchased from Lonza, Basil, Switzerland. Fetal bovine serum (FBS), GlutaMAX (L-alanyl-L-glutamine dipeptide in 0.85% NaCl), and 100× antibiotic-antimycotic were purchased from BioWest, Nuaillé, France. Carbon films were purchased from Lacey Formvar/Cu grids, SPI Supplies, West Chester, PA, USA. Agarose was purchased from Roth, Karlsruhe, Germany. The CellTiter-Glo 3D Viability Assay and RealTime-Glo Annexin V Apoptosis and Necrosis Assay were purchased from Promega, Madison, WI, USA.

4-Nitroquinoline N-oxide (NQNO), DMSO, l-histidine monochloride, yeast extract, levallorphan, NADP⁺, glucose-6-phosphate sodium salt, glucose-6-phosphate dehydrogenase, potassium hydroxide, DPPH, gallic acid, and ascorbic acid were purchased from Sigma-Aldrich (Seelze, Germany); Nutrient Broth No. 2, from Argenta (Poznań, Poland); glycerol and neomycin sulfate, from Pharma Cosmetic (Kraków, Poland); sodium sulfate, sodium chloride, d-glucose, and dipotassium hydrogen phosphate from Chempur (Piekary Śląskie, Poland); dichloromethane from Stanlab (Lublin, Poland); and agar-agar, bacto-peptone, beef extract, potato dextrose agar, and 0.2-mm silica-coated aluminum TLC plates from Merck (Darmstadt, Germany).

Medium-molecular-weight CS 80/50 (degree of deacetylation: 77.6–82.5%, viscosity of 1% solution in 1% acetic acid: 31–70 mPa·s, molecular weight: 80–200 kDa) was obtained from Heppe Medical CS GmbH (Haale, Germany). Low-methoxy amidated PC with low- (a type CF 010, degree of esterification 34%, degree of amidation 17%, pH 4.2 for 2.5% solution in distilled water at 20 °C) and high-calcium reactivity (a type CF 020, degree of esterification 31%, degree of amidation 19%, pH 4.1 for 2.5% solution in distilled water at 20 °C) were kindly gifted by Herbstreith & Fox and GmbH & Co. KG (Neuenbürg, Germany). Potassium dihydrogen phosphate, sodium chloride, calcium chloride dihydrate, and 85% lactic acid were purchased from Chempur (Piekary Śląskie, Poland). Glycerol was obtained from Fagron (Kraków, Poland).
SSS composed of Potassium dihydrogen phosphate (1.63 mg/mL), sodium chloride (2.32 mg/mL), and calcium chloride dihydrate (0.22 mg/mL) with pH 6.2 adjusted by disodium hydrogen phosphate addition (according to Nair et al. with modification [25 (link)]) was used for the research analyses.