Oleoyl chloride

Methanol, acetonitrile, methyl‐tert‐butyl ether (MTBE), dichloromethane, palmitoyl chloride, heptadecanoyl chloride, stearoyl chloride, oleoyl chloride, 4‐dimethylaminopyridine, ammonium hydrogen carbonate, ammonium formate, 2‐propanol, formic acid, and acetic acid were purchased from Sigma–Aldrich (St Louis, MO, USA), and pyridine was purchased from VWR (Radnor, PA, USA). Deionized water was obtained from a MilliQ Gradient A10 system (Millipore, Billerica, MA, USA).
1,2‐Di‐(9Z‐octadecenoyl)‐sn‐glycero‐3‐phosphoethanolamine‐N‐nonadecanoyl (PE 18:1/18:1‐N‐19:0) and 1,2‐dioleoyl‐sn‐glycero‐3‐phosphoethanolamine‐N‐arachidonoyl (ammonium salt) (PE 18:1/18:1‐N‐20:4) were purchased from Avanti Polar Lipids (Alabaster, AL, USA) and l‐α‐phosphatidylethanolamine from Larodan Fine Chemicals AB (Malmö, Sweden). Lipid standard stock solutions at concentrations of 1 mmol/L were prepared in chloroform/Methanol (1:1, v/v).

Micro fibrillated cellulose (MFC) slurry (Exilva F01V) with solid content of about 12 wt.% was purchased from Borregaard, Sarpsborg, Norway. Dimethylacetamide (DMAc) and tetrahydrofuran (THF) were purchased from Carl Roth (Karlsruhe, Germany). Oleoyl chloride (˃89%) and anhydrous pyridine were purchased from Sigma-Aldrich (St. Louis, MO, USA), while polybutadiene (PB), styrene butadiene rubber (SBR), treated distillate aromatic extract (TDAE oil), zinc oxide, stearic acid, nano silica (200 nm), Bis(triethoxysilylpropyl)disulfide (TESPD), N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD), sulfur, 2-mercaptobenzothiazole (MBT), diphenyl guanidine (DPG), and N-cyclohexyl-2-benzothiazylsulfenamide (CBS) were provided by Goodyear Tire and Rubber Company, Luxembourg.

Oleoyl
chloride, oleic,
and palmitic acids were purchased from Sigma. The standard 2′-deoxy
and 2′-O-methyl-ribonucleoside phosphoramidites,
reagents solutions, supports, and LCAA-CPG were purchased from Applied
Biosystems (PEBiosystems Hispania S.A., Spain) and Link Technologies
Ltd. (Lanarkshire, Scotland, UK). The rest of the chemicals were purchased
from Aldrich, Sigma, or Fluka (Sigma-Aldrich S.A., Spain), and used
without further purification. Anhydrous solvents and deuterated solvents
(CDCl₃ and MeOH-d₄) were obtained
from reputable sources and used as received. Thin-layer chromatography
(TLC) was carried out on aluminum-backed Silica-Gel 60 F₂₅₄ plates. The spots were visualized with UV light. Column chromatography
was performed using Silica Gel (60 Å, 230 × 400 mesh). Matrix
for MALDI-TOF experiments was composed of 2′,4′,6′-trihydroxyacetophenone
monohydrate (THAP, Aldrich) and ammonium citrate dibasic (Fluka).
Solvents for HPLC analysis were prepared using triethylammonium acetate
(TEAA) and acetonitrile (Merck) as a mobile phase. The desalted columns
with Sephadex G-25 (NAP-10 or NAP-5) were from GE Healthcare (Little
Chalfont, UK). The rest of the chemicals were analytical reagent grade
from commercial sources as specified. Ultrapure water (Millipore)
was used in all experiments.

Oxa and Cur were purchased from Merck Company (Darmstadt, Germany, 95% purity). For the stock solution preparation of Oxa, DMF and mQ water (1:5, v/v) was used as solvent while for Cur stock preparation, ethanol and DMSO was taken as solvent. For dendrosome preparation, PEG400, oleoyl chloride, triethylamine, and chloroform were procured from Sigma-Aldrich Company. The preparation of dendrosome and DNC was as per the previous reports [19 , 47 (link)–53 (link)].