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Sultana, Nazmun, Chandan Guria, and Vinod K. Saxena. Chemical Engineering Research and Design 190 (2023): 536-549.
This study investigates a renewable route for synthesizing AA-type monomers-adipic and azelaic acid-from linoleic acid (LA) through bromide-promoted catalytic oxidation. The liquid-phase oxidation was carried out in a stainless-steel autoclave using cobalt(II) acetate and manganese(II) acetate as catalysts, hydrogen bromide (HBr) as a co-catalyst, and acetic acid (AcA) as the reaction medium. The system operated under mild conditions (393-423 K, 5.8-8.8 bar) with compressed air as the oxidant.
The reactants-LA (5-20 wt%), catalysts, and HBr-were fully dissolved in AcA and charged into the reactor. The exothermic nature of the reaction was controlled by an internal cooling coil and external condenser. Constant mixing at 1000 rpm and regulated air feed through a pressure control valve ensured stable reaction conditions. The oxidation process yielded malonic acid, azelaic acid, and adipic acid at early reaction stages (<5 h), with malonic acid later decomposing to CO₂.
Product yields and LA conversion were strongly influenced by catalyst and co-catalyst loadings, temperature, and pressure. Optimal conditions favored selective formation of azelaic and adipic acids. Kinetic analysis revealed that the reaction is film-diffusion controlled, with Hatta numbers and enhancement factors indicating oxygen diffusion and reaction at the gas-liquid interface as the rate-limiting step.
This work provides a green and efficient pathway to produce industrially relevant dicarboxylic acids from linoleic acid, contributing to sustainable polymer precursor synthesis.
Yuan, Haoyang, et al. Journal of Controlled Release 382 (2025): 113744.
This study highlights the novel application of linoleic acid (LA) as a cell membrane fluidity regulator to enhance the oral absorption of nanocarrier-based therapeutics. Specifically, LA was used to modulate epithelial barrier properties, thereby facilitating the uptake and trans-epithelial transport of exenatide (EXT)-loaded hydroxyethyl starch nanocapsules (HES NCs) dual-functionalized with butyrate and octadecylamine (Bu-PEG-ODA NCs).
Pretreatment with LA significantly increased cell membrane fluidity and upregulated monocarboxylate transporter 1 (MCT1) expression by 3.26-fold in intestinal epithelial cells. As a result, the cellular uptake of Bu-PEG-ODA NCs was enhanced by 4.52-fold, while the energy requirement for endocytosis dropped to just 18.64% of that observed in untreated Caco-2 cells. Furthermore, LA treatment improved transcellular transport by 1.72-fold in a Caco-2/HT29-MTX-E12 co-culture model.
in vivo, co-administration of LA with Bu-PEG-ODA NCs significantly improved the oral bioavailability of EXT from 10.10% to 14.84%, leading to greater glycemic control and pancreatic function recovery in a type 2 diabetic rat model. This study establishes the first report of enhancing nanocarrier oral absorption by targeting the energy cost of endocytosis through LA-mediated membrane fluidization.
These findings underscore linoleic acid's potential as a powerful bioenhancer in nanomedicine, particularly for improving the efficacy of orally administered peptide drugs by overcoming epithelial absorption barriers.
Yu, Xiaoming, et al. Biomedicine & Pharmacotherapy 176 (2024): 116798.
This study demonstrates the successful application of linoleic acid in the synthesis of amphiphilic hydroxyethyl starch (LHES) polymers for the formulation of anticancer nanoparticles. Linoleic acid was grafted onto hydroxyethyl starch via DCC/DAMP-mediated esterification in DMSO, yielding a series of LHES carriers with varying degrees of substitution. These carriers were then employed to fabricate LHES-B nanoparticles by encapsulating a linoleic acid-modified berberine derivative (L-BBR), forming a nanoplatform with high drug loading efficiency (29%) and pH-responsive release behavior.
The LHES-B nanoparticles exhibited rapid L-BBR release under acidic conditions (pH 4.5), simulating the tumor microenvironment. in vitro studies showed significantly enhanced cytotoxicity against HepG2 hepatocellular carcinoma cells compared to free L-BBR, indicating improved cellular uptake and drug delivery efficiency. Furthermore, in vivo efficacy was demonstrated using a transgenic zebrafish model expressing the krasv12 oncogene, where LHES-B nanoparticles markedly suppressed oncogene expression.
This linoleic acid-based drug delivery system not only improves berberine's solubility and tumor-targeted release but also enhances its antitumor potency. These results highlight linoleic acid's critical role as a hydrophobic modifier in constructing amphiphilic nanocarriers, offering a promising strategy for developing potent, biocompatible anticancer therapeutics. The LHES-B nanoparticles thus represent a significant advancement in linoleic acid-mediated nanomedicine design for targeted cancer therapy.
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