The selective synthesis of biomass-derived 2,5-bis(aminomethyl)furan in 94.1% yield was achieved via enhancing the catalytic dehydration–hydrogenation of 2,5-diformylfuran dioxime.
The tandem reaction is a growing field to yield important advances toward green and sustainable chemistry. Herein, we report a bifunctional manganese oxide catalyst with an interface binding redox phase (α-MnO2) and a basic phase (NaxMnO2). The molar ratio of NaOH/Mn plays a great role in the formation of α-MnO2/NaxMnO2. The sodium cation is essential for the formation of a basic NaxMnO2 phase while the potassium cation promotes the formation of a redox-active α-MnO2 phase. The interface structure of α-MnO2/NaxMnO2 geometrically favors the ammoxidation–Pinner tandem reaction to synthesize imidates in a 58–96% yield from aldehydes. Thus a phase collaborative effect is observed. In the ammoxidation process, the redox cycle of MnIV/MnIII is involved and the lattice oxygen in the α-MnO2 phase acts as an active oxygen species. The O–H in methanol is activated and dissociated on the basic sites of NaxMnO2 to the adsorbed methoxyl species to facilitate the Pinner synthesis. This approach bypasses the conventional synthesis of imidates, which suffer from harsh reaction conditions and the requirement for multiple steps.
Pancreatic cancer (PC), known as the ″king of cancer," is a prevalent and aggressive form of malignant tumor affecting the digestive tract. Triptolide (TP), an epoxidized diterpenoid lactone extracted from Tripterygium wilfordii, shows promising antitumor activity. However, the systemic toxicity and poor water solubility of TP inhibit its clinical application. In this work, Lycium barbarum polysaccharide (LBP)-modified selenium nanoparticles (SeNPs), capable of reducing severe toxicity and enhancing solubility, have been designed, synthesized, and applied for the treatment of PC. In vitro release results revealed that TP showed an acid-dependent and sustained-release effect. In Pan02 cells, the IC50 values of TP and LBP-SeNPs@TP were 26.03 ± 2.82 ng/mL and 11.80 ± 2.64 ng/mL, respectively. Similarly, the IC50 values of TP and LBP-SeNPs@TP for L02 cells were 15.76 ± 0.58 ng/mL and 32.73 ± 2.61 ng/mL, suggesting enhanced antitumor efficacy along with reduced toxicity. Flow cytometry analysis demonstrated that LBP-SeNPs@TP exerted the most potent apoptotic effect, achieving an early apoptosis rate of 24.5% and a late apoptosis rate of 45.3%. Notably, the mitochondrial membrane potential was significantly reduced, while ROS production was increased in the LBP-SeNPs@TP group. LBP-SeNPs@TP could significantly inhibit tumor growth while minimizing toxicity. RT-qPCR analysis demonstrated that LBP-SeNPs@TP upregulated the mRNA expression of Bax, Cyt C, and Caspase-3, while downregulating Bcl-2 expression in vitro and in vivo. The immunohistochemical analysis of the tumor tissue further confirmed these results. Overall, LBP-SeNPs emerge as a promising platform for poorly soluble drugs, offering a potential therapeutic approach for pancreatic cancer.
30 March 2023 in European Journal of Medicinal Chemistry