A silver-coated copper wire as inexpensive drug eluting stent model: determination of the relative releasing properties of leoligin and derivatives

Investigation of Leoligin Derivatives as NF-κΒ Inhibitory Agents

“…Nuclear magnetic resonance spectroscopy (NMR) spectra were recorded from CDCl 3 or DMSO-d6 solutions on a Bruker AC 200 (200 MHz proton resonance frequency) or a Bruker Advanced UltraShield (400 MHz) spectrometer (as indicated individually) from Bruker Daltonik GmbH, Bremen, Germany, and chemical shifts are reported in ascending order in ppm relative to the nominal residual solvent signals, i.e., 1H: δ = 2.50 ppm (DMSO-d6); 13C: δ = 77.16 ppm (CDCl 3 ), δ = 39.52 ppm (DMSO-d6) [ 5 , 6 ]. For all 1H spectra in CDCl 3 , however, shifts are reported relative to tetramethyl silane (TMS) as an internal standard (δ = 0 ppm) due to the interference of aromatic signals of many samples with the residual solvent signal of CDCl 3 .…”

“…In the context of a multi-disciplinary project on the synthesis of furan-type lignans with anti-inflammatory activity, several leoligin analogs were synthesized in our group and subjected to cell-based assays, which led to analogs that selectively inhibited VSMC (vascular smooth muscle cell) versus EC (endothelial cell) proliferation, which is advantageous in the treatment of vascular neointima formation [ 5 ]. Based on this finding and taking into account that drug-eluting stents releasing immunosuppressant drugs are able to reduce local VSMC proliferation, leoligin and derivatives thereof were exploited in drug-releasing experiments using an inexpensive stent model, aiming to determine their relative releasing properties [ 6 ]. Additionally, particular emphasis has been put on 5-methoxyleoligin, an interesting lignan that induces CYP26B1-dependent angiogenesis in vitro, and arteriogenesis in vivo, which are important benefits for post-myocardial infarction therapy [ 7 ].…”

“…It is therefore interesting to investigate how modifications to the parent leoligin motif would impact this activity. Within a previous study, we studied leoligin and a small set of leoligin analogs to identify structural features [ 4 , 5 , 6 , 13 ], that can improve either NF-κB inhibition or inhibition of the proliferation of VSMCs [ 5 ]. The present contribution is dedicated to reveal the structure–activity relationships of leoligin-like lignans affecting NF-κB.…”