The four most prominent forms of biomass are cellulose, hemicellulose, lignin and chitin. In efforts to develop sustainable sources of platform molecules there has been an increasing focus on examining how these biopolymers could be exploited as feedstocks that support the chemical supply chain, including in the production of fine chemicals. Many different approaches are possible and some of the ones being developed in the authors’ laboratories are emphasised.
To exploit the interaction of the aryl hydrocarbon receptor (AhR) pathway in developing breast‐cancer‐specific cytotoxic compounds, we examined the breast cancer selectivity and the docking pose of the AhR ligands (Z)‐2‐(2‐aminophenyl)‐1H‐benzo[de]isoquinoline‐1,3(2H)‐dione (NAP‐6; 5) and 10‐chloro‐7H‐benzo[de]benzo[4,5]imidazo[2,1‐a]isoquinolin‐7‐one (10‐Cl‐BBQ; 6). While the breast cancer selectivity of 5 in vitro is known, we discuss the SAR around this lead and, by using phenotypic cell‐line screening and the MTT assay, show for the first time that 6 also presents with breast cancer selectivity, notably in the triple‐negative (TN) receptor breast cancer cell line MDA‐MB‐468, the ER+ breast cancer cell lines T47D, ZR‐75‐1 and the HER2+ breast cancer cell line SKBR3 (GI50 values of 0.098, 0.97, 0.13 and 0.21 μM, respectively). Indeed, 6 is 55 times more potent in MDA‐MB‐468 cells than normal MCF10A breast cells (GI50 of 0.098 vs 5.4 μM) and more than 130 times more potent than in cell lines derived from pancreas, brain and prostate (GI50 of 0.098 vs 10–13 μM). Molecular docking poses of 5 and 6 together with analogue synthesis and phenotypic screening show the importance of the naphthalene moiety, and an ortho‐disposed substituent on the N‐phenyl moiety for biological activity.
The bio-derived platform molecule levoglucosenone (LGO, 1), which is the precursor to the green solvent Cyrene® (2), has been converted, at multi-gram scale, into its pseudo-enantiomer (iso-LGO, 2) and then reduced to iso-Cyrene (4). A less effective synthesis of this last compound from D-glucose is also described. Various physicochemical as well as certain toxicological properties of compound 4 are reported and compared to those established for the now commercially available Cyrene® (2). Such studies reveal that there are significant enough differences in the properties of the sustainably-derived Cyrene® (2) and isomer 4 (iso-Cyrene) to suggest they will exert complementary effects as solvents in a range of settings.
It is a great challenge to develop polymeric materials possessing multiple functionalities for their intrinsic properties. In our efforts to overcome this dilemma, we report a carbon nanotube (CNT)-doped polymer architecture design in this paper using a soft matrix synthesized from methacrylic acid and poly(ethylene glycol) methacrylate via reversible addition− fragmentation chain-transfer polymerization and further functionalized by 1-pyrenemethanol and doped with hard, stiff CNTs as fillers. The CNTs were dispersed evenly into the pyrenefunctionalized copolymers obtained via the solution blending method. Our approach is simple, low-energy-consuming, facile in operation, and highly efficient. The developed composites demonstrate high mechanical strength, self-healing ability, and high electrical conductivity. To further maximize the potential of our CNT-filled composites, we introduced a simple but effective means to align CNTs by directional stretching at elevated temperatures and so achieved significant mechanical and electrical reinforcement. The multifunctional composites produced in this paper have desirable properties for future applications such as conductive bioskins, healthcare monitoring sensors, and other functional conductive electronics.
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