Abstract
Allylated biphenol neolignans contain a variety of chemopreventive entities that have been used as anti-tumor drug leads. Herein, 37 allylated biphenols were evaluated for anti-proliferative activity by the MTT assay and inhibitory effect on the migration and tube formation of HUVECs featuring anti-angiogenic properties. 3-(2-Methylbut-3-en-2-yl)-3′,5′-bis(trifluoromethyl)-[1,1′-biphenyl]-4-ol (5c) exerted an inhibitory effect on HUVECs compared to honokiol (IC50 = 47.0 vs. 52.6 μM) and showed significant blocking effects on the proliferation of C26, Hela, K562, A549, and HepG2 (IC50 = 15.0, 25.0, 21.2, 29.5, and 13.0 μM, respectively), superior to those of honokiol (IC50 = 65.1, 62.0, 42.0, 75.0, and 55.4 μM, respectively). Importantly, compound 5c inhibited the migration and capillary-like tube formation of HUVECs in vitro.
Highlights
Angiogenesis is a complicated multistep process involving endothelial cell (EC) activation, invasion, migration, proliferation, tube formation, and capillary network formation in several solid tumors and haematological malignancies [1]
By a convenient procedure starting from commercially available p-bromophenol and employing 1.1 equiv of allyl bromide in the presence of anhydrous K2CO3 (1.3 equiv) as base and acetone as solvent
Two cross-coupling methods were developed for the condensation of appropriate arylboronic acids with 2 under palladium catalysis under a N2 atmosphere
Summary
Angiogenesis is a complicated multistep process involving endothelial cell (EC) activation, invasion, migration, proliferation, tube formation, and capillary network formation in several solid tumors and haematological malignancies [1]. Tumor growth depends on the recruitment of new blood vessels from pre-existing vasculature. Without the development and progression of new blood vessels, tumors cannot deteriorate beyond a critical size or metastasize to other organs [2,3,4]. Endothelial cells play crucial roles in a series of physiological processes (e.g., wound healing, reproduction, and embryonic development) and pathophysiological events (e.g., solid tumor growth, psoriasis, and diabetic retinopathy). When tumor cells secrete pro-angiogenic growth factors that bind to receptors on dormant ECs, leading to ECs activation, stimulation, vasodilatation and an up-regulation of vessel permeability, the activated ECs rapidly detach from the extracellular matrix and basement membrane by secreting proteases (matrix metalloproteinases)
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