Spectroscopic characterization and efflux pump modulation of a thiophene curcumin derivative

Curcumin, along with its derivatives, form a large class of natural and synthetic compounds with notable biological activity. However, their highly reactive beta-diketone moiety renders this type of compounds unstable at pH above 6.5. The substitution of this group for a mono-carbonyl solves this problem, while improving antibacterial and anti-inflammatory activities. A thiophene curcuminoid, (1E,4E)-1,5-Di(thiophen-2-yl)penta-1,4-dien-3-one (DB Thiophene), has been synthesised and its molecular and spectroscopic characterization is reported, as well as a complete vibrational assignment. An efflux pump inhibition assay determined that DB Thiophene exhibits a remarkable NorA and MepA efflux pump inhibition activity. Molecular docking studies were carried out in order to understand this inhibition mechanism. (C) 2020 Elsevier B.V. All rights reserved.