Spectroscopic characterization and efflux pump modulation of a thiophene curcumin derivative

• Published in: Journal of molecular structure Vol. 1215; p. 128291
• Main Authors: Oliveira, Mauro M., Santos, Helcio S., Coutinho, Henrique D.M., Bandeira, Paulo N., da Silva, Priscila T., Freitas, Thiago S., Rocha, Janaina E., Xavier, Jayze C., Campina, Fabia F., Barbosa, Cristina R.S., Araújo Neto, José B., Pereira, Raimundo L.S., Silva, Maria M.C., Muniz, Débora F., Teixeira, Alexandre M.R., Frota, Vanessa M., Rodrigues, Tigressa H.S., Amado, Ana M., Marques, Maria P.M., Batista de Carvalho, Luis A.E., Nogueira, Carlos E.S.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05-09-2020
• Subjects: Chalcone; Curcumin; DFT; Docking; Efflux pump; Spectroscopy; Spectroscopy; Docking; Curcumin; DFT; Chalcone; Efflux pump
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2020.128291

Curcumin, along with its derivatives, form a large class of natural and synthetic compounds with notable biological activity. However, their highly reactive β-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.
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•A thiophene curcuminoid was synthetized.•Spectroscopic characterization and complete vibrational assignment is provided.•DFT calculations were done.•Efflux pump inhibition confirms modulatory antibacterial activity.•Docking calculations on NorA models were carried out.