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Spectroscopic characterization and efflux pump modulation of a thiophene curcumin derivative

2020; Elsevier BV; Volume: 1215; Linguagem: Inglês

10.1016/j.molstruc.2020.128291

1872-8014

Mauro Macêdo de Oliveira, Hélcio Silva dos Santos, Henrique Douglas Melo Coutinho, Paulo Nogueira Bandeira, Priscila T. da Silva, Thiago Sampaio de Freitas, Janaína Esmeraldo Rocha, Jayze da Cunha Xavier, Fábia F. Campina, Cristina Rodrigues dos Santos Barbosa, José Bezerra de Araújo Neto, Raimundo Luíz Silva Pereira, Maria Milene Costa da Silva, Débora Feitosa Muniz, Alexandre Magno Rodrigues Teixeira, Vanessa Moreira Frota, Tigressa Helena Soares Rodrigues, Ana M. Amado, M. Paula M. Marques, Luís A. E. Batista de Carvalho, C.E.S. Nogueira,

Synthesis and biological activity

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.