Synthesis, structural characterization and biological activity of novel Knoevenagel condensates on DLD-1 human colon carcinoma. Issue 11 (1st June 2017)

• Record Type: Journal Article
• Authors: Rišiaňová, Lucia; Fischer-Fodor, Eva; Valentová, Jindra; Tatomir, Corina; Corina Decea, Nicoleta; Virag, Piroska; Pechová, Iveta; Devínsky, Ferdinand; Miklášová, Natalia
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 27:Issue 11(2017)
• Page Start: 2345
• Page End: 2349
• Publication Date: 2017-06-01
• Subjects: ABTS 2, 2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) -- DPPH di(phenyl)-(2, 4, 6-trinitrophenyl)iminoazanium -- MDR1 multidrug resistance gene 1 -- MRP1 multidrug resistance-associated protein 1 -- PBS Phosphate-buffered saline -- SOD superoxide dismutase -- GSH glutathione -- GSSG glutathione disulfide; Knoevenagel condensates -- Curcuminoids -- Antioxidant activity -- Cytotoxicity -- SOD-mimetic activity -- Multidrug resistance; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2017.04.031
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: Biologically active Knoevenagel condensates (1 –14 ) of diarylheptanoids: 1, 7-bis(3-methoxy-4-hydroxyphenyl)hepta-1, 7-diene-3, 5-dione and 1, 7-bis(3-ethoxy-4-hydroxyphenyl)hepta-1, 7-diene-3, 5-dione, were synthesized and structurally characterized. Compounds1 –14 exhibited cytotoxicity against colon carcinoma cells, and their antiproliferative effect was associated with a significant decrease of multidrug resistance proteins. One of the underlying mechanisms of these effects is the reduction of intracellular and extracellular SOD enzymes by compounds1, 12 and14, which render the tumor cells more vulnerable to oxidative stress.