Singlet molecular oxygen trapping by the fluorescent probe diethyl-3,3′-(9,10-anthracenediyl)bisacrylate synthesized by the Heck reaction

• Published in: Photochemical & photobiological sciences Vol. 10; no. 10; pp. 1546 - 1555
• Main Authors: Oliveira, Marilene S., Severino, Divinomar, Prado, Fernanda M., Angeli, José Pedro F., Motta, Flávia D., Baptista, Maurício S., Medeiros, Marisa H. G., Di Mascio, Paolo
• Format: Journal Article
• Language: English
• Published: Cham Springer International Publishing 01.10.2011
• Subjects: Acrylates - chemical synthesis; Acrylates - chemistry; Animals; Anthracenes - chemical synthesis; Anthracenes - chemistry; Biochemistry; Biomaterials; Cell Line; Chemistry; Chromatography, High Pressure Liquid; Cricetinae; Fluorescent Dyes - chemistry; Kinetics; Microscopy, Fluorescence; Peroxides - chemical synthesis; Peroxides - chemistry; Physical Chemistry; Plant Sciences; Polycyclic Aromatic Hydrocarbons - chemistry; Singlet Oxygen - chemistry; Tandem Mass Spectrometry
• ISSN: 1474-905X; 1474-9092
• DOI: 10.1039/c1pp05120b

Singlet molecular oxygen O 2 ( 1 Δ g ) is a potent oxidant that can react with different biomolecules, including DNA, lipids and proteins. Many polycyclic aromatic hydrocarbons have been studied as O 2 ( 1 Δ g ) chemical traps. Nevertheless, a suitable modification in the polycyclic aromatic ring must be made to increase the yield of O 2 ( 1 Δ g ) chemical trapping. With this goal, an anthracene derivative, diethyl-3,3′-(9,10-anthracenediyl)bisacrylate (DADB), was obtained from the reaction of 9,10-dibromoanthracene and ethyl acrylate through the Heck coupling reaction. The coupling of ethyl acrylate with the anthracene ring produced a new lipophilic, esterified, fluorescent probe reactive toward O 2 ( 1 Δ g ). This compound reacts with O 2 ( 1 Δ g ) at a rate of k r = 1.69 × 10 6 M −1 s −1 forming a stable endoperoxide (DADBO 2 ), which was characterized by UV-Vis, fluorescence, HPLC/MS and 1 H and 13 C NMR techniques. The photophysical, photochemical and thermostability features of DADB were also evaluated. Furthermore, this compound has the potential for great application in biological systems because it is easily synthetized in large amount and generates specific endoperoxide (DADBO 2 ), which can be easily detected by HPLC tandem mass spectrometry (HPLC/MS/MS).