40274-67-7Relevant academic research and scientific papers
Inhibitory activities of anthraquinone and xanthone derivatives against transthyretin amyloidogenesis
Kitakami, Ryota,Inui, Kishin,Nakagawa, Yusuke,Sawai, Yurika,Katayama, Wakana,Yokoyama, Takeshi,Okada, Takuya,Kanamitsu, Kayoko,Nakagawa, Shinsaku,Toyooka, Naoki,Mizuguchi, Mineyuki
, (2021/07/06)
Transthyretin is a tetrameric protein which functions as a transporter of thyroxine and retinol-binding protein. Misfolding and amyloid aggregation of transthyretin are known to cause wild-type and hereditary transthyretin amyloidosis. Stabilization of the transthyretin tetramer by low molecular weight compounds is an efficacious strategy to inhibit the aggregation pathway in the amyloidosis. Here, we investigated the inhibitory activities of anthraquinone and xanthone derivatives against amyloid aggregation, and found that xanthone-2-carboxylic acid with one chlorine or methyl group has strong inhibitory activity comparable with that of diflunisal, which is one of the best known stabilizers of transthyretin. X-ray crystallographic structures of transthyretin in complex with the compounds revealed that the introduction of chlorine, which is buried in a hydrophobic region, is important for the strong inhibitory effect of the stabilizer against amyloidogenesis. An in vitro absorption, distribution, metabolism and elimination (ADME) study and in vivo pharmacokinetic study demonstrated that the compounds have drug-like features, suggesting that they have potential as therapeutic agents to stabilize transthyretin.
The Photodynamic Covalent Bond: Sensitized Alkoxyamines as a Tool to Shift Reaction Networks Out-of-Equilibrium Using Light Energy
Herder, Martin,Lehn, Jean-Marie
, p. 7647 - 7657 (2018/06/26)
We implement sensitized alkoxyamines as "photodynamic covalent bonds" - bonds that, while being stable in the dark at ambient temperatures, upon photoexcitation efficiently dissociate and recombine to the bound state in a fast thermal reaction. This type of bond allows for the photochemically induced exchange of molecular building blocks and resulting constitutional variation within dynamic reaction networks. To this end, alkoxyamines are coupled to a xanthone unit as triplet sensitizer enabling their reversible photodissociation into two radical species. By studying the photochemical properties of three generations of sensitized alkoxyamines it became clear that the nature and efficiency of triplet energy transfer from the sensitizer to the alkoxyamine bond as well as the reversibility of photodissociation crucially depends on the structure of the nitroxide terminus. By employing the thus designed photodynamic covalent bonding motif, we demonstrate how to use light energy to shift a dynamic covalent reaction network away from its thermodynamic minimum into a photostationary state. The network could be repeatedly switched between its minimum and kinetically trapped out-of-equilibrium state by thermal scrambling and selective photoactivation of sensitized alkoxyamines, respectively.
Highly efficient and regiospecific photocyclization of 2,2′-diacyl bixanthenylidenes
Mao, Mao,Wu, Qing-Qing,Ren, Ming-Guang,Song, Qin-Hua
, p. 3165 - 3169 (2011/05/12)
In contrast to the reversible photochemistry of the 2,2′-substituted bixanthenylidenes (1a-f), the photocyclization of 2,2′-diacyl bixanthenylidenes (1g-j) reveals an irreversible process where the initial cyclic intermediate C(E) can undergo a rapid [1,1
Photoinduced signal amplification through controlled externally sensitized fragmentation in masked sensitizers
Kottani, Rudresha,Majjigapu, Janaki R. R.,Kurchan, Alexei,Majjigapu, Kavitha,Gustafson, Tiffany P.,Kutateladze, Andrei G.
, p. 14794 - 14795 (2008/02/04)
Addition of lithiated dithianes to diaryl ketones, potential electron-transfer sensitizers, disrupts conjugation between the two aromatic moieties, effectively masking the sensitizer. A novel photoamplification strategy is developed based on photosensitiz
Substituted xanthones as antimycobacterial agents*, part 1: Synthesis and assignment of 1H/13C NMR chemical shifts
Pickert, Martina,Frahm, August Wilhelm
, p. 177 - 192 (2007/10/03)
A series of substituted xanthones was synthesized in order to prove the hypothesis that electron-withdrawing substituents enhance the antimycobacterial activity of these compounds, which is described by means of a QSAR equation with 13C NMR che
