- An enantioselective fluorescence sensing assay for quantitative analysis of chiral carboxylic acids and amino acid derivatives
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A chiral 1,8-diacridylnaphthalene-derived fluorosensor exhibiting a C 2-symmetric cleft designed for stereoselective interactions with hydrogen bond donors has been used for the determination of both concentration and enantiomeric composition of carboxylic acids and amino acid derivatives. The Royal Society of Chemistry 2006.
- Wolf, Christian,Liu, Shuanglong,Reinhardt, Brian C.
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- Development of LM98, a Small-Molecule TEAD Inhibitor Derived from Flufenamic Acid
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The YAP-TEAD transcriptional complex is responsible for the expression of genes that regulate cancer cell growth and proliferation. Dysregulation of the Hippo pathway due to overexpression of TEAD has been reported in a wide range of cancers. Inhibition of TEAD represses the expression of associated genes, demonstrating the value of this transcription factor for the development of novel anti-cancer therapies. We report herein the design, synthesis and biological evaluation of LM98, a flufenamic acid analogue. LM98 shows strong affinity to TEAD, inhibits its autopalmitoylation and reduces the YAP-TEAD transcriptional activity. Binding of LM98 to TEAD was supported by 19F-NMR studies while co-crystallization experiments confirmed that LM98 is anchored within the palmitic acid pocket of TEAD. LM98 reduces the expression of CTGF and Cyr61, inhibits MDA-MB-231 breast cancer cell migration and arrests cell cycling in the S phase during cell division.
- Mélin, Léa,Abdullayev, Shuay,Fnaiche, Ahmed,Vu, Victoria,González Suárez, Narjara,Zeng, Hong,Szewczyk, Magdalena M.,Li, Fengling,Senisterra, Guillermo,Allali-Hassani, Abdellah,Chau, Irene,Dong, Aiping,Woo, Simon,Annabi, Borhane,Halabelian, Levon,LaPlante, Steven R.,Vedadi, Masoud,Barsyte-Lovejoy, Dalia,Santhakumar, Vijayaratnam,Gagnon, Alexandre
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p. 2982 - 3002
(2021/08/03)
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- Regioselective copper-catalyzed amination of chlorobenzoic acids: Synthesis and solid-state structures of N-aryl anthranilic acid derivatives
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A chemo- and regioselective copper-catalyzed cross-coupling reaction for effective amination of 2-chlorobenzoic acids with aniline derivatives has been developed. The method eliminates the need for acid protection and produces a wide range of N-aryl anthranilic acid derivatives in up to 99% yield. The amination was found to proceed with both electron-rich and electron-deficient aryl chlorides and anilines and also utilizes sterically hindered anilines such as 2,6-dimethylaniline and 2-tert-butylaniline. The conformational isomerism of appropriately substituted N-aryl anthranilic acids has been investigated in the solid state. Crystallographic analysis of seven anthranilic acid derivatives showed formation of two distinct supramolecular architectures exhibiting trans-anti and unprecedented trans-syn dimeric structures.
- Mei, Xuefeng,August, Adam T.,Wolf, Christian
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p. 142 - 149
(2007/10/03)
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