99833-19-9Relevant academic research and scientific papers
Development of photoswitchable inhibitors for β-galactosidase
Rustler, Karin,Mickert, Matthias J.,Nazet, Julian,Merkl, Rainer,Gorris, Hans H.,K?nig, Burkhard
, p. 7430 - 7437 (2018)
Azobenzenes are of particular interest as a photochromic scaffold for biological applications because of their high fatigue resistance, their large geometrical change between extended (trans) and bent (cis) isomer, and their diverse synthetic accessibility. Despite their wide-spread use, there is no reported photochromic inhibitor of the well-investigated enzyme β-galactosidase, which plays an important role for biochemistry and single molecule studies. Herein, we report the synthesis of photochromic competitive β-galactosidase inhibitors based on the molecular structure of 2-phenylethyl β-d-thiogalactoside (PETG) and 1-amino-1-deoxy-β-d-galactose (β-d-galactosylamine). The thermally highly stable PETG-based azobenzenes show excellent photochromic properties in polar solvents and moderate to high photostationary states (PSS). The optimized compound 37 is a strong competitive inhibitior of β-galactosidase from Escherichia coli and its inhibition constant (Ki) changes between 60 nM and 290 nM upon irradiation with light. Additional docking experiments supported the observed structure-activity relationship.
Electrosynthesis of Azobenzenes Directly from Nitrobenzenes
Ma, Yanfeng,Wu, Shanghui,Jiang, Shuxin,Xiao, Fuhong,Deng, Guo-Jun
, p. 3334 - 3338 (2021/10/29)
The electrochemical reduction strategy of nitrobenzenes is developed. The chemistry occurs under ambient conditions. The protocol uses inert electrodes and the solvent, DMSO, plays a dual role as a reducing agent. Its synthetic value has been demonstrated by the highly efficient synthesis of symmetric, unsymmetric and cyclic azo compounds.
Photoregulated Ion-binding to Azobenzene-linked Ethylenediamines and Iminodiacetic Acids
Shinkai, Seiji,Nakamura, Shinichiro,Nakashima, Mikio,Manabe, Osamu,Iwamoto, Masakazu
, p. 2340 - 2347 (2007/10/02)
New photoresponsive complexones bearing two iminodiacetic acid units or ethylenediamine units at the two sides of an azobenzene through CH2 or (CH2)2 (AzoIDA(n=1,2) and AzoED(n=1,2), respectively) have been synthesized.The CH2 and (CH2)2 spcers were selected in order to examine the influence of the spacer length on the intramolecular cooperativity for the two ligands in the cis-isomers to coordinate to one metal ion.The thermal cis-to-trans isomerization of AzoIDA was efficiently suppressed by Zn(II) and Cu(II) while that of AzoED was suppressed only by Cu(II).The rate suppression supports the formation of the intramolecular chelate complexes with the metal ion.The measurements of ESR spectra of the cis-isomer Cu(II) complexes indicated that the square-planar structure of the complexes is somewhat distorted and probably close to a lozenge.The stability constants (Ks) were determined by a displacement method.The Ks values for the cis-isomers were generally greater than those for the trans-isomers, and the Ks for n=2 series increased more clearly.In particular, the Ks for cis-AzoED(n=2)+Cu(II) was improved by 43.8 fold.The photoresponsive change in the stability constants suggests a possible application of the present system as light-driven ion pumps for heavy metal ions.
