14474-22-7Relevant academic research and scientific papers
Development of a photoswitchable antagonist of NMDA receptors
Hartrampf, Felix W.W.,Barber, David M.,Gottschling, Kevin,Leippe, Philipp,Hollmann, Michael,Trauner, Dirk
, p. 4905 - 4912 (2017/07/27)
N-methyl–Daspartate receptors (NMDARs) are vital for neurological processes such as learning, memory, and synaptic plasticity. As such, small molecules that modulate their function are of interest in the study of numerous neurological diseases. We have synthesized a small library of photoswitches that modulate NMDAR function. The most efficient photoswitch to date is based on a known ligand of the glycine binding site and shows significant subtype selectivity.
Structure requirements for anaerobe processing of azo compounds: Implications for prodrug design
Gavin, Jason,Ruiz, Juan F. Marquez,Kedziora, Kinga,Windle, Henry,Kelleher, Dermot P.,Gilmer, John F.
, p. 7647 - 7652 (2013/02/21)
This Letter generalizes the metabolism of the azo class of compounds by Clostridium perfringens, an anaerobe found in the human colon. A recently reported 5-aminosalicylic acid-based prednisolone prodrug was shown to release the drug when incubated with the bacteria, while the para-aminobenzoic acid (PABA) based analogue did not. Instead, it showed a new HPLC peak with a relatively close retention time to the parent which was identified by LCMS as the partially reduced hydrazine product. This Letter investigates azoreduction across a panel of substrates with varying degrees of electronic and steric similarity to the PABA-based compound. Azo compounds with an electron donating group on the azo-containing aromatic ring showed immediate disproportionation to their parent amines without any detection of hydrazine intermediates by HPLC. Compounds containing only electron withdrawing groups are partially and reversibly reduced to produce a stable detectable hydrazine. They do not disproportionate to their parent amines, but regenerate the parent azo compound. This incomplete reduction is relevant to the design of azo-based prodrugs and the toxicology of azo-based dyes.
Bis(azobenzene)-based photoswitchable, prochiral, Cα- tetrasubstituted α-amino acids for nanomaterials applications
Fatas, Paola,Longo, Edoardo,Rastrelli, Federico,Crisma, Marco,Toniolo, Claudio,Jimenez, Ana I.,Cativiela, Carlos,Moretto, Alessandro
supporting information; experimental part, p. 12606 - 12611 (2011/12/21)
Light-driven chirality: Sequential light-driven isomerization of prochiral, bis(azobenzene)-containing amino acids results in the formation of chiral entities that have been characterized by different techniques. Metal nanoparticles conjugated with these amino acids retain the photoswitching properties and show conformation-dependent magnetic susceptibility that can be reversibly controlled by irradiation (see figure).
