1284293-56-6Relevant articles and documents
Synthesis and hydrolytic evaluation of acid-labile imine-linked cytotoxic isatin model systems
Matesic, Lidia,Locke, Julie M.,Vine, Kara L.,Ranson, Marie,Bremner, John B.,Skropeta, Danielle
, p. 1771 - 1778 (2011)
In this study a series of isatin-based, pH-sensitive aryl imine derivatives with differing aromatic substituents and substitution patterns were synthesised and their acid-catalysed hydrolysis evaluated. These derivatives were functionalised at the C3 carbonyl group of a potent N-substituted isatin cytotoxin and were stable at physiological pH but readily cleaved at pH 4.5. Observed rates of hydrolysis for the embedded imine-acid moiety were in the order para-phenylpropionic acid > phenylacetic acid (para > meta) > benzoic acid (meta > para). The ability to fine-tune hydrolysis rates in this way has potential implications for optimising imine linked, tumour targeting cytotoxin-protein conjugates.
