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ID: ALA1681682
Journal: Bioorg Med Chem
Title: Synthesis and hydrolytic evaluation of acid-labile imine-linked cytotoxic isatin model systems.
Authors: Matesic L, Locke JM, Vine KL, Ranson M, Bremner JB, Skropeta D.
Abstract: 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.
CiteXplore: 21306903