14338-36-4Relevant 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
experimental part, p. 1771 - 1778 (2011/04/17)
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.
SELECTIVELY DELIVERABLE ISATIN-BASED CYTOTOXIC AGENTS
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Page/Page column 69, (2008/12/06)
The invention relates to compounds comprising a cytotoxic isatin derivative conjugated to a cell targeting moiety via a spacer group. These conjugates allow the cytotoxic isatin derivaties to be targeted to particular cell and tissue types. The invention
"Mercaptan-Tail" Porphyrins: Synthetic Analogues for the Active Site of Cytochrome P-450
Collman, James P.,Groh, Susan E.
, p. 1391 - 1403 (2007/10/02)
The synthesis and characterization of a series of tetraarylporphyrins which bear covalently attached alkyl and aryl mercaptans designed to serve as axial ligands are described.The coordination chemistry of the iron(II) complexes of these "mercaptan-tail" porphyrins has been investigated by 1H NMR, IR, and electronic absorption spectroscopy, magnetic circular dichroism, and magnetic susceptibility measurements.Ferrous complexes of the alkyl mercaptan-tail porphyrins appear to remain four-coordinate, intermediate spin (S = 1) in solution.The situation is less clear in the case of appended aryl mercaptans and a "tail-on/tail-off" equilibrium is implicated.In the presence of carbon monoxide, however, binding of thiol trans to CO is observed in both the alkyl and aryl cases.By the addition of an appropriate base, six-coordinate mercaptide-Fe(II)-CO complexes can be generated; these reproduce quite well the characteristic absorption and MCD spectra of cytochrome P-450, suggesting that such compounds are indeed viable models for the active site of cytochrome P-450.