Anticancer hydrolysis products

Epothilones are a class of molecules that show anticancer activity. Production of a synthetic intermediate was investigated through the action of an esterase on various sterically hindered 3-hydroxy esters [76]. No initial activity was observed, so a Pseudomonasfluorescens esterase was transformed into a mutator strain Epicurian coli and screened using an indicator in the growth plates that would produce a red color if hydrolysis occurred. An ee of 25% was achieved from a variant containing two mutations. 

Lock, C. J. L. (1980). Structural studies of the hydrolysis products of platinum anticancer drugs, and their complexes with DNA base. In A. E. Martell (ed.), ACS Symposium Series, Vol. 140 Inorganic Chemistry in Biology and Medicine, pp. 209-24. 

Amygdalin, a compound isolated from the pits of apricots, peaches, and wild cherries, is commonly known as laetrile. Although it has no known therapeutic value, amygdalin has been used as an unsanctioned anticancer drug both within and outside of the United States. One hydrolysis product formed from amygdalin is mandelic acid, used in treating common skin problems caused by photo-aging and acne. 

Attention has also been paid to the TSM detection of the interaction of surface-bound nucleic acids with small molecules such as specific-binding cis-and ra splatin anticancer drugs. The results showed two distinct kinetic processes that were interpreted in terms of nucleic acid binding of the hydrolysis products of the two drugs by Thompson and co-workers [54]. 

Structural Studies of the Hydrolysis Products of Platinum Anticancer Drugs, and Their Complexes with DNA Bases... 

The anthracyciinone class of anticancer compounds (which includes daunomycin and adriamycin) can be made using a mercury (I I )-promoted alkyne hydration. You saw the synthesis of alkynes in this class on Chapter 9 where we discussed additions of metallated alkynes to ketones. Here is the final step in a synthesis of the anticancer compound deoxydaunomycinone the alkyne is hydrated using Hg2+ in dilute sulfuric acid the sulfuric acid also catalyses the hydrolysis of the phenolic acetate to give the final product. 

The isatin products from the Sandmeyer synthesis can serve as a source of ortto-arylaminoacids through degradation. Hydrolysis of isatin 42, yielded aminoacid 43, which was converted to the anticancer compound DMXAA (44). ... 

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