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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Genetic activity spectra of some antischistosomal compounds, with particular emphasis on thioxanthenones and benzothiopyranoindazoles.

In this review we note that hycanthone (Etrenol) is mutagenic for bacteriophage, bacteria, yeast, Neurospora, Drosophila, and for mammalian tissue culture cells, and we point out other genetic activities of this thioxanthenone and of related compounds. One alarming genetic activity is the ability of hycanthone to cause transformation of tissue culture cells in vitro in a test designed to detect carcinogens, results that parallel the direct demonstration of carcinogenic activity of hycanthone in the mouse in vivo. These and other results are compatible with the somatic mutation theory of cancer induction. Factors likely to affect the quantitative genetic activity of hycanthone and its congeners are summarized. Attempts are made to weave the more critical experimental evidence into a molecular model that accounts for the genetic activities of this series of compounds. We conclude that hycanthone is a directly acting mutagen that intercalates into DNA and preferentially alkylates deoxyguanosine residues via formation of a strongly electrophilic molecular species, the carbonium ion. Finally, we show that genetic activity can be dissociated from schistosomicidal activity by appropriate modifications in the thioxanthenone molecule. Preliminary experiments on a newly synthesized piperazinyl N-oxide derivative demonstrate no detectable mutagenic activity; yet considerable schistosomicidal activity is retained.[1]


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