Structure-activity relationship and design of an antimutagen against the UV-induced mutation of Escherichia coli.

Abstract

Structure-activity relationships of antimutagens were studied by assaying analogues and derivatives of 2(5//)furanone designed on the basis of the structures of natual antimutagens by the method of observing UV-induced reversion ofE. coli WP2B/r uvr A~trp E~. It is shown that an a,/?-unsaturated carbonyl system is required for antimutagenic activity. Further modification of 3(2i/)furanones resulted in the development of a highly potent antimutagen. The possibility that the antimutagenic effects maybe due to alteration of proteins involved in the DNArepair system by trapping thiol groups is also discussed.

INHIBITION OF LISTERIA MONOCYTOGENES BY CINNAMIC ACID: POSSIBLE INTERACTION OF THE ACID WITH CYSTEINYL RESIDUES

“…Cinnamic acid is also a natural antimutagenic agent (Mitscher et al 1992;Liu et al 1995). The reactive a$-unsaturated carbonyl is a common factor in compounds showing antimutagenic activity (Kakinuma et al 1986). It is speculated that a, P-unsaturated carbonyl systems react with nucleophiles and exert their antimutagenic activity by trapping thiol groups of target proteins (Ishibashi et al 1987;Kakinuma ef al.…”

Antimutagenic and Anticarcinogenic Effect of Methanol Extracts of Sweetpotato (Ipomea batata) Leaves

“…Antimutagens are classified desmutagens which can inactivate mutagens by directly binding mutagens before gene damage occurs, and bioantimutagens which can affect the recovery or replication of damaged genes (Kuroda and Hara, 1999) . Antimutagens exhibit their activities either by correction of the error-prone SOS response or enhancement of an error-free recombinational repair system (Kakinuma et al ., 1986) .…”

Synthesis of 4-Hydroxy-2-alkenals and 4-Oxo-2-alkenols from 4-Tetrahydropyranyloxy-2-butenal and Their Antimutagenic Effect against UV-InducedEscherichia coliWP2 B/rTrp

“…Among the ketonic compounds, 2,2-dimethyl-5-vinyl-3-furanone has been described to haveAD so = 0.9 ,ugjm1. 4 ) 2d was less active. The mutation frequency4) of II-formyl-undeca-2, 10-dienaP 4 ) and 1,5-bis( l-hydroxy-3-formyl-2-propenyl)pentane (14) was constant in concentrations of 0.2 to 40,ugjml, although the number of colonies of UV-induced Trp + cells decreased to about Ij2at 40,ugjm1.…”