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Chemical Compound Review:

CCRIS 341 1-benzo[1,3]dioxol-5-ylprop- 2-en-1-ol

Synonyms: AGN-PC-00DFI2, AG-F-77121, SureCN6869336, HSDB 3492, LS-7453, ...

Swanson, A.B. et al., Delaforge, M. et al., Miller, E.C. et al., Wiseman, R.W. et al., Falany, C.N. et al., et al.

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Disease relevance of CCRIS 341

Of the mice given a total dose of 4.4 mumoles of 1'-hydroxysafrole, 59developed hepatocellular carcinomas; 39% of the mice bore multiple liver tumors [1].

High impact information on CCRIS 341

Further characterization of the DNA adducts formed by electrophilic esters of the hepatocarcinogens 1'-hydroxysafrole and 1'-hydroxyestragole in vitro and in mouse liver in vivo, including new adducts at C-8 and N-7 of guanine residues [2].
However, the 2',3'-oxides of safrole, estragole, eugenol, 1'-hydroxysafrole, and 1'-hydroxyestragole, when administered topically to female CD-1 mice at relatively high doses, initiated benign skin tumors that could be promoted with croton oil [3].
The metabolic activation of the carcinogen 1'-hydroxysafrole in vivo and in vitro and the electrophilic reactivities of possible ultimate carcinogens [4].
The hepatocarcinogen 1'-hydroxysafrole (HOS) exhibited weak initiating activity and strong promoting activity for the induction of enzyme-altered foci and tumors in rat liver [5].
Supplementation with NADPH-fortified rat-liver microsomes and cytosol converted 3'-hydroxyanethole to a mutagen(s) and increased the mutagenic activities for strain TA100 of 1'-hydroxyestragole, 1'-hydroxysafrole, estragole, and anethole [6].

Anatomical context of CCRIS 341

Highly purified 1'-hydroxyestragole and 1'-hydroxysafrole were mutagenic (approximately 15 and 10 revertants/micromole, respectively) for strain TA100 in the absence of fortified liver microsomes; trans-anethole and estragole appeared to have very weak activity [6].

Associations of CCRIS 341 with other chemical compounds

Epoxysafrole and 1'-hydroxysafrole administered to phenobarbital-pretreated rats resulted in slight inhibition of the type I binding of safrole to liver microsomal P-450 in vitro; in contrast, with 3-methylcholanthrene-pretreated animals marked competitive inhibition was observed [7].
Hydroxymethyl PAHs are sulfated and bioactivated at a relatively rapid rate by DHEA-ST, whereas 1'-hydroxysafrole and N-hydroxy-2-acetylaminofluorene are bioactivated to a lesser extent [8].

References

Hepatocarcinogenicity of estragole (1-allyl-4-methoxybenzene) and 1'-hydroxyestragole in the mouse and mutagenicity of 1'-acetoxyestragole in bacteria. Drinkwater, N.R., Miller, E.C., Miller, J.A., Pitot, H.C. J. Natl. Cancer Inst. (1976) [Pubmed]
Further characterization of the DNA adducts formed by electrophilic esters of the hepatocarcinogens 1'-hydroxysafrole and 1'-hydroxyestragole in vitro and in mouse liver in vivo, including new adducts at C-8 and N-7 of guanine residues. Wiseman, R.W., Fennell, T.R., Miller, J.A., Miller, E.C. Cancer Res. (1985) [Pubmed]
Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole. Miller, E.C., Swanson, A.B., Phillips, D.H., Fletcher, T.L., Liem, A., Miller, J.A. Cancer Res. (1983) [Pubmed]
The metabolic activation of the carcinogen 1'-hydroxysafrole in vivo and in vitro and the electrophilic reactivities of possible ultimate carcinogens. Wislocki, P.G., Borchert, P., Miller, J.A., Miller, E.C. Cancer Res. (1976) [Pubmed]
Inhibition by pentachlorophenol of the initiating and promoting activities of 1'-hydroxysafrole for the formation of enzyme-altered foci and tumors in rat liver. Boberg, E.W., Liem, A., Miller, E.C., Miller, J.A. Carcinogenesis (1987) [Pubmed]
The mutagenicities of safrole, estragole, eugenol, trans-anethole, and some of their known or possible metabolites for Salmonella typhimurium mutants. Swanson, A.B., Chambliss, D.D., Blomquist, J.C., Miller, E.C., Miller, J.A. Mutat. Res. (1979) [Pubmed]
Ligand-complex formation between cytochromes P-450 and P-448 and methylenedioxyphenyl compounds. Delaforge, M., Ioannides, C., Parke, D.V. Xenobiotica (1985) [Pubmed]
Human dehydroepiandrosterone sulfotransferase. Purification, molecular cloning, and characterization. Falany, C.N., Comer, K.A., Dooley, T.P., Glatt, H. Ann. N. Y. Acad. Sci. (1995) [Pubmed]

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