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Chemical Compound Review:

SureCN6806973 (13S,14R)-3,4-dihydroxy-13- methyl-12,14,15...

Synonyms: LS-64745, AR-1E9217, AC1L33BC, AC1Q6OA1, 4-Hydroxyequilenin

Li, Y. et al., Embrechts, J. et al., Yasui, M. et al., Zhang, F. et al., Cuendet, M. et al., et al.

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Disease relevance of 4-Hydroxyequilenin

A metabolite of equine estrogens, 4-hydroxyequilenin, induces DNA damage and apoptosis in breast cancer cell lines [1].

High impact information on 4-Hydroxyequilenin

These equine estrogens are metabolized primarily to 4-hydroxyequilin (4-OHEQ) and 4-hydroxyequilenin, respectively, which are autoxidized to react with DNA, resulting in the various DNA damages [2].
These results suggest that the catechol metabolites of equine estrogens have the ability to cause alkylation/redox damage in vivo primarily through formation of 4-hydroxyequilenin quinoids [3].
Response of human mammary epithelial cells to DNA damage induced by 4-hydroxyequilenin: Lack of p53-mediated G1 arrest [4].
In the present study, Ala22Ser and Ala52Thr variants of human S-COMT were produced using recombinant DNA techniques, and then COMT properties were measured including enzymatic activity, thermostability, and sensitivity to inhibition mediated by 4-hydroxyequilenin (4-OHEN) [5].

Analytical, diagnostic and therapeutic context of 4-Hydroxyequilenin

In order to be able to analyze these adducts in in vivo samples a method based upon the coupling of miniaturized liquid chromatography (LC) to electrospray tandem mass spectrometry (ES-MS/MS) was developed for the analysis of the adducts formed with 4-hydroxyequilenin [6].

References

A metabolite of equine estrogens, 4-hydroxyequilenin, induces DNA damage and apoptosis in breast cancer cell lines. Chen, Y., Liu, X., Pisha, E., Constantinou, A.I., Hua, Y., Shen, L., van Breemen, R.B., Elguindi, E.C., Blond, S.Y., Zhang, F., Bolton, J.L. Chem. Res. Toxicol. (2000) [Pubmed]
Mutagenic events induced by 4-hydroxyequilin in supF shuttle vector plasmid propagated in human cells. Yasui, M., Matsui, S., Laxmi, Y.R., Suzuki, N., Kim, S.Y., Shibutani, S., Matsuda, T. Carcinogenesis (2003) [Pubmed]
The major metabolite of equilin, 4-hydroxyequilin, autoxidizes to an o-quinone which isomerizes to the potent cytotoxin 4-hydroxyequilenin-o-quinone. Zhang, F., Chen, Y., Pisha, E., Shen, L., Xiong, Y., van Breemen, R.B., Bolton, J.L. Chem. Res. Toxicol. (1999) [Pubmed]
Response of human mammary epithelial cells to DNA damage induced by 4-hydroxyequilenin: Lack of p53-mediated G1 arrest. Cuendet, M., Bolton, J.L. Chem. Biol. Interact. (2006) [Pubmed]
Characterization of two new variants of human catechol O-methyltransferase in vitro. Li, Y., Yang, X., van Breemen, R.B., Bolton, J.L. Cancer Lett. (2005) [Pubmed]
Equilenin-2'-deoxynucleoside adducts: analysis with nano-liquid chromatography coupled to nano-electrospray tandem mass spectrometry. Embrechts, J., Lemière, F., Van Dongen, W., Esmans, E.L. Journal of mass spectrometry : JMS. (2001) [Pubmed]

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