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Chemical Compound Review:

p-XSC 1,4-bis(selenocyanatomethyl) benzene

Synonyms: CHEMBL113478, CCRIS 6548, AG-J-11464, AC1L1KYK, CTK8G2674, ...

el-Bayoumy, K. et al., Tillotson, J.K. et al., Uddin, A.N. et al., Youn, B.W. et al., Fleming, J. et al., et al.

El-Bayoumy, Narayanan, Desai, Narayanan, Pittman, Amin, Schwartz, Nixon, Bartram, Krüger, Dusel, El-Bayoumy, Upadhyaya, Scheppach, Fiala, Staretz, Pandya, El-Bayoumy, Hamilton, Rao, Wang, Simi, Rodriguez, Cooma, El-Bayoumy, Reddy, El-Bayoumy, Das, Boyiri, Desai, Sinha, Pittman, Amin, Guttenplan, Kosinska, von Pressentin, Rosa, El-Bayoumy, El-Bayoumy, Rose, Papanikolaou, Leszczynska, Swamy, Rao,

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Disease relevance of CCRIS 6548

Chemoprevention of colon cancer by a glutathione conjugate of 1,4-phenylenebis(methylene)selenocyanate, a novel organoselenium compound with low toxicity [1].
We synthesized a novel organoselenium compound, 1,4-phenylenebis(methylene)selenocyanate (XSC), possessing low toxicity by comparison with inorganic Na2SeO3, and several other synthetic organoselenium compounds (K. El-Bayoumy, Cancer Res., 45: 3631-3636, 1985) [2].
We employed cDNA microarray analysis to identify, in mammary adenocarcinomas induced by 7,12-dimethylbenz[a] anthracene (DMBA) in the rat, target genes as potential biomarkers for cancer chemoprevention by 1,4-phenylenebis(methylene)selenocyanate (p-XSC) [3].
To identify mechanisms by which the organoselenium compound 1,4-phenylenebis(methylene)selenocyanate (p-XSC) mediates its chemopreventive activities, we have examined its effects on cell lines derived from breast cancer of humans and rats [4].
Recently, we showed that arsenite in drinking water greatly potentiates solar ultraviolet radiation (UVR) induced skin cancer in mice, at concentrations as low as 1.25 mg/l. In this study, we examined the protective efficacy of vitamin E and 1,4-phenylenebis(methylene)selenocyanate (p-XSC) against tumors induced by UVR and UVR + arsenite [5].

High impact information on CCRIS 6548

Inhibition of 7,12-dimethylbenz(a)anthracene-induced tumors and DNA adduct formation in the mammary glands of female Sprague-Dawley rats by the synthetic organoselenium compound, 1,4-phenylenebis(methylene)selenocyanate [2].
The organoselenium compounds benzyl selenocyanate (BSC) and 1,4-phenylenebis(methylene)selenocyanate (p-XSC), as well as sodium selenite, are effective chemopreventive agents for various chemically induced tumors in animal models at both the initiation and postinitiation stages [6].
Elevated 8-hydroxy-2'-deoxyguanosine levels in lung DNA of A/J mice and F344 rats treated with 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and inhibition by dietary 1,4-phenylenebis(methylene)selenocyanate [7].
Effects of dietary 1,4-phenylenebis(methylene)selenocyanate on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced DNA adduct formation in lung and liver of A/J mice and F344 rats [8].
In the present study we have elucidated the effect of the organoselenium chemopreventive agent 1,4-phenylenebis(methylene)selenocyanate (p-XSC, on UV-mediated JNK activation [9].

Biological context of CCRIS 6548

The role of apoptosis in the modulation of colon carcinogenesis by dietary fat and by the organoselenium compound 1,4-phenylenebis(methylene)selenocyanate [10].
The effects of dietary administration of 1,4-phenylenebis(methylene)selenocyanate (p-XSC) and Vitamin E on 4-nitroquinoline-N-oxide (4-NQO)-induced mutagenesis in lacZ mouse upper aerodigestive tissues were investigated [11].
We also examined the effects of 1,4-phenylenebis(methylene)selenocyanate (p-XSC), a highly effective chemopreventive organoselenium compound and known inhibitor of COX-2 expression, in vivo, on cell growth and COX-2 expression in vitro in the NCI-H460 cancer cell line [12].
Comparative excretion and tissue distribution of selenium in mice and rats following treatment with the chemopreventive agent 1,4-phenylenebis(methylene)selenocyanate [13].
Comparative action of 1,4-phenylenebis(methylene)selenocyanate and its metabolites against 7,12-dimethylbenz[a]anthracene-DNA adduct formation in the rat and cell proliferation in rat mammary tumor cells [14].

Anatomical context of CCRIS 6548

Organoselenium compound 1,4-phenylenebis(methylene)selenocyanate (p-XSC) was investigated for its effects on endothelial cell proliferation in vitro and angiogenesis in vivo [15].
Antiproliferative effect of 1,4-phenylenebis(methylene)selenocyanate (p-XSC) on colonic epithelium of patients with adenomatous polyps in vitro [16].

Gene context of CCRIS 6548

We assessed the in vitro and in vivo effects of the organoselenium compound 1,4-phenylenebis(methylene)selenocyanate (p-XSC) on the binding activities of the transcription factors nuclear factor-kappa B (NF-kappa B), activator protein-1 (AP-1), Sp1, and Sp3 using the HCT-116 (human colorectal adenocarcinoma) cell line as a model system [17].
In contrast, although the potent pharmacological selenium chemopreventive agent 1,4-phenylenebis(methylene)selenocyanate (p-XSC) also induces Fas ligand, heme oxygenase, and stress kinase pathways, apoptosis/Fas induction is not so strongly JNK-dependent and p-XSC does not show tumor selectivity [18].
Inhibition of thymidine kinase in cultured mammary tumor cells by the chemopreventive organoselenium compound, 1,4-phenylenebis(methylene)selenocyanate [4].

Analytical, diagnostic and therapeutic context of CCRIS 6548

Chemoprevention of colon carcinogenesis by the synthetic organoselenium compound 1,4-phenylenebis(methylene)selenocyanate [19].
1,4-Phenylenebis(methylene)selenocyanate (p-XSC) inhibits chemically induced tumors in several laboratory animal models [20].

References

Chemoprevention of colon cancer by a glutathione conjugate of 1,4-phenylenebis(methylene)selenocyanate, a novel organoselenium compound with low toxicity. Rao, C.V., Wang, C.Q., Simi, B., Rodriguez, J.G., Cooma, I., El-Bayoumy, K., Reddy, B.S. Cancer Res. (2001) [Pubmed]
Inhibition of 7,12-dimethylbenz(a)anthracene-induced tumors and DNA adduct formation in the mammary glands of female Sprague-Dawley rats by the synthetic organoselenium compound, 1,4-phenylenebis(methylene)selenocyanate. el-Bayoumy, K., Chae, Y.H., Upadhyaya, P., Meschter, C., Cohen, L.A., Reddy, B.S. Cancer Res. (1992) [Pubmed]
Elucidation of molecular targets of mammary cancer chemoprevention in the rat by organoselenium compounds using cDNA microarray. El-Bayoumy, K., Narayanan, B.A., Desai, D.H., Narayanan, N.K., Pittman, B., Amin, S.G., Schwartz, J., Nixon, D.W. Carcinogenesis (2003) [Pubmed]
Inhibition of thymidine kinase in cultured mammary tumor cells by the chemopreventive organoselenium compound, 1,4-phenylenebis(methylene)selenocyanate. Tillotson, J.K., Upadhyaya, P., Ronai, Z. Carcinogenesis (1994) [Pubmed]
Vitamin E and organoselenium prevent the cocarcinogenic activity of arsenite with solar UVR in mouse skin. Uddin, A.N., Burns, F.J., Rossman, T.G. Carcinogenesis (2005) [Pubmed]
Inhibition of DNA cytosine methyltransferase by chemopreventive selenium compounds, determined by an improved assay for DNA cytosine methyltransferase and DNA cytosine methylation. Fiala, E.S., Staretz, M.E., Pandya, G.A., El-Bayoumy, K., Hamilton, S.R. Carcinogenesis (1998) [Pubmed]
Elevated 8-hydroxy-2'-deoxyguanosine levels in lung DNA of A/J mice and F344 rats treated with 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and inhibition by dietary 1,4-phenylenebis(methylene)selenocyanate. Rosa, J.G., Prokopczyk, B., Desai, D.H., Amin, S.G., El-Bayoumy, K. Carcinogenesis (1998) [Pubmed]
Effects of dietary 1,4-phenylenebis(methylene)selenocyanate on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced DNA adduct formation in lung and liver of A/J mice and F344 rats. Prokopczyk, B., Cox, J.E., Upadhyaya, P., Amin, S., Desai, D., Hoffmann, D., el-Bayoumy, K. Carcinogenesis (1996) [Pubmed]
Effects of chemopreventive selenium compounds on Jun N-kinase activities. Adler, V., Pincus, M.R., Posner, S., Upadhyaya, P., El-Bayoumy, K., Ronai, Z. Carcinogenesis (1996) [Pubmed]
The role of apoptosis in the modulation of colon carcinogenesis by dietary fat and by the organoselenium compound 1,4-phenylenebis(methylene)selenocyanate. Samaha, H.S., Hamid, R., el-Bayoumy, K., Rao, C.V., Reddy, B.S. Cancer Epidemiol. Biomarkers Prev. (1997) [Pubmed]
Effects of 1,4-phenylenebis(methylene)selenocyanate (p-XSC) and vitamin E on 4-nitroquinoline-N-oxide (4-NQO)-induced mutagenesis in lacZ mouse upper aerodigestive tissue. Guttenplan, J.B., Kosinska, W., von Pressentin, M.M., Rosa, J., El-Bayoumy, K. Mutat. Res. (2002) [Pubmed]
Cyclooxygenase-2 expression influences the growth of human large and small cell lung carcinoma lines in athymic mice: impact of an organoselenium compound on growth regulation. El-Bayoumy, K., Rose, D.P., Papanikolaou, N., Leszczynska, J., Swamy, M.V., Rao, C.V. Int. J. Oncol. (2002) [Pubmed]
Comparative excretion and tissue distribution of selenium in mice and rats following treatment with the chemopreventive agent 1,4-phenylenebis(methylene)selenocyanate. Sohn, O.S., Desai, D.H., Das, A., Rodriguez, J.G., Amin, S.G., El-Bayoumy, K. Chem. Biol. Interact. (2005) [Pubmed]
Comparative action of 1,4-phenylenebis(methylene)selenocyanate and its metabolites against 7,12-dimethylbenz[a]anthracene-DNA adduct formation in the rat and cell proliferation in rat mammary tumor cells. El-Bayoumy, K., Das, A., Boyiri, T., Desai, D., Sinha, R., Pittman, B., Amin, S. Chem. Biol. Interact. (2003) [Pubmed]
Inhibition of vascular endothelial cells by 1,4-phenylenebis (methylene)selenocyanate--a novel chemopreventive organoselenium compound. Schumacher, J.J., Upadhyaya, P., Ramakrishnan, S. Anticancer Res. (2001) [Pubmed]
Antiproliferative effect of 1,4-phenylenebis(methylene)selenocyanate (p-XSC) on colonic epithelium of patients with adenomatous polyps in vitro. Bartram, H.P., Krüger, S., Dusel, G., El-Bayoumy, K., Upadhyaya, P., Scheppach, W. Eur. J. Cancer Prev. (2003) [Pubmed]
Mechanisms of organoselenium compounds in chemoprevention: effects on transcription factor-DNA binding. Youn, B.W., Fiala, E.S., Sohn, O.S. Nutrition and cancer. (2001) [Pubmed]
Molecular mechanisms of cancer prevention by selenium compounds. Fleming, J., Ghose, A., Harrison, P.R. Nutrition and cancer. (2001) [Pubmed]
Chemoprevention of colon carcinogenesis by the synthetic organoselenium compound 1,4-phenylenebis(methylene)selenocyanate. Reddy, B.S., Rivenson, A., Kulkarni, N., Upadhyaya, P., el-Bayoumy, K. Cancer Res. (1992) [Pubmed]
Synthesis and excretion profile of 1,4-[14C]phenylenebis(methylene)selenocyanate in the rat. El-Bayoumy, K., Upadhyaya, P., Sohn, O.S., Rosa, J.G., Fiala, E.S. Carcinogenesis (1998) [Pubmed]

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