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

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Fedorov, S.N. et al.

Evaluation of cancer-preventive activity and structure-activity relationships of 3-demethylubiquinone Q2, isolated from the ascidian Aplidium glabrum, and its synthetic analogs.

PURPOSE: 3-Demethylubiquinone Q2 was isolated from the ascidian Aplidium glabrum. The cancer-preventive properties and the structure-activity relationship for 3-demethylubiquinone Q2 and 12 of its synthetic analogs are reported. METHODS: Compounds, having one or several di- or triprenyl substitutions and quinone moieties with methoxyls in different positions, were synthesized. The cancer-preventive properties of compounds and were tested in JB6 Cl41 mouse skin cells, using a variety of assessments, including the methanethiosulfonate (MTS) assay, flow cytometry, and soft agar assay. Statistical nonparametric methods were used to confirm statistical significance. RESULTS: All quinones tested were shown to inhibit JB6 Cl41 cell transformation, to induce apoptosis, AP-1, and NF-kappaB activity, and to inhibit p53 activity. The most promising effects were indicated for compounds containing two isoprene units in a side chain and a methoxyl group at the para-position to a polyprenyl substitution. CONCLUSIONS: Quinones and demonstrated cancer-preventive activity in JB6 Cl41 cells, which may be attributed to the induction of p53-independent apoptosis. These activities depended on the length of side chains and on the positions of the methoxyl groups in the quinone part of the molecule.[1]

References

Evaluation of cancer-preventive activity and structure-activity relationships of 3-demethylubiquinone Q2, isolated from the ascidian Aplidium glabrum, and its synthetic analogs. Fedorov, S.N., Radchenko, O.S., Shubina, L.K., Balaneva, N.N., Bode, A.M., Stonik, V.A., Dong, Z. Pharm. Res. (2006) [Pubmed]

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