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Evaluation of Cancer-Preventive Activity and Structure–Activity Relationships of 3-Demethylubiquinone Q2, Isolated from the Ascidian Aplidium glabrum, and its Synthetic Analogs

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Purpose

3-Demethylubiquinone Q2 (1) was isolated from the ascidian Aplidium glabrum. The cancer-preventive properties and the structure–activity relationship for 3-demethylubiquinone Q2 (1) and 12 of its synthetic analogs (3–14) are reported.

Methods

Compounds 3–14, having one or several di- or triprenyl substitutions and quinone moieties with methoxyls in different positions, were synthesized. The cancer-preventive properties of compounds 1 and 3–14 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-κB 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 1 and 3–14 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.

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Scheme 1
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Abbreviations

3-demethylubiquinone Q2:

2,3-dimethoxy-5-(3′,7′-dimethyl-octa-2′(E),6′-dienyl)-[1,4]benzoquinone (1)

EGF:

epidermal growth factor

FBS:

fetal bovine serum

MEM:

minimum essential medium

TPA:

12-O-tetradecanoyl-phorbol-13-acetate

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Acknowledgments

This work was supported in part by The Hormel Foundation and National Institutes of Health grants CA81064, CA77646, and CA88961. The Russian co-authors are grateful for financial support by the RFFI Grant no. 05-04-48246, Russian Federation President Grant no. 725.2003.4, Program of Presidium of RAS “Molecular and Cell Biology” Grant no. 05-I-05-005, and FEB Grant no. 05-III-A-05-129.

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Authors and Affiliations

  1. Hormel Institute, University of Minnesota, 801 16th Avenue NE, Austin, Minnesota, 55912, USA

    Sergey N. Fedorov, Oleg S. Radchenko, Larisa K. Shubina, Nadezhda N. Balaneva & Valentin A. Stonik

  2. Pacific Institute of Bioorganic Chemistry, 159 Prospect 100-let Vladivostoku, Vladivostok, 690022, Russia

    Sergey N. Fedorov, Ann M. Bode & Zigang Dong

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  1. Sergey N. Fedorov
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Correspondence to Zigang Dong.

Appendix A

Appendix A

Tables A1–A4

Table A1 Effect of Quinones 1, 3–14 on the Viability of JB6 P+ Cl41 Cells
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Table A2 Inhibition of the Colony Growth of the Transformed Mouse JB6 P+ Cl41cells by the Quinones 1, 3–14 Evaluated by the Method of Anchorage-Independent Assay
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Table A3 The Induction of Apoptosis by the Quinones 1, 3–14 in JB6 P+ Cl41 Cells Evaluated by the Method of Flow Cytometry
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Table A4 The Effect of Quinones 1, 3–14 on the NF-κB-, AP-1-, or p53-Dependent Transcriptional Activity in JB6 Cl41 NF-κB, JB6 Cl41 AP-1, or PG-13 Cells
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Fedorov, S.N., Radchenko, O.S., Shubina, L.K. 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. Pharm Res 23, 70–81 (2006). https://doi.org/10.1007/s11095-005-8813-4

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