Boron trifluoride etherate on silica-A modified lewis acid reagent (VII). Antitumor activity of cannabigerol against human oral epitheloid carcinoma cells

Abstract

Geraniol (1), olivetol (2), cannabinoids (3 and4) and 5-fluorouracil (5) were tested for their growth inhibitory effects against human oral epitheloid carcinoma cell lines (KB) and NIH 3T3 fibroblasts using two different 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay and sulforhodamine B protein (SRB) assay. Cannabigerol (3) exhibited the highest growth-inhibitory activity against the cancer cell lines.

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References Cited

  1. Baek, S. H., Yook, C. N., and Han, D. S.: Boron trifluoride etherate on alumina-A modified Lewis acid reagent (V). A convenient single step synthesis of cannabinoids.Bull. Kor. Chem. Soc. 16, 293–296 (1995).

    CAS  Google Scholar 

  2. Baek, S. H., Han, D. S., Yook, C. N., Kim, Y. C., and Kwak, J. S.: Synthesis and antitumor activity of cannabigerol.Arch. Pharm. Res. 19, 228–230 (1996).

    Article  CAS  Google Scholar 

  3. Baik, K. U., and Ahn, B. Z.: Cytotoxic activities of some geranylated flavones against L 1210 cell.J. Pharm. Soc. Korea 32, 125–128, (1988).

    CAS  Google Scholar 

  4. Boersma, H. H., Woerdenbag, H. J., Kampinga, H. H., Konings, A. W. T., Bauer, J. and Scheithauer, W.: Modulation of 5-fluorouracil-induced cytotoxity by quercetin in two human colorectal cancer cell lines.Planta Med. 59, A682 (1993).

    Article  Google Scholar 

  5. Carmichael, J., Degraff, W. G., Gazdar, A. F., Minna, J. D., and Mitchell, J. B.: Evaluation of a tetrazolium-based semiautomated colorimetric assay: Assessment of chemosensitivity testing.Cancer Res. 47, 936–942 (1987).

    PubMed  CAS  Google Scholar 

  6. Dewey, W. L.: Cannabinoid pharmacology.Pharmacol. Rev., 38, 151–178 (1986).

    PubMed  CAS  Google Scholar 

  7. Eisohly, H. N., Turner, C. E., Clark, A. M., and Eisohly, M. A.; Synthesis and antimicrobial activities of certain cannabichromene and cannabigerol related compounds.J. Pharm. Sci. 71, 1319–1323 (1982).

    PubMed  Article  CAS  Google Scholar 

  8. Evans, A. T., Formukong, E. A., and Evans, F. J., Actions of cannabis constituents on enzymes of arachidonate metabolism. Anti-inflammatory potential.Biochem. Pharmacol. 36, 2037–2040 (1987a).

    Article  Google Scholar 

  9. Evans, A. T., Formukong, E. A., and Evans, F. J.; Activation of phospholipase A2 by cannabinoids: lack of correlation with CNS effects.FEB. Lett. 211, 119–122 (1987b).

    Article  CAS  Google Scholar 

  10. Formukong, E. A., Evans, A. T., and Evans, F. J.: The inhibitory effects of cannabinoids, The active constituents ofCannabis sativa L. on human and rabbit platelet aggregation.J. Pharm. Pharmacol. 41, 305–309 (1989).

    Google Scholar 

  11. Keepers, Y. P., Pozao, P. E., Peters, G. J., Otte, J. A., Winograd, B., and Pinedo, H. M.: Comparison of the sulforhodamine B protein and tetrazolium (MTT) assys forin vitro chemosensitivity testing.Eur. J. Cancer. 27, 897–900 (1991).

    PubMed  CAS  Article  Google Scholar 

  12. Martin, B.: Cellular effects of cannabinoids.Pharmacol. Rev., 38, 45–74 (1986).

    PubMed  CAS  Google Scholar 

  13. Mechoulam, R.: InCannabinoid as therapeutic agents, Boca Raton, CRC Press Inc., (1986).

    Google Scholar 

  14. Mosmann, T. J.: Rapid colorimetric assays for cellular growth and survival: application to proliferation and cytotoxicity assays.Immunol. Methods. 65, 55–63 (1983).

    Article  CAS  Google Scholar 

  15. Plasse, T. F., Gorter, R. W., Krasnow, S. H., Lane, M., Shepard, K. V., and Wadleig H. R. G.: Recent clinical experience with dronabinol.Pharmacol. Biochem. Behav 40, 695–700 (1991).

    PubMed  Article  CAS  Google Scholar 

  16. Skehan, P., Storeng, S., Studiero, D., Monke, A., McMahon, J., Vistica, D., Warren, J. T., Bodesh, H., Kenny, S. and Boyd, M. R.: New colorimetric cytotoxicity assay for anticancer-drug screeningJ. Natl. Cancer Inst, 82, 1107–1112, 1990.

    PubMed  Article  CAS  Google Scholar 

  17. Watson, E. S., Murphy, J. C., and Turner, C. E.: Allergenic properties of naturally occurring cannabinoids.Ibid.. 72, 954–955 (1983).

    CAS  Google Scholar 

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Correspondence to Seung Hwa Baek.

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Baek, S.H., Kim, Y.O., Kwag, J.S. et al. Boron trifluoride etherate on silica-A modified lewis acid reagent (VII). Antitumor activity of cannabigerol against human oral epitheloid carcinoma cells. Arch. Pharm. Res. 21, 353 (1998). https://doi.org/10.1007/BF02975301

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Key words

  • Cannabinoid
  • 5-Fluorouracil
  • Cannabigerol
  • Antitumor activity
  • Human oral epitheloid carcinoma cell
  • MTT assay
  • SRB assay