Abstract
Several diacetoxy acetal analogues have been synthesized from santonin and assessed for their ability of inducing or enhancing the differentiation of human HL-60 leukemia cells. The compounds themselves had little effect on HL-60 cell differentiation. However, three analogues,2a, 3a, and5b, synergistically enhanced 1,25-dihydroxyvitamin D3 [1,25-(OH)2D3]-induced HL-60 cell differentiation when combined with 5 nM of dihydroxyvitamin D3 [1,25-(OH)2D3], a well-known differentiation inducer. Especially, the compound5b profoundly enhanced the 1,25-(OH)2D3]-induced HL-60 cell differentiation.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Ando, M., Wada, T., Kusaka, H., Takase, K., Hirata, N., and Yanagi, Y., Studies on the synthesis of sesquiterpene lactones 10. Improved synthesis of (+)-tuberiferin and the related alpha-methylene gamma-lactones and their biological activities.J. Org. Chem., 52, 4782–4786 (1987).
Beere, H. M. and Hickman, J. A., Differentiation: a suitable strategy for cancer chemotherapy.Anti-Cancer Drug Design, 8, 299–322 (1993).
Breitman, T. R., Selonick, S. E., and Collins, S. J., Induction of differentiation of the human promyelocytic leukemia cell line (HL-60) by retinoic acid.Proc. Natl. Acad. Sci., U.S.A., 77, 2936–2940 (1980).
Collins, S. J., Ruscetti, F. W., Gallagher, R. E., and Gallo, R. C., Normal functional characteristics of cultured human promyelocytic leukemia cells (HL-60) after induction of differentiation by dimethylsulfoxide.J. Exp. Med., 149, 969–974 (1979).
Hall, I. H., Williams, W. L. Jr., Grippo, A. A., Lee, K. H., Holbrook, D. J., and Chaney, S. G., Inhibition of nucleic acid synthesis in P-388 lymphocytic leukemia cells in culture by sesquiterpene lactones.Anticancer Res., 8, 33–42 (1988).
Hehner, S. P., Hofmann, T. G., Droge, W., and Schmitz, M. L., The antiinflammatory sesquiterpene lactone parthenolide inhibits NF-κB by targeting the lkB kinase complex.J. Immunol., 163, 5617–5623 (1999).
Hershberger, P. A., Yu, W. D., Modzelewski, R. A., Rueger, R. M., Johnson, C. S., and Trump, D. L., Calcitriol (1, 25-dihydroxycholecalciferol) enhances paclitaxel antitumor activityin vitro andin vivo and accelerates paclitaxel-induced apoptosis.Clin. Cancer Res., 7, 1043–1051 (2001).
Kang, S. N., Lee, M. H., Kim, K. M., Cho, D., and Kim, T. S., Induction of human promyelocytic leukemia HL-60 cell differentiation into monocytes by silibinin: involvement of protein kinase C.Biochem. Pharmacol., 61, 1487–1495 (2001).
Kato, K., Hirata, Y., and Yamamura, S., Synthesis of shyobunone and related sesquiterpene.Tetrahedron, 27, 5987–92 (1971).
Ohnishi, M., Yoshimi, N., Kawamori, T., Ino, N., Hirose, Y., Tanaka, T., Yamahara, J., Miyata, H., and Mori, H., Inhibitory effects of dietary protocatechuic acid and costunolide on 7,12-dimethylbenz[a]anthracene-induced hamster cheek pouch carcinogenesis.Jpn. J. Cancer Res., 88, 111–119 (1997).
Ross, J. J., Armason, J. T., and Bimboim, H. C., Low concentrations of the feverfew component parthenolide inhibitin vitro growth of tumor lines in a cytostatic fashion.Planta Med., 65, 126–129 (1999).
Shibata, T., Okura, T., and Inayama, Dithioacetal; As a chiroptical Functional group to determine absolute and and relative configurations by CD and 1H-NMR spectra.Herocycle, 24, 897–900 (1986).
Simonvic, D. M., Rao, A. S., and Bhattacharyya, S. C., The synthesis of tetrahydro-sussurea lactone.Tetrahedron, 9, 1061–1071 (1963).
Sokoloski, J. A., Shyam, K., and Sartorelli, A. C., Induction of the differentiation of HL-60 promyelocytic leukemia cells by curcumin in combination with low levels of vitamin D3.Oncol. Res., 9, 31–39 (1997).
Studzinski, G. P. and Moore, D. C., Sunlight-can it prevent as well as cause cancer?Cancer Res., 55, 4014–4022 (1995).
Tanaka, H., Abe, E., Miyaura, C., Shiina, Y., and Suda, T., 1a,25-dihydroxyvitamin D3 Induces differentiation of human promyelocytic leukemia cells (HL-60) into monocytic macrophage, but not into granulocytes.Biochem. Biophys. Res. Commun., 117, 86–92 (1983).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kim, S.H., Chung, S.Y., Kim, T.S. et al. Synthesis of diacetoxy acetal derivatives of santonin and their enhancing effects on HL-60 leukemia cell differentiation. Arch Pharm Res 29, 40–45 (2006). https://doi.org/10.1007/BF02977466
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02977466