Abstract
DAAS is the diacetoxy acetal derivative of a-santonin and induces HL-60 cell differentiation into granulocytes. In this report, we investigated the structure-activity relationship (SAR) of DAAS derivatives in the differentiation of human HL-60 leukemia cells. Although its derivatives themselves had less effect on HL-60 cell differentiation than DAAS, the monoacetyl derivative, 2, mainly induced HL-60 cell differentiation. Moreover, compound 2 synergistically enhanced all-trans retinoic acid (ATRA)-induced HL-60 cell differentiation when combined with 50 nM ATRA, a well-known differentiation inducer. This enhancing effect is similar to that of DAAS in ATRA-induced differentiation.
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Beere, H. M. and Hickman, J. A., Differentiation: a suitable strategy for cancer chemotherapy. Anti-Cancer Drug Design, 8, 299–322 (1993).
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 IkB 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,α25-dihydroxycholecalciferol) enhances paclitaxel antitumor activity in vitro and in 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, 5987–5992 (1971).
Kim, S. H., Song, J. H., Choi, B. G., Kim, H. J., and Kim, T. S., Chemical modification of santonin into a diacetoxy acetal form confers the ability to induce differentiation of human promyelocytic leukemia cells via the down-regulation of NF-kappaB DNA binding activity. J. Biol. Chem., 281, 13117–13125 (2006).
Kim, S. H., Chung, S. Y., Kim, T. S., and Choi, B. G., Synthesis of diacetoxy acetal derivatives of santonin and their enhancing effects on HL-60 leukemia cell differentiation. Arch. Pharm. Res., 29, 40–45 (2006).
Kupchan, S.M., Hemingway, R., Werner, D., Karim, A., McPhail, A. T., and Sim, G. A., Vernolepin, a novel elemanolide diactone, tumor inhibition from vernonia hymenolepsois, J. Am. Chem. Soc., 90, 3596–3597 (1968).
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).
Shibata, T., Ohkura, T., and Inayama, S., Dithioacetal; As a chiroptical Functional group to determine absolute and and relative configurations by CD and 1H-NMR spectra, Heterocycle, 24, 897–900 (1986).
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Kim, S.H., Chung, S.Y., Kim, Y.W. et al. Synthesis of DAAS derivatives and their enhancement of HL-60 leukemia cell differentiation. Arch. Pharm. Res. 31, 300–304 (2008). https://doi.org/10.1007/s12272-001-1155-z
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DOI: https://doi.org/10.1007/s12272-001-1155-z