Unsaturated genistein disaccharide glycoside as a novel agent affecting microtubules

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 17, 2009, Pages 4939-4943

  Rusin, Aleksandra ^a   Gogler, Agnieszka ^a   Głowala Kosińska, Magdalena ^a   Bochenek, Daria ^a   Gruca, Aleksandra ^a   Grynkiewicz, Grzegorz ^b   Zawisza, Jadwiga ^c   Szeja, Wiesław ^c   Krawczyk, Zdzisław ^a,c  

^a INSTITUTE OF ONCOLOGY   (Poland)

^b INDUSTRIAL CHEMISTRY RESEARCH INSTITUTE   (Poland)

^c SILESIAN UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Genistein glycoside; Microtubule interfering drugs

Indexed keywords

7 O (2,3,4,6 TETRA O ACETYL BETA GALACTOPYRANOSYL)(1-4)(6 O ACETYL HEX 2 ENE ALPHA DEXTRO ERYTHROPYRANOSYL)GENISTEIN; DISACCHARIDE; GENISTEIN; GLYCOSIDE; ISOFLAVONOID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL CYCLE; CELL PROLIFERATION; CHEMOPROPHYLAXIS; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; HUMAN; HUMAN CELL; INTERPHASE; MICROTUBULE; MITOSIS INHIBITION; MITOSIS SPINDLE; STEREOCHEMISTRY;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DISACCHARIDES; GENISTEIN; GLYCOSIDES; HUMANS; MICROTUBULES; TUBULIN MODULATORS;

TETRA;

EID: 68349144404     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.07.089     Document Type: Article

References (34)

1. Middleton E., Kandaswami C., and Theoharides T.C. Pharmacol. Rev. 52 (2000) 673
2. Dixon R.A., and Ferreira D. Phytochemistry 60 (2002) 205
3. Banerjee S., Li Y., Wang Z., and Sarkar F.H. Cancer Lett. 269 (2008) 226
4. Somjen D., Amir-Zaltsman Y., Gayer B., Kulik T., Knoll E., Stern N., Lu L.J., Toldo L., and Kohen F. J. Endocrinol. 173 (2002) 415
5. Wang S.F., Jiang Q., Ye Y.H., Li Y., and Tan R.X. Bioorg. Med. Chem. 13 (2005) 4880
6. Meng Q.H., Lewis P., Wahala K., Adlercreutz H., and Tikkanen M.J. Biochim. Biophys. Acta 1438 (1999) 369
7. Matsumoto T., Kobayashi T., Kikuchi T., Honda T., and Kamata K. J. Smooth Muscle Res. 41 (2005) 23
8. Wang J., Shang F., Jing R., Liu L., Wang S., Hou J., Huan M., and Mei Q. J. Pharmacol. Sci. 104 (2007) 82
9. Zhang L.N., Xiao Z.P., Ding H., Ge H.M., Xu C., Zhu H.L., and Tan R.X. Chem. Biodivers. 4 (2007) 248
10. Kohen F., Gayer B., Kulik T., Frydman V., Nevo N., Katzburg S., Limor R., Sharon O., Stern N., and Somjen D. J. Med. Chem. 50 (2007) 6405
11. Ogawara H., Akiyama T., Watanabe S., Ito N., Kobori M., and Seoda Y. J. Antibiot. 42 (1989) 340
12. Booth C., Hargreaves D.F., Hadfield J.A., McGown A.T., and Potten C.S. Br. J. Cancer 80 (1999) 1550
13. Uckun F.M., Narla R.K., Zeren T., Yanishevski Y., Myers D.E., Waurzyniak B., Ek O., Schneider E., Messinger Y., Chelstrom L.M., Gunther R., and Evans W. Clin. Cancer Res. 4 (1998) 1125
14. Messinger Y., Yanishevski Y., Ek O., Zeren T., Waurzyniak B., Gunther R., Chelstrom L., Chandan-Langlie M., Schneider E., Myers D.E., Evans W., and Uckun F.M. Clin. Cancer Res. 4 (1998) 165
15. Grynkiewicz G., Szeja W., and Boryski J. Acta Pol. Pharm. 65 (2008) 655
16. Polkowski K., Popiolkiewicz J., Krzeczyński P., Ramza J., Pucko W., Zegrocka-Stendel O., Boryski J., Skierski J.S., Mazurek A.P., and Grynkiewicz G. Cancer Lett. 203 (2004) 59
17. Popiolkiewicz J., Polkowski K., Skierski J.S., and Mazurek A.P. Cancer Lett. 2005 229 (2005) 67
18. Achmatowicz, O.; Grynkiewicz, G.; Pucko, W.; Mazurek, A.; Polkowski, K.; Boryski, J.; Szeja, W.; Szelejewski W.; Opolski, A.; Pastuch-Gawolek, G.; Radzikowski, C.; Szechner, B.; Wietrzyk, J.; Skierski, J.; Wandzik, I.; Krzeczyński, P. Polish Patent P-346955; PCT/PL02/000029, 2002.
19. Lewis P.T., Wahala K., Hoikkala A., Mutikainen I., Meng Q.H., Adlercreutz H., and Tikkanen M.J. Tetrahedron 56 (2000) 7805
20. Wang S.F., Jiang Q., Ye Y.H., Li Y., and Tan R.X. Bioorg. Med. Chem. 13 (2005) 4880
21. Chern J.H., Shia K.S., Hsu T.A., Tai C.L., and Lee C.C. Bioorg. Med. Chem. Lett. 14 (2004) 2519
22. ElAshry H.S.H., Awad L.F., and Atta A.I. Tetrahedron 62 (2006) 2943
23. Szeja W., and Grynkiewicz G. In: Demchenko A. (Ed). Handbook of Glycosylation (2008), Wiley-VCH, Weinheim 329-361
24. Ferrieres V., Blanchard S., Fischer D., and Plusquellec D. Bioorg. Med. Chem. Lett. 12 (2002) 3515
25. Priebe W., and Zamojski A. Tetrahedron 36 (1980) 287
26. Demchenko A.V., Malysheva N.N., and De Meo C. Org. Lett. 5 (2003) 455
27. 4) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (chloroform) to allow the genistein glycoside as amorphous solid (630 mg, yield 76%).
28. -1; Sigma-Aldrich, Germany).
29. -1). The DNA content was analyzed using Becton Dickinson FACSCanto cytometer (BD Company, USA).
30. ® Fluorescent Mounting Medium (Dako, USA). Slides were examined under Nikon ECLIPSE E800 microscope using 40× objective. The mitotic cells were counted per 500 cells of the specimen.
31. ® slides, Nalgen Nunc International, Rochester, NY, USA) after treatment with genistein, G21, vinblastine or paclitaxel. Microtubules were immunostained as described by Huang, Y. T.; Huang, D. M.; Guh, J. H.; Chen, I. L.; Tzeng C. C.; Teng, C. M. J. Biol. Chem. 2005, 280, 2771. Cells were examined under an Nikon ECLIPSE E800 microscope using an oil immersion objective 100×. The type of mitotic spindle (bipolar = normal, multipolar or monopolar) was counted in 100 of mitotic cells per treatment. Experiments were repeated three times.
32. Hornik J.E., Bader J.R., Tribble E.K., Trimble K., Breunig J.S., Halpin E.S., Vaughan K.T., and Hinchcliffe E.H. Cell Motil. Cytoskeleton 65 (2008) 595
33. Jordan M.A., Thrower D., and Wilson L. J. Cell Sci. 102 (1992) 401
34. Metzler M., and Pheiffer E. Health Perspect. 103 (1995) 21