New insight for fluoroquinophenoxazine derivatives as possibly new potent topoisomerase I inhibitor

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 4, 2008, Pages 1520-1524

  Kang, Da Hye ^a   Kim, Jung Sook ^b   Jung, Mi Ja ^a   Lee, Eung Seok ^c   Jahng, Yurngdong ^c   Kwon, Youngjoo ^a   Na, Younghwa ^b  

^a Ewha Womans University   (South Korea)

^b Catholic University of Daegu   (South Korea)

^c Yeungnam University   (South Korea)

Author keywords

Anti cancer agents; Fluoroquinophenoxazines; Topoisomerases I and II inhibition

Indexed keywords

1 (3 AMINO 1 PYRROLIDINYL) 2 FLUORO 4 OXO 4H QUINO[8,1A,1 B,C][1,4]BENZOXAZINE 5 CARBOXYLIC ACID; ANTINEOPLASTIC AGENT; CAMPTOTHECIN; DNA TOPOISOMERASE; DNA TOPOISOMERASE (ATP HYDROLYSING); DNA TOPOISOMERASE INHIBITOR; DOXORUBICIN; ETOPOSIDE; GYRASE INHIBITOR; PHENOXAZINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL DIVISION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG EFFICACY; DRUG POTENCY; ENZYME INHIBITION; HUMAN; HUMAN CELL;

ANTINEOPLASTIC AGENTS; DNA TOPOISOMERASES, TYPE I; DNA TOPOISOMERASES, TYPE II; ENZYME INHIBITORS; FLUOROQUINOLONES; HCT116 CELLS; HELA CELLS; HL-60 CELLS; HUMANS; OXAZINES;

EID: 38949162250     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.12.053     Document Type: Article

References (23)

1. Wise R., Andrew J.M., and Edwards J.M. Antimicrob. Agents Chemother. 23 (1983) 559
2. Koga H., Itoh A., Murayama S., Suzue S., and Irikura T. J. Med. Chem. 23 (1980) 1358
3. Bhanot S.K., Singh M., and Chartterjee N.R. Curr. Pharm. Des. 7 (2001) 313
4. Anderson V.E., and Osheroff N. Curr. Pharm. Des. 7 (2001) 339
5. Derilca K. Curr. Opin. Microbiol. 2 (1999) 504
6. Chu D.T.W., and Maleczka Jr. R.E. J. Heterocyclic. Chem. 24 (1987) 453
7. Chu D.T.W., Hallas R., Clement J.J., Alder J., and McDonald E. Drugs Exp. Clin. Res. 18 (1992) 275
8. Chu D.T.W., Hallas R., Tanaka S.K., Alder J., Balli D., and Plattner J.J. Drugs Exp. Clin. Res. 20 (1994) 177
9. Zeng Q., Kwok Y., Kerwin S.M., Mangold G., and Hurley L.H. J. Med. Chem. 41 (1998) 4273
10. Duan W., Rangan A., Vankayalapati H., Kim M.-Y., Zeng Q., Sun D., Han H., Federoff O.Y., Nishioka D., Rha S.Y., Izbicka D., Von Hoff D.D., and Hurley L.H. Mol. Cancer Ther. 1 (2001) 103
11. Kim M.-Y., Duan W., Gleason-Guzman M., and Hurley L.H. J. Med. Chem. 46 (2003) 571
12. Na Y., and Kwon Y. Chem. Pharm. Bull. 54 (2006) 248
13. Robinson M.J., Martin B.A., Gootz T.D., McGuirk P.R., and Osheroff N. Antimicrob. Agents Chemother. 36 (1992) 751
14. Kwok Y., Zeng Q., and Hurley L.H. J. Biol. Chem. 274 (1999) 17226
15. Kwok Y., Sun D., Clement J., and Hurley L.H. Anti-Cancer Drug Des. 14 (1999) 443
16. Whitten, J.P.; Schwaebe, M.; Siddiqui-Jain, A.; Moran, T. US pat. Appl. Publ. 2006. 8pp, U.S. Ser. No. 903, 975.
17. C-F = 8.1 Hz), 121.2, 141.3, 152.3, 153.7, 162.7, 168.3, 177.9. Other peaks were not observed due to low concentration of this compound.
18. 2, 5 mM dithiothreitol, 2 mM spermidine, and 0.01% bovine serum albumin). The reaction in the final volume of 10 μL was terminated by adding 2.5 μL of the stop solution containing 10% SDS, 0.2% bromophenol blue, 0.2% xylene cyanol, and 30% glycerol. DNA samples were then electrophoresesed on a 1% agarose gel at 15 V for 7 h with a running buffer of TAE. Gels were stained for 30 min in an aqueous solution of ethidium bromide (0.5 μg/mL). DNA bands were visualized by transillumination with UV light and were quantitated using AlphaImager™ (Alpha Innotech Corporation).
19. 2, 1 mM EDTA, 1 mM ATP, and 15 μg/mL bovine serum albumin) for 30 min at 30 °C. The reaction in a final volume of 20 μL was terminated by the addition of 3μL of 7 mM EDTA. Reaction products were analyzed on a 1% agarose gel at 25 V for 4 h with a running buffer of TAE. Gels were stained for 30 min in an aqueous solution of ethidium bromide (0.5 μg/mL). DNA bands were visualized by transillumination with UV light and supercoiled DNA was quantitated using AlphaImagerTM (Alpha Innotech Corporation)
20. 50 values, the absorbance readings at 450 nm were fitted to the four-parameter logistic equation. The compounds of adriamycin, etoposide, and camptothecin were purchased from Sigma and used as positive controls.
21. Zhao L.X., Kim T.S., Ahn S.H., Kim T.H., Kim E.K., Cho W.J., Choi H., Lee C.S., Kim J.A., Jeong T.C., Chang C.-j., and Lee E.-S. Bioorg. Med. Chem. Lett. 11 (2001) 2659
22. Cho W.J., Le Q.M., Van H.T.M., Lee K.Y., Kang B.Y., Lee E.-S., Lee S.K., and Kwon Y. Bioorg. Med. Chem. Lett. 17 (2007) 3531
23. Seo C.S., Li G., Kim C.H., Lee C.S., Jahng Y., Chang H.W., and Son J.K. Arch. Pharm. Res. 30 (2007) 1404