Synthesis and biological evaluation of novel β-carbolines as potent cytotoxic and DNA intercalating agents

Chemical and Pharmaceutical Bulletin

Volumn 58, Issue 7, 2010, Pages 901-907

  Chen, Zhiyong ^a   Cao, Rihui ^a   Shi, Buxi ^a   Yi, Wei ^a,b   Yu, Liang ^a   Song, Huacan ^a   Ren, Zhenhua ^a  

^a SUN YAT SEN UNIVERSITY   (China)

^b Laboratoire de Pharmacochimie   (France)

Author keywords

Cytotoxic; Intercalating; Melting temperature; Synthesis; carboline

Indexed keywords

3 [N (3 DIMETHYLAMINO)PROPYL]AMINOMETHYL 1 METHYL BETA CARBOLINE; 3 [N (3 DIMETHYLAMINO)PROPYL]AMINOMETHYL 1,9 DIMETHYL BETA CARBOLINE; 3 [N (3 DIMETHYLAMINO)PROPYL]AMINOMETHYL 9 (3 PHENYL)PROPYL 1 METHYL BETA CARBOLINE; 3 [N (3 DIMETHYLAMINO)PROPYL]AMINOMETHYL 9 BENZYL 1 METHYL BETA CARBOLINE; 3 [N (3 DIMETHYLAMINO)PROPYL]AMINOMETHYL 9 N BUTYL 1 METHYL BETA CARBOLINE; ALKYL GROUP; BETA CARBOLINE DERIVATIVE; CISPLATIN; CYTOTOXIC AGENT; INTERCALATING AGENT; PACLITAXEL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG; CARBOLINE DERIVATIVE; DNA;

ARTICLE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INTERCALATION COMPLEX; STRUCTURE ACTIVITY RELATION; CHEMISTRY; DNA DENATURATION; METABOLISM; SPECTROFLUOROMETRY; SYNTHESIS; TOXICITY; TRANSITION TEMPERATURE; TUMOR CELL LINE;

CARBOLINES; CELL LINE, TUMOR; DNA; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INTERCALATING AGENTS; NUCLEIC ACID DENATURATION; SPECTROMETRY, FLUORESCENCE; TRANSITION TEMPERATURE;

EID: 77954298116     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.58.901     Document Type: Article

References (33)

1. Cao R., Peng W., Wang Z., Xu A., Curr. Med. Chem., 14, 479-500 (2007).
2. Cain M., Weber R. W., Guzman F., Cook J. M., Barker S. A., Rice K. C., Crawley J. N., Paul S. M., Skolnick P., J. Med. Chem. , 25, 1081-1091 (1982).
3. Hollinshead S. P., Trudell M. L., Skolnick P., Cook J. M., J. Med. Chem., 33, 1062-1069 (1990).
4. Allen M. S., LaLoggia A. J., Dorn L. J., Martin M. J., Costantino G., Hagen T. J., Koehler K. F., Skolnick P., Cook J. M., J. Med. Chem., 35, 4001-4010 (1992).
5. Cox E. D., Diaz-Arauzo H., Huang Q., Reddy M. S., Ma C., Harris B., McKernan R., Skolnick P., Cook J. M., J. Med. Chem., 41, 2537-2552 (1998).
6. Grella B., Teitler M., Smith C., Herrick-Davis K., Glennon R. A., Bioorg. Med. Chem. Lett., 13, 4421-4425 (2003).
7. Audia J. E., Evrard D. A., Murdoch G. R., Droste J. J., Nissen J. S., Schenck K. W., Fludzinski P., Lucaites V. L., Nelson D. L., Cohen M. L., J. Med. Chem., 39, 2773-2780 (1996).
8. Husbands S. M., Glennon R. A., Gorgerat S., Gough R., Tyacke R., Crosby J., Nutt D. J., Lewis J. W., Hudson A. L., Drug Alcohol Depend., 64, 203-208 (2001).
9. Miralles A., Esteban S., Sastre-Coll A., Moranta D., Asensio V. J., Garcia-Sevilla J. A., Eur. J. Pharmacol., 518, 234-242 (2005).
10. Ishida J., Wang H. K., Bastow K. F., Hu C. Q., Lee K. H., Bioorg. Med. Chem. Lett., 9, 3319-3324 (1999).
11. Xiao S., Lin W., Wang C., Yang M., Bioorg. Med. Chem. Lett., 11, 437-441 (2001).
12. Shen Y. C., Chen C. Y., Hsieh P. W., Duh C. Y., Lin Y. M., Ko C. L., Chem. Pharm. Bull., 53, 32-36 (2005).
13. Deveau A.M., Labroli M. A., Dieckhaus C. M., Barthen M. T., Smith K. S., Macdonald T. L., Bioorg. Med. Chem. Lett., 11, 1251-1255 (2001).
14. Zhao M., Bi L., Wang W., Wang C., Baudy-Floc'h M., Ju J., Peng S., Bioorg. Med. Chem., 14, 6998-7010 (2006).
15. Formagio A. S. N., Dusman L. T. D., Foglio M. A., Madjarof C., Carvalho J. E., Costa W. F., Cardoso F. P., Sarragiotto M. H., Bioorg. Med. Chem., 16, 9660-9667 (2008).
16. Wu J., Zhao M., Qian K., Lee K.-H., Morris-Natschke S., Peng S., Eur. J. Med. Chem., 44, 4153-4161 (2009).
17. Boursereau Y., Coldham I., Bioorg. Med. Chem. Lett., 14, 5841-5844 (2004).
18. Hayashi K., Nagao M., Sugimura T., Nucleic Acids Res., 4, 3679-3685 (1977).
19. Song Y., Wang J., Teng S. F., Kesuma D., Deng Y., Duan J., Wang J. H., Qi R. Z., Sim M. M., Bioorg. Med. Chem. Lett., 12, 1129-1132 (2002).
20. Song Y., Kesuma D., Wang J., Deng Y., Duan J., Wang J. H., Qi R. Z., Biochem. Biophys. Res. Commun., 317, 128-132 (2004).
21. Li Y., Liang F., Jiang W., Yu F., Cao R., Ma Q., Dai X., Jiang J., Wang Y., Si S., Cancer Biol. Ther., 6, 1193-1199 (2007).
22. Castro A. C., Dang L. C., Soucy F., Grenier L., Mazdiyasni H., Hottelet M., Parent L., Pien C., Palombella V., Adams J., Bioorg. Med. Chem. Lett., 13, 2419-2422 (2003).
23. Trujillo J. I., Meyers M. J., Anderson D. R., Hegde S., Mahoney M. W., Vernier W. F., Buchler I. P.,. Wu K. K, Yang S., Hartmann S. J., Reitz D. B., Bioorg. Med. Chem. Lett., 17, 4657-4663 (2007).
24. Zhang J., Li Y., Guo L., Cao R., Zhao P., Jiang W., Ma Q., Yi H., Li Z., Jiang J., Wu J., Wang Y., Si S., Cancer Biol. Ther., 8, 2374-2383 (2009).
25. Barsanti P. A., Wang W., Ni Z., Duhl D., Brammeier N., Martin E., Bussiere O., Walter A. O., Bioorg. Med. Chem. Lett., 20, 157-160 (2010).
26. Cao R., Chen Q., Hou X., Chen H., Guan H., Ma Y., Peng W., Xu A., Bioorg. Med. Chem., 12, 4613-4623 (2004).
27. Cao R., Peng W., Chen H., Hou X., Guan H., Chen Q., Ma Y., Xu A., Eur. J. Med. Chem., 40, 249-257 (2005).
28. Cao R., Chen H., Peng W., Ma Y., Hou X., Guan H., Liu X., Xu A., Eur. J. Med. Chem., 40, 991-1001 (2005).
29. Guan H., Chen H., Peng W., Ma Y., Cao R., Liu X., Xu A., Eur. J. Med. Chem., 41, 1167-1179 (2006).
30. Cao R., Yi W., Wu Q., Guan X., Feng M., Ma C., Chen Z., Song H., Peng W., Bioorg. Med. Chem. Lett., 18, 6558-6561 (2008).
31. Wu Q., Cao R., Feng M., Guan X., Ma C., Liu J., Song H., Peng W., Eur. J. Med. Chem., 44, 533-540 (2009).
32. Lemster T., Pindur U., Lenglet G., Depauw S., Dassi C., David-Cordonnier M., Eur. J. Med. Chem., 44, 3235-3252 (2009).
33. Tan C., Liu J., Chen L., Shi S., Ji L., J. Inorg. Biochem., 102, 1644-1653 (2008).