Polymer conjugates of acridine-type anticancer drugs with pH-controlled activation

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 13, 2012, Pages 4056-4063

  Sedláček, Ondřej ^a   Hrubý, Martin ^a   Studenovský, Martin ^a   Větvička, David ^b,c   Svoboda, Jan ^d   Kaňková, Dana ^a   Kovář, Jan ^e   Ulbrich, Karel ^a  

^a INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

^c CancerTech sro   (Czech Republic)

^d INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^e INSTITUTE FOR CLINICAL AND EXPERIMENTAL MEDICINE   (Czech Republic)

Author keywords

Acridines; Cancer therapy; Controlled release; Drug delivery systems; Hydrazone

Indexed keywords

3 (9 ACRIDINYLAMINO) 5 HYDROXYMETHYLANILINE; 3 (9 ACRIDINYLAMINO) 5 HYDROXYMETHYLANILINE N (4 ACETYLBENZOATE); 3 (9 ACRIDINYLAMINO) 5 HYDROXYMETHYLANILINE N (4 OXOPROPYLBENZOATE); 3 (9 ACRIDINYLAMINO) 5 HYDROXYMETHYLANILINE N (5 METHYL 4 OXOHEXANOATE); 3 (9 ACRIDINYLAMINO) 5 HYDROXYMETHYLANILINE N (5,5 DIMETHYL 4 OXOHEXANOATE); 3 (9 ACRIDINYLAMINO) 5 HYDROXYMETHYLANILINE N LEVULINATE; 9 ANILINOACRIDINE DERIVATIVE; ANTINEOPLASTIC AGENT; ETHIDIUM BROMIDE; HYDRAZIDE; UNCLASSIFIED DRUG; WATER;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BINDING COMPETITION; BIOCOMPATIBILITY; BLOOD PH; CELL NUCLEUS; CELL STRAIN HEPG2; CELL STRAIN MCF 7; CONFOCAL MICROSCOPY; CONTROLLED DRUG RELEASE; DRUG ACTIVATION; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG DETERMINATION; DRUG DNA BINDING; DRUG POTENCY; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; ENDOSOME; FLUORESCENCE MICROSCOPY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; INTERCALATION COMPLEX; INTERNALIZATION; MALE; PH; PROSTATE ADENOCARCINOMA; STEREOSPECIFICITY;

AMSACRINE; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL NUCLEUS; CELL SURVIVAL; DNA; DRUG CARRIERS; HEP G2 CELLS; HUMANS; HYDROGEN-ION CONCENTRATION; INTERCALATING AGENTS; MICROSCOPY, FLUORESCENCE; POLYMERS; WATER;

EID: 84862207656     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.05.007     Document Type: Article

References (39)

1. G.J. Atwell, B.F. Cain, and R.N. Seelye J. Med. Chem. 15 1972 611
2. B.C. Baguley, and R. Nash Eur. J. Cancer 1981 17 1965 671
3. L.R. Ferguson, D.G. Macphee, and B.C. Baguley Chem. Biol. Interact. 44 1983 53
4. S.S. Legha, M.J. Keating, A.R. Zander, K.B. McCredie, G.P. Bodey, and E.J. Freireich Ann. Intern. Med. 93 1980 17
5. B.C. Baguley, W.A. Denny, G.J. Atwell, and B.F. Cain J. Med. Chem. 24 1981 170
6. W.A. Denny, B.F. Cain, G.J. Atwell, C. Hansch, A. Panthananickal, and A. Leo J. Med. Chem. 25 1982 276
7. L.R. Ferguson, and W.A. Denny J. Med. Chem. 22 1979 251
8. T.-L. Su, T.-C. Chou, J.Y. Kim, J.-T. Huang, G. Ciszewska, W.-Y. Ren, G.M. Otter, F.M. Sirotnak, and K.A. Watanabe J. Med. Chem. 38 1995 3226
9. J.L. Jurlina, A. Lindsay, J.E. Packer, B.C. Baguley, and W.A. Denny J. Med. Chem. 30 1987 473
10. I.G.C. Robertson, B.D. Palmer, J.W. Paxton, and G.J. Shaw Xenobiotica 22 1992 657
11. J.-Y. Chang, C.-F. Lin, W.-Y. Pan, V. Bacherikov, T.-C. Chou, C.-H. Chen, H. Dong, S.-Y. Cheng, T.-J. Tasi, Y.-W. Lin, K.-T. Chen, L.-T. Chen, and T.-L. Su Bioorg. Med. Chem. 11 2003 4959
12. T.-L. Su, C.-H. Chen, L.-F. Huang, C.-H. Chen, M.K. Basu, X.-G. Zhang, and T.-C. Chou J. Med. Chem. 42 1999 4741
13. G. Boos, and H. Stopper Toxicol. Lett. 116 2000 7
14. M.G. Ferlin, C. Marzano, G. Chiarelotto, F. Baccichetti, and F. Bordin Eur. J. Med. Chem. 35 2000 827
15. D. Fyfe, C. Price, R.E. Langley, C. Pagonis, J. Houghton, L. Osborne, P.J. Woll, C. Gardner, B.C. Baguley, and J. Carmichael Cancer Chemother. Pharmacol. 47 2001 333
16. S.H. Allan J. Controlled Release 132 2008 153
17. H. Maeda Bioconjugate Chem. 21 2010 797
18. K. Knop, R. Hoogenboom, D. Fischer, and U.S. Schubert Angew. Chem., Int. Ed. 49 2010 6288
19. M. Talelli, C.J.F. Rijcken, C.F. van Nostrum, G. Storm, and W.E. Hennink Adv. Drug Deliv. Rev. 62 2010 231
20. D.B. Pike, and H. Ghandehari Adv. Drug Deliv. Rev. 62 2010 167
21. T. Etrych, P. Chytil, M. Jelinkova, B. Rihova, and K. Ulbrich Macromol. Biosci. 2 2002 43
22. T. Kaneko, D. Willner, I. Monkovic, J.O. Knipe, G.R. Braslawsky, R.S. Greenfield, and D.M. Vyas Bioconjugate Chem. 2 1991 133
23. K. Ulbrich, T. Etrych, P. Chytil, M. Jelinkova, and B. Rihova J. Controlled Release 87 2003 33
24. K. Ulbrich, and V. Subr Adv. Drug Deliv. Rev. 56 2004 1023
25. H. Krakovicova, T. Etrych, and K. Ulbrich Eur. J. Pharm. Sci. 37 2009 405
26. M. Barberis, and J. Pérez-Prieto Tetrahedron Lett. 44 2003 6683
27. T. Etrych, T. Mrkvan, P. Chytil, C. Konak, B. Rihova, and K. Ulbrich J. Appl. Polym. Sci. 109 2008 3050
28. In Drug-DNA Interaction Protocols, 2nd ed.; Fox, K. R., Ed., 2010; Vol. 613, p. 1.
29. T. Mosmann J. Immunol. Methods 65 1983 55
30. O. Hovorka, T. Etrych, V. Subr, J. Strohalm, K. Ulbrich, and B. Rihova J. Drug Target. 14 2006 391
31. V. Šubr, and K. Ulbrich React. Funct. Polym. 66 2006 1525
32. K. Ulbrich, and V. Subr Adv. Drug Deliv. Rev. 62 2010 150
33. M.N. Khan, and A.F. Kuliyaumar Bioorg. Med. Chem. 3 1995 881
34. M.N. Khan, and L. Malspeis J. Org. Chem. 47 1982 2731
35. A. Paul, and S. Ladame Org. Lett. 11 2009 4894
36. T.K. Yeung, J.W. Hopewell, R.H. Simmonds, L.W. Seymour, R. Duncan, O. Bellini, M. Grandi, F. Spreafico, J. Strohalm, and K. Ulbrich Cancer Chemother. Pharmacol. 29 1991 105
37. J. Yang, H.T. Chen, I.R. Vlahov, J.X. Cheng, and P.S. Low J. Pharmacol. Exp. Ther. 321 2007 462
38. L.P.G. Wakelin, G.J. Atwell, G.W. Rewcastle, and W.A. Denny J. Med. Chem. 30 1987 855
39. G.A. Hill, V. Salvin, and W.T.M. O'Brien J. Am. Chem. Soc. 59 1937 2385