Synthesis, biological evaluation, and structure-activity relationships of novel substituted N-phenyl ureidobenzenesulfonate derivatives blocking cell cycle progression in s-phase and inducing DNA double-strand breaks

Journal of Medicinal Chemistry

Volumn 55, Issue 13, 2012, Pages 6194-6208

  Turcotte, Vanessa ^a,b   Fortin, Sébastien ^a,b   Vevey, Florence ^a   Coulombe, Yan ^b   Lacroix, Jacques ^a   Côté, Marie France ^a   Masson, Jean Yves ^b   C Gaudreault, René ^a,b  

^a LAVAL UNIVERSITY   (Canada)

^b UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2 ETHYLPENYL 4 [3 (3 CHLOROETHYL)UREIDO]BENZENESULFONATE; 2 ETHYLPHENYL 3 [3 (2 CHLOROETHYL)UREIDO]BENZENESULFONATE; 2 ETHYLPHENYL 4 [3 (2 CHLOROETHYL)UREIDO] N 2 TOLYLBENZENESULFONAMIDE; 2 ETHYLPHENYL 4 [3 (2 CHLOROETHYL)UREIDO]BENZENESULFONATE; 2 PROPYLPHENYL 3 [3 (2 CHLOROETHYL)UREIDO]BENZENESULFONATE; 2 PROPYLPHENYL 4 [3 (2 CHLOROETHYL)UREIDO]BENZENESULFONATE; 2 TOLYL 3 [3 (2 CHLOROETHYL)UREIDO] N (2 PROPYLPHENYL)BENZENESULFONATE; 2 TOLYL 3 [3 (2 CHLOROETHYL)UREIDO]BENZENESULFONATE; 2 TOLYL 4 [3 (2 CHLOROETHYL)UREIDO]BENZENESULFONATE; 2 TOLYL 4 [3 (3 CHLOROETHYL)UREIDO]BENZENESULFONATE; 3 (3 ETHYLUREIDO) N 2 TOLYLBENZENESULFONAMIDE; 3 [3 (2 CHLOROETHYL)UREIDO] N (2 ETHYLPHENYL)BENZENESULFONAMIDE; 3 [3 (2 CHLOROETHYL)UREIDO] N (2 PROPYLPHENYL)BENZENESULFONAMIDE; 3 TOLYL 4 [3 (2 CHLOROETHYL)UREIDO]BENZENESULFONATE; 4 (DIMETHYLAMINO)PHENYL 4 [3 (2 CHLOROETHYL)UREIDO]BENZENESULFONATE; 4 (TERT BUTYLDIMETHYLSILYLOXY)PHENYL 3 [3 (2 CHLOROETHYL)UREIDO]BENZENESULFONATE; 4 (TERT BUTYLDIMETHYLSILYLOXY)PHENYL 4 [3 (2 CHLOROETHYL)UREIDO]BENZENESULFONATE; 4 [3 (2 CHLOROETHYL)UREIDO] N (2 ETHYLPHENYL)BENZENESULFONAMIDE; 4 [3 (2 CHLOROETHYL)UREIDO] N (2 PROPYLPHENYL)BENZENESULFONAMIDE; 4 [3 (2 CHLOROETHYL)UREIDO] N 2 TOLYLBENZENESULFONAMIDE; 4 HYDROXYPHENYL 3 [3 (2 CHLOROETHYL)UREIDO]BENZENESULFONATE; 4 HYDROXYPHENYL 4 [3 (2 CHLOROETHYL)UREIDO]BENZENESULFONATE; 4 TOLYL 4 [3 (2 CHLOROETHYL)UREIDO]BENZENESULFONATE; ANTINEOPLASTIC AGENT; CISPLATIN; COMBRETASTATIN A4; GAMMA H2AX; HISTONE H2AX; N PHENYLUREIDOBENZENESULFONAMIDE DERIVATIVE; N PHENYLUREIDOBENZENESULFONATE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL CYCLE PROGRESSION; CELL CYCLE S PHASE; CELL PROLIFERATION; DOUBLE STRANDED DNA BREAK; DRUG STRUCTURE; DRUG SYNTHESIS; EMBRYO; HUMAN; HUMAN CELL; IC 50; NONHUMAN; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANIMALS; ANTICARCINOGENIC AGENTS; BENZENESULFONATES; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; CHICK EMBRYO; CHORIOALLANTOIC MEMBRANE; CISPLATIN; DNA BREAKS, DOUBLE-STRANDED; HISTONES; HT29 CELLS; HUMANS; IMIDAZOLIDINES; JURKAT CELLS; NEOPLASMS; PHENYLUREA COMPOUNDS; PHOSPHORYLATION; S PHASE; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84863848847     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3006492     Document Type: Article

References (29)

1. Fortin, J. S.; Lacroix, J.; Desjardins, M.; Patenaude, A.; Petitclerc, E.; C.-Gaudreault, R. Alkylation potency and protein specificity of aromatic urea derivatives and bioisosteres as potential irreversible antagonists of the colchicine-binding site Bioorg. Med. Chem. 2007, 15, 4456-4469 (Pubitemid 46777295)
2. Fortin, S.; Moreau, E.; Lacroix, J.; Teulade, J. C.; Patenaude, A.; C.-Gaudreault, R. N -Phenyl- N -(2-chloroethyl)urea analogues of combretastatin A-4: Is the N -phenyl- N -(2-chloroethyl)urea pharmacophore mimicking the trimethoxy phenyl moiety? Bioorg. Med. Chem. Lett. 2007, 17, 2000-2004 (Pubitemid 46389583)
3. Fortin, S.; Moreau, E.; Patenaude, A.; Desjardins, M.; Lacroix, J.; Rousseau, J. L.; C.-Gaudreault, R. N -Phenyl- N -(2-chloroethyl)ureas (CEU) as potential antineoplastic agents. Part 2: Role of ?-hydroxyl group in the covalent binding to β-tubulin Bioorg. Med. Chem. 2007, 15, 1430-1438 (Pubitemid 46043436)
4. Moreau, E.; Fortin, S.; Desjardins, M.; Rousseau, J. L.; Petitclerc, E.; C.-Gaudreault, R. Optimized N -phenyl- N -(2-chloroethyl)ureas as potential antineoplastic agents: synthesis and growth inhibition activity Bioorg. Med. Chem. 2005, 13, 6703-6712 (Pubitemid 41571214)
5. Moreau, E.; Fortin, S.; Lacroix, J.; Patenaude, A.; Rousseau, J. L.; C.-Gaudreault, R. N -Phenyl- N -(2-chloroethyl)ureas (CEUs) as potential antineoplastic agents. Part 3: Role of carbonyl groups in the covalent binding to the colchicine-binding site Bioorg. Med. Chem. 2008, 16, 1206-1217 (Pubitemid 351200485)
6. Mounetou, E.; Legault, J.; Lacroix, J.; C.-Gaudreault, R. Antimitotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of N -aryl- N -(2-chloroethyl)ureas as new selective alkylating agents J. Med. Chem. 2001, 44, 694-702 (Pubitemid 32171666)
7. Mounetou, E.; Legault, J.; Lacroix, J.; C.-Gaudreault, R. A new generation of N -aryl- N -(1-alkyl-2-chloroethyl)ureas as microtubule disrupters: synthesis, antiproliferative activity, and β-tubulin alkylation kinetics J. Med. Chem. 2003, 46, 5055-5063 (Pubitemid 37352042)
8. II-tubulin and thioredoxin-1 by structurally related subsets of aryl chloroethylureas leading to either anti-microtubules or redox modulating agents Bioorg. Med. Chem. 2008, 16, 7277-7290
9. Fortin, J. S.; Cote, M. F.; Lacroix, J.; Patenaude, A.; Petitclerc, E.; C.-Gaudreault, R. Cycloalkyl-substituted aryl chloroethylureas inhibiting cell cycle progression in G0/G1 phase and thioredoxin-1 nuclear translocation Bioorg. Med. Chem. Lett. 2008, 18, 3526-3531 (Pubitemid 351787570)
10. Fortin, J. S.; Cote, M. F.; Lacroix, J.; Petitclerc, E.; C.-Gaudreault, R. Aromatic 2-chloroethyl urea derivatives and bioisosteres. Part 2: Cytocidal activity and effects on the nuclear translocation of thioredoxin-1, and the cell cycle progression Bioorg. Med. Chem. 2008, 16, 7477-7488
11. 1 arrest in B16 cells Br. J. Pharmacol. 2007, 152, 449-455 (Pubitemid 47585042)
12. Patenaude, A.; Deschesnes, R. G.; Rousseau, J. L.; Petitclerc, E.; Lacroix, J.; Cote, M. F.; C.-Gaudreault, R. New soft alkylating agents with enhanced cytotoxicity against cancer cells resistant to chemotherapeutics and hypoxia Cancer Res. 2007, 67, 2306-2316 (Pubitemid 46424251)
13. Bouchon, B.; Chambon, C.; Mounetou, E.; Papon, J.; Miot-Noirault, E.; Gaudreault, R.; Madelmont, J. C.; Degoul, F. Alkylation of β-tubulin on Glu 198 by a microtubule disrupter Mol. Pharmacol. 2005, 68, 1415-1422 (Pubitemid 41539997)
14. Fortin, S.; Wei, L.; Moreau, E.; Labrie, P.; Petitclerc, E.; Kotra, L. P.; C.-Gaudreault, R. Mechanism of action of N -phenyl- N -(2-chloroethyl)ureas in the colchicine-binding site at the interface between α- and β-tubulin Bioorg. Med. Chem. 2009, 17, 3690-3697
15. Wiesen, K. M.; Xia, S.; Yang, C. P.; Horwitz, S. B. Wild-type class I β-tubulin sensitizes Taxol-resistant breast adenocarcinoma cells harboring a β-tubulin mutation Cancer Lett. 2007, 257, 227-235 (Pubitemid 47538828)
16. Fortin, S.; Wei, L.; Moreau, E.; Lacroix, J.; Cote, M. F.; Petitclerc, E.; Kotra, L. P.; C.-Gaudreault, R. Design, synthesis, biological evaluation, and structure-activity relationships of substituted phenyl 4-(2-oxoimidazolidin- 1-yl)benzenesulfonates as new tubulin inhibitors mimicking combretastatin A-4 J. Med. Chem. 2011, 54, 4559-4580
17. Screening Services. NCI-60 DTP Human Tumor Cell Line Screen. http://dtp.nci.nih.gov/branches/btb/ivclsp.html (accessed September 25, 2011).
18. Paull, T. T.; Rogakou, E. P.; Yamazaki, V.; Kirchgessner, C. U.; Gellert, M.; Bonner, W. M. A critical role for histone H2AX in recruitment of repair factors to nuclear foci after DNA damage Curr. Biol. 2000, 10, 886-895 (Pubitemid 30647617)
19. Ivashkevich, A. N.; Martin, O. A.; Smith, A. J.; Redon, C. E.; Bonner, W. M.; Martin, R. F.; Lobachevsky, P. N. γH2AX foci as a measure of DNA damage: a computational approach to automatic analysis Mutat. Res., Fundam. Mol. Mech. Mutagen. 2011, 711, 49-60
20. Bonner, W. M.; Redon, C. E.; Dickey, J. S.; Nakamura, A. J.; Sedelnikova, O. A.; Solier, S.; Pommier, Y. γH2AX and cancer Nat. Rev. Cancer. 2008, 8, 957-967
21. Rogakou, E. P.; Pilch, D. R.; Orr, A. H.; Ivanova, V. S.; Bonner, W. M. DNA double-stranded breaks induce histone H2AX phosphorylation on serine 139 J. Biol. Chem. 1998, 273, 5858-5868 (Pubitemid 28124064)
22. Rogakou, E. P.; Nieves-Neira, W.; Boon, C.; Pommier, Y.; Bonner, W. M. Initiation of DNA fragmentation during apoptosis induces phosphorylation of H2AX histone at serine 139 J. Biol. Chem. 2000, 275, 9390-9395 (Pubitemid 30185164)
23. Rodrigue, A.; Lafrance, M.; Gauthier, M. C.; McDonald, D.; Hendzel, M.; West, S. C.; Jasin, M.; Masson, J. Y. Interplay between human DNA repair proteins at a unique double-strand break in vivo EMBO J. 2006, 25, 222-231 (Pubitemid 43077310)
24. Brooks, P. C.; Silletti, S.; von Schalscha, T. L.; Friedlander, M.; Cheresh, D. A. Disruption of angiogenesis by PEX, a noncatalytic metalloproteinase fragment with integrin binding activity Cell 1998, 92, 391-400 (Pubitemid 28093016)
25. Petitclerc, E.; Boutaud, A.; Prestayko, A.; Xu, J.; Sado, Y.; Ninomiya, Y.; Sarras, M. P., Jr.; Hudson, B. G.; Brooks, P. C. New functions for non-collagenous domains of human collagen type IV. Novel integrin ligands inhibiting angiogenesis and tumor growth in vivo J. Biol. Chem. 2000, 275, 8051-8061 (Pubitemid 30159718)
26. Uchibayashi, T.; Lee, S. W.; Kunimi, K.; Ohkawa, M.; Endo, Y.; Noguchi, M.; Sasaki, T. Studies of effects of anticancer agents in combination with/without hyperthermia on metastasized human bladder cancer cells in chick embryos using the polymerase chain reaction technique Cancer Chemother. Pharmacol. 1994, 35, 84-87
27. Petitclerc, E.; Deschesnes, R. G.; Cote, M. F.; Marquis, C.; Janvier, R.; Lacroix, J.; Miot-Noirault, E.; Legault, J.; Mounetou, E.; Madelmont, J. C.; C.-Gaudreault, R. Antiangiogenic and antitumoral activity of phenyl-3-(2-chloroethyl)ureas: a class of soft alkylating agents disrupting microtubules that are unaffected by cell adhesion-mediated drug resistance Cancer Res. 2004, 64, 4654-4663 (Pubitemid 38856940)
28. Lyu, M. A.; Choi, Y. K.; Park, B. N.; Kim, B. J.; Park, I. K.; Hyun, B. H.; Kook, Y. H. Over-expression of urokinase receptor in human epidermoid-carcinoma cell line (HEp3) increases tumorigenicity on chorio-allantoic membrane and in severe-combined-immunodeficient mice Int. J. Cancer 1998, 77, 257-263
29. Kim, J.; Yu, W.; Kovalski, K.; Ossowski, L. Requirement for specific proteases in cancer cell intravasation as revealed by a novel semiquantitative PCR-based assay Cell 1998, 94, 353-362 (Pubitemid 28376079)