The complex role of the triphenylmethyl motif in anticancer compounds

Journal of the American Chemical Society

Volumn 130, Issue 31, 2008, Pages 10274-10281

  Palchaudhuri, Rahul ^a   Nesterenko, Vitaliy ^a   Hergenrother, Paul J ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARSENIC COMPOUNDS; BIOCHEMISTRY; CALCIUM; CELL CULTURE; CELL DEATH; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; CYTOLOGY; MECHANISMS; MONOMERS; POLYMERS; POTASSIUM COMPOUNDS;

ANTI-CANCER AGENTS; ANTICANCER COMPOUNDS; BIOLOGICAL ASSAYS; CANCER CELL LINES; CANCER CELLS; CELL-CYCLE ARREST; HEXOKINASE; MECHANISM OF ACTIONS; PHARMACOPHORE; PHOSPHONATE; POTASSIUM ION CHANNELS; SMALL MOLECULES; TUBULIN POLYMERIZATION;

CELLS;

ANTINEOPLASTIC AGENT; BIFONAZOLE; CALCIUM; CHLORINE DERIVATIVE; CLOTRIMAZOLE; ECONAZOLE; HEXOKINASE; KETOCONAZOLE; MICONAZOLE; NOCODAZOLE; PACLITAXEL; PHOSPHONIC ACID DERIVATIVE; POTASSIUM CHANNEL; TRITYL DERIVATIVE;

ARTICLE; BIOASSAY; CANCER CELL; CELL CULTURE; CELL CYCLE ARREST; CELL DEATH; CONTROLLED STUDY; DRUG MECHANISM; FEMALE; HUMAN; HUMAN CELL; MICROTUBULE ASSEMBLY;

ANTINEOPLASTIC AGENTS; CELL CYCLE; CELL DEATH; CELL LINE, TUMOR; HEXOKINASE; HUMANS; PHOSPHONIC ACIDS; POTASSIUM CHANNELS, CALCIUM-ACTIVATED; STRUCTURE-ACTIVITY RELATIONSHIP; TRITYL COMPOUNDS; TUBULIN;

EID: 48749090995     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8020999     Document Type: Article

References (40)

1. American Cancer Society. In American Cancer Society Statistics for 2007, see: http://www.cancer.org/docroot/PRO/content/ PRO_1_1_Cancer_Statistics_2007_Presentation.asp.
2. Dothager, R. S.; Putt, K. S.; Allen, B. J.; Leslie, B. J.; Nesterenko, V.; Hergenrother, P. J. J. Am. Chem. Soc. 2005, 127, 8686-96.
3. Benzaquen, L. R.; Brugnara, C.; Byers, H. R.; Gatton-Celli, S.; Halperin, J. A. Nat. Med. 1995, 1, 534-40.
4. Khalid, M. H.; Tokunaga, Y.; Caputy, A. J.; Walters, E. J. Neurosurg. 2005, 103, 79-86.
5. Al-Qawasmeh, R. A.; Lee, Y.; Cao, M. Y.; Gu, X.; Vassilakos, A.; Wright, J. A.; Young, A. Bioorg. Med. Chem. Lett. 2004, 14, 347-50.
6. Snajdrova, L.; Xu, A.; Narayanan, N. J. Biol. Chem. 1998, 273, 28032-9.
7. Uddin, M. K.; Reignier, S. G.; Coulter, T.; Montalbetti, C.; Granas, C.; Butcher, S.; Krog-Jensen, C.; Felding, J. Bioorg. Med. Chem. Lett. 2007, 17, 2854-7.
8. Natarajan, A.; Fan, Y. H.; Chen, H.; Guo, Y.; Iyasere, J.; Harbinski, F.; Christ, W. J.; Aktas, H.; Halperin, J. A. J. Med. Chem. 2004, 47, 1882-5.
9. Natarajan, A.; Guo, Y.; Harbinski, F.; Fan, Y. H.; Chen, H.; Luus, L.; Diercks, J.; Aktas, H.; Chorev, M.; Halperin, J. A. J. Med. Chem. 2004, 47, 4979-82.
10. Cao, M. Y.; Lee, Y.; Feng, N. P.; Al-Qawasmeh, R. A.; Viau, S.; Gu, X. P.; Lau, L.; Jin, H.; Wang, M.; Vassilakos, A.; Wright, J. A.; Young, A. H. J. Pharmacol. Exp. Ther. 2004, 308, 538-46.
11. Skoufias, D. A.; DeBonis, S.; Saoudi, Y.; Lebeau, L.; Crevel, I.; Cross, R.; Wade, R. H.; Hackney, D.; Kozielski, F. J. Biol. Chem. 2006, 281, 17559-69.
12. For NCI standard agent database, see: http://dtp.nci.nih.gov/docs/cancer/ searches/standard_agent_table.html.
13. Ogo, N.; Oishi, S.; Matsuno, K.; Sawada, J.; Fujii, N.; Asai, A. Bioorg. Med. Chem. Lett. 2007, 17, 3921-4.
14. Iliopulos, M. I.; Wieder, H. Angew. Chem. 1965, 77, 618-19.
15. The Cancer Genome Project. http://www.sanger.ac.uk/perl/genetics/CGP/ cosmic?action=sample&id=905976.
16. Soengas, M. S.; Capodieci, P.; Polsky, D.; Mora, J.; Esteller, M.; Opitz-Araya, X.; McCombie, R.; Herman, J. G.; Gerald, W. L.; Lazebnik, Y. A.; Cordon-Cardo, C.; Lowe, S. W. Nature 2001, 409, 207-211.
17. HyperCLDB. http://www.biotech.ist.unige.it/cldb/cl7123.html.
18. The Cancer Genome Project. http://www.sanger.ac.uk/perl/genetics/CGP/ cosmic?action=sample&id=905956.
19. Hegemann, L.; Toso, S. M.; Lahijani, K. L.; Webster, G. F.; Uitto, J. J. Investig. Dermatol. 1993, 100, 343-346.
20. Beitner, R. Mol. Genet. Metab. 1998, 64, 161-168.
21. Glass-Marmor, L.; Beitner, R. Eur. J. Pharmacol. 1997, 328, 241-248.
22. Penso, J.; Beitner, R. Eur. J. Pharmacol. 1998, 342, 113-117.
23. Glass-Marmor, L.; Morgenstern, H.; Beitner, R. Eur. J. Pharmacol. 1996, 313, 265-271.
24. Pelicano, H.; Martin, D. S.; Xu, R. H.; Huang, P. Oncogene 2006, 25, 4633-4646.
25. Xu, R.-h.; Pelicano, H.; Zhou, Y.; Carew, J. S.; Feng, L.; Bhalla, K. N.; Keating, M. J.; Huang, P. Cancer Res. 2005, 65, 613-621.
26. Pastorino, J. G.; Shulga, N.; Hoek, J. B. J. Biol. Chem. 2002, 277, 7610-7618.
27. Brugnara, C.; Armsby, C. C.; Sakamoto, M.; Rifai, N.; Alper, S. L.; Platt, O. J. Pharm. Exper. Ther. 1995, 273, 266-272.
28. Wulff, H.; Gutman, G. A.; Cahalan, M. D.; Chandy, K. G. J. Biol. Chem. 2001, 276, 32040-32045.
29. Wulff, H.; Kolski-Andreaco, A.; Sankaranarayanan, A.; Sabatier, J.-M.; Shakkottai, V. Curr. Med. Chem. 2007, 14, 1437-1457.
30. Wulff, H.; Miller, M. J.; Hansel, W.; Grissmer, S.; Cahalan, M. D.; Chandy, K. G. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 8151-8156.
31. Nilius, B.; Wohlrab, W. J. Physiol. 1992, 445, 537-548.
32. Lepple-Wienhues, S.; Berweck, M.; Böhmig, C. P.; Leo, B.; Meyling; Garbe, C.; Wiederholt, M. J. Membr. Biol. 1996, 151, 149-157.
33. Stocker, J. W.; De Franceschi, L.; McNaughton-Smith, G. A.; Corrocher, R.; Beuzard, Y.; Brugnara, C. Blood 2003, 101, 2412-2418.
34. Gemma, S.; et al. J. Med. Chem. 2008, 51, 1278-94.
35. Wins, P.; Wilson, I. B. Biochim. Biophys. Acta 1974, 334, 137-145.
36. Hovanec, J. W.; Lieske, C. N. Biochemistry 1972, 11, 1051-1056.
37. Bjorkling, F.; Dahl, A.; Patkar, S.; Zundel, M. Bioorg. Med. Chem. 1994, 2, 697-705.
38. Feng, B. Y.; Simeonov, A.; Jadhav, A.; Babaoglu, K.; Inglese, J.; Shoichet, B. K.; Austin, C. P. J. Med. Chem. 2007, 50, 2385-2390.
39. Loscher, W.; Potschka, H. Prog. Neurobiol. 2005, 76, 22-76.
40. Khalid, M. H.; Tokunaga, Y.; Caputy, A. J.; Walters, E. J. Neurosurg. 2005, 103, 79-86.