Ferrocenyl flavonoid-induced morphological modifications of endothelial cells and cytotoxicity against B16 murine melanoma cells

Journal of Organometallic Chemistry

Volumn 734, Issue , 2013, Pages 78-85

  Monserrat, Jean Philippe ^a,b   Tiwari, Keshri Nath ^a,b   Quentin, Lionel ^b,c,d,e   Pigeon, Pascal ^a,b   Jaouen, Gérard ^a,b   Vessières, Anne ^a,b   Chabot, Guy G ^b,c,d,e   Hillard, Elizabeth A ^a,b  

^a PSL RESEARCH UNIVERSITY   (France)

^b CNRS   (France)

^c PSL RESEARCH UNIVERSITY   (France)

^d UNIVERSITÉ PARIS DESCARTES   (France)

^e INSERM   (France)

Author keywords

Antivascular agents; Aurones; Bioorganometallic chemistry; Cytotoxicity; Ferrocene; Flavones

Indexed keywords

ANTIVASCULAR; AURONES; BIO-ORGANOMETALLIC CHEMISTRY; FERROCENES; FLAVONES;

CELL CULTURE; DERMATOLOGY; DISEASES; ENDOTHELIAL CELLS; FLAVONOIDS; ONCOLOGY; ORGANOMETALLICS;

CYTOTOXICITY;

MURINAE;

EID: 84876672830     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2012.12.031     Document Type: Conference Paper

References (62)

1. Using the query "flavonoid" at clinicaltrials.gov on October 15, 2012, one finds some 60 clinical trials where flavonoids have been/are currently being studied.
2. J. Molnár, H. Engi, J. Hohmann, P. Molnár, J. Deli, O. Wesolowska, K. Michalak, and Q. Wang Curr. Top. Med. Chem. 10 2010 1757 1768
3. L. Gamet-Payrastre, S. Manenti, M.-P. Gratacap, J. Tulliez, H. Chap, and B. Payrastre Gen. Pharmacol. 32 1999 279 286
4. P.C. Ferriola, V. Cody, and E. Middleton Jr. Biochem. Pharmacol. 38 1989 1617 1624
5. B. Halder, S. Das Gupta, and A. Gomes FEBS J. 279 2012 2876 2891
6. A. Boumendjel, X. Ronot, and J. Boutonnat Curr. Drug Targets 10 2009 363 371
7. F. Li, C. Li, H. Zhang, Z. Lu, Z. Li, Q. You, N. Lu, and Q. Guo Toxicol. Appl. Pharmacol. 261 2012 217 226
8. C.J. Weng, and G.C. Yen Cancer Metastasis Rev. 31 2012 323 351
9. B.C. Baguley Clin. Lung Cancer 12 2011 81 86
10. B.C. Baguley, and M.J. McKeage Future Oncol. 6 2010 1537 1543
11. M.J. McKeage, and B.C. Baguley Cancer 116 2010 1859 1871
12. M. Patra, G. Gasser, and N. Metzler-Nolte Dalton Trans. 41 2012 6350 6358
13. M. Navarro, W. Castro, and C. Biot Organometallics 31 2012 5715 5727
14. M. Patra, and G. Gasser ChemBioChem 13 2012 1232 1252
15. G. Jaouen, and N. Metzler-Nolte Medicinal Organometallic Chemistry 2010 Springer-Verlag Berlin Heidelberg
16. G. Gasser, and N. Metzler-Nolte Curr. Opin. Chem. Biol. 16 2012 84 91
17. C.G. Hartinger, N. Metzler-Nolte, and P.J. Dyson Organometallics 31 2012 5677 5685
18. J. Spencer, J. Amin, M. Wang, G. Packham, S.S. Alwi, G.J. Tizzard, S.J. Coles, R.M. Paranal, J.E. Bradner, and T.D. Heightman ACS Med. Chem. Lett. 2 2011 358 362
19. C. Biot, N. Chavain, F. Dubar, B. Pradines, X. Trivelli, J. Brocard, I. Forfar, and D. Dive J. Organomet. Chem. 694 2009 845 854
20. E.A. Hillard, A. Vessières, L. Thouin, G. Jaouen, and C. Amatore Angew. Chem. Int. Ed. 45 2006 285 290
21. W.H. Ang, A. Casini, G. Sava, and P.J. Dyson J. Organomet. Chem. 696 2010 989 998
22. Z. Liu, A. Habtemariam, A. Pizarro, S. Fletcher, A. Kisova, O. Vrana, L. Salassa, P. Bruijnincx, G. Clarkson, V. Brabec, and P. Sadler J. Med. Chem. 54 2011 3011 3026
23. S. Chatterjee, I. Biondi, P.J. Dyson, and A. Bhattacharyya J. Biol. Inorg. Chem. 16 2011 715 724
24. N. Metzler-Nolte, and M. Salmain The bioorganometallic chemistry of ferrocene P. Stepnicka, Ferrocenes: Ligands, Materials and Biomolecules 2008 Wiley Chichester 499 639
25. E.A. Hillard, A. Vessières, and G. Jaouen Ferrocene functionalized endocrine modulators as anticancer agents N. Metzler-Nolte, G. Jaouen, Top. Organ. Chem., Medicinal Organometallic Chemistry 32 2010 Springer Verlag Berlin Heidelberg 81 117
26. I. Damljanovic, M. Vukicevic, N. Radulovic, R. Palic, E. Ellmerer, Z. Ratkovic, M.D. Joksovic, and R.D. Vukicevic Bioorg. Med. Chem. Lett. 19 2009 1093 1096
27. F. Dubar, T.J. Egan, B. Pradines, D. Kuter, K.K. Ncokazi, D. Forge, J.F. Paul, C. Pierrot, H. Kalamou, J. Khalife, E. Buisine, C. Rogier, H. Vezin, I. Forfar, C. Slomianny, X. Trivelli, S. Kapishnikov, L. Leiserowitz, D. Dive, and C. Biot ACS Chem. Biol. 6 2011 275 287
28. J.-P. Monserrat, R.I. Al-Safi, K.N. Tiwari, L. Quentin, G.G. Chabot, A. Vessières, G. Jaouen, N. Neamati, and E.A. Hillard Bioorg. Med. Chem. Lett. 20 2011 6195 6197
29. R. Schobert, S. Seibt, K. Mahal, A. Ahmad, B. Biersack, K. Effenberger-Neidnicht, S. Padhye, F.H. Sarkar, and T. Mueller J. Med. Chem. 54 2011 6177 6182
30. N.T. Huynh, M. Morille, J. Bejaud, P. Legras, A. Vessieres, G. Jaouen, J.P. Benoit, and C. Passirani Pharmaceut. Res. 28 2011 3189 3198
31. N.T. Huynh, C. Passirani, E. Allard-Vannier, L. Lemaire, J. Roux, E. Garcion, A. Vessieres, and J.-P. Benoit Int. J. Pharma. 423 2012 55 62
32. M. Roger, A. Clavreul, N.T. Huynh, C. Passirani, P. Schiller, A. Vessieres, C. Montero-Menei, and P. Menei Int. J. Pharma. 423 2012 63 68
33. For a recent review see: M. Grazul, and E. Budzisz Coord. Chem. Rev. 253 2009 2588 2598
34. X. Wu, P. Wilairat, and M.-L. Goa Bioorg. Med. Chem. Lett. 12 2002 2299 2302
35. L. Nagy, H. Mehner, A.A. Christy, E. Sletten, F.T. Edelmann, and Q.M. Andersen J. Radioanal. Nucl. Chem. 227 1998 89 98
36. C.E. Anson, C.S. Creaser, A.V. Malkov, L. Mojovic, and G.R. Stephanson J. Organomet. Chem. 668 2003 101 122
37. V. Guerchais, and J.-L. Fillaut Coord. Chem. Rev. 255 2011 2448 2457
38. J.-L. Fillaut, J. Andriès, R.D. Marwaha, P.-H. Lanoë, O. Lohio, L. Toupet, and J.A.G. Williams J. Organomet. Chem. 693 2008 228 234
39. C.E. Anson, C.S. Creaser, J.A. Downie, O. Egyed, A.V. Malkov, L. Mojovic, G.R. Stephenson, A.T. Turner, and K.E. Wilson Bioorg. Med. Chem. Lett. 8 1998 3549 3554
40. W. Langseth Inorg. Chim. Acta 90 1984 53 56
41. A. Kurzwernhart, W. Kandioller, C. Bartel, S. Bächler, R. Trondl, G. Mühlgassner, M.A. Jakupec, V.B. Arion, D. Marko, B.K. Keppler, and C.G. Hartinger Chem. Commun. 48 2012 4839 4841
42. K.N. Tiwari, J.-P. Monserrat, F. de Montigny, G. Jaouen, M.-N. Rager, and E. Hillard Organometallics 30 2011 5424 5432
43. K.N. Tiwari, J.-P. Monserrat, A. Hequet, C. Ganem-Elbaz, T. Cresteil, G. Jaouen, A. Vessières, E.A. Hillard, and C. Jolivalt Dalton Trans. 41 2012 6451 6457
44. N.N. Agrawal, and P.A. Soni Indian J. Chem. 44B 2005 2601 2603
45. Z. Du, H. Ng, K. Zhang, H. Zeng, and J. Wang Org. Biomol. Chem. 9 2011 6930 6933
46. T. Patonay, J. Jeko, and E. Riman Syn. Commun. 32 2002 2403 2415
47. K. Dahlén, E.A.A. Wallén, M. Grøtli, and K. Luthman J. Org. Chem. 71 2006 6863 6871
48. M. Yoshida, Y. Fujino, and T. Doi Org. Lett. 13 2011 4526 4529
49. J.I. Lee, H.S. Son, and H. Park Bull. Korean Chem. Soc. 25 2004 1945 1947
50. G.A. Kraus, and V. Gupta Org. Lett. 22 2010 5278 5280
51. O.V. Singh, and M. Muthukrishnan Indian J. Chem. 44B 2005 2575 2581
52. C.J. Edgell, C.C. McDonald, and J.B. Graham Proc. Natl. Acad. Sci. U S A 80 1983 3734 3737
53. D. Bouis, G.A. Hospers, C. Meijer, G. Molema, and N.H. Mulder Angiogenesis 4 2001 91 102
54. C.R. Hauser, and J.K. Lindsay J. Org. Chem. 22 1957 482 485
55. A. Arezki, E. Brulé, and G. Jaouen Organometallics 28 2009 1606 1609
56. N. Mur Blanch, G.G. Chabot, L. Quentin, D. Scherman, S. Bourg, and D. Dauzonne Eur. J. Med. Chem. 54 2012 22 32
57. A. Vessières, S. Top, P. Pigeon, E. Hillard, L. Boubeker, D. Spera, and G. Jaouen J. Med. Chem. 48 2005 3937 3940
58. B.S.J. Winkel The biosynthesis of flavonoids E. Grotewold, The Science of Flavonoids 2006 Springer New York 71 95
59. P. Mladenka, K. Macáková, T. Filipský, L. Zatloukalová, L. Jahodár, P. Bovicelli, I.P. Silvestri, R. Hrdina, and L. Saso J. Inorg. Biochem. 105 2011 693 701
60. S. Huang, Y. Zhao, X.L. Zhao, Y. Wu, P. Wu, T. Liu, B. Yang, Y. Hu, and X. Dong Med. Chem. Res. 2012 10.1007/s00044-011-9959-8
61. J. Mojzis, L. Varinska, G. Mojzisova, I. Kostova, and L. Mirossay Pharmacol. Res. 57 2008 259 265
62. G.M. Tozer, C. Kanthou, and B.C. Baguley Nat. Rev. Cancer 5 2005 423 435