Modulation of DNA binding by reversible metal-controlled molecular reorganizations of scorpiand-like ligands

Journal of the American Chemical Society

Volumn 134, Issue 23, 2012, Pages 9644-9656

  Inclán, Mario ^a   Albelda, M Teresa ^a   Frías, Juan C ^a,c   Blasco, Salvador ^a   Verdejo, Begoña ^a   Serena, Carolina ^b   Salat Canela, Clàudia ^b   Díaz, Maria Luisa ^b   García España, Antonio ^b   García España, Enrique ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

^b HOSPITAL UNIVERSITARI JOAN XXIII   (Spain)

^c UNIVERSIDAD CEU CARDENAL HERRERA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AZA MACROCYCLES; BINDING AFFINITIES; CALF THYMUS DNA (CT-DNA); DNA BINDING; DNA INTERACTION; EXPERIMENTAL TECHNIQUES; INTERCALATIVE MODE; MOLECULAR REORGANIZATIONS;

BINDING ENERGY;

LIGANDS;

6 (2 AMINOETHYL) 3,6,9 TRIAZA 1 (2,6) PYRIDINECYCLODECAPHANE; 6 (6 AMINO 3 AZAHEXYL) 3,6,9 TRIAZA 1 (2,6) PYRIDINECYCLODECAPHANE; 6 [4 (9 ANTHRYL) 3 AZABUTYL] 3,6,9 TRIAZA 1 (2,6) PYRIDINECYCLODECAPHANE; 6 [8 (1 PYRENYL) 3,7 DIAZAOCTYL] 3,6,9 TRIAZA 1 (2,6) PYRIDINECYCLODECAPHANE; 6 [8 (9 ANTHRYL) 3,7 DIAZAOCTYL] 3,6,9 TRIAZA 1 (2,6) PYRIDINECYCLODECAPHANE; ANTHRACENE; CHLOROPLAST DNA; COPPER ION; ETHIDIUM BROMIDE; LIGAND; PROTEIN P53; PYRIDINE; UNCLASSIFIED DRUG; ZINC ION;

ACIDITY; ARTICLE; BINDING AFFINITY; CELL ACTIVITY; CELL VIABILITY; CHELATION; CHEMICAL STRUCTURE; CHROMATOPHORE; CIRCULAR DICHROISM; CONFORMATION; CONTROLLED STUDY; CYTOTOXICITY; DNA BINDING; ELECTRON TRANSPORT; ENERGY TRANSFER; FLUORESCENCE; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; IN VIVO STUDY; MOLECULAR RECOGNITION; PH; POTENTIOMETRY; PROTEIN DNA INTERACTION; PROTEIN PHOSPHORYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; RETINOBLASTOMA; SPECTROSCOPY; VISCOSITY;

ANIMALS; ANTINEOPLASTIC AGENTS; CATTLE; CELL LINE, TUMOR; CELL SURVIVAL; CIRCULAR DICHROISM; DNA; HUMANS; INTERCALATING AGENTS; MACROCYCLIC COMPOUNDS; METALS; MODELS, MOLECULAR; NEOPLASMS; NUCLEIC ACID DENATURATION; PROTONS; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 84862217575     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja300538s     Document Type: Article

References (69)

1. Chenoweth, D. M.; Dervan, P. B. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 13175-13179
2. Chaires, J. B. Energetics of Anthracycline-DNA Interactions. In Small Molecule DNA and RNA Binders: From Synthesis to Nucleic Acid Complexes; Demeunynck, M.; Bailly, C.; Wilson, W. D., Eds; Wiley-VCH: Weinheim, Germany, 2004; Chapter 17.
3. Gurova, K. Future Oncol. 2009, 5, 1685-1704
4. Liu, Y; Wilson, W. D. Methods Mol. Biol. 2010, 613, 1-23
5. Havelka, A. M.; Berndtsson, M.; Olofsson, M. H.; Shoshan, M. C.; Linder, S. Mini-Rev. Med. Chem. 2007, 7, 1035-1039
6. Hannon, M. J. Chem. Soc. Rev. 2007, 36, 280-295
7. Long, E. C.; Barton, J. K. Acc. Chem. Res. 1990, 23, 271-273
8. Kim, R. Cancer 2005, 103, 1551-1560
9. Liu, H. K.; Sadler, P. J. Acc. Chem. Res. 2011, 44, 349-359
10. Lenglet, G.; David-Cordonnier, M.-H. J. Nucleic Acids 2010, 290935
11. Hendry, L. B.; Mahesh, V. B.; Bransome, E. D., Jr.; Ewing, D. E. Mutat. Res., Fundam. Mol. Mech. Mutagen. 2007, 623, 53-71
12. Liang, F.; Wan, S.; Li, Z.; Xiong, X.; Yang, L.; Zhou, X.; Wu, C. Curr. Med. Chem. 2006, 13, 711-727
13. Granzhan, A.; Largy, E.; Saettel, N.; Teulade-Fichou, M. P. Chem.-Eur. J. 2010, 16, 878-889
14. Chand, D. K.; Schneider, H.-J.; Aguilar, J. A.; Escartí, F.; García-España, E.; Luis, S. V. Inorg. Chim. Acta 2001, 316, 71-78
15. Lotz, T. J.; Kaden, T. A. J. Chem. Soc., Chem. Commun. 1977, 15-16
16. Pallavicini, P. S.; Perotti, A.; Poggi, A.; Segui, B.; Fabbrizzi, L. J. Am. Chem. Soc. 1987, 109, 5139-5144
17. Verdejo, B.; Ferrer, A.; Blasco, S.; Castillo, C. E.; González, J.; Latorre, J.; Máñez, M. A.; Basallote, M. G.; Soriano, C.; García-España, E. Inorg. Chem. 2007, 46, 5707-5719
18. Ikeda, T.; Yoshida, K.; Schneider, H.-J. J. Am. Chem. Soc. 1995, 117, 1453-1454
19. Lomadze, N.; Gogritchiani, E.; Schneider, H.-J.; Albelda, M. T.; Aguilar, J.; García-España, E.; Luis, S. V. Tetrahedron Lett. 2002, 43, 7801-7803
20. Malojcic, G.; Piantanida, I.; Marinic, M.; Zinic, M.; Marjanovic, M.; Kralj, M.; Pavelic, K.; Schneider, H.-J. Org. Biomol. Chem. 2005, 3, 4373-4381
21. Lomadze, N.; Schneider, H.-J.; Albelda, M. T.; García- España, E.; Verdejo, B. Org. Biomol. Chem. 2006, 4, 1755-1759
22. Sarnesky, J. E.; Surprenant, H. L.; Molen, F. K.; Reiley, C. N. Anal. Chem. 1975, 47, 2116-2124
23. Bencini, A.; Bianchi, A.; García-España, E.; Micheloni, M.; Ramírez, J. A. Coord. Chem. Rev. 1999, 188, 97-156
24. Albelda, M. T.; García-España, E.; Jiménez, H. R.; Llinares, J. M.; Soriano, C.; Sornosa-Ten, A.; Verdejo, B. Dalton Trans. 2006, 4474-4481
25. Frassineti, C.; Ghelli, S.; Gans, P.; Sabatini, A.; Moruzzi, M. S.; Vacca, A. Anal. Biochem. 1995, 231, 374-382
26. Frassineti, C.; Alderighi, L.; Gans, P.; Sabatini, A.; Vacca, A.; Ghelli, S. Anal. Bioanal. Chem. 2003, 376, 1041-1052
27. Dagnall, S. P.; Hague, D. N.; McAdam, M. E.; Moreton, A. D. J. Chem. Soc., Faraday Trans. 1 1985, 81, 1483-1494
28. Hague, D. N.; Moreton, A. D. J. Chem. Soc., Perkin Trans. 2 1994, 265-270
29. Julliard, M.; Chanon, M. Chem. Rev. 1983, 83, 425-506
30. de Silva, A. P.; Dayasiri Rupasinghe, R. A. D. J. Chem. Soc., Chem. Commun. 1985, 1669-1670
31. Zhang, S.-C.; Tu, C.; Wang, X.-Y.; Yang, Z.; Zhang, J.-Y.; Lin, L.-P.; Ding, J.; Guo, Z.-J. Eur. J. Inorg. Chem. 2004, 4028-4035
32. Sheng, X.; Lu, X.-M.; Chen, Y.-T.; Lu, G.-Y.; Zhang, J.-J.; Shao, Y.; Liu, F.; Qiang, X. Chem.-Eur. J. 2007, 13, 9703-9712
33. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566
34. de Silva, A. P.; Gunaratne, H. Q. N.; McCoy, C. P. Chem. Commun. 1996, 2399-2400
35. Addison, A. W.; Rao, T. N.; Reedijk, J.; van Rijn, J.; Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349-1356
36. Pyle, A. M.; Rehmann, J. P.; Meshoyrer, R.; Kumar, C. V.; Turro, N. J.; Barton, J. K. J. Am. Chem. Soc. 1989, 111, 3051-3058
37. Long, E. C.; Barton, J. K. Acc. Chem. Res. 1990, 23, 271-273
38. Tan, W. B.; Bhambhani, A.; Duff, M. R.; Rodger, A.; Kumar, C. V. Photochem. Photobiol. 2006, 82, 20-30
39. Bush, C. A. In Basic Principles in Nucleic Acid Chemistry; Tso, P. O. P., Ed.; Academic Press: New York, 1974; Vol. 2, p 102.
40. Lyng, R.; Härd, T.; Norden, B. Biopolymers 1987, 26, 1327-1345
41. Norden, B.; Tjerneld, F. Biopolymers 1982, 21, 1713-1734
42. Schipper, P. E.; Norden, B.; Tjerneld, F. Chem. Phys. Lett. 1980, 70, 17-21
43. Modukuru, N. K.; Snow, K. J.; Perrin, B. S., Jr.; Bhambhani, A.; Duff, M.; Kumar, C. V. J. Photochem. Photobiol., A 2006, 177, 43-54
44. Duff, M. R.; Tan, W. B.; Bhambhani, A.; Perrin, B. S., Jr.; Thota, J.; Rodger, A.; Kumar, C. V. J. Phys. Chem. B 2006, 110, 20693-20701
45. Modukuru, N. K.; Snow, K. J.; Perrin, B. S., Jr.; Thota, J.; Kumar, C. V. J. Phys. Chem. B 2005, 109, 11810-11818
46. Rodger, A.; Taylor, S.; Adlam, G.; Blagbrough, I. S.; Haworth, I. S. Bioorg. Med. Chem. 1995, 3, 861-872
47. Haq, I.; Jenkins, T. C.; Chowdhry, B. Z.; Ren, J. S.; Chaires, J. B. Methods Enzymol. 2000, 323, 373-405
48. Kumar, C. V.; Asuncion, E. H. J. Am. Chem. Soc. 1993, 115, 8547-8553
49. Suh, D.; Chaires, J. B. Bioorg. Med. Chem. 1995, 3, 723-728
50. López-Knowles, E.; Hernández, S.; Malats, N.; Kogevinas, M.; Lloreta, J.; Carrato, A.; Tardón, A.; Serra, C.; Real, F. X. Cancer Res. 2006, 66, 7401-7404
51. Sanchez-Carbayo, M.; Socci, N. D.; Charytonowicz, E.; Lu, M. L.; Prystowsky, M.; Childs, G.; Cordon-Cardo, C. Cancer Res. 2002, 62, 6973-6980
52. Shieh, S. Y.; Ikeda, M.; Taya, Y.; Prives, C. Cell 1997, 91, 325-334
53. Verma, R.; Rigatti, M. J.; Belinsky, G. S.; Godman, C. A.; Giardina, C. Biochem. Pharmacol. 2010, 79, 565-574
54. Makovski, A.; Yaffe, E.; Shpungin, S.; Nir, U. Cell. Signalling 2012, 24, 1369-1374
55. García-España, E.; Ballester, M. J.; Lloret, F.; Moratal, J. M.; Faus, J.; Bianchi, A. J. Chem. Soc., Dalton Trans. 1988, 101-104
56. Fontanelli, M.; Micheloni, M. In Proceedings of the First Spanish-Italian Congress on Thermodynamics of Metal Complexes, Diputación de Castellón, Spain, 1990.
57. Gran, G. Analyst 1952, 77, 661-671
58. Rossotti, F. J. C.; Rossotti, H. J. Chem. Educ. 1965, 42, 375-378
59. Avdeef, A.; Box, K. J.; Comer, J. E. A.; Gilges, M.; Hadley, M.; Hibbert, C.; Patterson, W.; Tam, K. Y. J. Pharm. Biomed. Anal. 1999, 20, 631-641
60. Gans, P.; Sabatini, A.; Vacca, A. Talanta 1996, 43, 1739-1753
61. Glasoe, P. K.; Long, F. A. J. Phys. Chem. 1960, 64, 188-190
62. Covington, A. K.; Paabo, M.; Robinson, R. A.; Bates, R. G. Anal. Chem. 1968, 40, 700-706
63. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122
64. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A. J. Appl. Crystallogr. 2008, 41, 466-470
65. Chaires, J. B.; Dattagupta, N.; Crothers, D. M. Biochemistry 1982, 21, 3933-3940
66. Cohen, G.; Eisenberg, H. Biopolymers 1969, 8, 45-55
67. Mosmann, T. J. Immunol. Methods 1983, 65, 55-63
68. Alley, M. C.; Scudiero, D. A.; Monks, A.; Hursey, M. L.; Czerwinski, M. J.; Fine, D. L.; Abbott, B. J.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Cancer Res. 1988, 48, 589-601
69. García-España, A.; Salazar, E.; Sun, T. T.; Wu, X. R.; Pellicer, A. Cancer Res. 2005, 65, 1150-1157