Guanidiniocarbonylpyrrole-aryl derivatives: Structure tuning for spectrophotometry; recognition of specific DNA and RNA sequences and for antiproliferative activity

Chemistry - A European Journal

Volumn 16, Issue 10, 2010, Pages 3036-3056

  Hernandez Folgado, Laura ^a,b   Baretić, Domagoj ^c   Piantanida, Ivo ^c   Marjanović, Marko ^c   Kralj, Marijeta ^a   Rehm, Thomas ^a   Schmuck, Carsten ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^c RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Antiproliferation; Dna recognition; Intercalations; Rna recognition; Structure activity relationships

Indexed keywords

ANTIPROLIFERATION; ANTIPROLIFERATIVE ACTIVITIES; AROMATIC MOIETIES; AROMATIC RINGS; BASE STACKS; BINDING AFFINITIES; BINDING GROUPS; BIOLOGICAL EFFECTS; DNA BINDING; DNA RECOGNITION; EFFICIENT INTERACTION; FLEXIBLE LINKERS; FLUORESCENCE AND CD SPECTROSCOPY; GROOVE BINDING; PH VALUE; PHYSIOLOGICAL PH; POSITIVE CHARGES; RNA RECOGNITION; RNA SEQUENCES; SELECTIVE RECOGNITION; STRUCTURE ACTIVITY RELATIONSHIPS; STRUCTURE TUNING; SYSTEMATIC STUDY; TUMOUR CELLS;

AROMATIC COMPOUNDS; BENZENE; BINDING ENERGY; CELL CULTURE; DNA; GENES; INTERCALATION; NAPHTHALENE; PH EFFECTS; POLYPEPTIDES; RNA; TUMORS;

DNA SEQUENCES;

DNA; GUANIDINE DERIVATIVE; PYRENE DERIVATIVE; PYRROLE DERIVATIVE; RNA;

ARTICLE; BASE PAIRING; BINDING SITE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HUMAN; METABOLISM; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; SPECTROFLUOROMETRY; SPECTROPHOTOMETRY; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE; ULTRAVIOLET SPECTROPHOTOMETRY;

BASE PAIRING; BASE SEQUENCE; BINDING SITES; CELL LINE, TUMOR; CELL PROLIFERATION; DNA; GUANIDINES; HUMANS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; NUCLEIC ACID CONFORMATION; PYRENES; PYRROLES; RNA; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY; SPECTROPHOTOMETRY, ULTRAVIOLET; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77649215635     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901999     Document Type: Article

References (74)

1. R. B. Silverman, The Organic Chemistry of Drug Design and Drug Action, Elsevier, New York, 2004.
2. W. D. Wilson, L. Ratmeyer, M. Zhao, L. Strekowski, D. Boykin, Biochemistry 1993, 32, 4098-4104.
3. N. Stevens, N. O'Connor, H. Vishwasrao, D. Samaroo, E. R. Kandel, D. L. Akins, C. M. Drain, N. J. Turro, J. Am. Chem. Soc. 2008, 130, 7182-7183.
4. M. Demeunynck, C. Bailly, W. D. Wilson, DNA and RNA Bnders, Wiley-VCH, Weinheim, 2002.
5. C. Bailly, R. K. Arafa, F. A. Tanious, W. Laine, C. le Tardy, A. Lansiaux, P. Colson, D. W. Boykin, W. D. Wilson, Biochemistry 2005, 44, 1941-1952.
6. V. Peytou, R. Condom, N. Patino, R. Guedj, A.-M. Aubertin, N. Gelus, C. Bailly, R. Terreux, D. Cabrol-Bass, J. Med. Chem. 1999, 42, 4042-4053.
7. L. Hernandez-Folgado, C. Schmuck, S. Tomić, I. Piantanida, Bioorg. Med. Chem. Lett. 2008, 18, 2977-2981.
8. a) F. M. Winnik, Chem. Rev. 1993, 93, 587-614;
9. b) K. Kalyanasundaram, J. K. Thomas, J. Am. Chem. Soc. 1977, 99, 2039-2044;
10. c) D. C. Dong, M. A. Winnik, Photochem. Photobiol 1982, 35, 17.
11. a) J. R. Lakowicz, Principles of Fluorescence Spectroscopy, Kluwer Academic/Plenum, New York, 1999;
12. b) F. M. Winnik, Chem. Rev. 1993, 93, 587-614;
13. c) S. S. Lehrer, Methods Enzymol. 1997, 278, 286-295.
14. a) P. C. Bevilacqua, R. Kierzek, K. A. Johnson, D. H. Turner, Science 1992, 258, 1355-1358;
15. b) K. Yamana, T. Gokota, H. Ozaki, H. Nakano, O. Sangen, T. Shimidzu, Nucleosides Nucleotides 1992, 11, 383-390;
16. c) R. Kierzek, Y. Li, D. H. Turner, P. C. Bevilacqua, J. Am. Chem. Soc. 1993, 115, 4985-4992;
17. d) Y. Li, P. C. Bevilacqua, D. Mathews, D. H. Turner, Biochemistry 1995, 34, 14394-14399;
18. e) M. Manoharan, K. L. Tivel, M. Zhao, K. Nafisi, T. L. Netzel, J. Phys. Chem. 1995, 99, 17461-17472;
19. f) J. Yguerabide, E. Talavera, J. M. Alvarez, M. Afkir, Anal. Biochem. 1996, 241, 238-247;
20. g) J. Dapprich, N. G. Walter, F. Salingue, H. Staerk, J. Fluoresc. 1997, 7, 87S-89S;
21. h) R. Preuß, J. Dapprich, N. G. Walter, J. Mol. Biol. 1997, 273, 600-613;
22. i) K. Yamana, R. Iwase, S. Furutani, H. Tsuchida, H. Zako, T. Yamaoka, A. Murakami, Nucleic Acids Res. 1999, 27, 2387-2392;
23. j) S. K. Silverman, T. R. Cech, Biochemistry 1999, 38, 14224-14237;
24. k) K. Yamana, H. Zako, K. Asazuma, R. Iwase, H. Nakano, A. Murakami, Angew. Chem. 2001, 113, 1138-1140;
25. Angew. Chem. Int. Ed. 2001, 40, 1104-1106;
26. V. A. Korshun, D. A. Stetsenko, M. J. Gait, J. Chem. Soc. Perkin Trans. 1 2002, 1092-1104.
27. a) H. Fritzsche, A. Akhebat, E. Taillandier, K. Rippe, T. M. Jovin, Nucleic Acids Res. 1993, 21, 5085-5091;
28. b) K. Ebata, M. Masuko, H. Ohtani, M. Kashiwasake-Jibu, Photochem. Photobiol. 1995, 62, 836-839;
29. c) G. Tong, J. M. Lawlor, G. W. Tregear, J. Haralambidis, J. Am. Chem. Soc. 1995, 117, 12151-12158;
30. d) F. D. Lewis, Y. Zhang, R. L. Letsinger, J. Am. Chem. Soc. 1997, 119, 5451-5452;
31. e) K. V. Balakin, V. A. Korshun, I. A. Prokhorenko, G. V. Maleev, I. A. Kudelina, S. V. Gontarev, Y. A. Berlin, Bioorg. Khim. 1997, 23, 33-41;
32. f) P. L. Paris, J. M. Langenhan, E. T. Kool, Nucleic Acids Res. 1998, 26, 3789-3793;
33. g) K. V. Balakin, V. A. Korshun, I. I. Mikhalev, G. V. Maleev, A. D. Malakhov, I. A. Prokhorenko, Y. A. Berlin, Biosens. Bioelectron. 1998, 13, 771-778;
34. h) M. Masuko, H. Ohtani, K. Ebata, A. Shimadzu, Nucleic Acids Res. 1998, 26, 5409-5416;
35. i) V. A. Korshun, K. V. Balakin, T. A. Proskurina, I. I. Mikhalev, A. D. Malakhov, Y. A. Berlin, Nucleosides Nucleotides 1999, 18, 2661-2676;
36. j) E. Kostenko, M. Dobrikov, D. Pyshnyi, V. Petyuk, N. Komarova, V. Vlassov, M. Zenkova, Nucleic Acids Res. 2001, 29, 3611-3620;
37. k) A. Mahara, R. Iwase, T. Sakamoto, K. Yamana, T. Yamaoka, A. Murakami, Angew. Chem. 2002, 114, 3800-3802;
38. Angew. Chem. Int. Ed. 2002, 41, 3648-3650.
39. a) K. M. Guckian, B. A. Schweitzer, R. X.-F. Ren, C. J. Sheils, P. L. Paris, D. C. Tahmassebi, E. T. Kool, J. Am. Chem. Soc. 1996, 118, 8182-8183;
40. b) B. Ravindra Babu, A. K. Prasad, S. Trikha, N. Thorup, V. S. Parmar, J. Wengel, J. Chem. Soc. Perkin Trans. 1 2002, 22, 2509-2519;
41. c) U. B. Christensen, E. B. Pedersen, Nucleic Acids Res. 2002, 30, 4918-4925;
42. d) V. V. Filichev, E. B. Pedersen, Org. Biomol. Chem. 2003, 7, 100-103;
43. e) J. Michel, K. Bathany, J.-M. Schmitter, J.-P. Monti, S. Moreau, Tetrahedron 2002, 58, 7975-7982.
44. C. Schmuck, L. Hernandez-Folgado, Org. Biomol. Chem. 2007, 5, 2390-2394.
45. R. Houssin, J.-L. Bernier, J.-P. Hénichart, Synthesis 1988, 259-261.
46. C. Schmuck, V. Bickert, M. Merschky, L. Geiger, D. Rupprecht, J. Dudaczek, P. Wich, T. Rehm, U. Machon, Eur. J. Org. Chem. 2008, 324-329.
47. J.-F. Pons, J.-L. Fauchère, F. Lamaty, A. Molla, R. Lazaro, Eur. J. Org. Chem. 1998, 853-859.
48. C. Schmuck, L. Geiger, Chem. Commun. 2005, 772-774.
49. G. Malojčić, I. Piantanida, M. Marinić, M. Žinić, M. Marjanović, M. Kralj, K. Pavelić, H.-J. Schneider, Org. Biomol. Chem. 2005, 3, 4373-4381.
50. C. R. Cantor, P. R. Schimmel, Biophysical Chemistry, Vol.3, Freeman and Co., San Francisco, 1980.
51. a) J. Ramstein, M. Leng, Biochim. Biophys. Acta Nucleic Acids Protein Synth. 1972, 281, 18;
52. b) M. G. Badea, S. Georghiou, Photochem. Photobiol. 1976, 24, 417;
53. c) S. Georghiou, Photochem. Photobiol. 1977, 26, 59.
54. I. Piantanida, B. S. Palm, M. Žinić, H.-J. Schneider, J. Chem. Soc. Perkin Trans. 2 2001, 1808-1816.
55. a) S. O. Kelley, J. K. Barton, Science 1999, 283, 375-381;
56. b) S. A. E. Marras, F. R. Kramer, S. Tyagi, Nucleic Acids Res. 2002, 30, 122e.
57. W. D. Wilson, Y.-H, Wang, C. R. Krishnamoorthy, J. C. Smith, Biochemistry 1985, 24, 3991-3999.
58. G. Scatchard, Ann. N. Y. Acad. Sci. 1949, 51, 660-672;
59. J. D. McGhee, P. H. von Hippel, J. Mol. Biol. 1976, 103, 679-684.
60. B. S. Palm I. Piantanida, M. Žinić, H.-J. Schneider, J. Chem. Soc. Perkin Trans. 2 2000, 385-392.
61. A. Rodger, B. Norden, Circular Dichroism and Linear Dichroism, Oxford University Press, New York, 1997.
62. N. Berova, K. Nakanishi, R. W. Woody, Circular Dichroism Principles and Applications, 2nd ed., Wiley-VCH, Weinheim, 2000.
63. M. Eriksson, B. Norden, Methods Enzymol. 2001, 340, 68-98.
64. a) B. Nordén, F. Tjerneld, Biopolymers 1982, 21, 1713-1734;
65. b) R. Lying, A. Rodger, B. Norden, Biopolymers 1991, 31, 1709-1820;
66. c) P. E. Schipper, B. Norden, F. Tjerneld, Chem. Phys. Lett. 1980, 70, 17-21.
67. a) I. F. Tannock, D. Rotin, Cancer Res. 1989, 49, 4373-4384;
68. b) P. Wong, C. Lee, I. F. Tannock, Clin. Cancer Res. 2005, 11, 3553-3557;
69. c) R. J. Gillies, I. Robey, R. A. Gatenby, J. Nucl. Med. 2008, 49, 24S-42S.
70. N. Raghunand, R. J. Gillies, Drug Resist. Updates 2000, 3, 39-47.
71. J. N. Miller in Standards for Fluorescence Spectrometry, Chapman and Hall, London, 1981.
72. M. R. Eftink, Y. Jia, D. Hu, C. A. Ghiron, J. Phys. Chem. 1995, 99, 5713-5723.
73. M. Marjanović, M. Kralj, F. Supek, L. Frkanec, I. Piantanida, T. Šmuc, L. Tušek-Božić, J. Med. Chem. 2007, 50, 1007-1018.
74. M. R. Boyd, D. P. Kenneth, Drug Dev. Res. 1995, 34, 91-109.