DyNAs: Constitutional dynamic nucleic acid analogues

Chemistry - A European Journal

Volumn 12, Issue 33, 2006, Pages 8581-8588

  Sreenivasachary, Nampally ^a,b   Hickman, David T ^a,b   Sarazin, Dominique ^c   Lehn, Jean Marie ^a  

^a UNIVERSITÉ LOUIS PASTEUR   (France)

^b EPFL   (Switzerland)

^c INSTITUT CHARLES SADRON   (France)

Author keywords

Combinatorial chemistry; Dynamers; Imines; Polymers; Supramolecular chemistry

Indexed keywords

BIOPOLYMERS; ELECTROSTATICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PROTONS; SUPRAMOLECULAR CHEMISTRY;

ANIONIC CHARGE; COMBINATORIAL CHEMISTRY; DYNAMERS;

DNA;

ALDEHYDE; ANION; CATION; HYDRAZINE; HYDRAZINE DERIVATIVE; NUCLEIC ACID; PEPTIDE; POLYASPARTIC ACID; POLYMER; POLYPHOSPHATE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRICITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TIME;

ALDEHYDES; ANIONS; CATIONS; ELECTROSTATICS; HYDRAZINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NUCLEIC ACIDS; PEPTIDES; POLYMERS; POLYPHOSPHATES; TIME FACTORS;

EID: 33751339831     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600625     Document Type: Article

References (78)

1. a) J.-M. Lehn, Proc. Natl. Acad. Sci. USA 2002, 99, 4763-4768;
2. b) J.-M. Lehn, Science 2002, 295, 2400-2403;
3. c) J.-M. Lehn, Prog. Polym. Sci. 2005, 30, 814-831.
4. Reviews on dynamic combinatorial chemistry see: a) J.-M. Lehn, Chem. Eur. J. 1999, 5, 2455-2463;
5. b) G. R. L. Cousins, S.-A. Poulsen, J. K. M. Sanders, Curr. Opin. Chem. Biol. 2000, 4, 270-279;
6. c) S. Otto, R. L. E. Furlan, J. K. M. Sanders, Curr. Opin. Chem. Biol. 2002, 6, 321-327;
7. d) J.-M. Lehn, A. V. Eliscev, Science 2001, 291, 2331-2332;
8. e) O. Ramström, J.-M. Lehn, Nat. Rev. Drug Discovery 2002, 1, 26-36;
9. f) O. Ramström, T. Bunyapaiboonsri, S. Lohmann, J.-M. Lehn, Biochim. Biophys. Acta 2002, 1572, 178-186.
10. a) I. Hue, J.-M. Lehn, Proc. Natl. Acad. Sci. USA 1997, 94, 2106-2110;
11. b) O. Ramström, J.-M. Lehn, ChemBioChem 2000, 1, 41-48;
12. c) T. Bunyapaiboonsri, O. Ramström, S. Lohmann, J.-M. Lehn, L. Peng, M. Goeldner, ChemBioChem 2001, 2, 438-444;
13. d) T. Bunyapaiboonsri, H. Ramström, O. Ramström, J. Haiech, J.-M. Lehn, J. Med. Chem. 2003, 46, 5803-5811;
14. e) S. Zameo, B. Vauzeilles, J.-M. Beau, Angew. Chem. 2005, 117, 987-991;
15. Angew. Chem. Int. Ed. 2005, 44, 965-969;
16. f) M. S. Congreve, D. J. Davis, L. Devine, C. Granata, M. O. Reilly, P. G. Wyatt, H. Jhoti, Angew. Chem. 2003, 115, 4617-4620;
17. Angew. Chem. Int. Ed. 2003, 42, 4479-4482.
18. a) M. Hochgürtel, H. Kroth, D. Piecha, M. W. Hofmann, C. Nicolau, S. Krause, O. Schaaf, G. Sonnenmoser, A. V. Eliseev, Proc. Natl. Acad. Sci. USA 2002, 99, 3382-3387;
19. b) O. Ramström, S. Lohmann, T. Bunyapaiboonsri, J.-M. Lehn, Chem. Eur. J. 2004, 10, 1711-1715;
20. c) R. Larsson, Z. Pei, O. Ramström, Angew. Chem. 2004, 116, 3802-3804;
21. Angew. Chem. Int. Ed. 2004, 43, 3716-3718;
22. d) H. Li, P. Williams, J. Micklefield, J. M. Gardiner, G. Stephens, Tetrahedron 2004, 60, 753-758.
23. a) W. G. Skene, J.-M. Lehn, Proc. Natl. Acad. Sci. USA 2004, 101, 8270-8275;
24. b) T. One, T. Nobori, J.-M. Lehn, Chem. Commun. 2005, 1522-1524;
25. c) E. Kolomiets, J.-M. Lehn, Chem. Commun. 2005, 1519-1521;
26. d) J.-L. Schmitt, J.-M. Lehn, Helv. Chim. Acta 2003, 86, 3417-3426.
27. a) Supramolecular Polymers, 2nd ed. (Ed.: A. Ciferri), Taylor & Francis, Boca Raton 2005;
28. b) L. Brunsveld, B. J. B. Folmer, E. W. Meijer, R. P. Sijbesma, Chem. Rev. 2001, 101, 4071-4098;
29. c) J.-M. Lehn, Polym. Int. 2002, 51, 825-839;
30. d) J.-M. Lehn in Supramolecular Polymers, 2nd ed. (Ed.: A. Ciferri), Taylor & Francis, Boca Raton 2005 Chapter 1.
31. a) N. Giuseppone, J.-M. Lehn, J. Am. Chem. Soc. 2004, 126, 11448-11449;
32. b) N. Giuseppone, J.-M. Lehn, Chem. Eur. J. 2006, 12, 1715-1722;
33. c) N. Giuseppone, G. Fuks, J.-M. Lehn, Chem. Eur. J. 2006, 12, 1723-1735;
34. for the effect of gelation on constitutional exchange and selection, see: N. Sreenivasachary, J.-M. Lehn, Proc. Natl. Acad. Sci. USA 2005, 102, 5938-5943.
35. S. Lohmann, 2003, Ph.D. thesis, Université louis Pasteur, Strasbourg (France).
36. a) Y. Ruff, J.-M. Lehn, unpublished results;
37. b) I. Nakazawa, S. Suda, M. Masuda, M. Asai, T. Shimizu, Chem. Commun. 2000, 881-882.
38. For nucleic acid systems involving a reversible bond, see: a) J. T. Goodwin, D. G. Lynn, J. Am. Chem. Soc. 1992, 114, 9197-9198;
39. b) Y. Krishnan-Ghosh, A. M. Whitney, S. Balasubramanian, Chem. Commun. 2005, 3068-3070;
40. c) A. Bugaut, J.-J. Toulmé, B. Rayner, Angew. Chem. 2004, 116, 3206-3209;
41. Angew. Chem. Int. Ed. 2004, 43, 3144-3147;
42. for dynamic selection by binding to DNA, sec: d) B. Klekota, M. H. Hammond, B. L. Miller, Tetrahedron Lett. 1997, 38, 8639-8642;
43. e) B. Klekota, B. L. Miller, Tetrahedron 1999, 55, 11687-11697;
44. f) C. Karan, B. L. Miller, J. Am. Chem. Soc. 2001, 123, 7455-7456.
45. a) I. Chemin, D. Moradpour, S. Wieland, W. B. Offensperger, E. Walter, J.-P. Behr, H. E. Blum, J. Viral Hepatitis 1998, 5, 369-375;
46. b) P. Erbacher, J. S. Remy, J.-P. Behr. Gene Ther. 1999, 6, 138-145;
47. c) W. Zauner, M. Ogris, E. Wagner, Adv. Drug Delivery Rev. 1998, 30, 97-113;
48. d) B. Ochietti, N. Guérin, S. V. Vinogradov, Y. S. Pierre, P. Lemieux, A. V. Kabanov, V. Y. Alakhov, J. Drug Targeting 2002, 10, 113-121.
49. a) A. V. Kabanov, V. A. Kabanov, Bioconjugate Chem. 1995, 6, 7-20;
50. b) O. Boussif, F. Lezoualc'h, M. A. Zanta, M. D. Mergny, D. Scherman, B. Demeneix, J.-P. Behr, Proc. Natl. Acad. Sci. USA 1995, 92, 7297-7301.
51. a) D. Putnam, R. Langer, Macromolecules 1999, 32, 3658-3662;
52. b) Y. Lim, Y. H. Choi, J.-S. Park, J. Am. Chem. Soc. 1999, 121, 5633-5639.
53. a) J. Summerton, D. Weller, Antisense Nucleic Acid Drug Dev. 1997, 7, 187-195;
54. b) O. Chakhmakhcheva, M. Andrianov, A. Buryakova, M. Choob, V. Efimov, Nucleosides Nucleotides 1999, 18, 1427-1428;
55. c) T. Vilaivan, G. Lowe, J. Am. Chem. Soc. 2002, 124, 9326-9327;
56. d) A. D. Mesmaeker, K.-H. Altmann, A. Waldmer, S. Wendeborn, Curr. Biol. Curr. Opin. Stru. Bio. 1995, 5, 343-355;
57. e) O. Almarsson, T. C. Bruice, J. Kerr. R. N. Zuckermann, Proc. Natl. Acad. Sci. USA 1993, 90, 7518-7522;
58. f) J. Micklefield, Curr. Med. Chem. 2001, 8, 1157-1179;
59. g) S. M. Freier, K.-H. Altmann, Nucleic Acids Res. 1997, 25, 4429-4443.
60. a) M. Egholm, O. Buchardt, P. E. Nielsen, R. H. Berg, J. Am. Chem. Soc. 1992, 114, 1895-1897;
61. b) M. Egholm, O. Buchardt, L. Christensen, C. Behrens, S. M. Freier, D. A. Driver, R. H. Berg, S. K. Kim, B. Norden, P. E. Nielsen, Nature 1993, 365, 566-568
62. c) O. Buchardt, M. Egholm, R. H. Berg, P. E. Nielsen, Trends Biotechnol. 1993, 11, 384-386.
63. Related compounds were also prepared: D. T. Hickman, N. Sreenivasachary, J.-M. Lehn, unpubllished results.
64. a) G. R. L. Cousins, S.-A. Poulsen, J. K. M. Sanders, Chem. Commun. 1999, 1575-1576;
65. b) R. L. E. Furlan, Y.-F. Ng, S. Otto. J. K. M. Sanders, J. Am. Chem. Soc. 2001, 123, 8876-8877;
66. c) L. F. Bornaghi, B. L. Wilkinson, M. J. Kiefel, S.-A Poulsen. Tetrahedron Lett. 2004, 45, 9281-9284;
67. d) R. L. Furlan, Y.-F. Ng, S. Otto, J. K. M. Sanders, J. Am. Chem. Soc. 2001, 123, 8876-8877;
68. e) R. Nguyen, I. Huc, Chem. Commun. 2003, 942-943.
69. a) P. Wyatt, Anal. Chim. Acta 1993, 272, 1-40;
70. b) R. Mendichi, G. Giammona, G. Cavallaro, A. G. Schieroni, Polymer 1999, 40, 7109-7116.
71. K. C. Fylaktakidou, J.-M. Lehn, R. Greferath, C. Nicolau, Bioorg. Med. Chem. Lett. 2005, 15, 1605-1608;
72. L. F. Johnson, M. E. Tate, Can. J. Chem. 1969, 47, 63-73.
73. a) P. Debye, J. Phys. Coll. Chem. 1947, 57, 18-32;
74. b) B. H. Zimm, J. Chem. Phys. 1948, 16, 1099-1116.
75. H. C. Benoit, J. S. Higgins, Polymers and Neutron scattering, Oxford Science, Clarendon, Oxford 1994;
76. B. Chu, Laser light scattering, 2nd ed., Academic Press, New York, 1991.
77. A. Libeyre, D. Sarazin, J. François, Polym. Bull. 1981, 4, 53-60.
78. G. G. Fuller, Optical Rheometry of Complex Fluids: Theory and Practice of Optical Rheometry, Oxford University Press, Oxford, 1995.