Urea derivatives of 1,4,7,10-tetraazacyclododecane - Synthesis and binding properties

European Journal of Organic Chemistry

Volumn , Issue 10, 2001, Pages 1943-1949

  König, Burkhard ^a   Pelka, Mario ^a   Subat, Michael ^a   Dix, Ina ^b   Jones, Peter G ^b  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Azacrown ether; DNA binding; Macrocycles; Supramolecular chemistry; Urea

Indexed keywords

1,4,7,10 TETRAAZACYCLODODECANE; AMINE; COPPER ION; DODECANE; DOUBLE STRANDED DNA; ETHIDIUM BROMIDE; ISOCYANIC ACID DERIVATIVE; MACROCYCLIC COMPOUND; METAL COMPLEX; UNCLASSIFIED DRUG; UREA DERIVATIVE; ZINC ION;

ARTICLE; BINDING AFFINITY; CHEMICAL BINDING; CHEMICAL STRUCTURE; POTENTIOMETRY; PROTON TRANSPORT; SYNTHESIS;

EID: 0035030928     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200105)2001:10<1943::AID-EJOC1943>3.0.CO;2-O     Document Type: Article

References (48)

1. B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry, VCH, Weinheim 1993.
2. G. Gokel, Crown Ethers and Cryptands in: Monographs in Supramolecular Chemistry (Ed.: J. F. Stoddart), The Royal Society of Chemistry, Cambridge, 1991.
3. T. A. Kaden, Pure & Appl. Chem. 1988, 60, 1117-1122.
4. P. V. Bernhardt, G. A. Lawrence, Coord. Chem. Rev. 1990, 104, 297-343.
5. R. S. Dickins, J. A. K. Howard, C. W. Lehmann, J. Moloney, D. Parker, R. D. Peacock, Angew. Chem. 1997, 109, 541-543;
6. Angew. Chem. Int. Ed. Engl. 1997, 36, 521-523.
7. S. Aime, M. Botta, S. G. Crich, B. G. Giovenzana, G. Jommi, R. Pagliarin, M. Sisti, J. Chem. Soc., Chem. Commun. 1995, 1885-1886.
8. T. J. Norman, D. Parker, F. C. Smith, J. D. King, J. Chem. Soc., Chem. Commun. 1995, 1877-1878 and 1879-1880.
9. E. Kimura, A. Sakonaka, T. Yatsunami, M. Kodama, J. Am. Chem. Soc. 1981, 103, 3041-3045.
10. J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim 1995, p. 31-35 and cited ref.
11. E. Kimura, T. Koike, Chem. Commun. 1998, 1495-1500 and ref. cited.
12. S. Aoki, M. Shiro, T. Koike, E. Kimura, J. Am. Chem. Soc. 2000, 122, 576-584.
13. B. König, M. Pelka, H. Zieg, T. Ritter, H. Bouas-Laurent, R. Bonneau, J.-P. Desvergne, J. Am. Chem. Soc. 1999, 121, 1681-1687.
14. E. Kikuta, T. Koike, E. Kimura, J. Inorg. Biochem. 2000, 79, 253-259.
15. H. Fujioka, T. Koike, N. Yamanda, E. Kimura, M. Shiro, Heterocycles 1996, 42, 775-787
16. T. Koike, M. Takashige, E. Kimura, H. Fujioka, M. Shiro, Chem. Eur. J. 1996, 2, 617-623.
17. E. Kimura, S. Aoki, T. Koike, M. Shiro, J. Am. Chem. Soc. 1997, 119, 3068-3076.
18. As revealed by a recent study, phenylene(bismethylene)-bridged bistetraazamacrocycles inhibit HIV replication: G. J. Bridger, R. T. Skerlj, S. Padmanabhan, D. Thornton, J. Org. Chem. 1996, 61, 1519-1522.
19. V. Patinec, J. J. Yaouanc, J. C. Clément, H. Handel, H. des Abbayes, Tetrahedron Lett. 1995, 36, 79-82.
20. A. Urfer, T. A. Kaden, Helv. Chim. Acta 1994, 77, 23-35.
21. J.-L. Kraus, J. Heterocyc. Chem. 1985, 22, 1307-1312.
22. S. Brandés, C. Gros, F. Denat, P. Pullumbi, R. Guilard, Bull Soc. Chim. Fr. 1996, 133, 65-73.
23. B. König, M. Pelka, M. Klein, I. Dix, P. G. Jones, J. Lex, J. Ind. Phenom. 2000, 37, 39-57.
24. The cyclen resonances are observed as sharp signals without broadening. The carbamoyl N-H proton shows a well resolved coupling to the adjacent methylene group.
25. B. König, M. Pelka, H. Zieg, P. G. Jones, I. Dix, Chem. Commun. 1996, 471-472.
26. B. König, M. Pelka, O. Möller, I. Dix, P. G. Jones, Chem. Ber./Recueil 1997, 512-518.
27. M. Kalesse, A. Loos, Liebigs Ann. 1996, 935-939.
28. P. Kocienski, Protecting Groups, Thieme, Stuttgart, 1994, 192-195.
29. E. Kimura, S. Aoki, T. Koike, M. Shiro, J. Am. Chem. Soc. 1997, 119, 3068-3076.
30. No metal ion binding under these conditions was observed with compound 2.
31. T. Koike, S. Kajitani, I. Nakamura, E. Kimura, M. Shiro, J. Am. Chem. Soc. 1995, 117, 1210-1219.
32. Compound 8b was stirred in aqueous, slightly basic solution at room temperature, resulting in significant decomposition as confirmed by NMR spectroscopy.
33. H. J. Schneider, T. Blatter, Angew. Chem. 1992, 104, 1244-1245;
34. Angew. Chem. Int. Ed. Engl. 1992, 31, 1207-1208.
35. K. D. Stewart, T. A. Gray, J. Org. Phy. Chem. 1992, 5, 461-466.
36. E. Kikuta, M. Murata, N. Katsube, T. Koike, E. Kimura, J. Am. Chem. Soc. 1999, 121, 5426-5436.
37. T. C. Jenkins, Optical Absorbance and Fluorescence Techniques for Measuring DNA-Drug Interactions in: Drug-DNA Interaction Protocols (Ed.: K. R. Fox), Humana Press, New Jersey, 1997, p. 195-218.
38. M. Lee, A. L. Rhodes, M. D. Wyatt, S. Forrow, J. A. Hartley, Biochemistry 1993, 32, 4237-4242.
39. The method is sensitive to intercalating and nonintercalating compounds. Information about sequence specificity of binding is not obtained.
40. K. G. Hardy (Ed.), Plasmids - A Practical Approach, IRL Press, Oxford, 2nd Ed., 1993, p. 200.
41. R. Moss, K. Ragunathan, Langmuir 1999, 15, 107-110.
42. R. Moss, K. Ragunathan, to be published.
43. For a detailed discussion of the structure dependence of amine DNA binding, see: A. R. Morgan, J. S. Lee, P. E. Pulleyblank, N. L. Murry, D. H. Evans, Nuc. Acids Res. 1979, 7, 547-569.
44. All complexes were used as their perchlorate salts, so that any influence of the counterion can be neglected.
45. 11 = 2 L/mol. The results indicate that 6d does not interact with heterocyclic imide moieties under physiological conditions, and hence an interaction with the phosphate backbone of DNA is likely.
46. E. Kimura, T. Ikeda, M. Shionoya, Pure Appl. Chem. 1997, 69, 2187-2195.
47. G. Gran, Analyst 1952, 77, 661.
48. P. Gans, University of Leeds, 1995.