Intercalating nucleic acids (INAs) containing insertions of 6H-indolo[2,3-b]quinoxaline

Tetrahedron

Volumn 62, Issue 48, 2006, Pages 11187-11199

  Wamberg, Michael C ^a   Hassan, Allam A ^a   Bond, Andrew D ^a   Pedersen, Erik B ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

6H Indolo 2,3 b quinoxaline; DNA; Intercalating nucleic acids; Oligonucleotides with a covalently bound intercalator; Thermal stability

Indexed keywords

DNA; DOUBLE STRANDED DNA; DOUBLE STRANDED RNA; INTERCALATING AGENT; NUCLEIC ACID; OLIGONUCLEOTIDE; QUINOXALINE DERIVATIVE; RNA;

ALKYLATION; ARTICLE; COVALENT BOND; INTERCALATION COMPLEX; MELTING POINT; MOLECULAR STABILITY; PRIORITY JOURNAL; PURIFICATION; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 33749991823     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.09.017     Document Type: Article

References (59)

1. Lerman L.S. J. Mol. Biol. 3 (1961) 18-30
2. Pigram W.J., Fuller W., and Davies M.E. J. Mol. Biol. 80 (1973) 361-365
3. Wang J.C. J. Mol. Biol. 89 (1974) 783-801
4. Miller K.J. Biopolymers 18 (1979) 2683-2719
5. Wang A.H.J., Ughetto G., Quingley G.J., and Rich A. Biochemistry 26 (1987) 1152-1163
6. Calendi E., Di Marco A., Reggiani M., Scarpinato B., and Valentini L. Biochim. Biophys. Acta 103 (1965) 25-49
7. Gellert M., Smith C.E., Neville D., and Felsenfeld G. J. Mol. Biol. 11 (1965) 445-457
8. Müller W., and Crothers D.M. J. Mol. Biol. 35 (1968) 251-290
9. Glisson B.S., and Ross W.E. Pharmacol. Ther. 32 (1987) 89-106
10. Ross W.E., and Bradley M.O. Biochim. Biophys. Acta 654 (1981) 129-134
11. Martinez R., and Chacón-Garcia L. Curr. Med. Chem. 12 (2005) 127-151
12. Braña M.F., Cacho M., Gradillas A., de Pascual-Teresa B., and Ramos A. Curr. Pharm. Des. 7 (2001) 1745-1780
13. Graves D.E., and Velea L.M. Curr. Org. Chem. 4 (2000) 915-929
14. Christensen U.B., Wamberg M., El-Essawy F.A.G., Ismail A.E.-H., Nielsen C.B., Filichev V.V., Jessen C.H., Petersen M., and Pedersen E.B. Nucleosides Nucleotides Nucleic Acids 23 (2004) 207-225
15. Christensen U.B., and Pedersen E.B. Nucleic Acids Res. 30 (2002) 4918-4925
16. Christensen U.B., and Pedersen E.B. Helv. Chim. Acta 86 (2003) 2090-2097
17. Louët S. Nat. Biotechnol. (23 June 2003). http://dx.doi.org/10.1038/bioent748 INA™ is commercially available from Human Genetic Signatures Pty Ltd., Sydney, Australia
18. Ren J., Qu X., Dattagupta N., and Chaires J.B. J. Am. Chem. Soc. 123 (2001) 6742-6743
19. Goodwin S., Smith A.F., and Horning E.C. J. Am. Chem. Soc. 81 (1959) 1903-1908
20. Kansal V.K., and Potier P. Tetrahedron 42 (1986) 2389-2408
21. Patel N., Bergman J., and Gräslund A. Eur. J. Chem. 197 (1991) 597-604
22. Zegar I., Gräslund A., Bergman J., Eriksson M., and Nordén B. Chem. Biol. Interact. 72 (1989) 277-293
23. Bergman J., Damberg C., and Valberg H. Recl. Trav. Chim. Pays-Bas 115 (1996) 31-36
24. Harmenberg J., Wahren B., Bergman J., Åkerfeldt S., and Lundblad L. Antimicrob. Agents Chemother. 32 (1988) 1720-1724
25. Harmenberg J., Åkesson-Johansson A., Gräslund A., Malmfors T., Bergman J., Wahren B., Åkerfeldt S., Lundblad L., and Cox S. Antiviral Res. 15 (1991) 193-204
26. Kohn K.W., Waring M.J., Glaubiger D., and Friedman C.A. Cancer Res. 35 (1975) 71-76
27. Feigon J., Denny W.A., Leupin W., and Kearns D.R. J. Med. Chem. 27 (1984) 450-465
28. Paoletti C., Lesca C., Cros S., Malvy C., and Auclair C. Biochem. Pharmacol. 28 (1979) 345-350
29. Filipski J., and Kohn K.W. Biochim. Biophys. Acta 698 (1982) 280-286
30. Arimondo P.B., Baldeyrou B., Laine W., Bal C., Alphonse F.-A., Routier S., Coudert G., Mérour J.-Y., Colson P., Houssier C., and Bailly C. Chem. Biol. Interact. 138 (2001) 59-75
31. Kim H.S., Barak D., Harden T.K., Boyer J.L., and Jacobson K.A. J. Med. Chem. 44 (2001) 3092-3108
32. Kawakami Y., Asai T., Umeyama K., and Yamashita Y. J. Org. Chem. 47 (1982) 3581-3585
33. Augustyns K., Aerschot A.V., Schepdael A.V., Urbanke C., and Herdewijn P. Nucleic Acid Res. 19 (1991) 2587-2593
34. Mori K., and Ikunaka M. Tetrahedron 40 (1984) 3471-3479
35. Hayashi H., Nakanishi K., Brandon C., and Marmur J. J. Am. Chem. Soc. 95 (1973) 8749-8757
36. Herdeis C. Synthesis (1986) 232-233
37. Brunner H., and Lautenschalger H.-J. Synthesis (1989) 706-709
38. Dostert P., Langlois M., Guerret P., Ancher J.-F., Bucher B., and Mocquet G. Eur. J. Med. Chem. 15 (1980) 199-206
39. Schunck E., and Marchlewski L. Chem. Ber. 28 (1895) 2525-2531
40. Buraczewski J., and Marchlewski L. Chem. Ber. 34 (1901) 4008-4015
41. Cassel S., Debaig C., Benvegnu T., Chaimbault P., Lafosse M., Plusquellec D., and Rollin P. Eur. J. Org. Chem. (2001) 875-896
42. Börjesson L., and Welch C.J. Tetrahedron 48 (1992) 6325-6334
43. Bergman J. Tetrahedron Lett. 30 (1989) 1837-1840
44. Knotz F. Sci. Pharm. 38 (1970) 20-25
45. Rolland V., Kotera M., and Lhomme J. Synth. Commun. 27 (1997) 3505-3511
46. Abdel-Megied A.E.-S., Hansen P., Pedersen E.B., and Nielsen C.M. Acta Chem. Scand. 45 (1991) 1060-1063
47. Varma R.S., and Khan I.A. J. Indian Chem. Soc. 55 (1978) 1043-1045
48. Badger G.M., and Nelson J.P. J. Chem. Soc. (1962) 3926-3931
49. Bair K.W., Tuttle R.L., Knick V.C., Cory M., and McKee D.D. J. Med. Chem. 33 (1990) 2385-2393
50. Tirosh O., Kohen R., Katzhendler J., Gorodetsky R., and Barenholz Y. J. Chem. Soc., Perkin Trans. 2 (1997) 383-389
51. Mujeeb A., Kerwin S.M., Kenyon G.L., and James T.L. Biochemistry 32 (1993) 13419-13431
52. Filichev V.V., Christensen U.B., Pedersen E.B., Babu B.R., and Wengel J. ChemBioChem 5 (2004) 1673-1679
53. Nielsen C.B., Petersen M., Pedersen E.B., Hansen P.E., and Christensen U.B. Bioconjugate Chem. 15 (2004) 260-269
54. Filichev V.V., Hilmy K.H.M., Christensen U.B., and Pedersen E.B. Tetrahedron Lett. 45 (2004) 4907-4910
55. Koshkin A.A., Singh S.K., Nielsen P., Rajwanshi V.K., Kumar R., Meldgaard M., Olsen C.E., and Wengel J. Tetrahedron 54 (1998) 3607-3630
56. Petersen M., Nielsen C.B., Nielsen K.E., Jensen G.A., Bondensgaard K., Singh S.K., Rajwanshi V.K., Koshkin A.A., Dahl B.M., Wengel J., and Jacobsen J.P. J. Mol. Recognit. 13 (2000) 44-53
57. Jensen G.A., Singh S.K., Kumar R., Wengel J., and Jacobsen J.P. J. Chem. Soc., Perkin Trans. 2 (2001) 1224-1232
58. Bergman, J. O. E.; Åkerfeldt, S. G. Patent WO 8704436, 1987.
59. Alphonse F.-A., Routier S., Coudert G., and Mérour J.-Y. Heterocycles 55 (2001) 925-940