A facile solid-phase strategy for the synthesis of oligonucleotide- tetraphenylporphyrin conjugates

European Journal of Organic Chemistry

Volumn , Issue 6, 2000, Pages 1013-1018

  De Napoli, Lorenzo ^a   De Luca, Stefania ^b   Di Fabio, Giovanni ^a   Messere, Anna ^a   Montesarchio, Daniela ^a   Morelli, Giancarlo ^b   Piccialli, Gennaro ^c   Tesauro, Diego ^b  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b Ctro di Stud di Biocristallografia   (Italy)

^c UNIVERSITY OF MOLISE   (Italy)

Author keywords

Conjugation; Oligonucleotides; Porphyrinoids; Solid phase synthesis

Indexed keywords

COMPLEMENTARY DNA; DNA FRAGMENT; LYSINE DERIVATIVE; OLIGONUCLEOTIDE; POLYMER; TETRAPHENYLPORPHYRIN;

ARTICLE; CONJUGATION; DNA DENATURATION; HYBRIDIZATION; SOLID STATE; SYNTHESIS; THERMAL ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0034095906     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. T. Le Doan, L. Perroault, C. Hélène, Biochemistry 1986, 25, 6736.
2. C. Casas, C. J. Lacey, B. Meunier, Bioconjugate Chem. 1993, 4, 366.
3. J. F. Ramalho Ortigao, A. Ruck, K. C. Gupta, R. Rosch, R. Steiner, H. Seliger, Biochimie, 1994, 75, 29.
4. E. Wickstrom, Prospect for Antisense Nucleic Acids Therapy of Cancer and AIDS, Wiley-Liss, New York, 1991.
5. H. E. Moser, P. B. Dervan, Science, 1987, 238, 645.
6. E. Uhlmann, A. Peyman, Chem. Rev. 1990, 90, 543.
7. U. Englisch, D. H. Gauss, Angew. Chem. Int. Engl. Ed. 1991, 30, 613.
8. N. T. Thuong, C. Hélène, Angew. Chem. Int. Engl. Ed. 1993, 32, 666.
9. [9a] R. J. Fiel, J. C. Howard, E. H. Mark, N. Datta-Gupta, Nucleic Acids Res., 1979, 6, 3093.
10. [9b] D. S. Sigman, A. Mazumder, D. M. Perrin, Chem. Rev. 1993, 93, 2295 and references cited therein.
11. G. Pratviel, J. Bernardou, B. Meunier in "Metal Ions in Biological Systems", vol. 33, pp. 399-426 A. and H. Sigel Eds, M. Dekker, 1996.
12. M. Pitiè, C. Casas, C. J. Lacey, G. Pratviel, J. Bernadou, B. Meunier, Angew. Chem. Int. Ed. Engl. 1993, 32, 557.
13. G. Pratviel, V. Duarte, J. Bernardou, B. Meunier, J. Am. Chem. Soc. 1993, 115, 7939.
14. M. Pitiè, J. Bernadou, B. Meunier, J. Am. Chem. Soc. 1995, 117, 2935.
15. P. Bigey, G. Pratviel, B. Meunier, J. Chem. Soc., Chem. Commun. 1995, 181.
16. B. Mestre, A. Jacobs, G. Pratviel, B. Meunier, Biochemistry, 1996, 35, 9140.
17. Y. Adam, J. Bernadou, B. Meunier, New Journal of Chem. 1992, 18, 525.
18. J. R. Fiel, T. A. Beerman, E. H. Mark, N. Datta-Gupta, Biochem. Biophys. Res. Commun.,1982, 107, 1067.
19. J. L. Sessler, P. I. Sansom, V. Kral, D. O'Connor, B. L. Iverson, J. Am. Chem. Soc. 1996, 118, 12322.
20. D. Magda, S. Crofts, J. L. Sessler, P. Sansom, L. Springs, Y. Ohya, Tetrahedron Lett. 1997, 38, 5759.
21. A similar polymeric support is commercially available from Novabiochem [Fmoc-Lys(Boc)Nova Syn TGA resin] in which the lysine residue is linked to the matrix through a benzyl ester group, which shows remarkable lability to acids. Since the ODN chain assembly requires repeated acidic treatments to deprotect the 5′-hydroxy functions of the nucleotide building blocks, its use was discarded.
22. S. De Luca, G. Bruno, R. Fattorusso, C. Isernia, C. Pedone, G. Morelli. Letters in Peptide Science, 1989, 5, 269.
23. V. K. Sarin, S. B. H. Kent, J. P. Tam, R. B. Merrifield, Analytical Biochem. 1981, 117, 147.
24. J. S. Lindsey, R. W. Wagner, J. Org. Chem. 1989, 54, 828.
25. [24a] Oligonucleotides and Analogues: A Practical Approach, F. Eckstein, Ed., IRL Press, Oxford, 1991, pp. 1-23.
26. [24b] Oligonucleotide Synthesis: A Practical Approach, M. Gait, Ed., IRL Press, Oxford, 1984, pp. 35-81.
27. 2O could not be directly obtained due to its extremely scarce solubility in this solvent, the above assumption is supported by spectra of 1 dissolved in other solvents, such as methanol or DMF, which all showed a close to zero absorbance in the 260-nm region.
28. [26a] Handbook of Biochemistry and Molecular Biology, volume I, Nucleic Acids, G. D. Fasman Ed., 3rd ed., CRC Press, 1975, p.589.
29. [26b] Cantor, C. R., Warshaw, M. M., Shapiro, H., Biopolymers, 1970, 9, 1059.