Esterase-triggered fluorescence of fluorogenic oligonucleotides

Bioconjugate Chemistry

Volumn 8, Issue 6, 1997, Pages 856-861

  Laurent, Alain ^a   Debart, Françoise ^a   Lamb, Ned ^b   Rayner, Bernard ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CELL CULTURE; ENZYMES; FLUORESCENCE; NUCLEIC ACIDS; OLIGOMERS; OLIGONUCLEOTIDES;

ANTISENSE OLIGONUCLEOTIDES; CELL-BE; CELL/B.E; CELL/BE; CELLULAR ESTERASE; FLUOROGENICS; INTRACELLULAR DELIVERY; LABELINGS; PHENOLICS; PHOSPHOROTHIOATES;

ESTERS;

EID: 0031281837     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc970168i     Document Type: Article

References (23)

1. Barber, I., Rayner, B., and Imbach, J. L. (1995) The prooligonucleotide approach I: Esterase-mediated reversibility of dithymidine S-alkyl-phosphorothiolates to dithymidine phosphorothioates. Bioorg. Med. Chem. Lett. 5, 563-568.
2. Barber, I., Tosquellas, G., Morvan, F., Rayner, B., and Imbach, J. L. (1995) The prooligonucleotide approach II: Synthesis and stability studies of chimeric oligonucleotide models. Bioorg. Med. Chem. Lett. 5, 1441-1444.
3. Iyer, R. P., Yu, D., and Agrawal, S. (1995) Prodrugs of oligonucleotides: the acyloxyalkyl esters of oligodeoxyribo-nucleoside phosphorothioates. Bioorg. Chem. 23, 1-21.
4. Tosquellas, G., Barber, I., Morvan, F., Rayner, B., and Imbach, J. L. (1996) The prooligonucleotide approach III: Synthesis and bioreversibility of a chimeric phosphorodithioate prooligonucleotide. Bioorg. Med. Chem. Lett. 6, 457-462.
5. Tosquellas, G., Morvan, F., Rayner, B., and Imbach, J. L. (1997) The prooligonucleotide approach IV: Synthesis of chimeric prooligonucleotides with 6 enzymolabile masking groups and unexpected desulfurization side reaction. Bioorg. Med. Chem. Lett. 7, 263-268.
6. Temsamani, J., Kubert, M., Tang, J. Y., Padmapriya, A., and Agrawal, S. (1994) Cellular uptake of oligodeoxynucleotide phosphorothioates and their analogs. Antisense Res. Dev. 4, 35-42.
7. Spiller, D. G., and Tidd, D. M. (1992) The uptake kinetics of chimeric oligodeoxynucleotide analogues in human leukaemia MOLT-4 cells. Anti-Cancer Drug Design 7, 115-129.
8. Giles, R. V., Spiller, D. G., and Tidd, D. M. (1993) Chimeric oligodeoxynucleotide analogues enhanced cell uptake of structures which direct ribonuclease-H with high specificity. Anti-Cancer Drug Design 8, 33-51.
9. Milligan, J. F., Matteucci, M. D., and Martin, J. C. (1993) Currents concepts in antisense drug design. J. Med. Chem. 36, 1923-1937.
10. Iyer, R. P., Phillips, L. R., Egan, W., Regan, J. B., and Beaucage, S. L. (1990) The automated synthesis of sulfur-containing oligodeoxyribonucleotides using 3H-1,2-benzodithiol-3-one 1,1-dioxide as a sulfur-transfer reagent. J. Org. Chem. 55, 4693-4699.
11. Hogrefe, R. I., Reynolds, M. A., Vaghefi, M. M., Young, K. M., Riley, T. A., Klem, R. E., and Arnold, L. J., Jr. (1993). An improved method for the synthesis and deprotection of methylphosphonate oligonucleotides. Methods in Molecular Biology: Protocols for Oligonucleotides and Analogs (S. Agrawal, Ed.) pp 143-164, Humana Press, Totowa, NJ.
12. Wachter, L., Jablonski, J.-A., and Ramachandran, K. L. (1986) A simple and efficient procedure for the synthesis of 5′-aminoalkyl oligodeoxynucleotides. Nucleic Acids Res. 14, 7985-7994.
13. Hogrefe, R. I., Vaghefi, M. M., Reynolds, M. A., Young, K. M., and Arnold Jr., L. J. (1993) Deprotection of methylphosphonate oligonucleotides using a novel one-pot procedure. Nucleic Acids Res. 21, 2031-2038.
14. Pompon, A., Lefebvre, I., Imbach, J.-L., Kahn, S., and Farquhar, D. (1994) Decomposition pathways of the mono-and bis(pivaloyloxymethyl)esters of azidothymidine 5′-monophosphate in cell extract and in tissue culture medium: an application of the 'on-line ISRP-cleaning' HPLC technique. Antiviral Chem. Chemother. 5, 91-98.
15. Girard, F., Fernandez, A., and Lamb, N. (1995) Delayed cyclin A and B1 degradation in nontransformed mammalian cells. J. Cell Sci. 108, 2599-2608.
16. Agrawal, S. (1994) Functionalization of oligonucleotides with amino groups and attachment of amino specific reporter groups. Methods in Molecular Biology: Protocols for Oligonucleotides Conjugates (S. Agrawal, Ed.) pp 93-120, Humana Press, Totowa, NJ.
17. Theisen, P., McCollum, C., Upadhya, K., Jacobson, K., Vu, H., and Andrus, A. (1992) Fluorescent dye phosphoramidite labelling of oligonucleotides. Tetrahedron Lett. 33, 5033-5036.
18. Acedo, M., Tarrason, G., Piulats, J., Mann, M., Wilm, M., and Eritja, R. (1995) Preparation of oligonucleotide-dexamethasone conjugates. Bioorg. Med. Chem. Lett. 5, 1577-1580.
19. Fukui, K., Morimoto, M., Segawa, H., Tanaka, K., and Shimidzu, T. (1996) Synthesis and properties of an oligonucleotide modified with an acridine derivative at the artificial abasic site. Bioconjugate Chem. 7, 349-355.
20. Telser, J., Cruickshank, K. A., Morrison, L. E., and Netzel, T. L. (1989) Synthesis and characterization of DNA oligomers and duplexes containing covalently attached molecular labels: comparison of biotin, fluorescein, and pyrene labels by thermodynamic and optical spectroscopic measurements. J. Am. Chem. Soc. 111, 6966-6976.
21. Fisher, T. L., Terhorst, T., Cao, X., and Wagner, R. W. (1993) Intracellular disposition and metabolism of fluorescently-labeled unmodified and modified oligonucleotides microinjected into mammalian cells. Nucleic Acids Res. 21, 3857-3865.
22. Chin, D. J., Green, G. A., Zon, G., Szoka Jr., F. C., and Straubinger, R. M. (1990) Rapid nuclear accumulation of injected oligodeoxyribonucleotides. New Biol. 2, 1091-1100.
23. Leonetti, J.-P., Mechti, N., Degols, G., Gagnor, C., and Lebleu, B. (1991) Intracellular distribution of microinjected antisense oligonucleotides. Proc. Natl. Acad. Sci. U.S.A. 88, 2702-2706.