Energy transfer assemblies composed of expanded porphyrin-oligonucleotide conjugates

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5759-5762

  Magda, Darren ^a   Crofts, Shaun ^a   Sessler, Jonathan L ^b   Sansom, Petra ^b   Springs, Stacy L ^b   Ohya, Yuichi ^b  

^a PHARMACYCLICS INC   (United States)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGONUCLEOTIDE; PORPHYRIN DERIVATIVE;

ARTICLE; ENERGY TRANSFER; IN VITRO STUDY; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0030858749     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01288-4     Document Type: Article

References (26)

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10. Clegg, R. M.; Murchie, A. I. H.; Zechel, A.; Lilley, D. M. J. Proc. Natl. Acad. Sci. USA 1993, 90, 2994-2998.
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18. Electron transfer in oligonucleotide assemblies has been studied: (a) Dandliker, P. J.; Holmlin, R. E.; Barton, J. K. Science 1997, 275, 1465-1468.
19. (b) Murphy, C. J.; Arkin, M. R.; Jenkins, Y.; Ghatlia, N. D.; Bossmann, S. H.; Turro, N. J.; Barton, J. K. Science 1993, 262, 1025-1029.
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21. (d) Meade, T. J.; Kayyem, J. F. Angew. Chem. Int. Ed. Engl. 1995, 34, 352-354.
22. An ancillary advantage of conjugates 1-3 is that they could define nucleic acid probes with improved, red-shifted spectral characteristics. For a discussion of the advantages that could accrue for in vivo applications of such properties, see: Sessler, J. L.; Sansom, P. I.; Král, V.; O'Connor, D.; Iverson, B. L. J. Am. Chem. Soc. 1996, 118, 12322-12330.
23. Magda, D.; Crofts, S.; Lin, A.; Miles, D.; Wright, M.; Sessler, J. L. J. Am. Chem. Soc. 1997, 119, 2293-2294.
24. Eaton, D. F. Pure & Appl. Chem. 1988, 60, 1107-1114.
25. The difference between the efficiency (50%) at the calculated Förster critical distance (36 Å) and the observed efficiency (65%) in the conjugate-derived ensemble reflects the fact that the overlap integrals and orientation factors used to calculate Förster critical distances are approximate. Moreover, the actual center-to-center distance between the chromophores in the duplex formed between the oligonucleotide conjugates is difficult to estimate because of the flexible attachment to the oligonucleotide. This distance is, however, expected to be less than 35 Å, which is consistent with the greater efficiency which is observed.
26. Under the concentration conditions of this control experiment, we were surprised to see quenching at all. The modest quenching observed with the 3′-sapphyrin conjugate 1 and the Y(III) texaphyrin monomer may be rationalized by the fact that lanthanide texaphyrins bind well to anionic phosphate esters: Lisowski, J.; Sessler, J. L.; Lynch, V.; Mody, T. D. J. Am. Chem. Soc. 1995, 117, 2273-2285. Thus, the "bimolecular" quenching observed may not be purely diffusional in character, but rather due in part to this association.