Phototriggered drug release from functionalized oligonucleotides by a molecular beacon strategy

Angewandte Chemie - International Edition

Volumn 42, Issue 22, 2003, Pages 2502-2504

  Okamato, Akimitsu ^a   Tanabe, Kazuhito ^a   Inasaki, Takaheshi ^a   Saito, Isao ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Drug delivery; Molecular devices; Oligonucleotides; Photolysis

Indexed keywords

MOLECULES; QUENCHING;

MOLECULAR BEACONS;

DRUG PRODUCTS;

1 NAPHTHYLACETIC ACID; 4 HYDROXYACETOPHENONE; NAPHTHALENE DERIVATIVE; NAPHTHALENE PHOSPHORAMIDITE; OLIGONUCLEOTIDE; PHOTOACTIVE PROBE OLIGODEOXYNUCLEOTIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOSENSOR; DNA HYBRIDIZATION; DNA PROBE; DRUG RELEASE; GENETIC ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYBRIDIZATION; INTRAMOLECULAR TRIPLET QUENCHING; IRRADIATION; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR BEACON; MOLECULAR DEVICE; MOLECULAR DYNAMICS; PHOTOCHEMICAL QUENCHING; PHOTOLYSIS; PHOTOREACTIVITY; PHOTOTRIGGERED DRUG RELEASE; PROTEIN DEGRADATION;

BIOSENSING TECHNIQUES; BIOTIN; MOLECULAR STRUCTURE; OLIGONUCLEOTIDES; PHARMACEUTICAL PREPARATIONS; PHOTOCHEMISTRY; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 0037663896     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250832     Document Type: Article

References (16)

1. S. Tyagi, F. R. Kramer, Nat. Biotechnol. 1996, 14, 303-308.
2. S. Tyagi, D. P. Btaru, F. R. Kramer, Nat. Biotechnol. 1998, 16, 49-53.
3. A.S. Piatek, S. Tyagi, A. C. Pol, A. Telenti, L. P. Miller, F. R. Kramer, D. Alland, Nat. Biotechnol. 1998, 16, 359-363.
4. Z. Ma, J.-S. Taylor, Proc. Natl. Acad. Sci. USA 2000, 97, 11159-11163.
5. Z. Ma, J.-S. Taylor, Bioorg. Med. Chem. 2001, 9, 2501-2510.
6. J. C. Sheehan, K. Umezawa, J. Org. Chem. 1973, 38, 3771-3774.
7. K. Zhang, J. E. T. Corrie, V. R. N. Munasinghe, P. Wan, J. Am. Chem. Soc. 1999, 121, 5625-5632.
8. P. G. Conrad II, R. S. Givens, J. F. W. Weber, K. Kandler, Org. Lett. 2000, 2, 1545-1547.
9. R. S. Givens, A. Jung, C.-H. Park, J. Weber, W. Bartlett, J. Am. Chem. Soc. 1997, 119, 8369-8370.
10. R. S. Givens, J. F. W. Weber, P. G. Conrad II, G. Orosz, S. L. Donahue, S. A. Thayer, J. Am. Chem. Soc. 2000, 122, 2687-2697.
11. m was 40.4°C in 10 mM sodium cacodylate (pH 7.0) and 1 mM NaCl.
12. A control ODN that does not have a 5′ triplet quencher 9a-naph was also tested. Very rapid degradation was observed for both closed form 9a-naph and open form 9a-naph hybridized with the complementary strand (59% and 55% conversion, respectively).
13. A solution of 4-methoxyphenacyl ester of biotin (0.14 mmol) in acetonitrile/2-propanol/water (1:4:2, v/v/v) was irradiated at 312 nm with a transilluminator for 3.5 h at room temperature. The reaction mixture was purified by silica gel chromatography to give 4-methoxyacetophenone and biotin in 59% yield.
14. Several peaks were detected by HPLC in the reaction mixture of 9b, suggesting that the mixture contains several photoproducts in addition to product 10b as given by MALDI-TOF mass. For a solution containing duplex ODN 5′-d(GCGAGAAGTTAAGACCTATGCTCGC)-3′/5′-d (CATAGGTCTTAACTT)-3′ and 4-methoxyphenacyl ester of biotin, 8% consumptions of ODN were observed for 60 s irradiation. Further conversion of 10b by irradiation was not observed.
15. N. M. Green, Biochem. J. 1965, 94, 23c-24c.
16. H. Hofstetter, M. Morpurgo, O. Hofstetter, E. A. Bayer, M. Wilchek, Anal. Biochem. 2000, 284, 354-366.