Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of 3β [L-Lysinamide-carbamoyl] Cholesterol Derivatives by Solid-Phase Method and Characteristics of Complexes with Antisense Oligodeoxynucleotides

  • Lee, Eun-Jung (School of Chemistry, Seoul National University) ;
  • Lee, Min-hyung (Department of Bioengineering, College of Engineering, Hanyang University) ;
  • Park, Jong-Sang (School of Chemistry, Seoul National University) ;
  • Choi, Joon-Sig (Department of Biochemistry, College of Natural Sciences, Chungnam National University)
  • Published : 2006.01.20
Download PDF
⟨ Previous Next ⟩

Abstract

In this report, we describe the synthesis of mono- and di-valent cationic $3\beta$ [L-Lysinamide-carbamoyl] cholesterol (K-Chol) derivatives by solid-phase peptide synthesis method and the characteristics of K-Chol/antisense oligodeoxynucleotide (ODN) complexes. K-Chol was able to interact with antisense ODNs electrostatically and constructed nanometer-sized complexes of 50-100 nm in diameter. The formation of K-Chol/antisense ODN complexes was demonstrated by non-denaturing polyacrylamide gel electrophoresis assay and atomic force microscopy. The cell-associated radioactivity was measured to monitor the cellular uptake of the complexes containing radioactive antisense ODNs using HL 60 cells.

Keywords

References

  1. Lu, Q. L.; Rabinowitz, A.; Chen, Y. C.; Yokota, T.; Yin, H.; Alter, J.; Jadoon, A.; Bou-Gharios, G.; Partridge, T. Proc. Natl. Acad. Sci. USA 2005, 102, 198 https://doi.org/10.1073/pnas.0406700102
  2. Mercatante, D. R.; Sazani, P.; Kole, R. Curr. Cancer Drug Targets 2001, 1, 211 https://doi.org/10.2174/1568009013334124
  3. Morrison, R. S. J. Biol. Chem. 1991, 266, 728
  4. Milligan, J. F.; Krawczyk, S. H.; Wadwani, S.; Matteucci, M. D. Nucleic Acids Res. 1993, 21, 327 https://doi.org/10.1093/nar/21.2.327
  5. Rao, T. S.; Durland, R. H.; Seth, D. M.; Myrick, M. A.; Bodepudi, V.; Revankar, G. R. Biochemistry 1995, 34, 765 https://doi.org/10.1021/bi00003a009
  6. Bennett, C. F.; Chiang, M. Y.; Chan, H.; Shoemaker, J. E.; Mirabelli, C. K. Mol. Pharmacol. 1992, 41, 1023
  7. Gao, X.; Huang, L. Biochem. Biophys. Res. Commun. 1991, 179, 280 https://doi.org/10.1016/0006-291X(91)91366-K
  8. Trubetskoy, V. S.; Torchilin, V. P.; Kennel, S.; Huang, L. Biochim. Biophys. Acta 1992, 1131, 311 https://doi.org/10.1016/0167-4781(92)90030-4
  9. Guy-Caffey, J. K.; Bodepudi, V.; Bishop, J. S.; Jayaraman, K.; Chaudhary, N. J. Biol. Chem. 1995, 270, 31391 https://doi.org/10.1074/jbc.270.52.31391
  10. Lewis, J. G.; Lin, K. Y.; Kothavale, A.; Flanagan, W. M.; Matteucci, M. D.; DePrince, R. B.; Mook, R. A., Jr.; Hendren, R. W.; Wagner, R. W. Proc. Natl. Acad. Sci. USA 1996, 93, 3176 https://doi.org/10.1073/pnas.93.8.3176
  11. Wang, S.; Lee, R. J.; Cauchon, G.; Gorenstein, D. G.; Low, P. S. Proc. Natl. Acad. Sci. USA 1995, 92, 3318 https://doi.org/10.1073/pnas.92.8.3318
  12. Choi, J. S.; Lee, E. J.; Jang, H. S.; Park, J. S. Bioconjug. Chem. 2001, 12, 108 https://doi.org/10.1021/bc000081o
  13. Choi, J. S.; Choi, Y. H.; Park, J. S. Bull. Korean Chem. Soc. 2004, 25, 1025 https://doi.org/10.5012/bkcs.2004.25.7.1025
  14. Kim, T.; Seo, H. J.; Baek, J.; Park, J. H.; Park, J. S. Bull. Korean Chem. Soc. 2005, 26, 175 https://doi.org/10.1007/s11814-009-0029-6
  15. Lee, S.; Suraiya, R. BioTechniques 1990, 9, 676
  16. Ausubel, F. M.; Brent, R.; Kingston, R. E.; Moore, D. D.; Smith, A. A.; Seidman, J. G.; Struhl, K. Current Protocols in Molecular Biology; John Wily & Sons: New York, 1998
  17. Kim, S.; Choi, J. S.; Jang, H. S.; Suh, H.; Park, J. S. Bull. Korean Chem. Soc. 2001, 22, 1069
  18. Hansen, M. B.; Nielsen, S. E.; Berg, K. J. Immunol. Methods 1989, 119, 203 https://doi.org/10.1016/0022-1759(89)90397-9
  19. Wickstrom, E. L.; Bacon, T. A.; Gonzalez, A.; Freeman, D. L.; Lyman, G. H.; Wickstrom, E. Proc. Natl. Acad. Sci. USA 1988, 85, 1028 https://doi.org/10.1073/pnas.85.4.1028
  20. Wickstrom, E.; Bacon, T. A.; Wickstrom, E. L. Cancer Res. 1992, 52, 6741
  21. Zon, G. Methods Mol. Biol. 1993, 20, 165