Development of thiol-responsive amide bond cleavage device and its application for peptide nucleic acid-based DNA releasing system

Tetrahedron Letters

Volumn 51, Issue 18, 2010, Pages 2525-2528

  Shigenaga, Akira ^a   Yamamoto, Jun ^a   Hirakawa, Hiroko ^a   Ogura, Keiji ^a   Maeda, Nami ^a   Morishita, Ko ^a   Otaka, Akira ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; COMPLEMENTARY DNA; PEPTIDE NUCLEIC ACID; THIOL;

ARTICLE; DISSOCIATION; DRUG RELEASE; REACTION ANALYSIS; SYNTHESIS;

EID: 77950002639     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.006     Document Type: Article

References (29)

1. Mintzer M.A., and Simanek E.E. Chem. Rev. 109 (2009) 259-302
2. Recent reviews covering a thiol-responsive gene delivery system:. Lin C., and Engbersen J.F.J. J. Controlled Release 132 (2008) 267-272
3. Ganta S., Devalapally H., Shahiwala A., and Amiji M. J. Controlled Release 126 (2008) 187-204
4. Harada A., and Kataoka K. Prog. Polym. Sci. 31 (2006) 949-982
5. Anderson E. Chem. Biol. Interact. 112 (1998) 1-14 and references therein
6. Jones D.P., Carlson J.L., Samiec P.S., Sternberg P., Mody V.C., Reed R.L., and Brown L.A.S. Clin. Chem. Acta 275 (1998) 175-184
7. Shigenaga A., Yamamoto J., Hirakawa H., Yamaguchi K., and Otaka A. Tetrahedron 65 (2009) 2212-2216
8. Shigenaga A., Tsuji D., Nishioka N., Tsuda S., Itoh K., and Otaka A. ChemBioChem 8 (2007) 1929-1931
9. Trimethyl lock system:. Jung M.E., and Piizzi G. Chem. Rev. 105 (2005) 1735-1766 and references therein
10. Amsberry K.L., and Borchardt R.T. J. Org. Chem. 55 (1990) 5867-5877
11. Caswell M., and Schmir G.L. J. Am. Chem. Soc. 102 (1980) 4815-4821
12. Milstien S., and Cohen L.A. J. Am. Chem. Soc. 94 (1972) 9158-9165
13. Borchardt R.T., and Cohen L.A. J. Am. Chem. Soc. 94 (1972) 9166-9174
14. Milstien S., and Cohen L.A. Proc. Natl. Acad. Sci. U.S.A. 67 (1970) 1143-1147
15. Kan T., and Fukuyama T. Chem. Commun. (2004) 353-359
16. Fukuyama T., Jow C.K., and Cheung M. Tetrahedron Lett. 36 (1995) 6373-6374
17. Yang X.-F., Wang L., Xu H., and Zhao M. Anal. Chim. Acta 631 (2009) 91-95
18. Zhou W., Shultz J.W., Murphy N., Hawkins E.M., Bernad L., Good T., Moothart L., Frackman S., Klaubert D.H., Bulleit R.F., and Wood K.V. Chem. Commun. (2006) 4620-4622
19. Maeda H., Matsuno H., Ushida M., Katayama K., Saeki K., and Itoh N. Angew. Chem., Int. Ed. 44 (2005) 2922-2925
20. Nielsen P.E. Chem. Biodivers. 4 (2007) 1996-2002
21. Nielsen P.E., and Michael E. In: Nielsen P.E. (Ed). Peptide Nucleic Acid. second ed. (2004), Horizon Bioscience, Wymondham 1-36
22. +): 1390.6, found; 1390.7 and 1390.7.
23. Because glutathione and its disulfide derivative make HPLC chart complicated, thiol 11 was used as a model thiol.
24. Time dependent epimerization of processing product 8 to its epimer 8′ was observed under reaction conditions.
25. 2+): 1369.1, found; 1369.1.
26. Synthesis of Fmoc-t-OH, see:. Thomson S.A., Josey J.A., Cadilla R., Gaul M.D., Hassman C.F., Luzzio M.J., Pipe A.J., Reed K.L., Ricca D.J., Wiethe R.W., and Noble S.A. Tetrahedron 51 (1995) 6179-6194
27. Rahman S.M., Seki S., Obika S., Yoshikawa H., Miyashita K., and Imanishi T. J. Am. Chem. Soc. 130 (2008) 4886-4896
28. Because UV-absorption of thiol or disulfide was observed at 260 nm, standard UV-absorption-based method was not applicable to this experiment.
29. m value of PNA, see:. Giesen U., Kleider W., Berding C., Geiger A., Orum H., and Nielsen P.E. Nucleic Acids Res. 26 (1998) 5004-5006