Synthesis of conformationaly preorganized and cell-permeable guanidine-based γ-peptide nucleic acids (γGPNAs)

Journal of Organic Chemistry

Volumn 74, Issue 4, 2009, Pages 1509-1516

  Sahu, Bichismita ^a   Chenna, Venugopal ^a,e   Lathrop, Kira L ^b   Thomas, Sufi M ^c   Zon, Gerald ^a,d   Livak, Kenneth J ^d   Ly, Danith H ^a  

^a CARNEGIE MELLON UNIVERSITY   (United States)

^b University of Pittsburgh School of Medicine   (United States)

^c UNIVERSITY OF PITTSBURGH SCHOOL OF MEDICINE   (United States)

^d APPLIED BIOSYSTEMS   (United States)

^e DEPARTMENT OF PATHOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELL-PERMEABLE; D-AMINO ACIDS; GENERAL METHODS; GUANIDINIUM; HIGH AFFINITIES; L-AMINO ACIDS; MAMMALIAN CELLS; NUCLEOBASES; PEPTIDE NUCLEIC ACIDS; RIGHT-HANDED HELIXES; SEQUENCE SELECTIVITIES;

AMINATION; AMINES; AMINO ACIDS; MAMMALS; ORGANIC ACIDS; RNA; SYNTHESIS (CHEMICAL);

NUCLEIC ACIDS;

AMINO ACID; ARGININE; DNA; GLYCINE; GUANIDINE; MONOMER; OLIGOMER; PEPTIDE NUCLEIC ACID; RNA;

ARTICLE; BINDING AFFINITY; CARBON NUCLEAR MAGNETIC RESONANCE; CIRCULAR DICHROISM; DNA BINDING; ELECTROSPRAY MASS SPECTROMETRY; FLUORINE NUCLEAR MAGNETIC RESONANCE; HELA CELL; MAMMAL CELL; MOLECULAR DYNAMICS; NUCLEIC ACID ANALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; RNA BINDING; SYNTHESIS; ANIMAL; CELL MEMBRANE PERMEABILITY; CHEMISTRY; CONFORMATION; CYTOLOGY; ENZYME SPECIFICITY; HUMAN; LIVER; METABOLISM; NUCLEIC ACID HYBRIDIZATION; NUCLEOTIDE SEQUENCE; STEREOISOMERISM;

ANIMALS; BASE SEQUENCE; CELL MEMBRANE PERMEABILITY; DNA; GUANIDINE; HELA CELLS; HUMANS; LIVER; NUCLEIC ACID CONFORMATION; NUCLEIC ACID HYBRIDIZATION; PEPTIDE NUCLEIC ACIDS; RNA; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 64349120434     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802211n     Document Type: Article

References (48)

1. De Mesmaeker, A.; Haener, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366-374.
2. Wengel, J. Acc. Chem. Res. 1999, 32, 301-310.
3. Nielsen, P. E. Acc. Chem. Res. 1999, 32, 624-630.
4. Summerton, J. E. Lett. Pept. Sci. 2004, 10, 215-236.
5. Juliano, R. L.; Yoon, H. Curr. Opin. Mol. Therap. 2000, 2, 297-303.
6. Lebedeva, I.; Benimetskaya, L.; Stein, C. A.; Vilenchik, M. Eur. J. Pharm. Biopharm 2000, 50, 101-119.
7. Stein, C. A. Nat. Biotechnol. 1999, 17, 209.
8. Nielsen, P. E.; Egholm, M.; Berg, R. H.; Buchardt, O. Science 1991, 254, 1497-1500.
9. Nielsen, P. E. Mol. Biotech. 2004, 26, 233-248.
10. Nielsen, P. E. Q. Rev. Biophys. 2005, 38, 345-350.
11. Koppelhus, U.; Nielsen, P. E. Adv. Drue Deliv.Rev. 2003, 55, 267-280.
12. Frankel, A. D.; Pabo, C. O. Cell 1988, 55, 1189-1193.
13. Green, M.; Loewenstein, P. M. Cell 1988, 55, 1179-1188.
14. Schwarze, S. R.; Ho, A.; Vocero-Akbani, A.; Dowdy, S. F. Science 1999, 285, 1569-1572.
15. Gratton, J.-P.; Yu, J.; Griffith, J. W.; Babbitt, R. W.; Scotland, R. S.; Hickey, R.; Giordano, F. J.; Sessa, W. C. Nat. Med. 2003, 9, 357-362.
16. Lewin, M.; Carlesso, N.; Tung, C.-H.; Tang, X.-W.; Cory, D.; Scadden, D. T.; Weissleder, R. Nat. Biotechnol. 2000, 18, 410-414.
17. Wender, P. A.; Mitchell, D. J.; Pattabiraman, K.; Pelkey, E. T.; Steinman, L.; Rothbard, J. B. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 13003-13008.
18. Umezawa, N.; Gelman, M. A.; Haigis, M. C.; Raines, R. T.; Gellman, S. H. J. Am. Chem. Soc. 2002, 124, 368-369.
19. Zhou, P.; Wang, M.; Du, L.; Fisher, G. W.; Waggoner, A.; Ly, D. H. J. Am. Chem. Soc. 2003, 125, 6878-6879.
20. Zhou, P.; Dragulescu-Andrasi, A.; Bhattacharya, B.; O'keefe, H.; Vatta, P.; Hyldig-Nielsen, J. J.; Ly, D. H. Bioorg. Med. Chem. Lett. 2006, 16, 4931-4935.
21. Dragulescu-Andrasi, A.; Zhou, P.; He, G.; Ly, D. H. Chem. Comm. 2005, 244-246.
22. Zasloff, M. Nature 2002, 415, 389-395.
23. Dragulescu-Andrasi, A.; Rapireddy, S.; He, G.; Bhattacharya, B.; Hyldig- Nielsen, J. J.; Zon, G.; Ly, D. H. J. Am. Chem. Soc. 2006, 128, 16104-16112.
24. Kosynkina, L.; Wang, W.; Liang, T. C. Tetrahedron Lett. 1994, 35, 5173-5176.
25. Wu, Y.; Xu, J. C. Tetrahedron 2001, 57, 8107-8113.
26. Englund, E. A.; Appella, D. H. Org. Lett. 2005, 7, 3465-3467.
27. Tedeschi, T.; Sforza, S.; Corradini, R.; Marchelli, R. Tetrahedron Lett. 2005, 46, 8395-8399.
28. Dose, C.; Seitz, O. Org. Lett. 2005, 7, 4365-4368.
29. Englund, E. A.; Appella, D. H. Aneew. Chem., Int. Ed. 2007, 46, 1414-1418.
30. Falkiewicz, B.; Kolodziejczyk, A. S.; Liberek, B.; Wisniewski, K. Tetrahedron 2001, 57, 7909-7917.
31. Stanfield, C. F.; Parker, J. E.; Kanellis, P. J. Org. Chem. 1981, 46, 4797-4798.
32. Rittle, K. E.; Homnick, C. F.; Ponticello, G. S.; Evans, B. E. J. Org. Chem. 1982, 47, 3016-3018.
33. Dueholm, K. L.; Egholm, M.; Behrens, C.; Christensen, L.; Hansen, H. F.; Vulpius, T.; Petersen, K. H.; Berg, R. H.; Nielsen, P. E.; Buchardt, O. J. Org. Chem. 1994, 59, 5767-5773.
34. Seco, J. M.; Quinoa, E.; Riguera, R. Chem. Rev. 2004, 104, 17-117.
35. Christensen, L.; Fitzpatrick, R.; Gildea, B.; Petersen, K. H.; Hansen, H. F.; Koch, T.; Egholm, M.; Buchardt, O.; Nielsen, P. E.; Coull, J.; Berg, R. H. J. Pept. Sci. 1995, 1, 175-183.
36. Sen, S.; Nilsson, L. J. Am. Chem. Soc. 2001, 123, 7414-7422.
37. Dragulescu-Andrasi, A.; Rapireddy, S.; Frezza, B. M.; Gayathri, C.; Gil, R. R.; Ly, D. H. J. Am. Chem. Soc. 2006, 128, 10258-10267.
38. Seitz, O. Angew. Chem., Int. Ed. 2000, 39, 3249-3252.
39. Ranasinghe, R. T.; Brown, T. J.; Brown, L. J. Chem. Comm. 2001, 1480-1481.
40. Kuhn, H.; Demidov, V. V.; Coull, J. M.; Fiandaca, M. J.; Gildea, B. D.; Frank-Kameneteskii, M. D. J. Am. Chem. Soc. 2002, 124, 1097-1103.
41. Egholm, M.; Buchardt, O.; Christensen, L.; Behrens, C.; Freier, S. M.; Driver, D. A.; Berg, R. H.; Kim, S. K.; Norden, B.; Nielsen, P. E. Nature 1993, 365, 566-568.
42. Wittung, P.; Nielsen, P. E.; Buchardt, O.; Egholm, M.; Norden, B. Nature 1994, 368, 561-563.
43. Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860-1866.
44. Green, M. M.; Cheon, K.-S.; Yang, S.-Y.; Park, J.-W.; Swansburg, S.; Liu, W. Acc. Chem. Res. 2001, 34, 672-680.
45. Haaima, G.; Lohse, A.; Buchardt, O.; Nielsen, P. E. Angew. Chem., Int. Ed. 1996, 35, 1939-1941.
46. Jensen, K. K.; Orum, H.; Nielsen, P. E.; Norden, B. Biochemistry 1997, 36, 5072-5077.
47. Wimley, W. C.; White, S. H. Biochemistry 2000, 39, 4432-4442.
48. Potocky, T. B.; Menon, A. K.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 3686-3687.