Binding of HIV-1 TAR mRNA to a peptide nucleic acid oligomer and its conjugates with metal-ion-binding multidentate ligands

Journal of Biological Inorganic Chemistry

Volumn 14, Issue 2, 2009, Pages 287-300

  Belousoff, Matthew J ^a,b   Gasser, Gilles ^a   Graham, Bim ^c   Tor, Yitzhak ^b   Spiccia, Leone ^a  

^a MONASH UNIVERSITY   (Australia)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c MONASH UNIVERSITY   (Australia)

Author keywords

Bis((pyridin 2 yl)methyl)amine peptide nucleic acid hybrids; Macrocycle peptide nucleic acid hybrids; Peptide nucleic acids; Targeting HIV 1 TAR stem loop; Zinc(II) complexes

Indexed keywords

MESSENGER RNA; METAL ION; OLIGOMER; PEPTIDE NUCLEIC ACID; RNA; SINGLE STRANDED RNA; ZINC;

ARTICLE; BASE PAIRING; CONJUGATION; CONTROLLED STUDY; DENATURATION; ELECTRICITY; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROGEN BOND; METAL BINDING; NONHUMAN; PRIORITY JOURNAL; PROTON TRANSPORT; REPRODUCIBILITY; RNA BINDING; RNA STRUCTURE; VIRUS ATTACHMENT;

BASE SEQUENCE; BINDING SITES; HETEROCYCLIC COMPOUNDS; HIV LONG TERMINAL REPEAT; HYDROGEN BONDING; LIGANDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PEPTIDE NUCLEIC ACIDS; PROTEIN DENATURATION; PYRIDINES; RNA, MESSENGER; RNA, VIRAL; STEREOISOMERISM; TEMPERATURE; ZINC;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 58849094920     PISSN: 09498257     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00775-008-0448-6     Document Type: Article

References (64)

1. PE Nielsen M Egholm RH Berg O Buchardt 1991 Science 254 1497 1500
2. J Wang E Palecek PE Nielsen G Rivas X Cai H Shiraishi N Dontha D Luo PAM Farias 1996 J Am Chem Soc 118 7667 7670
3. PE Nielsen 1999 Curr Opin Struct Biol 9 353 357
4. Koppelhus U, Nielsen PE (2001) Antisense drug technology, 1st Ed., Netlibrary, pp 359-374
5. Hanvey JC, Babiss LE (1995) Delivery strategies for antisense oligonucleotide therapeutics. CRC press, pp 151-60
6. R Gambari 2004 Curr Top Pharmacol 8 313 324
7. S Cogoi A Codognotto V Rapozzi LE Xodo 2005 Nucleosides Nucleotides Nucleic Acids 24 971 974
8. VL Marin S Roy BA Armitage 2004 Expert Opin Biol Ther 4 337 348
9. F Le Floch H-A Ho P Harding-Lepage M Pedard R Neagu-Plesu M Leclerc 2005 J Adv Mater 17 1251 1254
10. HF Arlinghaus M Schoreoder JC Feldner O Brandt JD Hoheisel D Lipinsky 2004 Appl Surf Sci 231-232 392 396
11. J Wang 1998 Biosens Bioelectron 13 757 762
12. Ratilainen T, Holmen A, Norden B (2004) Peptide nucleic acids. 2nd edn, Taylor & Francis, pp 77-105
13. K Hashimoto Y Ishimori 2001 Lab Chip 1 61 63
14. H Aoki P Buhlmann Y Umezawa 2000 Electroanalysis 12 1272 1276
15. J Wang PE Nielsen M Jiang X Cai JR Fernandes DH Grant M Ozsoz A Beglieter M Mowat 1997 Anal Chem 69 5200 5202
16. G Gasser MJ Belousoff AM Bond L Spiccia 2006 J Org Chem 71 7565 7573
17. Hess A, Metzler-Nolte, N (1999) Chem Commun 885-886
18. Baldoli C, Falciola L, Licandro E, Maiorana S, Mussini P, Ramani P, Rigamonti C, Zinzalla G (2004) J Organomet Chem 689:4791-4802
19. Baldoli C, Giannini C, Licandro E, Maiorana S, Zinzalla G (2004) Synlett 6:1044-1048
20. Hudson RHE, Li G, Tse J (2002) Tetrahedron Letters 43:1381-1386
21. Gasser G, Spiccia L (2008) J Organomet Chem 693:2478-2482
22. JC Verheijen GA van der Marel JH van Boom N Metzler-Nolte 2000 Bioconjug Chem 11 741 743
23. C Baldoli P Cerea C Giannini E Licandro C Rigamonti S Maionara 2005 Synlett 13 1984 1994
24. R Hamzavi T Happ K Weitershaus N Metzler-Nolte 2004 J Organomet Chem 689 4745 4750
25. Maurer A, Kraatz H-B, Metzler-Nolte N (2005) Eur J Inorg Chem 3207-3210
26. A Füssl A Schleifenbaum M Göritz A Riddell C Schultz R Kraemer 2006 J Am Chem Soc 128 5986 5987
27. A Mokhir R Stiebing R Kraemer 2003 Bioorg Med Chem Lett 13 1399 1401
28. A Mokhir R Kraemer H Wolf 2004 J Am Chem Soc 126 6208 6209
29. RM Watson YA Skorik GK Patra C Achim 2005 J Am Chem Soc 127 14628 14639
30. D-L Popescu TJ Parolin C Achim 2003 J Am Chem Soc 125 6354 6355
31. Küsel A, Zhang J, Gil MA, Stückl AC, Meyer-Klaucke W, Meyer F, Diederichsen U (2005) Eur J Inorg Chem 4317-4325
32. RM Franzini RM Watson D-L Popescu GK Patra C Achim 2004 Polymer Prepr 45 337 338
33. O Kornyushyna AJ Stemmler DM Graybosch I Bergenthal CJ Burrows 2005 Bioconjug Chem 16 178 183
34. FH Zelder J Brunner R Kraemer 2003 Chem Commun 7 902 903
35. I Boll R Kraemer J Brunner A Mokhir 2005 J Am Chem Soc 127 7849 7856
36. J Brunner A Mokhir R Kraemer 2003 J Am Chem Soc 125 12410 12411
37. M Shionoya E Kimura M Shiro 1993 J Am Chem Soc 115 6730 6737
38. S Aoki E Kimura 2004 Chem Rev 104 769 787
39. DA Barawkar RK Kumar KN Ganesh 1992 Tetrahedron 48 8505 8514
40. G Gasser MJ Belousoff AM Bond Z Kosowski L Spiccia 2007 Inorg Chem 46 1665 1674
41. E Kikuta N Katsube E Kimura 1999 J Biol Inorg Chem 4 431 440
42. S Aoki Y Honda E Kimura 1998 J Am Chem Soc 120 10018 10026
43. E Kikuta S Aoki E Kimura 2001 J Am Chem Soc 123 7911 7912
44. L-J Ma G-L Zhang S-Y Chen B Wu J-S You C-Q Xia X-Q Yu 2005 J Pept Sci 11 812 817
45. A Mokhir B Zohm A Fuessl R Kraemer 2003 R Bioorg Med Chem Lett 13 2489 2492
46. Armarego WLF, Perrin DD (1996) Purification of laboratory chemicals, 4th edn. Butterworth-Heinemann, Oxford
47. JW Jeon SJ Son CE Yoo IS Hong JB Song J Suh 2002 Org Lett 4 4155 4158
48. S Brandes C Gros F Denat P Pullumbi R Guilard 1996 Bull Soc Chim Fr 133 65 73
49. SI Kirin P Duebon T Weyhermueller E Bill N Metzler-Nolte 2005 Inorg Chem 44 5405 5415
50. Hartley FR, Burgess C, Alcock RM (1980) Solution equilibria, 1st edn. Wiley, London
51. R Lee N Kaushik MJ Modak R Vinayak VN Pandey 1998 Biochemistry 37 900 910
52. JC Hanvey NJ Peffer JE Bisi SA Thomson R Cadilla JA Josey DJ Ricca CF Hassman MA Bonham KG Au 1992 Science 258 1481 1485
53. NJ Peffer JC Hanvey JE Bisi SA Thomson CF Hassman SA Noble LE Babiss 1993 Proc Natl Acad Sci USA 90 10648 10652
54. ET Kool 1997 New J Chem 21 33 45
55. JL Asensio R Carr T Brown AN Lane 1999 J Am Chem Soc 121 11063 11070
56. Tam VK, Liu Q, Tor Y (2006) Chem Commun 2684-2686
57. A Avino M Frieden JC Morales BG De la Torre R Gueimil-Garcia M Orozco C Gonzalez R Eritja 2003 Nucleosides Nucleotides Nucleic Acids 22 645 648
58. KL Duehom PE Nielsen 1997 New J Chem 21 19 31
59. KK Jensen H Oerum PE Nielsen B Norden 1997 Biochemistry 36 5072 5077
60. SK Kim PE Nielsen M Egholm O Buchardt RH Berg B Norden 1993 J Am Chem Soc 115 6477 6481
61. J Brahms 1967 Proc R Soc Lond Ser A 297 150 162
62. Smith RM, Martell AE, Motekaitis RJ (1997) NIST standard reference data 46
63. A Warden M Warren TW Milton L Spiccia 2004 New J Chem 28 1160 1167
64. A Warden M Warren MTW Hearn L Spiccia 2004 Inorg Chem 43 6936 6943