Synthesis and studies of modified oligonucleotides-directed triple helix formation at the purine-pyrimidine interrupted site

Nucleosides, Nucleotides and Nucleic Acids

Volumn 22, Issue 5-8, 2003, Pages 1277-1280

  Jazouli, Mohamed ^a   Guianvarc'h, Dominique ^b   Bougrin, Khalid ^a   Soufiaoui, Mohamed ^a   Vierling, Pierre ^c   Benhida, Rachid ^c  

^a FACULTÉ DES SCIENCES   (Morocco)

^b MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

^c UNIVERSITÉ CÔTE D'AZUR   (France)

Author keywords

Artificial nucleobases; AT inversion; Triple helix

Indexed keywords

ADENINE; OLIGONUCLEOTIDE; PURINE; PYRIMIDINE; THYMIDINE;

BASE PAIRING; CONFERENCE PAPER; DNA SEQUENCE; DNA STRUCTURE; MOLECULAR GENETICS; NUCLEOTIDE METABOLISM; NUCLEOTIDE SEQUENCE; TRIPLE HELIX;

BASE PAIRING; BASE SEQUENCE; HYDROGEN BONDING; NUCLEIC ACID CONFORMATION; NUCLEIC ACID DENATURATION; OLIGODEOXYRIBONUCLEOTIDES; PURINES; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 0141484689     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120022945     Document Type: Conference Paper

References (20)

1. (a) Le Doan, T.; Perrouault, L.; Praseuth, D.; Habhoub, N.; Decout, J.L. ; Thuong, N.T.; Lhomme, J.; Hélène, C. Sequence-specific recognition, photocrosslinking and cleavage of the DNA double helix by an oligo-[alpha]-thymidylate covalently linked to an azidoproflavine derivative. Nucleic Acids Res. 1987, 15, 7749-7760;
2. (b) Moser, H.E.; Dervan, P.B. Sequence-specific cleavage of double helical DNA by triple helix formation. Science 1987, 238, 645-650;
3. For reviews see (c) Thuong, N.T.; Hélène, C. Sequence-specific recognition and modification of double-helical DNA by oligonucleotides. Angew. Chem. Int. Ed. Engl. 1993, 32, 666-690;
4. (d) Frank-Kamenetskii, M.D.; Mirkin, S.M. Triplex DNA structures. Annu. Rev. Biochem. 1995, 64, 65-95;
5. (e) Neidle, S. Recent developments in triple-helix regulation of gene expression. Anti-Cancer Drug Design 1997, 12, 433-442.
6. (a) Giovannangeli, C.; Hélène, C. Progress in developments of triplex-based strategies. Antisense Nucleic Acid Drug Dev. 1997, 7, 413-421;
7. (b) Vasquez, K.M.; Wilson, J.H. Triplex-directed modification of genes and gene activity. Trends Biochem. Sci. 1998, 23, 4-9;
8. (c) Praseuth, D.; Guieysse-Peugeot, A.L.; Hélène, C. Triple helix formation and the antigene strategy for sequence-specific control of gene expression. Biochim. Biophys. Acta. 1999, 1489, 181-206.
9. (a) Mergny, J.L.; Sun, J.S.; Rougée, M.; Garestier, T.; Barcelo, F.; Chomilier, J.; Hélène, C. Sequence specificity in triple-helix formation: experimental and theoretical studies of the effect of mismatches on triplex stability. Biochemistry 1991, 30, 9791-9798;
10. (b) Greenberg, W.A.; Dervan, P.B. Energetics of formation of sixteen triple helical complexes which vary at a single position within a purine motif. J. Am. Chem. Soc. 1995, 117, 5016-5022;
11. (c) Best, G.C.; Dervan, P.B. Energetics of formation of sixteen triple helical complexes which vary at a single position within a pyrimidine motif. J. Am. Chem. Soc. 1995, 117, 1187-1193.
12. (a) Griffin, L.C.; Kiessling, L.L.; Beal, P.A.; Gillespie, P.; Dervan, P.B. Recognition of all four base pairs of double-helical DNA by triple-helix formation: design of nonnatural deoxyribonucleosides for pyrimidine-purine base pair binding. J. Am. Chem. Soc. 1992, 114, 7976-7982;
13. (b) Koshlap, K.M.; Gillespie, P.; Dervan, P.B.; Feigon, J. Nonnatural deoxyribonucleoside D3 incorporation in an intramolecular DNA triplex binds sequence-specifically by intercalation. J. Am. Chem. Soc. 1993, 115, 7908-7909;
14. (c) Huang, C.Y.; Cushman, C.D.; Miller, P.S. Triplex formation by an oligonucleotide containing N4-(3-acetamidopropyl)cytosine. J. Org. Chem. 1993, 58, 5048-5049;
15. (d) Huang, C.Y.; Miller, P.S. Triplex formation by an oligodeoxyribonucleotide containing N4-(6-aminopyridinyl)-2′ -deoxycytidine. J. Am. Chem. Soc. 1993, 115, 10,456-10,457;
16. (e) Huang, C.Y.; Bi, G.; Miller, P.S. Triplex formation by oligonucleotides containing novel deoxycytidine derivatives. Nucleic Acids Res. 1996, 24, 2606-2613;
17. (f) Lehmann, T.E.; Greenberg, W.A.; Liberles, D.A.; Wada, C.K.; Dervan, P.B. Triple-helix formation by pyrimidine oligonucleotides containing nonnatural nucleosides with extended aromatic nucleobases: intercalation from the major groove as a method for recognizing CG and AT base pairs. Helv. Chim. Acta. 1997, 80, 2002-2022;
18. (g) Obika, S.; Hari, Y.; Sekiguchi, M.; Imanishi, T. A 2′,4′-bridged nucleic acid containing 2-pyridone as a nucleobase: efficient recognition of a CG interruption by triplex formation with a pyrimidine motif. Angew. Chem. Int. Ed. 2001, 40, 2079-2081.
19. Guianvarc'h, D.; Benhida, R.; Fourrey, J.-L.; Maurisse, R.; Sun, J.S. Incorporation of a novel nucleobase allows stable oligonucleotide-directed triple helix formation at the target sequence containing a purine-pyrimidine interruption. J. Chem. Soc. Chem. Commun. 2001, 1814-1815.
20. Guianvarc'h, D.; Fourrey, J.-L.; Maurisse, R.; Sun, J.S.; Benhida, R. Synthesis, incorporation into triplex-forming oligonucleotide, and binding properties of a novel 2′-deoxy-C-nucleoside featuring a 6-(thiazolyl-5)benzimidazole nucleobase. Org. Lett. 2002, 4 (24), 4209-4212.