Synthesis of triazole-linked oligonucleotides with high affinity to DNA complements and an analysis of their compatibility with biosystems

Journal of Organic Chemistry

Volumn 78, Issue 12, 2013, Pages 5964-5969

  Varizhuk, Anna M ^a,b   Kaluzhny, Dmitry N ^b   Novikov, Roman A ^b   Chizhov, Alexandr O ^c   Smirnov, Igor P ^a   Chuvilin, Andrey N ^a   Tatarinova, Olga N ^a   Fisunov, Gleb Y ^a   Pozmogova, Galina E ^a   Florentiev, Vladimir L ^b  

^a FEDERAL RESEARCH AND CLINICAL CENTER OF PHYSICAL CHEMICAL MEDICINE OF FEDERAL MEDICAL BIOLOGICAL AGENCY   (Russian Federation)

^b ENGELHARDT INSTITUTE OF MOLECULAR BIOLOGY   (Russian Federation)

^c N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

BIO-SYSTEMS; DNA BINDING AFFINITY; HIGH AFFINITY; MODIFIED OLIGONUCLEOTIDES; PCR PRIMERS;

BINDING ENERGY; NITROGEN COMPOUNDS; POLYMERASE CHAIN REACTION;

OLIGONUCLEOTIDES;

DNA; NUCLEASE; OLIGONUCLEOTIDE; TRIAZOLE;

ARTICLE; BINDING AFFINITY; CHEMICAL PARAMETERS; CONTROLLED STUDY; DNA BINDING; HYDROLYSIS; INTERNUCLEOTIDE LINKAGE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; POLYMERASE CHAIN REACTION; PROTEIN MODIFICATION; SYNTHESIS;

DEOXYRIBONUCLEASES; DNA; HYDROLYSIS; MOLECULAR MIMICRY; MOLECULAR PROBES; NUCLEIC ACID DENATURATION; NUCLEIC ACID HYBRIDIZATION; OLIGONUCLEOTIDES; POLYMERASE CHAIN REACTION; TRIAZOLES;

EID: 84879373269     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400651k     Document Type: Article

References (20)

1. El-Sagheer, A. H.; Brown, T. Chem. Soc. Rev. 2010, 39, 1388-1405
2. Mutisya, D.; Selvam, C.; Kennedy, S. D.; Rozners, E. Bioorg. Med. Chem. Lett. 2011, 21, 3420-3422
3. Sau, S. P.; Hrdlicka, P. J. J. Org. Chem. 2012, 77, 5-16
4. El-Sagheer, A. H.; Brown, T. Acc. Chem. Res. 2012, 45, 1258-1267
5. Nuzzi, A.; Massi, A.; Dondoni, A. QSAR Comb. Sci. 2007, 26, 1191-1199
6. Lucas, R.; Neto, V.; Bouazza, A. H.; Zerrouki, R.; Granet, R.; Champavier, Y. K. Tetrahedron 2008, 64, 5467-5471
7. Chandrasekhar, S.; Srihari, P.; Nagesh, C.; Kiranmai, N.; Nagesh, N.; Idris, M. M. Synthesis 2010, 21, 3710-3714
8. Madhuri, V.; Kumar, V. A. Nucleosides, Nucleotides Nucleic Acids 2012, 31, 97-111
9. Isobe, H.; Fujino, T.; Yamazaki, N.; Guillot-Nieckowski, M.; Nakamura, E. Org. Lett. 2008, 10, 3729-3732
10. Varizhuk, A.; Chizhov, A.; Smirnov, I.; Kaluzhny, D.; Florentiev, V. Eur. J. Org. Chem. 2012, 11, 2173-2179
11. Sanzone, A. P.; El-Sagheer, A. H.; Brown, T.; Tavassoli, A. Nucleic Acids Res. 2012, 40, 10567-10575
12. Dallmann, A.; El-Sagheer, A. H.; Dehmel, L.; Mügge, Griesinger, C.; Ernstinga, N. P.; Brown, T. Chem. Eur. J. 2011, 17, 14714-14717
13. El-Sagheer, A. H.; Sanzone, A. P.; Gao, R.; Tavassoli, A.; Brown, T. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 11338-11343
14. El-Sagheer, A. H.; Brown, T. Chem. Commun. 2011, 47, 12057-12058
15. Zavgorodny, S.; Polianski, M.; Besidsky, E.; Kriukov, V.; Sanin, A.; Pokrovskaya, M.; Gurskaya, G.; Lonnberg, H.; Azhayev, A. Tetrahedron Lett. 1991, 32, 7593-7596
16. Veeneman, G. H.; Van Der Marel, G. A.; H. Van Den Elst, H.; Van Boom, J. H. Tetrahedron 1991, 47 (8) 1547-1562
17. He, G. H.; Bischofberger, N. Tetrahedron Lett. 1997, 38 (6) 945-948
18. Zavgorodny, S. G.; Pechenov, A. E.; Shvets, V. I.; Miroshnikov, A. I. S,X-acetals in nucleoside chemistry. III Nucleosides Nucleotides Nucleic Acids 2000, 19, 1977-1991
19. Varizhuk, A.; Chizhov, A.; Florentiev, V. Bioorg. Chem. 2011, 39, 127-131
20. Hovinen, J.; Azhayeva, E.; Azhayev, A.; Guzaev, A.; Lonnberg, H. J. Chem. Soc., Perkin Trans. 1 1994, 211-217