Design and synthesis of LNA-based mercaptoacetamido-linked nucleoside dimers

Nucleosides, Nucleotides and Nucleic Acids

Volumn 32, Issue 5, 2013, Pages 256-272

  Sharma, Vivek K ^a   Singh, Sunil K ^a   Bohra, Kapil ^a   Chandra Shekhar Reddy, L ^a   Khatri, Vinod ^a   Olsen, Carl E ^b   Prasad, Ashok K ^a  

^a UNIVERSITY OF DELHI   (India)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Locked nucleic acid; mercaptoace tamido linkage; phosphate backbone modification; phosphoramidite derivative

Indexed keywords

2 (5' DEOXY 3' O TERT BUTYLDIPHENYLSILYL 2' O, 4' C METHYLENETHYMIDIN 5' YL)MERCAPTOACETIC ACID; 2 (5' DEOXY 3' O TERT BUTYLDIPHENYLSILYL BETA THYMIDIN 5' YL)MERCAPTOACETIC ACID; LOCKED NUCLEIC ACID; NUCLEOSIDE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG; OLIGONUCLEOTIDE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; DEACETYLATION; DESILYLATION; DRUG DESIGN; DRUG SYNTHESIS; CHEMISTRY; DIMERIZATION; SYNTHESIS;

CHEMISTRY TECHNIQUES, SYNTHETIC; DIMERIZATION; DRUG DESIGN; NUCLEOSIDES; OLIGONUCLEOTIDES; SULFHYDRYL COMPOUNDS;

EID: 84876351342     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770.2013.783218     Document Type: Article

References (31)

1. Snead, N.M.; Rossi, J.J. RNA interference trigger variants: getting the most out of RNA for RNA interference-based therapeutics. Nucleic Acid Ther. 2012, 22, 139-146.
2. Campbell, M.A.; Wengel, J. Locked vs. unlocked nucleic acids (LNA vs. UNA): contrasting structures work towards common therapeutic goals. Chem. Soc. Rev. 2011, 40, 5680-5689.
3. Herdewijn, P. Nucleic acids with a six-membered 'carbohydrate' mimic in the backbone. Chem. Biodivers. 2010, 7, 1-59.
4. Crooke, S.T. Progress in antisense technology. Annu. Rev. Med. 2004, 55, 61-95.
5. Novina, C.D.; Sharp, P.A. The RNAi revolution. Nature 2004, 430, 161-164.
6. Yan, H. Nucleic acid nanotechnology. Science 2004, 306, 2048-2049.
7. Wengel, J. Nucleic acid nanotechnology-towards A° ngstr̈om-scale engineering. Org. Biomol. Chem. 2004, 2, 277-280.
8. Chen, X.; Roloff, A.; Seitz, O. Consecutive signal amplification for DNA detection based on de novo fluorophore synthesis and host-guest chemistry. Angew. Chem. Int. Ed. Engl. 2012, 51, 4479-4483.
9. Corey, D.R. Chemical modification: the key to clinical application of RNA interference? J. Clin. Invest. 2007, 117, 3615-3622.
10. Mickelfield, J. Backbone modification of nucleic acids: synthesis, structure and therapeutic applications. Current Med. Chem. 2001, 8, 1157-1179.
11. Wengel, J. Synthesis of 3-C-and 4-C-branched oligodeoxynucleotides and the development of locked nucleic acid (LNA). Acc. Chem. Res. 1999, 32, 301-310.
12. Hildebrandt-Eriksen, E.S.; Aarup, V.; Persson, R.; Hansen, H.F.; Munk, M.E.; Ørum, H. A locked nucleic acid oligonucleotide targeting microRNA 122 is well-tolerated in cynomolgus monkeys. Nucleic Acid Ther. 2012, 22, 152-161.
13. Veedu, R.N.; Wengel, J. Locked nucleic acids: promising nucleic acid analogs for therapeutic applications. Chem Biodivers. 2010, 7, 536-542.
14. Baraasch, D.A.; Corey, D.R. Locked nucleic acid (LNA): fine-tuning the recognition of DNA and RNA. Chem. Biol. 2001, 8, 1-7.
15. Zhang, J.; Shaw, J.T.; Matteucci, M.D. Synthesis and hybridization property of an oligonucleotide containing a 3-thioformcetal linked pentathymidylate. Bioorg. Med. Chem. Lett. 1999, 9, 319-322.
16. Waldner, A.; Mesmaeker, A. De. Synthesis of oligodeoxyribonucleotides containing dimers with carbamate moieties as replacement of the natural phosphodiester linkage. Bioorg. Med. Chem. Lett. 1994, 4, 405-408.
17. Bhat, B.; Swayze, E.E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y.S. Synthesis of novel nucleic acid mimics via the stereoselective intermolecular radical coupling of 3-Iodo nucleosides and formaldoximes. J. Org. Chem. 1996, 61, 8186-8199.
18. Lauristen, A.; Wengel, J. Oligodeoxynucleotides containing amide-linked LNA-type dinucleotides: synthesis and high-affinity nucleic acid hybridization. Chem. Commun. 2002, 530-531.
19. Isobe, H.; Fujino, T.; Yamazaki, N.; Niekowski, M.G.; Nakamura, E. Triazole-linked analogue of deoxyribonucleic acid (TLDNA): design, synthesis, and double-strand formation with natural DNA. Org. Lett. 2008, 10, 3729-3732.
20. Gogoi, K.; Gunjal, A.D.; Phalgune, U.D.; Kumar, V.A. Synthesis and RNA binding selectivity of oligonucleotides modified with five-atom thioacetamido nucleic acid backbone structures. Org. Lett. 2007, 9, 2697-2700.
21. (a Martin, M.M. Synthesis of D-glucose derived oxetane: 1,2-O-isopropylidene-4-(S)-3-O,4-Cmethylene-5-O-methanesulfonyl-β-L-threo- pento-1,4-furanose. J. Appl. Sci. Res. 2008, 4, 1478-1482
22. (b Youssefyeh, R.D.; Verheyden, J.P.H.; Moffatt, J.G. 4-Substituted nucleosides: synthesis of some 4-hydroxymethyl nucleosides. J. Org. Chem. 1979, 44, 1301-1309.
23. Vorbr̈uggen, H.; Lagoja, I.M.; Herdewijn, P. Synthesis of ribonucleosides by condensation using trimethylsilyl triflate. Curr. Protoc. Nucleic Acid Chem. 2007, 1, 1131-11316.
24. Teng, B.; Bai, Y.; Chang, Y.; Chen, S.; Li, Z. Technetium-99m-labeling and synthesis of thymidine analogs: potential candidates for tumor imaging. Bioorg. Med. Chem. Lett., 2007, 17, 3440-3444.
25. (a Koshkin, A.A.; Singh, S.K.;Nielson, P.; Rajwanshi, V.K.; Kumar, R.; Meldgaard, M.; Wengel, J. LNA (Locked Nucleic Acids): synthesis of the adenine, cytosine, guanine, 5-methylcytosine, thymine and uracil bicyclonucleoside monomers, oligomerisation, and unprecedented nucleic acid recognition. Tetrahedron 1998, 54, 3607-3630
26. (b Koshkin, A.A.; Fensholdt, J.; Pfundheller, H.M.; Lomholt, C. A simplified and efficient route to 2-O, 4-C-methylene-linked bicyclic ribonucleosides (Locked Nucleic Acid). J. Org. Chem. 2001, 66, 8504-8512.
27. (a Obika, S.; Abdur Rahman, S.M.; Song, B.; Onoda, M.; Koizumi, M.; Morita, K.; Imanishi, T. Synthesis and properties of 3-amino-2,4-BNA, a bridged nucleic acid with a N3-P5phosphoramidate linkage Bioorg. Med. Chem. 2008, 16, 9230-9232.
28. Olsen, A. G.; Nielsen, C.; Wengel, J. Synthesis and evaluation of anti-HIV activity of 3-azido-4-(hydroxymethyl)tetrahydrofuran derivatives containing 2-(thymin-1-yl)methyl, 2-(cytosin-1-yl)methyl or 2-(adenin-9-yl) methyl substituents-a new series of AZT analogues. J. Chem. Soc. Perkin Trans. 1 2001, 900-904.
29. Czernecki, S.; Valery, J.M. U.S. Patent 5,124,442.
30. Bryld, T.; Sørensen, M.H.; Nielsen, P.; Koch, T.; Nielsen, C.; Wengel, J. Synthesis and antiviral evaluation of novel conformationally locked nucleosides andmasked 5-phosphate derivatives thereof. J. Chem. Soc. Perkin Trans. 1 2002, 1655-1662.
31. Obika, S.; Andoh, J.; Sugimoto, T.; Miyashita, K.; Imanishi, T. Synthesis of a conformationally locked AZT analogue, 3-azido-3-deoxy-2-O,4-C-methylene-5- methyluridine. Tetrahedron Lett. 1999, 40, 6465-6468.