Structure‐Based Design of a Highly Constrained Nucleic Acid Analogue: Improved Duplex Stabilization by Restricting Sugar Pucker and Torsion Angle γ
2012; Wiley; Volume: 51; Issue: 45 Linguagem: Inglês
10.1002/anie.201203680
ISSN1521-3773
AutoresStephen Hanessian, Benjamin R. Schroeder, Robert D. Giacometti, Bradley L. Merner, Michael E. Østergaard, Eric E. Swayze, Punit P. Seth,
Tópico(s)RNA Interference and Gene Delivery
ResumoAngewandte Chemie International EditionVolume 51, Issue 45 p. 11242-11245 Communication Structure-Based Design of a Highly Constrained Nucleic Acid Analogue: Improved Duplex Stabilization by Restricting Sugar Pucker and Torsion Angle γ† Prof. Dr. Stephen Hanessian, Corresponding Author Prof. Dr. Stephen Hanessian [email protected] Department of Chemistry, Université de Montréal, C.P. 6128, Succ. Centre-ville, Montréal, QC H3C 3J7 (Canada) Stephen Hanessian, Department of Chemistry, Université de Montréal, C.P. 6128, Succ. Centre-ville, Montréal, QC H3C 3J7 (Canada) Punit P. Seth, Department of Medicinal Chemistry, Isis Pharmaceuticals, 2855 Gazelle Court, Carlsbad, CA 92010 (USA)Search for more papers by this authorDr. Benjamin R. Schroeder, Dr. Benjamin R. Schroeder Department of Chemistry, Université de Montréal, C.P. 6128, Succ. Centre-ville, Montréal, QC H3C 3J7 (Canada)Search for more papers by this authorRobert D. Giacometti, Robert D. Giacometti Department of Chemistry, Université de Montréal, C.P. 6128, Succ. Centre-ville, Montréal, QC H3C 3J7 (Canada)Search for more papers by this authorDr. Bradley L. Merner, Dr. Bradley L. Merner Department of Chemistry, Université de Montréal, C.P. 6128, Succ. Centre-ville, Montréal, QC H3C 3J7 (Canada)Search for more papers by this authorDr. Michael Østergaard, Dr. Michael Østergaard Department of Medicinal Chemistry, Isis Pharmaceuticals, 2855 Gazelle Court, Carlsbad, CA 92010 (USA)Search for more papers by this authorDr. Eric E. Swayze, Dr. Eric E. Swayze Department of Medicinal Chemistry, Isis Pharmaceuticals, 2855 Gazelle Court, Carlsbad, CA 92010 (USA)Search for more papers by this authorDr. Punit P. Seth, Corresponding Author Dr. Punit P. Seth [email protected] Department of Medicinal Chemistry, Isis Pharmaceuticals, 2855 Gazelle Court, Carlsbad, CA 92010 (USA) Stephen Hanessian, Department of Chemistry, Université de Montréal, C.P. 6128, Succ. Centre-ville, Montréal, QC H3C 3J7 (Canada) Punit P. Seth, Department of Medicinal Chemistry, Isis Pharmaceuticals, 2855 Gazelle Court, Carlsbad, CA 92010 (USA)Search for more papers by this author Prof. Dr. Stephen Hanessian, Corresponding Author Prof. Dr. Stephen Hanessian [email protected] Department of Chemistry, Université de Montréal, C.P. 6128, Succ. Centre-ville, Montréal, QC H3C 3J7 (Canada) Stephen Hanessian, Department of Chemistry, Université de Montréal, C.P. 6128, Succ. Centre-ville, Montréal, QC H3C 3J7 (Canada) Punit P. Seth, Department of Medicinal Chemistry, Isis Pharmaceuticals, 2855 Gazelle Court, Carlsbad, CA 92010 (USA)Search for more papers by this authorDr. Benjamin R. Schroeder, Dr. Benjamin R. Schroeder Department of Chemistry, Université de Montréal, C.P. 6128, Succ. Centre-ville, Montréal, QC H3C 3J7 (Canada)Search for more papers by this authorRobert D. Giacometti, Robert D. Giacometti Department of Chemistry, Université de Montréal, C.P. 6128, Succ. Centre-ville, Montréal, QC H3C 3J7 (Canada)Search for more papers by this authorDr. Bradley L. Merner, Dr. Bradley L. Merner Department of Chemistry, Université de Montréal, C.P. 6128, Succ. Centre-ville, Montréal, QC H3C 3J7 (Canada)Search for more papers by this authorDr. Michael Østergaard, Dr. Michael Østergaard Department of Medicinal Chemistry, Isis Pharmaceuticals, 2855 Gazelle Court, Carlsbad, CA 92010 (USA)Search for more papers by this authorDr. Eric E. Swayze, Dr. Eric E. Swayze Department of Medicinal Chemistry, Isis Pharmaceuticals, 2855 Gazelle Court, Carlsbad, CA 92010 (USA)Search for more papers by this authorDr. Punit P. Seth, Corresponding Author Dr. Punit P. Seth [email protected] Department of Medicinal Chemistry, Isis Pharmaceuticals, 2855 Gazelle Court, Carlsbad, CA 92010 (USA) Stephen Hanessian, Department of Chemistry, Université de Montréal, C.P. 6128, Succ. Centre-ville, Montréal, QC H3C 3J7 (Canada) Punit P. Seth, Department of Medicinal Chemistry, Isis Pharmaceuticals, 2855 Gazelle Court, Carlsbad, CA 92010 (USA)Search for more papers by this author First published: 22 August 2012 https://doi.org/10.1002/anie.201203680Citations: 28 † R.D.G. is grateful to NSERC (CGS D) for a postgraduate scholarship. We thank Benoît Deschênes-Simard for X-ray crystallographic analyses. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Dual conformational restriction: A new, highly constrained modification of the α-L-locked nucleic acid (α-L-LNA) scaffold that locks the sugar furanose ring in an N-type configuration and also restricts rotation around torsion angle γ was synthesized (see scheme). This new modification increases the thermostability of an oligonucleotide duplex compared to using a single mode of constraint alone. Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_201203680_sm_miscellaneous_information.pdf12.2 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1E. E. Swayze, B. Bhat in Antisense Drug Technology: Principles, Strategies, and Applications, 2nd ed. ), CRC, Boca Raton, 2008, pp. 143–182. 2M. E. Østergaard, P. J. Hrdlicka, Chem. Soc. Rev. 2011, 40, 5771–5788. 3 3aB. Vester, J. Wengel, Biochemistry 2004, 43, 13233–13241; 3bC. J. Leumann, Bioorg. Med. Chem. 2002, 10, 841–854; 3cP. Herdewijn, Chem. Biodiversity 2010, 7, 1–59; 3dA. Eschenmoser, Pure Appl. Chem. 1993, 65, 1179–1188. 4D. Renneberg, C. J. Leumann, J. Am. Chem. Soc. 2002, 124, 5993–6002. 5C. Dupouy, N. Iche-Tarrat, M. P. Durrieu, F. Rodriguez, J. M. Escudier, A. Vigroux, Angew. Chem. 2006, 118, 3705–3709; Angew. Chem. Int. Ed. 2006, 45, 3623–3627. 6 6aJ. Wengel, Acc. Chem. Res. 1999, 32, 301–310; 6bT. Imanishi, S. Obika, Chem. Commun. 2002, 1653–1659. 7 7aV. K. Rajwanshi, A. E. Håkansson, M. D. Sørensen, S. Pitsch, S. K. Singh, R. Kumar, P. Nielsen, J. Wengel, Angew. Chem. 2000, 112, 1722–1725; Angew. Chem. Int. Ed. 2000, 39, 1656–1659; 7bM. D. Sørensen, L. Kværnø, T. Bryld, A. E. Håkansson, B. Verbeure, G. Gaubert, P. Herdewijn, J. Wengel, J. Am. Chem. Soc. 2002, 124, 2164–2176. 8M. Petersen, A. E. Håkansson, J. Wengel, J. P. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7431–7432. 9J. T. Nielsen, P. C. Stein, M. Petersen, Nucleic Acids Res. 2003, 31, 5858–5867. 10 10aP. P. Seth, J. Yu, C. R. Allerson, A. Berdeja, E. E. Swayze, Bioorg. Med. Chem. Lett. 2011, 21, 1122–1125; 10bP. P. Seth, C. A. Allerson, M. E. Østergaard, E. E. Swayze, Bioorg. Med. Chem. Lett. 2012, 22, 296–299. 11J. K. Maity, R. Ghosh, M. G. B. Drew, B. Achari, S. B. Mandal, J. Org. Chem. 2008, 73, 4305–4308. 12 12aA. Hosomi, M. Endo, H. Sakurai, Chem. Lett. 1976, 941–942; 12bA. Hosomi, H. Sakurai, Tetrahedron Lett. 1976, 17, 1295–1298; 12cS. J. Danishefsky, M. DeNinno, Tetrahedron Lett. 1985, 26, 823–824. 13U. Niedballa, H. Vorbrüggen, Angew. Chem. 1970, 82, 449–450; Angew. Chem. Int. Ed. Engl. 1970, 9, 461–462. 14See Supporting Information for details. 15A. Romieu, D. Gasparutto, J. Cadet, J. Chem. Soc., Perkin Trans. 1 1999, 1257–1264. 16S. M. Abdur Rahman, S. Seki, S. Obika, H. Yoshikawa, K. Miyashita, T. Imanishi, J. Am. Chem. Soc. 2008, 130, 4886–4896. 17 17aK. I. Shaikh, S. Kumar, L. Lundhus, A. D. Bond, P. K. Sharma, P. Nielsen, J. Org. Chem. 2009, 74, 1557–1566; 17bA. Stauffiger, C. J. Leumann, Eur. J. Org. Chem. 2009, 1153–1162; 17cM. Sekiguchi, S. Obika, Y. Harada, T. Osaki, R. Somjing, Y. Mitsuoka, N. Shibata, M. Masaki, T. Imanishi, J. Org. Chem. 2006, 71, 1306–1316; 17dJ. Ravn, N. Thorup, P. Nielsen, J. Chem. Soc., Perkin Trans. 1 2001, 1855–1861. 18 18aS. Kumar, M. H. Hansen, N. Albaek, S. I. Steffansen, M. Petersen, P. Nielsen, J. Org. Chem. 2009, 74, 6756–6769; 18bP. P. Seth, C. R. Allerson, A. Berdeja, A. Siwkowski, P. S. Pallan, H. Gaus, T. P. Prakash, A. T. Watt, M. Egli, E. E. Swayze, J. Am. Chem. Soc. 2010, 132, 14942–14950. Citing Literature Volume51, Issue45November 5, 2012Pages 11242-11245 ReferencesRelatedInformation
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