Literature DB >> 22614180

Structure and nuclease resistance of 2',4'-constrained 2'-O-methoxyethyl (cMOE) and 2'-O-ethyl (cEt) modified DNAs.

Pradeep S Pallan1, Charles R Allerson, Andres Berdeja, Punit P Seth, Eric E Swayze, Thazha P Prakash, Martin Egli.   

Abstract

Combining the structural elements of the second generation 2'-O-methoxyethyl (MOE) and locked nucleic acid (LNA) antisense oligonucleotide (AON) modifications yielded the highly nuclease resistant 2',4'-constrained MOE and ethyl bicyclic nucleic acids (cMOE and cEt BNA, respectively). Crystal structures of DNAs with cMOE or cEt BNA residues reveal their conformational preferences. Comparisons with MOE and LNA structures allow insights into their favourable properties for AON applications.

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Year:  2012        PMID： 22614180      PMCID： PMC3404228          DOI： 10.1039/c2cc32286b

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  9 in total

1.  Crystal structure and improved antisense properties of 2'-O-(2-methoxyethyl)-RNA.

Authors:  M Teplova; G Minasov; V Tereshko; G B Inamati; P D Cook; M Manoharan; M Egli
Journal:  Nat Struct Biol       Date:  1999-06

2.  Probing the influence of stereoelectronic effects on the biophysical properties of oligonucleotides: comprehensive analysis of the RNA affinity, nuclease resistance, and crystal structure of ten 2'-O-ribonucleic acid modifications.

Authors:  Martin Egli; George Minasov; Valentina Tereshko; Pradeep S Pallan; Marianna Teplova; Gopal B Inamati; Elena A Lesnik; Steve R Owens; Bruce S Ross; Thazha P Prakash; Muthiah Manoharan
Journal:  Biochemistry       Date:  2005-06-28       Impact factor: 3.162

Review 3.  RNA targeting therapeutics: molecular mechanisms of antisense oligonucleotides as a therapeutic platform.

Authors:  C Frank Bennett; Eric E Swayze
Journal:  Annu Rev Pharmacol Toxicol       Date:  2010       Impact factor: 13.820

4.  Potent reduction of apolipoprotein B and low-density lipoprotein cholesterol by short-term administration of an antisense inhibitor of apolipoprotein B.

Authors:  John J P Kastelein; Mark K Wedel; Brenda F Baker; John Su; JoAnn D Bradley; Rosie Z Yu; Emil Chuang; Mark J Graham; Rosanne M Crooke
Journal:  Circulation       Date:  2006-10-09       Impact factor: 29.690

5.  The ups and downs of nucleic acid duplex stability: structure-stability studies on chemically-modified DNA:RNA duplexes.

Authors:  S M Freier; K H Altmann
Journal:  Nucleic Acids Res       Date:  1997-11-15       Impact factor: 16.971

6.  Synthesis and biophysical evaluation of 2',4'-constrained 2'O-methoxyethyl and 2',4'-constrained 2'O-ethyl nucleic acid analogues.

Authors:  Punit P Seth; Guillermo Vasquez; Charles A Allerson; Andres Berdeja; Hans Gaus; Garth A Kinberger; Thazha P Prakash; Michael T Migawa; Balkrishen Bhat; Eric E Swayze
Journal:  J Org Chem       Date:  2010-03-05       Impact factor: 4.354

7.  Conformational influence of the ribose 2'-hydroxyl group: crystal structures of DNA-RNA chimeric duplexes.

Authors:  M Egli; N Usman; A Rich
Journal:  Biochemistry       Date:  1993-04-06       Impact factor: 3.162

8.  Short antisense oligonucleotides with novel 2'-4' conformationaly restricted nucleoside analogues show improved potency without increased toxicity in animals.

Authors:  Punit P Seth; Andrew Siwkowski; Charles R Allerson; Guillermo Vasquez; Sam Lee; Thazha P Prakash; Edward V Wancewicz; Donna Witchell; Eric E Swayze
Journal:  J Med Chem       Date:  2009-01-08       Impact factor: 7.446

Review 9.  Antisense technologies. Improvement through novel chemical modifications.

Authors:  Jens Kurreck
Journal:  Eur J Biochem       Date:  2003-04
  9 in total
  14 in total

Review 1.  Selective tissue targeting of synthetic nucleic acid drugs.

Authors:  Punit P Seth; Michael Tanowitz; C Frank Bennett
Journal:  J Clin Invest       Date:  2019-01-28       Impact factor: 14.808

Review 2.  From evolution to revolution: miRNAs as pharmacological targets for modulating cholesterol efflux and reverse cholesterol transport.

Authors:  Alberto Dávalos; Carlos Fernández-Hernando
Journal:  Pharmacol Res       Date:  2013-02-19       Impact factor: 7.658

3.  Oligonucleotide Therapies for the Lung: Ready to Return to the Clinic?

Authors:  Manish Kumar; Sterghios A Moschos
Journal:  Mol Ther       Date:  2017-11-23       Impact factor: 11.454

Review 4.  In vitro selection of BNA (LNA) aptamers.

Authors:  Masayasu Kuwahara; Satoshi Obika
Journal:  Artif DNA PNA XNA       Date:  2013 Apr-Jun

5.  High-throughput screening identifies small molecules that enhance the pharmacological effects of oligonucleotides.

Authors:  B Yang; X Ming; C Cao; B Laing; A Yuan; M A Porter; E A Hull-Ryde; J Maddry; M Suto; W P Janzen; R L Juliano
Journal:  Nucleic Acids Res       Date:  2015-02-06       Impact factor: 16.971

6.  Antisense oligonucleotide-mediated Dnm2 knockdown prevents and reverts myotubular myopathy in mice.

Authors:  Hichem Tasfaout; Suzie Buono; Shuling Guo; Christine Kretz; Nadia Messaddeq; Sheri Booten; Sarah Greenlee; Brett P Monia; Belinda S Cowling; Jocelyn Laporte
Journal:  Nat Commun       Date:  2017-06-07       Impact factor: 14.919

7.  Metabolite Profiling of the Antisense Oligonucleotide Eluforsen Using Liquid Chromatography-Mass Spectrometry.

Authors:  Jaeah Kim; Babak Basiri; Chopie Hassan; Carine Punt; Erik van der Hage; Cathaline den Besten; Michael G Bartlett
Journal:  Mol Ther Nucleic Acids       Date:  2019-07-22       Impact factor: 8.886

8.  Structure Activity Relationships of α-L-LNA Modified Phosphorothioate Gapmer Antisense Oligonucleotides in Animals.

Authors:  Punit P Seth; Ali Jazayeri; Jeff Yu; Charles R Allerson; Balkrishen Bhat; Eric E Swayze
Journal:  Mol Ther Nucleic Acids       Date:  2012-09-18       Impact factor: 10.183

9.  Rational design of antisense oligonucleotides targeting single nucleotide polymorphisms for potent and allele selective suppression of mutant Huntingtin in the CNS.

Authors:  Michael E Østergaard; Amber L Southwell; Holly Kordasiewicz; Andrew T Watt; Niels H Skotte; Crystal N Doty; Kuljeet Vaid; Erika B Villanueva; Eric E Swayze; C Frank Bennett; Michael R Hayden; Punit P Seth
Journal:  Nucleic Acids Res       Date:  2013-08-19       Impact factor: 16.971

10.  Hsp90 protein interacts with phosphorothioate oligonucleotides containing hydrophobic 2'-modifications and enhances antisense activity.

Authors:  Xue-Hai Liang; Wen Shen; Hong Sun; Garth A Kinberger; Thazha P Prakash; Joshua G Nichols; Stanley T Crooke
Journal:  Nucleic Acids Res       Date:  2016-03-03       Impact factor: 16.971
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