메뉴 건너뛰기




Volumn 53, Issue 23, 2010, Pages 8309-8318

Configuration of the 5′-methyl group modulates the biophysical and biological properties of locked nucleic acid (LNA) oligonucleotides

Author keywords

[No Author keywords available]

Indexed keywords

5' METHYL LOCKED NUCLEIC ACID; ANTISENSE OLIGONUCLEOTIDE; LOCKED NUCLEIC ACID; METHYL GROUP; UNCLASSIFIED DRUG; OLIGONUCLEOTIDE;

EID: 78649899322     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101207e     Document Type: Article
Times cited : (38)

References (47)
  • 1
    • 77949512140 scopus 로고    scopus 로고
    • RNA targeting therapeutics: Molecular mechanisms of antisense oligonucleotides as a therapeutic platform
    • Bennett, C. F.; Swayze, E. E. RNA targeting therapeutics: molecular mechanisms of antisense oligonucleotides as a therapeutic platform Annu. Rev. Pharmacol. Toxicol. 2010, 50, 259-293
    • (2010) Annu. Rev. Pharmacol. Toxicol. , vol.50 , pp. 259-293
    • Bennett, C.F.1    Swayze, E.E.2
  • 3
    • 34047190259 scopus 로고    scopus 로고
    • Hydrophobization and bioconjugation for enhanced siRNA delivery and targeting
    • De Paula, D.; Bentley, M. V.; Mahato, R. I. Hydrophobization and bioconjugation for enhanced siRNA delivery and targeting RNA 2007, 13, 431-456
    • (2007) RNA , vol.13 , pp. 431-456
    • De Paula, D.1    Bentley, M.V.2    Mahato, R.I.3
  • 6
    • 77949485460 scopus 로고    scopus 로고
    • Mipomersen, an apolipoprotein B synthesis inhibitor, for lowering of LDL cholesterol concentrations in patients with homozygous familial hypercholesterolaemia: A randomised, double-blind, placebo-controlled trial
    • Raal, F. J.; Santos, R. D.; Blom, D. J.; Marais, A. D.; Charng, M. J.; Cromwell, W. C.; Lachmann, R. H.; Gaudet, D.; Tan, J. L.; Chasan-Taber, S.; Tribble, D. L.; Flaim, J. D.; Crooke, S. T. Mipomersen, an apolipoprotein B synthesis inhibitor, for lowering of LDL cholesterol concentrations in patients with homozygous familial hypercholesterolaemia: a randomised, double-blind, placebo-controlled trial Lancet 2010, 375, 998-1006
    • (2010) Lancet , vol.375 , pp. 998-1006
    • Raal, F.J.1    Santos, R.D.2    Blom, D.J.3    Marais, A.D.4    Charng, M.J.5    Cromwell, W.C.6    Lachmann, R.H.7    Gaudet, D.8    Tan, J.L.9    Chasan-Taber, S.10    Tribble, D.L.11    Flaim, J.D.12    Crooke, S.T.13
  • 7
    • 0035043324 scopus 로고    scopus 로고
    • Pharmacokinetics of phosphorothioate antisense oligodeoxynucleotides
    • Geary, R. S.; Yu, R. Z.; Levin, A. A. Pharmacokinetics of phosphorothioate antisense oligodeoxynucleotides Curr. Opin. Invest. Drugs 2001, 2, 562-573
    • (2001) Curr. Opin. Invest. Drugs , vol.2 , pp. 562-573
    • Geary, R.S.1    Yu, R.Z.2    Levin, A.A.3
  • 8
    • 67649271530 scopus 로고    scopus 로고
    • Antisense oligonucleotide pharmacokinetics and metabolism
    • Geary, R. S. Antisense oligonucleotide pharmacokinetics and metabolism Expert Opin. Drug Metab. Toxicol. 2009, 5, 381-391
    • (2009) Expert Opin. Drug Metab. Toxicol. , vol.5 , pp. 381-391
    • Geary, R.S.1
  • 9
    • 34247586674 scopus 로고    scopus 로고
    • 2′-Modified oligonucleotides for antisense therapeutics
    • Prakash, T. P.; Bhat, B. 2′-Modified oligonucleotides for antisense therapeutics Curr. Top. Med. Chem. 2007, 7, 641-649
    • (2007) Curr. Top. Med. Chem. , vol.7 , pp. 641-649
    • Prakash, T.P.1    Bhat, B.2
  • 10
    • 0029099305 scopus 로고
    • Ein neuer zugang zu 2- O -alkylribonucleosiden und eigenschaften deren oligonucleotide
    • Martin, P. Ein neuer zugang zu 2- O -alkylribonucleosiden und eigenschaften deren oligonucleotide Helv. Chim. Acta 1995, 78, 486-504
    • (1995) Helv. Chim. Acta , vol.78 , pp. 486-504
    • Martin, P.1
  • 12
    • 0032909507 scopus 로고    scopus 로고
    • Synthesis of 3′- C - And 4′- C -branched oligodeoxynucleotides and the development of locked nucleic acid (LNA)
    • 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
    • (1999) Acc. Chem. Res. , vol.32 , pp. 301-310
    • Wengel, J.1
  • 13
    • 0036061380 scopus 로고    scopus 로고
    • BNAs: Novel nucleic acid analogs with a bridged sugar moiety
    • Imanishi, T.; Obika, S. BNAs: novel nucleic acid analogs with a bridged sugar moiety Chem. Commun. 2002, 1653-1659
    • (2002) Chem. Commun. , pp. 1653-1659
    • Imanishi, T.1    Obika, S.2
  • 15
    • 78649877710 scopus 로고    scopus 로고
    • Short locked nucleic acid antisense oligonucleotides potently reduce apolipoprotein B mRNA and serum cholesterol in mice and non-human primates
    • [Online early access]. DOI: 10.1093/nar/gkq457 Published Online: July 8, 2010
    • Straarup, E. M.; Fisker, N.; Hedtjarn, M.; Lindholm, M. W.; Rosenbohm, C.; Aarup, V.; Hansen, H. F.; Orum, H.; Hansen, J. B.; Koch, T. Short locked nucleic acid antisense oligonucleotides potently reduce apolipoprotein B mRNA and serum cholesterol in mice and non-human primates. Nucleic Acids Res. [Online early access]. DOI: 10.1093/nar/gkq457 Published Online: July 8, 2010.
    • Nucleic Acids Res.
    • Straarup, E.M.1    Fisker, N.2    Hedtjarn, M.3    Lindholm, M.W.4    Rosenbohm, C.5    Aarup, V.6    Hansen, H.F.7    Orum, H.8    Hansen, J.B.9    Koch, T.10
  • 17
    • 45749096229 scopus 로고    scopus 로고
    • An endogenous TNF-alpha antagonist induced by splice-switching oligonucleotides reduces inflammation in hepatitis and arthritis mouse models
    • Graziewicz, M. A.; Tarrant, T. K.; Buckley, B.; Roberts, J.; Fulton, L.; Hansen, H.; Orum, H.; Kole, R.; Sazani, P. An endogenous TNF-alpha antagonist induced by splice-switching oligonucleotides reduces inflammation in hepatitis and arthritis mouse models Mol. Ther. 2008, 16, 1316-1322
    • (2008) Mol. Ther. , vol.16 , pp. 1316-1322
    • Graziewicz, M.A.1    Tarrant, T.K.2    Buckley, B.3    Roberts, J.4    Fulton, L.5    Hansen, H.6    Orum, H.7    Kole, R.8    Sazani, P.9
  • 20
    • 59449093219 scopus 로고    scopus 로고
    • Short antisense oligonucleotides with novel 2′-4′ conformationaly restricted nucleoside analogues show improved potency without increased toxicity in animals
    • Seth, P. P.; Siwkowski, A.; Allerson, C. R.; Vasquez, G.; Lee, S.; Prakash, T. P.; Wancewicz, E. V.; Witchell, D.; Swayze, E. E. Short antisense oligonucleotides with novel 2′-4′ conformationaly restricted nucleoside analogues show improved potency without increased toxicity in animals J. Med. Chem. 2009, 52, 10-13
    • (2009) J. Med. Chem. , vol.52 , pp. 10-13
    • Seth, P.P.1    Siwkowski, A.2    Allerson, C.R.3    Vasquez, G.4    Lee, S.5    Prakash, T.P.6    Wancewicz, E.V.7    Witchell, D.8    Swayze, E.E.9
  • 21
    • 77949297395 scopus 로고    scopus 로고
    • Synthesis and biophysical evaluation of 2′,4′-constrained 2′O-methoxyethyl and 2′,4′-constrained 2′O-ethyl nucleic acid analogues
    • Seth, P. P.; Vasquez, G.; Allerson, C. A.; Berdeja, A.; Gaus, H.; Kinberger, G. A.; Prakash, T. P.; Migawa, M. T.; Bhat, B.; Swayze, E. E. Synthesis and biophysical evaluation of 2′,4′-constrained 2′O-methoxyethyl and 2′,4′-constrained 2′O-ethyl nucleic acid analogues J. Org. Chem. 2010, 75, 1569-1581
    • (2010) J. Org. Chem. , vol.75 , pp. 1569-1581
    • Seth, P.P.1    Vasquez, G.2    Allerson, C.A.3    Berdeja, A.4    Gaus, H.5    Kinberger, G.A.6    Prakash, T.P.7    Migawa, M.T.8    Bhat, B.9    Swayze, E.E.10
  • 22
    • 34447129727 scopus 로고    scopus 로고
    • Five- and six-membered conformationally locked 2′,4′- carbocyclic ribo -thymidines: Synthesis, structure, and biochemical studies
    • Srivastava, P.; Barman, J.; Pathmasiri, W.; Plashkevych, O.; Wenska, M. g.; Chattopadhyaya, J. Five- and six-membered conformationally locked 2′,4′-carbocyclic ribo -thymidines: synthesis, structure, and biochemical studies J. Am. Chem. Soc. 2007, 129, 8362-8379
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 8362-8379
    • Srivastava, P.1    Barman, J.2    Pathmasiri, W.3    Plashkevych, O.4    Wenska, M.G.5    Chattopadhyaya, J.6
  • 24
    • 77649230488 scopus 로고    scopus 로고
    • Antisense oligonucleotides containing conformationally constrained 2′,4′-(N -methoxy)aminomethylene and 2′,4′- aminooxymethylene and 2′- O,4′- C -aminomethylene bridged nucleoside analogues show improved potency in animal models
    • Prakash, T. P.; Siwkowski, A.; Allerson, C. R.; Migawa, M. T.; Lee, S.; Gaus, H. J.; Black, C.; Seth, P. P.; Swayze, E. E.; Bhat, B. Antisense oligonucleotides containing conformationally constrained 2′,4′-(N -methoxy)aminomethylene and 2′,4′-aminooxymethylene and 2′- O,4′- C -aminomethylene bridged nucleoside analogues show improved potency in animal models J. Med. Chem. 2010, 53, 1636-1650
    • (2010) J. Med. Chem. , vol.53 , pp. 1636-1650
    • Prakash, T.P.1    Siwkowski, A.2    Allerson, C.R.3    Migawa, M.T.4    Lee, S.5    Gaus, H.J.6    Black, C.7    Seth, P.P.8    Swayze, E.E.9    Bhat, B.10
  • 26
    • 0029978365 scopus 로고    scopus 로고
    • 5′-C-branched thymidines: Synthesis, stereochemistry, and incorporation into oligodeoxynucleotides
    • Wang, G.; Middleton, P. J. 5′-C-branched thymidines: synthesis, stereochemistry, and incorporation into oligodeoxynucleotides Tetrahedron Lett. 1996, 37, 2739-2742
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2739-2742
    • Wang, G.1    Middleton, P.J.2
  • 27
    • 2342476659 scopus 로고    scopus 로고
    • Amide-modified oligonucleotides with preorganized backbone and furanose rings: Highly increased thermodynamic stability of the duplexes formed with their RNA and DNA complements
    • De Mesmaeker, A.; Lebreton, J.; Jouanno, C.; Fritsch, V.; Wolf, R. M.; Wendeborn, S. Amide-modified oligonucleotides with preorganized backbone and furanose rings: highly increased thermodynamic stability of the duplexes formed with their RNA and DNA complements Synlett 1997, 1287-1290
    • (1997) Synlett , pp. 1287-1290
    • De Mesmaeker, A.1    Lebreton, J.2    Jouanno, C.3    Fritsch, V.4    Wolf, R.M.5    Wendeborn, S.6
  • 28
    • 0036169162 scopus 로고    scopus 로고
    • DNA analogues: From supramolecular principles to biological properties
    • Leumann, C. J. DNA analogues: from supramolecular principles to biological properties Bioorg. Med. Chem. 2002, 10, 841-854
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 841-854
    • Leumann, C.J.1
  • 29
    • 33746279446 scopus 로고    scopus 로고
    • Watson-Crick base-pairing properties of nucleic acid analogues with stereocontrolled alpha and beta torsion angles (alpha,beta-D-CNAs)
    • Dupouy, C.; Iche-Tarrat, N.; Durrieu, M. P.; Rodriguez, F.; Escudier, J. M.; Vigroux, A. Watson-Crick base-pairing properties of nucleic acid analogues with stereocontrolled alpha and beta torsion angles (alpha,beta-D-CNAs) Angew. Chem., Int. Ed. 2006, 45, 3623-3627
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 3623-3627
    • Dupouy, C.1    Iche-Tarrat, N.2    Durrieu, M.P.3    Rodriguez, F.4    Escudier, J.M.5    Vigroux, A.6
  • 32
    • 0032189581 scopus 로고    scopus 로고
    • Synthesis and pairing properties of oligoribonucleotide analogues containing a metal-binding site attached to β- D -allofuranosyl cytosine
    • Wu, X.; Pitsch, S. Synthesis and pairing properties of oligoribonucleotide analogues containing a metal-binding site attached to β- d -allofuranosyl cytosine Nucleic Acids Res. 1998, 26, 4315-4323
    • (1998) Nucleic Acids Res. , vol.26 , pp. 4315-4323
    • Wu, X.1    Pitsch, S.2
  • 34
    • 0002939707 scopus 로고    scopus 로고
    • Antisense molecules and furanose conformations-is it really that simple?
    • Kvaerno, L.; Wengel, J. Antisense molecules and furanose conformations-is it really that simple? Chem. Commun. 2001, 1419-1424
    • (2001) Chem. Commun. , pp. 1419-1424
    • Kvaerno, L.1    Wengel, J.2
  • 35
    • 0034714409 scopus 로고    scopus 로고
    • Synthesis of abasic locked nucleic acid and two seco-LNA derivatives and evaluation of their hybridization properties compared with their more flexible DNA counterparts
    • Kvrno, L.; Kumar, R.; Dahl, B. M.; Olsen, C. E.; Wengel, J. Synthesis of abasic locked nucleic acid and two seco-LNA derivatives and evaluation of their hybridization properties compared with their more flexible DNA counterparts J. Org. Chem. 2000, 65, 5167-5176
    • (2000) J. Org. Chem. , vol.65 , pp. 5167-5176
    • Kvrno, L.1    Kumar, R.2    Dahl, B.M.3    Olsen, C.E.4    Wengel, J.5
  • 37
    • 0034023314 scopus 로고    scopus 로고
    • Solution structure of an LNA hybridized to DNA: NMR study of the d(CTLGCTLTLCTLGC):d(GCAGAAGCAG) duplex containing four locked nucleotides
    • Nielsen, K. E.; Singh, S. K.; Wengel, J.; Jacobsen, J. P. Solution structure of an LNA hybridized to DNA: NMR study of the d(CTLGCTLTLCTLGC): d(GCAGAAGCAG) duplex containing four locked nucleotides Bioconj. Chem. 2000, 11, 228-238
    • (2000) Bioconj. Chem. , vol.11 , pp. 228-238
    • Nielsen, K.E.1    Singh, S.K.2    Wengel, J.3    Jacobsen, J.P.4
  • 38
    • 0037140761 scopus 로고    scopus 로고
    • Locked nucleic acid (LNA) recognition of RNA: NMR solution structures of LNA:RNA hybrids
    • Petersen, M.; Bondensgaard, K.; Wengel, J.; Jacobsen, J. P. Locked nucleic acid (LNA) recognition of RNA: NMR solution structures of LNA:RNA hybrids J. Am. Chem. Soc. 2002, 124, 5974-5982
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 5974-5982
    • Petersen, M.1    Bondensgaard, K.2    Wengel, J.3    Jacobsen, J.P.4
  • 39
    • 33745012353 scopus 로고    scopus 로고
    • Thermodynamic, counterion, and hydration effects for the incorporation of locked nucleic acid nucleotides into DNA duplexes
    • Kaur, H.; Arora, A.; Wengel, J.; Maiti, S. Thermodynamic, counterion, and hydration effects for the incorporation of locked nucleic acid nucleotides into DNA duplexes Biochemistry 2006, 45, 7347-7355
    • (2006) Biochemistry , vol.45 , pp. 7347-7355
    • Kaur, H.1    Arora, A.2    Wengel, J.3    Maiti, S.4
  • 40
    • 0035820423 scopus 로고    scopus 로고
    • X-ray crystal structure of a locked nucleic acid (LNA) duplex composed of a palindromic 10-mer DNA strand containing one LNA thymine monomer
    • Egli, M.; Teplova, M.; Minasov, G.; Kumar, R.; Wengel, J. X-ray crystal structure of a locked nucleic acid (LNA) duplex composed of a palindromic 10-mer DNA strand containing one LNA thymine monomer Chem. Commun 2001, 651-652
    • (2001) Chem. Commun , pp. 651-652
    • Egli, M.1    Teplova, M.2    Minasov, G.3    Kumar, R.4    Wengel, J.5
  • 42
    • 0015384762 scopus 로고
    • Crystal and molecular structure of a naturally occurring dinucleoside monophosphate. Uridylyl-(3′-5′)-adenosine hemihydrate. Conformational rigidity of the nucleotide unit and models for polynucleotide chain folding
    • Rubin, J.; Brennan, T.; Sundaralingam, M. Crystal and molecular structure of a naturally occurring dinucleoside monophosphate. Uridylyl-(3′- 5′)-adenosine hemihydrate. Conformational rigidity of the nucleotide unit and models for polynucleotide chain folding Biochemistry 1972, 11, 3112-3128
    • (1972) Biochemistry , vol.11 , pp. 3112-3128
    • Rubin, J.1    Brennan, T.2    Sundaralingam, M.3
  • 43
    • 0029051383 scopus 로고
    • The Crystal structure of r(CCCCGGGG) in two distinct lattices
    • Portmann, S.; Usman, N.; Egli, M. The Crystal structure of r(CCCCGGGG) in two distinct lattices Biochemistry 1995, 34, 7569-7575
    • (1995) Biochemistry , vol.34 , pp. 7569-7575
    • Portmann, S.1    Usman, N.2    Egli, M.3
  • 44
    • 0000831957 scopus 로고
    • Crystal structure of a parallel-stranded duplex of a deoxycytidylyl- (3′-5′)-deoxycytidine analog containing intranucleosidyl C(3′)-C(5′) ethylene bridges
    • Egli, M.; Lubini, P.; Bolli, M.; Dobler, M.; Leumann, C. Crystal structure of a parallel-stranded duplex of a deoxycytidylyl-(3′-5′)- deoxycytidine analog containing intranucleosidyl C(3′)-C(5′) ethylene bridges J. Am. Chem. Soc. 1993, 115, 5855-5856
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 5855-5856
    • Egli, M.1    Lubini, P.2    Bolli, M.3    Dobler, M.4    Leumann, C.5
  • 45
    • 84987491049 scopus 로고
    • Nucleic-acid analogs with constraint conformational flexibility in the sugar-phosphate backbone ("bicyclo-DNA"). Part 1. Preparation of (3′ S,5′ R)-2′-deoxy-3′,5′-ethano-ab- d -ribonucleosides (bicyclonucleosides)
    • Tarkov, M.; Bolli, M.; Schweizer, B.; Leumann, C. Nucleic-acid analogs with constraint conformational flexibility in the sugar-phosphate backbone ("bicyclo-DNA"). Part 1. Preparation of (3′ S,5′ R)-2′-deoxy-3′,5′-ethano-ab- d -ribonucleosides (bicyclonucleosides) Helv. Chim. Acta 1993, 76, 481-510
    • (1993) Helv. Chim. Acta , vol.76 , pp. 481-510
    • Tarkov, M.1    Bolli, M.2    Schweizer, B.3    Leumann, C.4
  • 46
    • 38849157057 scopus 로고    scopus 로고
    • Crystal structure of tricyclo-DNA: An unusual compensatory change of two adjacent backbone torsion angles
    • Pallan, P. S.; Ittig, D.; Heroux, A.; Wawrzak, Z.; Leumann, C. J.; Egli, M. Crystal structure of tricyclo-DNA: an unusual compensatory change of two adjacent backbone torsion angles Chem. Commun. 2008, 883-885
    • (2008) Chem. Commun. , pp. 883-885
    • Pallan, P.S.1    Ittig, D.2    Heroux, A.3    Wawrzak, Z.4    Leumann, C.J.5    Egli, M.6
  • 47
    • 0030727765 scopus 로고    scopus 로고
    • The ups and downs of nucleic acid duplex stability: Structure-stability studies on chemically-modified DNA:RNA duplexes
    • Freier, S. M.; Altmann, K. H. The ups and downs of nucleic acid duplex stability: structure-stability studies on chemically-modified DNA:RNA duplexes Nucleic Acids Res. 1997, 25, 4429-4443
    • (1997) Nucleic Acids Res. , vol.25 , pp. 4429-4443
    • Freier, S.M.1    Altmann, K.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.