메뉴 건너뛰기




Volumn 21, Issue 8, 2010, Pages 1537-1544

Properties of double-stranded oligonucleotides modified with lipophilic substituents

Author keywords

[No Author keywords available]

Indexed keywords

DNA SEQUENCES; FREE ENERGY;

EID: 77955835286     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc100201n     Document Type: Article
Times cited : (14)

References (36)
  • 1
    • 41549149109 scopus 로고    scopus 로고
    • Nucleoside, nucleotide and oligonucleotide based amphiphiles: A successful marriage of nucleic acids with lipids
    • Gissot, A., Camplo, M., Grinstaff, M. W., and Barthelemy, P. (2008) Nucleoside, nucleotide and oligonucleotide based amphiphiles: a successful marriage of nucleic acids with lipids Org. Biomol. Chem. 6, 1324-1333
    • (2008) Org. Biomol. Chem. , vol.6 , pp. 1324-1333
    • Gissot, A.1    Camplo, M.2    Grinstaff, M.W.3    Barthelemy, P.4
  • 2
    • 33751430435 scopus 로고    scopus 로고
    • Building oligonucleotide therapeutics using non-natural chemistries
    • Wilson, C. and Keefe, A. D. (2006) Building oligonucleotide therapeutics using non-natural chemistries Curr. Opin. Chem. Biol. 10, 607-614
    • (2006) Curr. Opin. Chem. Biol. , vol.10 , pp. 607-614
    • Wilson, C.1    Keefe, A.D.2
  • 3
    • 0027473513 scopus 로고
    • Modification of antisense phosphodiester oligodeoxynucleotides by a 5′ cholesteryl moiety increases cellular association and improves efficacy
    • Krieg, A. M., Tonkinson, J., Matson, S., Zhao, Q., Saxon, M., Zhang, L. M., Bhanja, U., Yakubov, L., and Stein, C. A. (1993) Modification of antisense phosphodiester oligodeoxynucleotides by a 5′ cholesteryl moiety increases cellular association and improves efficacy Proc. Natl. Acad. Sci. U.S.A. 90, 1048-1052
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 1048-1052
    • Krieg, A.M.1    Tonkinson, J.2    Matson, S.3    Zhao, Q.4    Saxon, M.5    Zhang, L.M.6    Bhanja, U.7    Yakubov, L.8    Stein, C.A.9
  • 4
    • 0035989886 scopus 로고    scopus 로고
    • Oligonucleotide conjugates as potential antisense drugs with improved uptake, biodistribution, targeted delivery, and mechanism of action
    • Manoharan, M. (2002) Oligonucleotide conjugates as potential antisense drugs with improved uptake, biodistribution, targeted delivery, and mechanism of action Antisense Nucleic Acid Drug Dev. 12, 103-128
    • (2002) Antisense Nucleic Acid Drug Dev. , vol.12 , pp. 103-128
    • Manoharan, M.1
  • 5
    • 0000800447 scopus 로고
    • Cholesteryl-conjugated oligonucleotides: Synthesis, properties, and activity as inhibitors of replication of human immunodeficiency virus in cell culture
    • Letsinger, R. L., Zhang, G. R., Sun, D. K., Ikeuchi, T., and Sarin, P. S. (1989) Cholesteryl-conjugated oligonucleotides: synthesis, properties, and activity as inhibitors of replication of human immunodeficiency virus in cell culture Proc. Natl. Acad. Sci. U.S.A. 86, 6553-6556
    • (1989) Proc. Natl. Acad. Sci. U.S.A. , vol.86 , pp. 6553-6556
    • Letsinger, R.L.1    Zhang, G.R.2    Sun, D.K.3    Ikeuchi, T.4    Sarin, P.S.5
  • 6
    • 0025333845 scopus 로고
    • Synthesis, hybridization properties and antiviral activity of lipid-oligodeoxynucleotide conjugates
    • Shea, R. G., Marsters, J. C., and Bischofberger, N. (1990) Synthesis, hybridization properties and antiviral activity of lipid-oligodeoxynucleotide conjugates Nucleic Acids Res. 18, 3777-3783
    • (1990) Nucleic Acids Res. , vol.18 , pp. 3777-3783
    • Shea, R.G.1    Marsters, J.C.2    Bischofberger, N.3
  • 7
    • 0025758178 scopus 로고
    • Mode of action of 5′-linked cholesteryl phosphorothioate oligodeoxynucleotides in inhibiting syncytia formation and infection by HIV-1 and HIV-2 in vitro
    • Stein, C. A., Pal, R., DeVico, A. L., Hoke, G., Mumbauer, S., Kinstler, O., Sarngadharan, M. G., and Letsinger, R. L. (1991) Mode of action of 5′-linked cholesteryl phosphorothioate oligodeoxynucleotides in inhibiting syncytia formation and infection by HIV-1 and HIV-2 in vitro Biochemistry 30, 2439-2444
    • (1991) Biochemistry , vol.30 , pp. 2439-2444
    • Stein, C.A.1    Pal, R.2    Devico, A.L.3    Hoke, G.4    Mumbauer, S.5    Kinstler, O.6    Sarngadharan, M.G.7    Letsinger, R.L.8
  • 8
    • 0027324730 scopus 로고
    • Reversible covalent attachment of cholesterol to oligodeoxyribonucleotides for studies of the mechanisms of their penetration into eucaryotic cells
    • Boutorine, A. S. and Kostina, E. V. (1993) Reversible covalent attachment of cholesterol to oligodeoxyribonucleotides for studies of the mechanisms of their penetration into eucaryotic cells Biochimie 75, 35-41
    • (1993) Biochimie , vol.75 , pp. 35-41
    • Boutorine, A.S.1    Kostina, E.V.2
  • 9
    • 49449098341 scopus 로고    scopus 로고
    • Lipid-conjugated oligonucleotides via "click chemistry" efficiently inhibit hepatitis C virus translation
    • Godeau, G., Staedel, C., and Barthelemy, P. (2008) Lipid-conjugated oligonucleotides via "click chemistry" efficiently inhibit hepatitis C virus translation J. Med. Chem. 51, 4374-4376
    • (2008) J. Med. Chem. , vol.51 , pp. 4374-4376
    • Godeau, G.1    Staedel, C.2    Barthelemy, P.3
  • 10
    • 0027723230 scopus 로고
    • Modulation of oligonucleotide duplex and triplex stability via hydrophobic interactions
    • Gryaznov, S. M. and Lloyd, D. H. (1993) Modulation of oligonucleotide duplex and triplex stability via hydrophobic interactions Nucleic Acids Res. 21, 5909-15
    • (1993) Nucleic Acids Res. , vol.21 , pp. 5909-5915
    • Gryaznov, S.M.1    Lloyd, D.H.2
  • 12
    • 2042516387 scopus 로고    scopus 로고
    • Enzymatic hydrolysis and biological activity of oligonucleotides containing 5-substituted pyrimidine bases
    • Otvos, L., Sagi, J., Sagi, G., Szemzo, A., Toth, F. D., and Jeney, A. (1999) Enzymatic hydrolysis and biological activity of oligonucleotides containing 5-substituted pyrimidine bases Nucleosides Nucleotides 18, 1665-1666
    • (1999) Nucleosides Nucleotides , vol.18 , pp. 1665-1666
    • Otvos, L.1    Sagi, J.2    Sagi, G.3    Szemzo, A.4    Toth, F.D.5    Jeney, A.6
  • 13
    • 0033597999 scopus 로고    scopus 로고
    • Solid support synthesis of ester linked hydrophobic conjugates of oligonucleotides
    • Guzaev, A. and Lonnberg, H. (1999) Solid support synthesis of ester linked hydrophobic conjugates of oligonucleotides Tetrahedron 55, 9101-9116
    • (1999) Tetrahedron , vol.55 , pp. 9101-9116
    • Guzaev, A.1    Lonnberg, H.2
  • 14
    • 0000876330 scopus 로고
    • Use of hydrophobic substituents in controlling self-assembly of oligonucleotides
    • Letsinger, R. L., Chaturvedi, S. K., Farooqui, F., and Salunkhe, M. (1993) Use of hydrophobic substituents in controlling self-assembly of oligonucleotides J. Am. Chem. Soc. 115, 7535-7536
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 7535-7536
    • Letsinger, R.L.1    Chaturvedi, S.K.2    Farooqui, F.3    Salunkhe, M.4
  • 15
    • 0026734668 scopus 로고
    • Synthesis and physical properties of anti-HIV antisense oligonucleotides bearing terminal lipophilic groups
    • MacKellar, C., Graham, D., Will, D. W., Burgess, S., and Brown, T. (1992) Synthesis and physical properties of anti-HIV antisense oligonucleotides bearing terminal lipophilic groups Nucleic Acids Res. 20, 3411-3417
    • (1992) Nucleic Acids Res. , vol.20 , pp. 3411-3417
    • MacKellar, C.1    Graham, D.2    Will, D.W.3    Burgess, S.4    Brown, T.5
  • 16
    • 0030768415 scopus 로고    scopus 로고
    • 7-deazaguanine DNA: Oligonucleotides with hydrophobic or cationic side chains
    • Ramzaeva, N., Mittelbach, C., and Seela, F. (1997) 7-deazaguanine DNA: Oligonucleotides with hydrophobic or cationic side chains Helv. Chim. Acta 80, 1809-1822
    • (1997) Helv. Chim. Acta , vol.80 , pp. 1809-1822
    • Ramzaeva, N.1    Mittelbach, C.2    Seela, F.3
  • 17
    • 34848907786 scopus 로고    scopus 로고
    • Protein lipidation
    • Nadolski, M. J. and Linder, M. E. (2007) Protein lipidation FEBS J. 274, 5202-5210
    • (2007) FEBS J. , vol.274 , pp. 5202-5210
    • Nadolski, M.J.1    Linder, M.E.2
  • 18
    • 15044352445 scopus 로고    scopus 로고
    • Fatty acylation and prenylation of proteins: Whats hot in fat
    • Magee, T. and Seabra, M. C. (2005) Fatty acylation and prenylation of proteins: whats hot in fat Curr. Opin. Cell Biol. 17, 190-196
    • (2005) Curr. Opin. Cell Biol. , vol.17 , pp. 190-196
    • Magee, T.1    Seabra, M.C.2
  • 19
    • 0037012847 scopus 로고    scopus 로고
    • Partitioning of lipid-modified monomeric GFPs into membrane microdomains of live cells
    • Zacharias, D. A., Violin, J. D., Newton, A. C., and Tsien, R. Y. (2002) Partitioning of lipid-modified monomeric GFPs into membrane microdomains of live cells Science 296, 913-916
    • (2002) Science , vol.296 , pp. 913-916
    • Zacharias, D.A.1    Violin, J.D.2    Newton, A.C.3    Tsien, R.Y.4
  • 20
    • 67749120313 scopus 로고    scopus 로고
    • Stabilization of conformationally dynamic helices by covalently attached acyl chains
    • Poschner, B. C. and Langosch, D. (2009) Stabilization of conformationally dynamic helices by covalently attached acyl chains Protein Sci. 18, 1801-1805
    • (2009) Protein Sci. , vol.18 , pp. 1801-1805
    • Poschner, B.C.1    Langosch, D.2
  • 22
    • 0019584302 scopus 로고
    • Effects of alkyl chain length on surface and micellar properties of octaethyleneglycol-n alkyl ethers
    • Ueno, M., Takasawa, Y., Miyashige, H., Tabata, Y., and Meguro, K. (1981) Effects of alkyl chain length on surface and micellar properties of octaethyleneglycol-n alkyl ethers Colloid Polym. Sci. 259, 761-766
    • (1981) Colloid Polym. Sci. , vol.259 , pp. 761-766
    • Ueno, M.1    Takasawa, Y.2    Miyashige, H.3    Tabata, Y.4    Meguro, K.5
  • 24
    • 0032576157 scopus 로고    scopus 로고
    • Perylene- and naphthalene-based linkers for duplex and triplex stabilization
    • Bevers, S., ODe, T. P., and McLaughlin, L. W. (1998) Perylene- and naphthalene-based linkers for duplex and triplex stabilization J. Am. Chem. Soc. 120, 11004-11005
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 11004-11005
    • Bevers, S.1    Ode, T.P.2    McLaughlin, L.W.3
  • 25
    • 0040520028 scopus 로고    scopus 로고
    • Naphthalene- and perylene-based linkers for the stabilization of hairpin triplexes
    • Bevers, S., Schutte, S., and McLaughlin, L. W. (2000) Naphthalene- and perylene-based linkers for the stabilization of hairpin triplexes J. Am. Chem. Soc. 122, 5905-5915
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 5905-5915
    • Bevers, S.1    Schutte, S.2    McLaughlin, L.W.3
  • 26
    • 0029166734 scopus 로고
    • Use of a stilbenedicarboxamide bridge in stabilizing, monitoring, and photochemically altering folded conformations of oligonucleotides
    • Letsinger, R. L. and Wu, T. (1995) Use of a stilbenedicarboxamide bridge in stabilizing, monitoring, and photochemically altering folded conformations of oligonucleotides J. Am. Chem. Soc. 117, 7323-7328
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 7323-7328
    • Letsinger, R.L.1    Wu, T.2
  • 27
    • 0037120876 scopus 로고    scopus 로고
    • Synthesis, structure, and photochemistry of exceptionally stable synthetic dna hairpins with stilbene diether linkers
    • Lewis, F. D., Wu, Y., and Liu, X. (2002) Synthesis, structure, and photochemistry of exceptionally stable synthetic dna hairpins with stilbene diether linkers J. Am. Chem. Soc. 124, 12165-12173
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 12165-12173
    • Lewis, F.D.1    Wu, Y.2    Liu, X.3
  • 28
    • 16844366807 scopus 로고    scopus 로고
    • A uniform mechanism correlating dangling-end stabilization and stacking geometry
    • Isaksson, J. and Chattopadhyaya, J. (2005) A uniform mechanism correlating dangling-end stabilization and stacking geometry Biochemistry 44, 5390-5401
    • (2005) Biochemistry , vol.44 , pp. 5390-5401
    • Isaksson, J.1    Chattopadhyaya, J.2
  • 29
    • 11144311174 scopus 로고    scopus 로고
    • Single-stranded adenine-rich DNA and RNA retain structural characteristics of their respective double-stranded conformations and show directional differences in stacking pattern
    • Isaksson, J., Acharya, S., Barman, J., Cheruku, P., and Chattopadhyaya, J. (2004) Single-stranded adenine-rich DNA and RNA retain structural characteristics of their respective double-stranded conformations and show directional differences in stacking pattern Biochemistry 43, 15996-6010
    • (2004) Biochemistry , vol.43 , pp. 15996-16010
    • Isaksson, J.1    Acharya, S.2    Barman, J.3    Cheruku, P.4    Chattopadhyaya, J.5
  • 30
    • 0034194135 scopus 로고    scopus 로고
    • Thermodynamic parameters for DNA sequences with dangling ends
    • Bommarito, S., Peyret, N., and SantaLucia, J., Jr. (2000) Thermodynamic parameters for DNA sequences with dangling ends Nucleic Acids Res. 28, 1929-1934
    • (2000) Nucleic Acids Res. , vol.28 , pp. 1929-1934
    • Bommarito, S.1    Peyret, N.2    Santalucia Jr., J.3
  • 31
    • 4444220551 scopus 로고    scopus 로고
    • Steroid and lipid conjugates of siRNAs to enhance cellular uptake and gene silencing in liver cells
    • Lorenz, C., Hadwiger, P., John, M., Vornlocher, H.-P., and Unverzagt, C. (2004) Steroid and lipid conjugates of siRNAs to enhance cellular uptake and gene silencing in liver cells Bioorg. Med. Chem. Lett. 14, 4975-4977
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 4975-4977
    • Lorenz, C.1    Hadwiger, P.2    John, M.3    Vornlocher, H.-P.4    Unverzagt, C.5
  • 35
    • 0026040132 scopus 로고
    • Mechanism of cellular uptake of modified oligodeoxynucleotides containing methylphosphonate linkages
    • Shoji, Y., Akhtar, S., Periasamy, A., Herman, B., and Juliano, R. L. (1991) Mechanism of cellular uptake of modified oligodeoxynucleotides containing methylphosphonate linkages Nucleic Acids Res. 19, 5543-5550
    • (1991) Nucleic Acids Res. , vol.19 , pp. 5543-5550
    • Shoji, Y.1    Akhtar, S.2    Periasamy, A.3    Herman, B.4    Juliano, R.L.5
  • 36
    • 0024804759 scopus 로고
    • Absorbance melting curves of RNA
    • Puglisi, J. D. and Tinoco, I., Jr. (1989) Absorbance melting curves of RNA Methods Enzymol. 180, 304-325
    • (1989) Methods Enzymol. , vol.180 , pp. 304-325
    • Puglisi, J.D.1    Tinoco Jr., I.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.