메뉴 건너뛰기




Volumn 5, Issue 3, 1995, Pages 343-355

Backbone modifications in oligonucleotides and peptide nucleic acid systems

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ANTISENSE OLIGONUCLEOTIDE; DEOXYRIBONUCLEOTIDE; NUCLEIC ACID; OLIGONUCLEOTIDE; PEPTIDE; PHOSPHORUS;

EID: 0029093853     PISSN: 0959440X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0959-440X(95)80096-4     Document Type: Article
Times cited : (136)

References (92)
  • 5
    • 0015168319 scopus 로고
    • Syntheses and properties of adenine and thymine nucleoside alkyl phosphotriesters, the neutral analogs of dinucleoside monophosphates
    • (1971) J Am Chem Soc , vol.93 , pp. 6657-6665
    • Miller1    Fang2    Kondo3    Ts'O4
  • 9
    • 85022440392 scopus 로고
    • Synthesis of Oligonucleotide Analogues with Modified Backbones
    • (1993) Synlett , pp. 621-637
    • Varma1
  • 11
    • 0027730294 scopus 로고
    • Evaluation of some properties of phosphorodithioate oligodeoxyribonucleotides for antisense application
    • of special interest, Melting temperatures, nuclease resistance, protein binding, and specific and non-specific hybridization of a phosphorodithioate-containing oligonucleotide are investigated and compared to the corresponding oligonucleotides containing phosphodiesters and phosphorothioates. The phosphorodithioate modification is reported to result in reduced protein binding, but produces higher non-specific translation inhibition and forms weaker duplexes with the complementary RNA sequence. The paper concludes that phosphorodithioated oligonucleotides have little advantage over phosphorothioate derivatives for antisense applications.
    • (1993) Nucleic Acids Res , vol.21 , pp. 5761-5766
    • Ghosh1    Ghosh2    Dahl3    Cohen4
  • 15
    • 0028136417 scopus 로고
    • Pharmacokinetics of an antisense phosphorothioate oligodeoxynucleotide against rev from human immunodeficiency virus type 1 in the adult male rat following single injections and continuous infusion.
    • (1994) Antisense Res Dev , vol.4 , pp. 43-52
    • Iversen1    Mata2    Tracewell3    Zon4
  • 16
    • 0027503286 scopus 로고
    • Characterization of the nuclear binding sites of oligodeoxyribonucleotides and their analogs
    • (1993) J Biol Chem , vol.268 , pp. 5600-5604
    • Clarenc1    Lebleu2    Leonetti3
  • 17
    • 0027492473 scopus 로고
    • Cellular pharmacology of phosphorothioate homooligodeoxynucleotides in human cells
    • (1993) Mol Pharmacol , vol.43 , pp. 45-50
    • Gao1    Storm2    Egan3    Cheng4
  • 18
    • 0027268608 scopus 로고
    • Cellular uptake of phosphorothioate oligodeoxynucleotides is negatively affected by the cell density in a transformed rat tracheal epithelial cell line: implication for antisense approaches
    • (1993) Biochem Biophys Res Commun , vol.191 , pp. 1152-1157
    • Iwanaga1    Ferriola2
  • 19
    • 0027433590 scopus 로고
    • Differential distribution of oligodeoxynucleotides in developing organs with epithelial-mesenchymal interactions
    • (1993) Nucleic Acids Res , vol.21 , pp. 4961-4966
    • Rothenpieler1    Dressler2
  • 21
    • 0027325137 scopus 로고
    • Comparison of cellular binding and uptake of antisense phosphodiester, phosphorothioate and mixed phosphorothioate and methylphosphonate oligonucleotides
    • (1993) Antisense Res Dev , vol.3 , pp. 53-66
    • Zhao1    Matson2    Herrera3    Fisher4    Yu5    Krieg6
  • 23
  • 25
    • 14744277298 scopus 로고
    • Oligonucleoside methylphosphonates as antisense reagents
    • (1991) Biotechnology , vol.9 , pp. 358
    • Miller1
  • 27
    • 0024561620 scopus 로고
    • Use of EDTA derivatisation to characterize interactions between oligodeoxyribonucleotide methylphosphonates and nucleic acids
    • (1989) Biochemistry , vol.28 , pp. 1054-1061
    • Lin1    Blake2    Miller3    Ts'o4
  • 28
    • 0024578843 scopus 로고
    • Effect of ionic strength on the hybridization of oligodeoxynucleotides with reduced charge due to methylphosphonate linkage to unmodified oligodeoxynucleotides containing the complementary sequence
    • (1989) Biochemistry , vol.28 , pp. 1040-1047
    • Quartin1    Wetmur2
  • 32
    • 0023261982 scopus 로고
    • Comparative inhibition of chloramphenicol acetyltransferase gene expression by antisense oligonucleotide analogues having alkyl phosphotriester, methylphosphonate and phosphorothioate linkage
    • (1987) Nucleic Acids Res , vol.15 , pp. 5749-5763
    • Marcus-Sekura1    Woerner2    Shinozuka3    Zon4    Quinnan5
  • 33
    • 0024826733 scopus 로고
    • Modulation of drug resistance in a Daunorubicin resistance subline with oligonucleoside methylphosphonates
    • (1989) Cancer Commun , vol.1 , pp. 225-232
    • Vasanthakumar1    Ahmed2
  • 39
    • 0025647806 scopus 로고
    • Boron-containing nucleic acids. 2. Synthesis of oligodeoxynucleotide boranophosphonates
    • (1990) J Am Chem Soc , vol.112 , pp. 9000-9001
    • Sood1    Shaw2    Spielvogel3
  • 40
    • 0028319151 scopus 로고
    • Hydroxymethylphosphonate: novel oligonucleotide analogue
    • (1994) Bioorg Chem , vol.22 , pp. 128-139
    • Lesnikowski1
  • 41
    • 0025777951 scopus 로고
    • Synthesis and selective cleavage of an oligodeoxynucleotide containing a bridged internucleotide 5'-phosphorothioate linkage
    • (1991) Nucleic Acids Res , vol.19 , pp. 1437-1441
    • Mag1    Lüking2    Engels3
  • 42
    • 0026555646 scopus 로고
    • Sequence-and strand-specific cleavage in oligodeoxyribonucleotides and DNA containing 3'-thiothymidine
    • (1992) Biochemistry , vol.31 , pp. 3012-3018
    • Vyle1    Connolly2    Kemp3    Cosstick4
  • 43
    • 0025271245 scopus 로고
    • Synthesis and properties of dithymidine phosphate analogues containing 3'-thiothymidine
    • (1990) Nucleic Acids Res , vol.18 , pp. 829-835
    • Cosstick1    Vyle2
  • 45
    • 0026471149 scopus 로고
    • Synthesis and selective cleavage of an oligodeoxynucleotide containing bridged non-chiral internucleotide 3'-phosphoramidate linkage
    • (1992) Tetrahedron Lett , vol.33 , pp. 7319-7322
    • Mag1    Schmidt2    Engels3
  • 46
    • 0028177581 scopus 로고
    • Oligodeoxyribonucleotide N3′→P5′ phosphoramidates: synthesis and hybridization properties
    • of special interest, Highly efficient solid phase synthesis of oligonucleotides containing 3′→P5′ phosphoramidate linkages using Atheron-Todd type coupling of a polymer-supported 5′-H-phosphonate diester with a 3′-aminonucleoside is reported. The hybridization properties of six different oligonucleotides with DNA and RNA target sequences are studied. The reported melting temperatures are impressive.
    • (1994) J Am Chem Soc , vol.116 , pp. 3143-3144
    • Gryaznov1    Chen2
  • 51
    • 0023638996 scopus 로고
    • Uncharged stereoregular nucleic acid analogues. 1. Synthesis of a cytosine containing oligomer with carbamate internucleoside linkages
    • (1987) J Org Chem , vol.52 , pp. 4202-4206
    • Stirchak1    Summerton2    Weller3
  • 52
    • 0028344671 scopus 로고
    • Synthesis of di-, tri- and tetrameric building blocks with novel carbamate internucleoside linkages and their incorporation into oligonucleotides
    • (1994) Bioorg Med Chem Lett , vol.4 , pp. 1065-1070
    • Habus1    Temsamani2    Agrawal3
  • 60
    • 33748217097 scopus 로고
    • Amides as a new type of backbone modification in oligonucleotides
    • of special interest, This paper reports that replacing the backbone with amides increases both the thermodynamic stability of the duplexes formed with complementary RNA and the nuclease resistance of the antisense oligonucleotide. Conformational analysis was used to assess various low-energy conformers of the amide-modified backbones. Molecular dynamics simulations were carried out to study the dynamic behavior of the modified duplexes.
    • (1994) Angew Chem Int Ed , vol.33 , pp. 226-229
    • De Mesmaeker1    Waldner2    Lebreton3    Hoffmann4    Fritsch5    Wolf6    Freier7
  • 64
    • 0028258927 scopus 로고
    • Oligodeoxynucleotides containing 3′-allylether, 3′-allylsulfide and their saturated derivatives as phosphate mimics
    • (1994) Tetrahedron Lett , vol.35 , pp. 2325-2328
    • Cao1    Matteucci2
  • 65
    • 0027971706 scopus 로고
    • An approach to the structure determination of nucleic acid analogues hybridized to RNA. NMR studies of a duplex between 2′-OMe RNA and an oligonucleotide containing a single amide backbone modification
    • (1994) Nucleic Acids Res , vol.22 , pp. 4187-4194
    • Blommers1    Pieles2    De Mesmaeker3
  • 67
    • 0026683445 scopus 로고
    • Oligonucleosides: synthesis of a novel methylhydroxylamine-linked nucleoside dimer and its incorporation into antisense sequences
    • (1992) J Am Chem Soc , vol.114 , pp. 4006-4007
    • Vasseur1    Debart2    Sanghvi3    Cook4
  • 70
    • 0027304997 scopus 로고
    • Synthesis and binding properties of pyrimidine oligodeoxynucleoside analogs containing neutral phosphodiester replacements: the formacetal and 3′-thioformacetal internucleoside linkages
    • of special interest, The 3′-thioformacetal moiety is one of the backbone replacements for the antisense oligonucleotides that stabilize the duplex formed with a complementary RNA. Its effect on stability is compared with that of the 5′-thioformacetal and formacetal analogs.
    • (1993) J Org Chem , vol.58 , pp. 2983-2991
    • Jones1    Lin2    Milligan3    Wadwani4    Matteucci5
  • 71
    • 0028018669 scopus 로고
    • Unusual conformation of a 3′-thioformacetal linkage in a DNA duplex
    • (1994) J Biomol NMR , vol.4 , pp. 17-34
    • Gao1    Jeffs2
  • 73
    • 0026341239 scopus 로고
    • Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide
    • (1991) Science , vol.254 , pp. 1497-1500
    • Nielsen1    Egholm2    Berg3    Buchardt4
  • 76
    • 0027364174 scopus 로고
    • PNA hybridizes to complementary oligonucleotides obeying the Watson-Crick hydrogen bonding rules
    • of special interest, The paper describes the binding properties of mixed sequence peptide nucleic acid (PNA) to complementary DNA and RNA. It is the first demonstration that mixed sequence (as opposed to homopyrimidine sequences) PNA in fact bind to DNA and RNA with 1:1 stoichiometry; so far it is the only piece of work that has systematically assessed the thermodynamic properties of PNA-DNA and PNA-RNA duplexes and compared them to those of the corresponding DNA-DNA and DNA-RNA duplexes.
    • (1993) Nature , vol.365 , pp. 566-568
    • Egholm1    Buchardt2    Christensen3    Behrens4    Freier5    Driver6    Berg7    Kim8    Nordén9    Nielsen10
  • 80
    • 0028260073 scopus 로고
    • DNA-like double helix formed by peptide nucleic acid
    • of special interest, This paper demonstrates that two complementary strands of PNA are actually capable of self-recognition via Watson-Crick base pairing, resulting in the formation of very stable PNA-PNA duplexes. The stability of these hybrids exceeds even that of natural DNa-DNA duplexes (see also [78]). Particularly intriguing is the finding that inherently achiral PNA-PNA duplexes can be transformed into chiral structures with a single handedness by the simple attachments of a single chiral amino acid to the end of the PNA.
    • (1994) Nature , vol.368 , pp. 561-563
    • Wittung1    Nielsen2    Buchardt3    Egholm4    Nordén5
  • 85
    • 0028066788 scopus 로고
    • NMR solution structure of a peptide nucleic acid complexed with RNA
    • of special interest, This paper is the first report to shed light on the structure of duplexes of PNA with complementary nucleic acids (in this case RNA) at the molecular level. This work could form the basis for the design of analogs of PNA that would retain its high RNA-binding affinity, but may otherwise exhibit more favorable properties than PNA itself, for example with respect to cellular uptake.
    • (1994) Science , vol.265 , pp. 777-780
    • Brown1    Thomson2    Veal3    Davis4
  • 87
    • 0027485066 scopus 로고
    • Single base pair mutation analysis by PNA directed PCR clamping
    • of special interest, Together with a series of other papers [81,88,89], this work illustrates the potential that peptide nucleic acids (PNA) may have for diagnostic purposes in the near future. It demonstrates that PNAs can be utilized to direct gene amplification mediated by the polymerase chain reaction in such a way as to enable the selective amplification of a specific mutant gene with only a single base pair mutation in the presence of the corresponding wild-type gene.
    • (1993) Nucleic Acids Research , vol.21 , pp. 5332-5336
    • Ørum1    Nielsen2    Egholm3    Berg4    Buchardt5    Stanley6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.