메뉴 건너뛰기




Volumn 7, Issue 4, 2010, Pages 213-223

Extension of the PNA world by functionalized PNA monomers eligible candidates for inverse diels alder click chemistry

Author keywords

Click chemistry; Diels alder reactioninvers (DARinv); Peptide nucleic acid (PNA); Pna building block functionalization

Indexed keywords

4 PENTENOIC ACID; ACID ANHYDRIDE; DNA; MALEIC ANHYDRIDE; MONOMER; PEPTIDE NUCLEIC ACID; POLYMER; REPPE ANHYDRIDE; RNA; UNCLASSIFIED DRUG;

EID: 77955529012     PISSN: None     EISSN: 14491907     Source Type: Journal    
DOI: 10.7150/ijms.7.213     Document Type: Article
Times cited : (11)

References (45)
  • 1
    • 0031047038 scopus 로고    scopus 로고
    • Peptide nucleic acids and prebiotic chemistry
    • Miller SL. Peptide nucleic acids and prebiotic chemistry. Nat Struct Biol. 1997; 4: 167-9.
    • (1997) Nat Struct Biol , vol.4 , pp. 167-169
    • Miller, S.L.1
  • 2
    • 34948883585 scopus 로고    scopus 로고
    • Peptide nucleic acids and the origin of life
    • Nielsen PE. Peptide nucleic acids and the origin of life. Chem Biodivers. 2007; 4: 1996-2002.
    • (2007) Chem Biodivers , vol.4 , pp. 1996-2002
    • Nielsen, P.E.1
  • 3
    • 0026341239 scopus 로고
    • Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide
    • Nielsen PE, Egholm M, Berg RH, et al. Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide. Science. 1991; 254: 1497-500.
    • (1991) Science , vol.254 , pp. 1497-1500
    • Nielsen, P.E.1    Egholm, M.2    Berg, R.H.3
  • 4
    • 0002490493 scopus 로고
    • Theory of 1,3-Dipolar Cycloadditions
    • In: Padwa A, editor, New York: Wiley
    • Huisgen R. Theory of 1,3-Dipolar Cycloadditions. In: Padwa A, editor. 1,3-Dipolar Cycloaddition Chemistry. New York: Wiley; 1984: 1-176.
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , pp. 1-176
    • Huisgen, R.1
  • 5
    • 14744278308 scopus 로고    scopus 로고
    • Mechanistic investigation of the staudinger ligation
    • Lin FL, Hoyt HM, van HH, et al. Mechanistic investigation of the staudinger ligation. J Am Chem Soc. 2005; 127: 2686-95.
    • (2005) J Am Chem Soc , vol.127 , pp. 2686-2695
    • Lin, F.L.1    Hoyt, H.M.2    Van, H.H.3
  • 6
    • 0342697550 scopus 로고    scopus 로고
    • Site-specific modification of enzymatically synthesized RNA: Transcription initiation and Diels-Alder reaction
    • Seelig B, Jaschke A. Site-specific modification of enzymatically synthesized RNA: Transcription initiation and Diels-Alder reaction. Tetrahedron Letters. 1997; 38: 7729-32.
    • (1997) Tetrahedron Letters , vol.38 , pp. 7729-7732
    • Seelig, B.1    Jaschke, A.2
  • 7
    • 0000096835 scopus 로고    scopus 로고
    • Click Chemistry: Diverse Chemical Function from a Few Good Reactions
    • Kolb HC, Finn MG, Sharpless KB. Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew Chem Int Ed Engl. 2001; 40: 2004-21.
    • (2001) Angew Chem Int Ed Engl , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 8
    • 77949857925 scopus 로고    scopus 로고
    • Click chemistry: Function follows form
    • Finn MG, Fokin VV. Click chemistry: function follows form. Chem Soc Rev. 2010; 39: 1231-2.
    • (2010) Chem Soc Rev , vol.39 , pp. 1231-1232
    • Finn, M.G.1    Fokin, V.V.2
  • 9
    • 33947446511 scopus 로고
    • The Diels Alder Reaction of 1-Vinyl-6-Methoxy-3,4-Dihydronaphthalene with Citraconic Anhydride
    • Bachmann WE, Chemerda JM. The Diels Alder Reaction of 1-Vinyl-6-Methoxy-3,4-Dihydronaphthalene with Citraconic Anhydride. J Americ Chem Soc. 1948; 70: 1468-73.
    • (1948) J Americ Chem Soc , vol.70 , pp. 1468-1473
    • Bachmann, W.E.1    Chemerda, J.M.2
  • 10
    • 77049363062 scopus 로고
    • Otto Diels and Kurt Alder; winners of the Nobel Prize in chemistry
    • Alder K, Diels O. [Otto Diels and Kurt Alder; winners of the Nobel Prize in chemistry.]. Cienc Invest. 1951; 7: 143-4.
    • (1951) Cienc Invest , vol.7 , pp. 143-144
    • Alder, K.1    Diels, O.2
  • 11
    • 0041810236 scopus 로고    scopus 로고
    • Chemistry and biology of biosynthetic Diels-Alder reactions
    • Stocking EM, Williams RM. Chemistry and biology of biosynthetic Diels-Alder reactions. Angew Chem Int Ed Engl. 2003; 42: 3078-115.
    • (2003) Angew Chem Int Ed Engl , vol.42 , pp. 3078-3115
    • Stocking, E.M.1    Williams, R.M.2
  • 12
    • 53849105464 scopus 로고    scopus 로고
    • Tetrazine ligation: Fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity
    • Blackman ML, Royzen M, Fox JM. Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity. J Am Chem Soc. 2008; 130: 13518-9.
    • (2008) J Am Chem Soc , vol.130 , pp. 13518-13519
    • Blackman, M.L.1    Royzen, M.2    Fox, J.M.3
  • 13
    • 54749123594 scopus 로고    scopus 로고
    • TMZ-BioShuttle--a reformulated temozolomide
    • Waldeck W, Wiessler M, Ehemann V, et al. TMZ-BioShuttle--a reformulated temozolomide. Int J Med Sci. 2008; 5: 273-84.
    • (2008) Int J Med Sci , vol.5 , pp. 273-284
    • Waldeck, W.1    Wiessler, M.2    Ehemann, V.3
  • 14
    • 58549090883 scopus 로고    scopus 로고
    • Diels-Alder route to steroids and associated structures
    • Ibrahim-Ouali M. Diels-Alder route to steroids and associated structures. Steroids. 2009 Feb;74(2):133-62.
    • (2009) Steroids , vol.74 , Issue.2 , pp. 133-162
    • Ibrahim-Ouali, M.1
  • 15
    • 0001105947 scopus 로고
    • Reactions of Tetrazines with Unsaturated Compounds - A New Synthesis of Pyridazines
    • Carboni RA, Lindsey RV. Reactions of Tetrazines with Unsaturated Compounds - A New Synthesis of Pyridazines. J Americ Chem So. 1959; 81: 4342-6.
    • (1959) J Americ Chem So , vol.81 , pp. 4342-4346
    • Carboni, R.A.1    Lindsey, R.V.2
  • 16
    • 0033301584 scopus 로고    scopus 로고
    • An introduction to peptide nucleic acid
    • Nielsen PE, Egholm M. An introduction to peptide nucleic acid. Curr Issues Mol Biol. 1999; 1: 89-104.
    • (1999) Curr Issues Mol Biol , vol.1 , pp. 89-104
    • Nielsen, P.E.1    Egholm, M.2
  • 17
    • 0027419756 scopus 로고
    • Peptide nucleic acids (PNAs): Potential antisense and anti-gene agents
    • Nielsen PE, Egholm M, Berg RH, et al. Peptide nucleic acids (PNAs): potential antisense and anti-gene agents. Anticancer Drug Des. 1993; 8: 53-63.
    • (1993) Anticancer Drug Des , vol.8 , pp. 53-63
    • Nielsen, P.E.1    Egholm, M.2    Berg, R.H.3
  • 18
    • 0030917307 scopus 로고    scopus 로고
    • Peptide nucleic acids: Expanding the scope of nucleic acid recognition
    • Corey DR. Peptide nucleic acids: expanding the scope of nucleic acid recognition. Trends Biotechnol. 1997; 15: 224-9.
    • (1997) Trends Biotechnol , vol.15 , pp. 224-229
    • Corey, D.R.1
  • 19
    • 0024296609 scopus 로고
    • Physicochemical properties of phosphorothioate oligodeoxynucleotides
    • Stein CA, Subasinghe C, Shinozuka K, et al. Physicochemical properties of phosphorothioate oligodeoxynucleotides. Nucleic Acids Res. 1988; 16: 3209-21.
    • (1988) Nucleic Acids Res , vol.16 , pp. 3209-3221
    • Stein, C.A.1    Subasinghe, C.2    Shinozuka, K.3
  • 20
    • 0027998151 scopus 로고
    • Target-specific arrest of mRNA translation by antisense 2'-O-alkyloligoribonucleotides
    • Johansson HE, Belsham GJ, Sproat BS, et al. Target-specific arrest of mRNA translation by antisense 2'-O-alkyloligoribonucleotides. Nucleic Acids Res. 1994; 22: 4591-8.
    • (1994) Nucleic Acids Res , vol.22 , pp. 4591-4598
    • Johansson, H.E.1    Belsham, G.J.2    Sproat, B.S.3
  • 21
    • 0030872852 scopus 로고    scopus 로고
    • RNase H-independent antisense activity of oligonucleotide N3 '-- > P5 ' phosphoramidates
    • Heidenreich O, Gryaznov S, Nerenberg M. RNase H-independent antisense activity of oligonucleotide N3 '-- > P5 ' phosphoramidates. Nucleic Acids Res. 1997; 25: 776-80.
    • (1997) Nucleic Acids Res , vol.25 , pp. 776-780
    • Heidenreich, O.1    Gryaznov, S.2    Nerenberg, M.3
  • 22
    • 84990238662 scopus 로고
    • Recognition of Guanine and Adenine in DNA by Cytosine and Thymine Containing Peptide Nucleic-Acids (PNA)(1,2)
    • Egholm M, Nielsen PE, Buchardt O, et al. Recognition of Guanine and Adenine in DNA by Cytosine and Thymine Containing Peptide Nucleic-Acids (PNA)(1,2). J AMER CHEM SOC. 1992; 114: 9677-8.
    • (1992) J AMER CHEM SOC , vol.114 , pp. 9677-9678
    • Egholm, M.1    Nielsen, P.E.2    Buchardt, O.3
  • 23
    • 0030862707 scopus 로고    scopus 로고
    • Morpholino antisense oligomers: Design, preparation, and properties
    • Summerton J, Weller D. Morpholino antisense oligomers: design, preparation, and properties. Antisense Nucleic Acid Drug Dev. 1997; 7: 187-95.
    • (1997) Antisense Nucleic Acid Drug Dev , vol.7 , pp. 187-195
    • Summerton, J.1    Weller, D.2
  • 24
    • 0032561794 scopus 로고    scopus 로고
    • LNA (locked nucleic acid): An RNA mimic forming exceedingly stable LNA: LNA duplexes
    • Koshkin AA, Nielsen P, Meldgaard M, et al. LNA (locked nucleic acid): An RNA mimic forming exceedingly stable LNA: LNA duplexes. Journal of the American Chemical Society. 1998; 120: 13252-3.
    • (1998) Journal of The American Chemical Society , vol.120 , pp. 13252-13253
    • Koshkin, A.A.1    Nielsen, P.2    Meldgaard, M.3
  • 25
    • 77955539789 scopus 로고    scopus 로고
    • Peptide Nucleic-Acid (PNA) a Structural DNA Mimic
    • Nielsen PE. Peptide Nucleic-Acid (PNA) a Structural DNA Mimic. PROG BIOPHYS MOL BIOL. 1996; 65: 103.
    • (1996) PROG BIOPHYS MOL BIOL , vol.65 , pp. 103
    • Nielsen, P.E.1
  • 26
    • 0028129843 scopus 로고
    • Stability of peptide nucleic acids in human serum and cellular extracts
    • Demidov VV, Potaman VN, Frank Kamenetskii MD, et al. Stability of peptide nucleic acids in human serum and cellular extracts. Biochem Pharmacol. 1994; 48: 1310-3.
    • (1994) Biochem Pharmacol , vol.48 , pp. 1310-1313
    • Demidov, V.V.1    Potaman, V.N.2    Frank Kamenetskii, M.D.3
  • 27
    • 84990238662 scopus 로고
    • Peptide Nucleic Acids (PNA). Oligonucleotide Analogues with an Achiral Peptide Backbone
    • Egholm M, Buchardt O, Nielsen PE, et al. Peptide Nucleic Acids (PNA). Oligonucleotide Analogues with an Achiral Peptide Backbone. J Am Chem Soc. 1992; 114: 1895-7.
    • (1992) J Am Chem Soc , vol.114 , pp. 1895-1897
    • Egholm, M.1    Buchardt, O.2    Nielsen, P.E.3
  • 28
    • 35948993819 scopus 로고    scopus 로고
    • BioShuttle-mediated plasmid transfer
    • Braun K, von Brasch L, Pipkorn R, et al. BioShuttle-mediated plasmid transfer. Int J Med Sci. 2007; 4: 267-77.
    • (2007) Int J Med Sci , vol.4 , pp. 267-277
    • Braun, K.1    von Brasch, L.2    Pipkorn, R.3
  • 29
    • 0032925881 scopus 로고    scopus 로고
    • Applications of peptide nucleic acids
    • Nielsen PE. Applications of peptide nucleic acids. Curr Opin Biotechnol. 1999; 10: 71-5.
    • (1999) Curr Opin Biotechnol , vol.10 , pp. 71-75
    • Nielsen, P.E.1
  • 31
    • 0033376405 scopus 로고    scopus 로고
    • Non-viral peptide-based approaches to gene delivery
    • Mahato RI. Non-viral peptide-based approaches to gene delivery. J Drug Target. 1999; 7: 249-68.
    • (1999) J Drug Target , vol.7 , pp. 249-268
    • Mahato, R.I.1
  • 32
    • 0346725016 scopus 로고    scopus 로고
    • Delivery of antisense peptide nucleic acids (PNAs) to the cytosol by disulphide conjugation to a lipophilic cation
    • Filipovska A, Eccles MR, Smith RAJ, et al. Delivery of antisense peptide nucleic acids (PNAs) to the cytosol by disulphide conjugation to a lipophilic cation. Febs Letters. 2004; 556: 180-6.
    • (2004) Febs Letters , vol.556 , pp. 180-186
    • Filipovska, A.1    Eccles, M.R.2    Smith, R.A.J.3
  • 33
    • 0037600638 scopus 로고    scopus 로고
    • Peptide-mediated cellular delivery of antisense oligonucleotides and their analogues
    • Gait MJ. Peptide-mediated cellular delivery of antisense oligonucleotides and their analogues. Cell Mol Life Sci. 2003; 60: 844-53.
    • (2003) Cell Mol Life Sci , vol.60 , pp. 844-853
    • Gait, M.J.1
  • 34
    • 0032580528 scopus 로고    scopus 로고
    • Effects of membrane-active agents in gene delivery
    • Wagner E. Effects of membrane-active agents in gene delivery. J Controlled Release. 1998; 53: 155-8.
    • (1998) J Controlled Release , vol.53 , pp. 155-158
    • Wagner, E.1
  • 35
    • 0032871488 scopus 로고    scopus 로고
    • In vitro membrane penetration of modified peptide nucleic acid (PNA)
    • Ardhammar M, Norden B, Nielsen PE, et al. In vitro membrane penetration of modified peptide nucleic acid (PNA). J Biomol Struct Dyn. 1999; 17: 33-40.
    • (1999) J Biomol Struct Dyn , vol.17 , pp. 33-40
    • Ardhammar, M.1    Norden, B.2    Nielsen, P.E.3
  • 36
    • 0037428953 scopus 로고    scopus 로고
    • Cellular delivery of peptide nucleic acid (PNA)
    • Koppelhus U, Nielsen PE. Cellular delivery of peptide nucleic acid (PNA). Adv Drug Deliv Rev. 2003; 55: 267-80.
    • (2003) Adv Drug Deliv Rev , vol.55 , pp. 267-280
    • Koppelhus, U.1    Nielsen, P.E.2
  • 37
    • 22544441597 scopus 로고    scopus 로고
    • Development and Characterization of Drug Delivery systems for Targeting Mammalian Cells and Tissues: A Review
    • Braun K, Pipkorn R, Waldeck W. Development and Characterization of Drug Delivery systems for Targeting Mammalian Cells and Tissues: A Review. Curr Med Chem. 2005; 12: 1841-58.
    • (2005) Curr Med Chem , vol.12 , pp. 1841-1858
    • Braun, K.1    Pipkorn, R.2    Waldeck, W.3
  • 38
    • 0029044163 scopus 로고
    • Fmoc Mediated Synthesis of Peptide Nucleic-Acids
    • Thomson SA, Josey JA, Cadilla R, et al. Fmoc Mediated Synthesis of Peptide Nucleic-Acids. TETRAHEDRON. 1995; 51: 6179-94.
    • (1995) TETRAHEDRON , vol.51 , pp. 6179-6194
    • Thomson, S.A.1    Josey, J.A.2    Cadilla, R.3
  • 40
    • 0002186442 scopus 로고
    • Sheppard RC
    • In: Undenfriend S, Meienhofer J, editors, Orlando: Academic Press
    • Atherton E, Sheppard RC. In: Undenfriend S, Meienhofer J, editors. The Peptides. Orlando: Academic Press; 1987: 1-38.
    • (1987) The Peptides , pp. 1-38
    • Atherton, E.1
  • 41
    • 20744456789 scopus 로고
    • Solid Phase Peptide Synthesis. I The Synthesis of a Tetrapeptide
    • Merriefield RB. Solid Phase Peptide Synthesis. I The Synthesis of a Tetrapeptide. J Americ Chem Soc. 1963; 85: 2149-54.
    • (1963) J Americ Chem Soc , vol.85 , pp. 2149-2154
    • Merriefield, R.B.1
  • 42
    • 33947091567 scopus 로고
    • The 9-Fluorenylmethoxycarbonyl Amino-Protecting Group
    • Carpino LA, Han GY. The 9-Fluorenylmethoxycarbonyl Amino-Protecting Group. J ORG CHEM. 1972; 37: 3404-9.
    • (1972) J ORG CHEM , vol.37 , pp. 3404-3409
    • Carpino, L.A.1    Han, G.Y.2
  • 43
    • 0036305495 scopus 로고    scopus 로고
    • A biological transporter for the delivery of peptide nucleic acids (PNAs) to the nuclear compartment of living cells
    • Braun K, Peschke P, Pipkorn R, et al. A biological transporter for the delivery of peptide nucleic acids (PNAs) to the nuclear compartment of living cells. J Mol Biol. 2002; 318: 237-43.
    • (2002) J Mol Biol , vol.318 , pp. 237-243
    • Braun, K.1    Peschke, P.2    Pipkorn, R.3
  • 44
    • 76149118438 scopus 로고    scopus 로고
    • The Diels-Alder-reaction with inverse-electron-demand, a very efficient versatile click-reaction concept for proper ligation of variable molecular partners
    • Wiessler M, Waldeck W, Kliem C, et al. The Diels-Alder-reaction with inverse-electron-demand, a very efficient versatile click-reaction concept for proper ligation of variable molecular partners. Int J Med Sci. 2009; 7: 19-28.
    • (2009) Int J Med Sci , vol.7 , pp. 19-28
    • Wiessler, M.1    Waldeck, W.2    Kliem, C.3
  • 45
    • 63449127358 scopus 로고    scopus 로고
    • Inverse-electron-demand Diels-Alder reaction as a highly efficient chemoselective ligation procedure: Synthesis and function of a BioShuttle for temozolomide transport into prostate cancer cells
    • Pipkorn R, Waldeck W, Didinger B, et al. Inverse-electron-demand Diels-Alder reaction as a highly efficient chemoselective ligation procedure: Synthesis and function of a BioShuttle for temozolomide transport into prostate cancer cells. J Pept Sci. 2009; 15: 235-41.
    • (2009) J Pept Sci , vol.15 , pp. 235-241
    • Pipkorn, R.1    Waldeck, W.2    Didinger, B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.