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Volumn 14, Issue 5, 2003, Pages 941-954

Modulation of the pharmacokinetic properties of PNA: Preparation of galactosyl, mannosyl, fucosyl, N-acetylgalactosaminyl, and N-acetylglucosaminyl derivatives of aminoethylglycine peptide nucleic acid monomers and their incorporation into PNA oligomers

Author keywords

[No Author keywords available]

Indexed keywords

MODULATION; MONOMERS; NUCLEIC ACIDS; OLIGOMERS; PEPTIDES; PHARMACOKINETICS;

EID: 0141681146     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc034022x     Document Type: Article
Times cited : (67)

References (40)
  • 1
    • 0033919830 scopus 로고    scopus 로고
    • Antisense peptide nucleic acids
    • Nielsen, P. E. (2000) Antisense peptide nucleic acids. Curr. Opin. Mol. Ther. 2, 282-287.
    • (2000) Curr. Opin. Mol. Ther. , vol.2 , pp. 282-287
    • Nielsen, P.E.1
  • 2
    • 0037046160 scopus 로고    scopus 로고
    • Novel antisense and peptide nucleic acid strategies for controlling gene expression
    • Braasch, D. A., and Corey, D. R. (2002) Novel Antisense and Peptide Nucleic Acid Strategies for Controlling Gene Expression. Biochemistry 41, 4503-4510.
    • (2002) Biochemistry , vol.41 , pp. 4503-4510
    • Braasch, D.A.1    Corey, D.R.2
  • 3
    • 0037428953 scopus 로고    scopus 로고
    • Cellular delivery of peptide nucleic acid (PNA)
    • Koppelhus, U., and Nielsen, P. E. (2003) Cellular delivery of peptide nucleic acid (PNA). Adv. Drug Delivery Rev. 55, 267-280.
    • (2003) Adv. Drug Delivery Rev. , vol.55 , pp. 267-280
    • Koppelhus, U.1    Nielsen, P.E.2
  • 4
    • 0035151066 scopus 로고    scopus 로고
    • Peptide nucleic acids as antibacterial agents via the antisense principle
    • Nielsen, P. E. (2001) Peptide nucleic acids as antibacterial agents via the antisense principle. Expert Opin. Invest. Drugs 10, 331-341.
    • (2001) Expert Opin. Invest. Drugs , vol.10 , pp. 331-341
    • Nielsen, P.E.1
  • 6
    • 0029905179 scopus 로고    scopus 로고
    • Peptide nucleic acids (PNAs) containing thymine monomers derived from chiral amino acids: Hybridization and solubility properties of D-lysine PNA
    • Haaima, G., Lohse, A., Buchardt, O., and Nielsen, P. E. (1996) Peptide nucleic acids (PNAs) containing thymine monomers derived from chiral amino acids: hybridization and solubility properties of D-lysine PNA. Angew. Chem., Int. Ed. Engl. 35, 1939-1941.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1939-1941
    • Haaima, G.1    Lohse, A.2    Buchardt, O.3    Nielsen, P.E.4
  • 8
    • 0036846909 scopus 로고    scopus 로고
    • A novel hepatic-targeting system for therapeutic cytokines that delivers to the hepatic asialoglycoprotein receptor, but avoids receptor-mediated endocytosis
    • Sato, H., Kato, Y., Hayasi, E., Tabata, T., Suzuki, M., Takahara, Y., and Sugiyama, Y. (2002) A novel hepatic-targeting system for therapeutic cytokines that delivers to the hepatic asialoglycoprotein receptor, but avoids receptor-mediated endocytosis. Pharm Res. 19, 1736-44.
    • (2002) Pharm Res. , vol.19 , pp. 1736-1744
    • Sato, H.1    Kato, Y.2    Hayasi, E.3    Tabata, T.4    Suzuki, M.5    Takahara, Y.6    Sugiyama, Y.7
  • 10
    • 0033805014 scopus 로고    scopus 로고
    • Lectin-mediated drug targeting: Selection of valency, sugar type (Gal/Lac), and spacer length for cluster glycosides as parameters to distinguish ligand binding to C-type asialoglycoprotein receptors and galectins
    • Andre, S., Frisch, B., Kaltner, H., Desouza, D. L., Schuber, F., and Gabius, H. J. (2000) Lectin-mediated drug targeting: selection of valency, sugar type (Gal/Lac), and spacer length for cluster glycosides as parameters to distinguish ligand binding to C-type asialoglycoprotein receptors and galectins. Pharm Res. 17, 985-90.
    • (2000) Pharm Res. , vol.17 , pp. 985-990
    • Andre, S.1    Frisch, B.2    Kaltner, H.3    Desouza, D.L.4    Schuber, F.5    Gabius, H.J.6
  • 11
    • 0031239051 scopus 로고    scopus 로고
    • Facile synthesis of a high-affinity ligand for mammalian hepatic lectin containing three terminal N-acetylgalactosamine residues
    • Lee, R. T., and Lee, Y. C. (1997) Facile synthesis of a high-affinity ligand for mammalian hepatic lectin containing three terminal N-acetylgalactosamine residues. Bioconjugate Chem. 8, 762-5.
    • (1997) Bioconjugate Chem. , vol.8 , pp. 762-765
    • Lee, R.T.1    Lee, Y.C.2
  • 17
    • 0030823838 scopus 로고    scopus 로고
    • Monitoring the solid-phase synthesis of analogues of lysobactin and the katanosins using in situ MALDI-TOF MS
    • Egner, B. J., and Bradley, M. (1997) Monitoring the solid-phase synthesis of analogues of lysobactin and the katanosins using in situ MALDI-TOF MS. Tetrahedron 53, 14021-14030.
    • (1997) Tetrahedron , vol.53 , pp. 14021-14030
    • Egner, B.J.1    Bradley, M.2
  • 18
    • 0345396975 scopus 로고
    • An efficient synthesis of Boc-aminoacetaldehyde and its application to the synthesis of N-(2-Boc-aminoethyl)glycine esters
    • Dueholm, K. L., Egholm, M., and Buchardt, O. (1993) An efficient synthesis of Boc-aminoacetaldehyde and its application to the synthesis of N-(2-Boc-aminoethyl)glycine esters. Org. Prep. Proced. Int. 25, 457-461.
    • (1993) Org. Prep. Proced. Int. , vol.25 , pp. 457-461
    • Dueholm, K.L.1    Egholm, M.2    Buchardt, O.3
  • 19
    • 0026341239 scopus 로고
    • Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide
    • Nielsen, P. E., Egholm, M., Berg, R. H., and Buchardt, O. (1991) Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide. Science 254, 1497-1500.
    • (1991) Science , vol.254 , pp. 1497-1500
    • Nielsen, P.E.1    Egholm, M.2    Berg, R.H.3    Buchardt, O.4
  • 21
    • 84985624827 scopus 로고
    • Facile synthesis of Alpha-O-glycosyl and Beta-O-glycosyl imidates - Praparation of glycosides and disaccharides
    • Schmidt, R. R., and Michel, J. (1980) Facile synthesis of Alpha-O-glycosyl and Beta-O-glycosyl imidates - Praparation of glycosides and disaccharides. Angew. Chem., Int. Ed. 19, 731-732.
    • (1980) Angew. Chem., Int. Ed. , vol.19 , pp. 731-732
    • Schmidt, R.R.1    Michel, J.2
  • 22
    • 0031916180 scopus 로고    scopus 로고
    • Investigation on the stability of the Dde protecting group used in peptide synthesis: Migration to an unprotected lysine
    • Augustyns, K., Kraas, W., and Jung, G. (1998) Investigation on the stability of the Dde protecting group used in peptide synthesis: migration to an unprotected lysine. J. Pept. Res. 51, 127-133.
    • (1998) J. Pept. Res. , vol.51 , pp. 127-133
    • Augustyns, K.1    Kraas, W.2    Jung, G.3
  • 23
    • 0032485517 scopus 로고    scopus 로고
    • Hydrazinolysis of Dde: Complete orthogonality with Aloc protecting groups
    • Rohwedder, B., Mutti, Y., Dumy, P., and Mutter, M. (1998) Hydrazinolysis of Dde: complete orthogonality with Aloc protecting groups. Tetrahedron Lett. 39, 1175-1178.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1175-1178
    • Rohwedder, B.1    Mutti, Y.2    Dumy, P.3    Mutter, M.4
  • 24
    • 0001320196 scopus 로고
    • Stereoselective synthesis of α-C-allylglycopyranosides
    • Giannis, A., and Sandhoff, K. (1985) Stereoselective synthesis of α-C-allylglycopyranosides. Tetrahedron Lett. 26, 1479-1482.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 1479-1482
    • Giannis, A.1    Sandhoff, K.2
  • 25
    • 0000136219 scopus 로고
    • Synthesis of the brevetoxin B IJK ring system
    • Nicolaou, K. C., Hwang, C. K., and Duggan, M. E. (1989) Synthesis of the brevetoxin B IJK ring system. J. Am. Chem. Soc. 111, 6682-6690.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6682-6690
    • Nicolaou, K.C.1    Hwang, C.K.2    Duggan, M.E.3
  • 27
    • 0023759880 scopus 로고
    • Analogues of uridine 5′-diphosphate glucose. Inhibition of glycolipid biosynthesis
    • Broxterman, H. J. G., Van der Marel, G. A., and Van Boom, J. H. (1988) Analogues of uridine 5′-diphosphate glucose. Inhibition of glycolipid biosynthesis. Tetrahedron Lett. 29, 4893-4896.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4893-4896
    • Broxterman, H.J.G.1    Van der Marel, G.A.2    Van Boom, J.H.3
  • 28
    • 0029801847 scopus 로고    scopus 로고
    • Generation of C-Glycoside peptide ligands for cell surface carbohydrate receptors using a four-component condensation on solid support
    • Sutherlin, D. P., Stark, T. M., Hughes, R., and Armstrong, R. W. (1996) Generation of C-Glycoside Peptide Ligands for Cell Surface Carbohydrate Receptors Using a Four-Component Condensation on Solid Support. J. Org. Chem. 61, 8350-8354.
    • (1996) J. Org. Chem. , vol.61 , pp. 8350-8354
    • Sutherlin, D.P.1    Stark, T.M.2    Hughes, R.3    Armstrong, R.W.4
  • 29
    • 0031031387 scopus 로고    scopus 로고
    • 2-NH) peptide bond with 2,4-dimethoxybenzyl group in solid-phase peptide synthesis
    • 2-NH) peptide bond with 2,4-dimethoxybenzyl group in solid-phase peptide synthesis. Chem. Pharm. Bull. 45, 13-17
    • (1997) Chem. Pharm. Bull. , vol.45 , pp. 13-17
    • Yusuke, S.1    Junko, A.2
  • 30
    • 0033427735 scopus 로고    scopus 로고
    • Stepwise solid-phase synthesis of peptide-oligonucleotide conjugates on new solid supports
    • Antopolsky, M., and Azhayev, A. (1999) Stepwise solid-phase synthesis of peptide-oligonucleotide conjugates on new solid supports. Helv. Chim. Acta 82 (12), 2130-2140.
    • (1999) Helv. Chim. Acta , vol.82 , Issue.12 , pp. 2130-2140
    • Antopolsky, M.1    Azhayev, A.2
  • 31
    • 0038726659 scopus 로고
    • The syntheses of various 1-N-(L-aspart-4-oyl)-glycosylamines and their analogues
    • Tanaka, M., and Yamashina, I. (1973) The syntheses of various 1-N-(L-aspart-4-oyl)-glycosylamines and their analogues. Carbohydr. Res. 27, 175-183.
    • (1973) Carbohydr. Res. , vol.27 , pp. 175-183
    • Tanaka, M.1    Yamashina, I.2
  • 32
    • 0032554856 scopus 로고    scopus 로고
    • Synthesis and activity of dipeptides, linked to targeting ligands, as specific NK cell enhancers
    • Abbot, S. D., Gagnon, L., Lagraoui, M., Kadhim, S., Attardo, G., Zacharie B., and Penney, C. L. (1998) Synthesis and Activity of Dipeptides, Linked to Targeting Ligands, as Specific NK Cell Enhancers. J. Med. Chem. 41, 1909-1926.
    • (1998) J. Med. Chem. , vol.41 , pp. 1909-1926
    • Abbot, S.D.1    Gagnon, L.2    Lagraoui, M.3    Kadhim, S.4    Attardo, G.5    Zacharie, B.6    Penney, C.L.7
  • 33
    • 0002237717 scopus 로고
    • Glycosyl fluorides and azides
    • Micheel, F., and Klemer, A. (1961) Glycosyl fluorides and azides. Adv. Carbohyd. Chem. 16, 85-103.
    • (1961) Adv. Carbohyd. Chem. , vol.16 , pp. 85-103
    • Micheel, F.1    Klemer, A.2
  • 34
    • 0004432239 scopus 로고
    • Amino acids and peptides. Part 36. Dehydroamino acids. Part 16. Simple preparation of N-acyl-2-(diethoxyphosphoryl)glycine esters and their application in the synthesis of dehydroamino acid esters
    • Schmidt, U., Lieberknecht, A., Schanbacher, U., Beuttler, T., and Wild, J. (1982) Amino acids and peptides. Part 36. Dehydroamino acids. Part 16. Simple preparation of N-acyl-2-(diethoxyphosphoryl)glycine esters and their application in the synthesis of dehydroamino acid esters. Angew. Chem. 94, 797-798.
    • (1982) Angew. Chem. , vol.94 , pp. 797-798
    • Schmidt, U.1    Lieberknecht, A.2    Schanbacher, U.3    Beuttler, T.4    Wild, J.5
  • 36
    • 0037077790 scopus 로고    scopus 로고
    • Racemization of chiral PNAs during solid-phase synthesis: Effect of the coupling conditions on enantiomeric purity
    • Tedeschi, T., Corradini, R., Marchelli, R., Pushl, A., and Nielsen, P. E. (2002) Racemization of chiral PNAs during solid-phase synthesis: effect of the coupling conditions on enantiomeric purity. Tetrahedron: Asymmetry 13, 1629-1636.
    • (2002) Tetrahedron: Asymmetry , vol.13 , pp. 1629-1636
    • Tedeschi, T.1    Corradini, R.2    Marchelli, R.3    Pushl, A.4    Nielsen, P.E.5
  • 37
    • 0033522742 scopus 로고    scopus 로고
    • Direct enantiomeric separation of N-aminoethylamino acids: Determination of the enantiomeric excess of chiral peptide nucleic acids (PNAs) by GC
    • Corradini, R., Di Silvestro, G., Sforza, S., Palla, G., Dossena, A., and Nielsen, P. E., et al. (1999) Direct enantiomeric separation of N-aminoethylamino acids: determination of the enantiomeric excess of chiral peptide nucleic acids (PNAs) by GC. Tetrahedron: Asymmetry 10, 2063-2066.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 2063-2066
    • Corradini, R.1    Di Silvestro, G.2    Sforza, S.3    Palla, G.4    Dossena, A.5    Nielsen, P.E.6
  • 38
    • 13044266375 scopus 로고    scopus 로고
    • Peptide nucleic acids targeted to the neurotensin receptor and administered i.p. cross the blood-brain barrier and specifically reduce gene expression
    • Tyler, B. M., Jansen, K., McCormick, D. J., Douglas, C. L., Boules, M., Stewart, J. A., et al. (1999) Peptide nucleic acids targeted to the neurotensin receptor and administered i.p. cross the blood-brain barrier and specifically reduce gene expression. Proc. Natl. Acad. Sci. U.S.A. 96, 7053-7058.
    • (1999) Proc. Natl. Acad. Sci. U.S.A. , vol.96 , pp. 7053-7058
    • Tyler, B.M.1    Jansen, K.2    McCormick, D.J.3    Douglas, C.L.4    Boules, M.5    Stewart, J.A.6
  • 39
    • 0037136420 scopus 로고    scopus 로고
    • Glycans as endocytosis signals: The cases of the asialoglycoprotein and hyaluronan/chondroitin sulfate receptors
    • Weigel, P., and Yik, J. (2002) Glycans as endocytosis signals: the cases of the asialoglycoprotein and hyaluronan/chondroitin sulfate receptors. Biochim. Biophys. Acta 1572, 341-363.
    • (2002) Biochim. Biophys. Acta , vol.1572 , pp. 341-363
    • Weigel, P.1    Yik, J.2
  • 40
    • 0032584664 scopus 로고    scopus 로고
    • Mechanism of N-acetylgalactosamine binding to a C-type animal lectin carbohydrate-recognition domain
    • Kolatkar, A. R., Leung, A. K., Isecke, R., Brossmer, R., Drickamer, K., and Weis, W. I. (1998) Mechanism of N-acetylgalactosamine binding to a C-type animal lectin carbohydrate-recognition domain. J. Biol. Chem. 273, 19502-19508.
    • (1998) J. Biol. Chem. , vol.273 , pp. 19502-19508
    • Kolatkar, A.R.1    Leung, A.K.2    Isecke, R.3    Brossmer, R.4    Drickamer, K.5    Weis, W.I.6


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