Synthesis of a novel Fmoc-protected nucleoaminoacid for the solid phase assembly of 4-piperidyl glycine/L-arginine-containing nucleopeptides and preliminary RNA interaction studies (464 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 Sep; 39(3): 795-800.
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Paper type: Journal Article,
Impact factor: 4.106, 5-year impact factor: 3.541
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-77956922342&partnerID=40&md5=039e2fe9a2d0edba14278d2161f6f795
Keywords: Nucleopeptide, Rna, Rt-Pcr, 4 Piperidyl Glycine, 9 Fluorenylmethoxycarbonyl N (4 Piperidyl)glycine, (thymin 1 Ylacetyl) 4, Piperidyl]glycine, Amino Acid Derivative, Arginine Derivative, Messenger Rna, Nucleic Acid Base, Nucleopeptide Derivative, Oligomer, Tetrapeptide, Unclassified Drug, Amino Acid Synthesis, Article, Carbon Nuclear Magnetic Resonance, Circular Dichroism, Electrospray Mass Spectrometry, Hela Cell, Priority Journal, Protein Interaction, Proton Nuclear Magnetic Resonance, Reverse Transcription Polymerase Chain Reaction, Reversed Phase High Performance Liquid Chromatography, Solid Phase Synthesis, Ultraviolet Spectroscopy, Humans, Molecular Structure, Peptide Nucleic Acids, Eukaryota,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, 80134 Naples, Italy
Dipartimento Delle Scienze Biologiche, Università di Napoli Federico II, 80134 Naples, Italy
References:
Bell, N.M., Micklefield, J., Chemical modification of oligonucleotides for therapeutic, bioanalytical and other applications (2009) Chembiochem, 10 (17), pp. 2691-2703. , doi:10.1002/cbic.20090034
Diederichsen, U., Pairing properties of alanyl peptide nucleic acids containing an amino acid backbone with alternating configuration (1996) Angew Chem Int Ed Engl, 35, pp. 445-448
Dragulescu-Andrasi, A., Rapireddy, S., He, G., Bhattacharya, B., Hyldig-Nielsen, J.J., Zon, G., Ly, D.H., Cell-permeable peptide nucleic acid designed to bind to the 5'-untranslated region of E-cadherin transcript induces potent and sequence-specific antisense effects (2006) J Am Chem Soc, 128, pp. 16104-16112
Geotti-Bianchini, P., Beyrath, J., Chaloin, O., Formaggio, F., Bianco, A., Design and synthesis of intrinsically cell-penetrating nucleopeptides (2008) Org Biomol Chem, 6, pp. 3661-3663
Katritzky, A.R., Narindoshvili, T., Chiral peptide nucleic acid monomers (PNAM) with modified backbones (2008) Org Biomol Chem, 6, pp. 3171-3176
Krzyzanowska, D., Lisowski, M., Kochman, M., UV-difference and CD spectroscopy studies on juvenile hormone binding to its carrier prote (1998) J Pept Res, 51, pp. 96-102
Lonkar, P.S., Kumar, V.A., Design and synthesis of conforma-tionally frozen peptide nucleic acid backbone: Chiral piperidine PNA as a hexitol nucleic acid surrogate (2004) Bioorg Med Chem Lett, 14, pp. 2147-2149
Moggio, L., Romanelli, A., Gambari, R., Bianchi, N., Borgatti, M., Fabbri, E., Mancini, I., Messere, A., Alternate PNA-DNA chimeras (PNA-DNA)(n): Synthesis binding properties and biological activity (2007) Biopolymers, 88, pp. 815-822
Nielsen, P.E., Egholm, M., Berg, R.M., Buchardt, O., Sequence selective recognition of DNA by strand displacement with thymine-substituted polyamide (1991) Science, 254, pp. 1497-1500
Rocchi, R., Borin, G., Marchiori, F., Moroder, L., Peggion, E., Scoffone, E., Crescenzi, V., Quadrifoglio, F., Interaction of S-protein with S-peptide and with synthetic S-peptide analogs. A spectroscopic and calorimetric investigation (1972) Biochemistry, 11, pp. 50-57
Roviello, G.N., Musumeci, D., De Cristofaro, A., Capasso, D., Di Gaetano, S., Bucci, E.M., Pedone, C., Alternate dab-aegPNAs: Synthesis, nucleic acid binding studies and biological activity (2010) Mol Biosyst, 6 (1), pp. 189-195. , doi:10.1039/b910278g
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 Sep; 39(3): 795-800.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 4.106, 5-year impact factor: 3.541
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-77956922342&partnerID=40&md5=039e2fe9a2d0edba14278d2161f6f795
Keywords: Nucleopeptide, Rna, Rt-Pcr, 4 Piperidyl Glycine, 9 Fluorenylmethoxycarbonyl N (4 Piperidyl)glycine, (thymin 1 Ylacetyl) 4, Piperidyl]glycine, Amino Acid Derivative, Arginine Derivative, Messenger Rna, Nucleic Acid Base, Nucleopeptide Derivative, Oligomer, Tetrapeptide, Unclassified Drug, Amino Acid Synthesis, Article, Carbon Nuclear Magnetic Resonance, Circular Dichroism, Electrospray Mass Spectrometry, Hela Cell, Priority Journal, Protein Interaction, Proton Nuclear Magnetic Resonance, Reverse Transcription Polymerase Chain Reaction, Reversed Phase High Performance Liquid Chromatography, Solid Phase Synthesis, Ultraviolet Spectroscopy, Humans, Molecular Structure, Peptide Nucleic Acids, Eukaryota,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, 80134 Naples, Italy
Dipartimento Delle Scienze Biologiche, Università di Napoli Federico II, 80134 Naples, Italy
References:
Bell, N.M., Micklefield, J., Chemical modification of oligonucleotides for therapeutic, bioanalytical and other applications (2009) Chembiochem, 10 (17), pp. 2691-2703. , doi:10.1002/cbic.20090034
Diederichsen, U., Pairing properties of alanyl peptide nucleic acids containing an amino acid backbone with alternating configuration (1996) Angew Chem Int Ed Engl, 35, pp. 445-448
Dragulescu-Andrasi, A., Rapireddy, S., He, G., Bhattacharya, B., Hyldig-Nielsen, J.J., Zon, G., Ly, D.H., Cell-permeable peptide nucleic acid designed to bind to the 5'-untranslated region of E-cadherin transcript induces potent and sequence-specific antisense effects (2006) J Am Chem Soc, 128, pp. 16104-16112
Geotti-Bianchini, P., Beyrath, J., Chaloin, O., Formaggio, F., Bianco, A., Design and synthesis of intrinsically cell-penetrating nucleopeptides (2008) Org Biomol Chem, 6, pp. 3661-3663
Katritzky, A.R., Narindoshvili, T., Chiral peptide nucleic acid monomers (PNAM) with modified backbones (2008) Org Biomol Chem, 6, pp. 3171-3176
Krzyzanowska, D., Lisowski, M., Kochman, M., UV-difference and CD spectroscopy studies on juvenile hormone binding to its carrier prote (1998) J Pept Res, 51, pp. 96-102
Lonkar, P.S., Kumar, V.A., Design and synthesis of conforma-tionally frozen peptide nucleic acid backbone: Chiral piperidine PNA as a hexitol nucleic acid surrogate (2004) Bioorg Med Chem Lett, 14, pp. 2147-2149
Moggio, L., Romanelli, A., Gambari, R., Bianchi, N., Borgatti, M., Fabbri, E., Mancini, I., Messere, A., Alternate PNA-DNA chimeras (PNA-DNA)(n): Synthesis binding properties and biological activity (2007) Biopolymers, 88, pp. 815-822
Nielsen, P.E., Egholm, M., Berg, R.M., Buchardt, O., Sequence selective recognition of DNA by strand displacement with thymine-substituted polyamide (1991) Science, 254, pp. 1497-1500
Rocchi, R., Borin, G., Marchiori, F., Moroder, L., Peggion, E., Scoffone, E., Crescenzi, V., Quadrifoglio, F., Interaction of S-protein with S-peptide and with synthetic S-peptide analogs. A spectroscopic and calorimetric investigation (1972) Biochemistry, 11, pp. 50-57
Roviello, G.N., Musumeci, D., De Cristofaro, A., Capasso, D., Di Gaetano, S., Bucci, E.M., Pedone, C., Alternate dab-aegPNAs: Synthesis, nucleic acid binding studies and biological activity (2010) Mol Biosyst, 6 (1), pp. 189-195. , doi:10.1039/b910278g
Synthesis of a novel Fmoc-protected nucleoaminoacid for the solid phase assembly of 4-piperidyl glycine/L-arginine-containing nucleopeptides and preliminary RNA interaction studies
In this work, we report the synthesis of a novel Fmoc-protected nucleoaminoacid, based on 4-piperidinyl glycine, carrying the DNA nucleobase on the secondary amino group, suitable for the solid-phase synthesis of nu-cleopeptides. After ESI-MS and NMR characterization this building block was used for the assembly of a thymine-functionalized tetrapeptide, composed of 4-piperidinyl glycine and L-arginine moieties alternated in the backbone. The ability to interact with RNA and the efficiency in interfering with the reverse transcription of eukaryotic mRNA of the novel nucleo-tetrapeptide found in this study are in favour of the employment of chiral nucleopeptides based on alternate 4-piperidinyl glycine/L-arginine backbone in biomedicine. © Springer-Verlag 2010.
In this work, we report the synthesis of a novel Fmoc-protected nucleoaminoacid, based on 4-piperidinyl glycine, carrying the DNA nucleobase on the secondary amino group, suitable for the solid-phase synthesis of nu-cleopeptides. After ESI-MS and NMR characterization this building block was used for the assembly of a thymine-functionalized tetrapeptide, composed of 4-piperidinyl glycine and L-arginine moieties alternated in the backbone. The ability to interact with RNA and the efficiency in interfering with the reverse transcription of eukaryotic mRNA of the novel nucleo-tetrapeptide found in this study are in favour of the employment of chiral nucleopeptides based on alternate 4-piperidinyl glycine/L-arginine backbone in biomedicine. © Springer-Verlag 2010.
Synthesis of a novel Fmoc-protected nucleoaminoacid for the solid phase assembly of 4-piperidyl glycine/L-arginine-containing nucleopeptides and preliminary RNA interaction studies
Synthesis of a novel Fmoc-protected nucleoaminoacid for the solid phase assembly of 4-piperidyl glycine/L-arginine-containing nucleopeptides and preliminary RNA interaction studies
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Impact Factor: 4.3
View Export to BibTeX Export to EndNote
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* A COMPUTER MODELING STUDY OF BINDING PROPERTIES OF CHIRAL NUCLEOPEPTIDE FOR BIOMEDICAL APPLICATIONS (430 views)
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Impact Factor: 0
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D
* Synthetic approaches to nucleopeptides containing all the four nucleobases, and nucleic acid-binding studies on a mixed-sequence nucleo-oligolysine (435 views)
Rsc Adv (ISSN: 2046-2069), 2016 Jun; 6: 63578-63585.
Impact Factor: 3.108
View Export to BibTeX Export to EndNote
Roviello GN, Vicidomini C, Di Gaetano S, Capasso D, Musumeci D, Roviello V
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Impact Factor: 3.108
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, Roviello V, Pirtskhalava M, Egoyan A, Mirtskhulava M
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Impact Factor: 2.778
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, D'Alessandro C, Pedone C
* Binding ability of a thymine-functionalized oligolysine towards nucleic acids (347 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 0968-0896linking), 2014 Feb 1; 22(3): 997-1002.
Impact Factor: 2.793
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, D'Alessandro C, Pedone C
* Synthesis of a thymine-functionalized nucleoamino acid for the solid phase assembly of cationic nucleopeptides (486 views)
Amino Acids (ISSN: 1438-2199, 0939-4451, 1438-2199electronic), 2013 Oct; 45(4): 779-784.
Impact Factor: 3.653
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, Bucci EM, Pedone C
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Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2012 Dec; 43(6): 2537-2543.
Impact Factor: 3.914
View Export to BibTeX Export to EndNote
Roviello GN, Roviello G, Musumeci D, Bucci EM, Pedone C
* Dakin-West reaction on 1-thyminyl acetic acid for the synthesis of 1, 3-bis(1-thyminyl)-2-propanone, a heteroaromatic compound with nucleopeptide-binding properties (439 views)
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Impact Factor: 3.914
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, Bucci EM, Pedone C
* Synthesis and characterization of a novel ester-based nucleoamino acid for the assembly of aromatic nucleopeptides for biomedical applications (531 views)
Int J Pharm (ISSN: 0378-5173, 1873-3476), 2011 Sep 30; 415(1-2): 206-210.
Impact Factor: 3.35
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, Bucci EM, Pedone C
* Evidences for supramolecular organization of nucleopeptides: Synthesis, spectroscopic and biological studies of a novel dithymine l-serine tetrapeptide (578 views)
Mol Biosyst (ISSN: 1742-206x, 1742-2051, 1742-2051electronic), 2011 Apr; 7(4): 1073-1080.
Impact Factor: 3.534
View Export to BibTeX Export to EndNote
Roviello GN, Benedetti E, Pedone C, Bucci EM
* Nucleobase-containing peptides: An overview of their characteristic features and applications (753 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 Jun; 39(1): 45-57.
Impact Factor: 4.106
View Export to BibTeX Export to EndNote
Roviello GN, Di Gaetano S, Capasso D, Cesarani A, Bucci EM, Pedone C
* Synthesis, spectroscopic studies and biological activity of a novel nucleopeptide with Moloney murine leukemia virus reverse transcriptase inhibitory activity (443 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 May; 38(5): 1489-1496.
Impact Factor: 4.106
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, Pedone C, Bucci EM
* Synthesis, Characterization And Hybridization Studies Of An Alternate Nucleo-Epsilon/Gamma-Peptide: Complexes Formation With Natural Nucleic Acids (494 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 Jan; 38(1): 103-111.
Impact Factor: 4.106
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, Moccia M, Castiglione M, Sapio R, Valente M, Bucci EM, Perretta G, Pedone C
* Dabpna: Design, Synthesis And Nucleic Acids Binding Studies (430 views)
Nucleosides Nucleotides Nucleic Acids (ISSN: 1525-7770), 2007; 26(10-12): 1307-1310.
Impact Factor: 0.723
View Export to BibTeX Export to EndNote
Roviello GN, Moccia M, Sapio R, Valente M, Bucci EM, Castiglione M, Pedone C, Perretta G, Benedetti E, Musumeci D
* Synthesis, Characterization And Hybridization Studies Of New Nucleo-Gamma-Peptides Based On Diaminobutyric Acid (493 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2006 Dec; 12(12): 829-835.
Impact Factor: 1.801
View Export to BibTeX Export to EndNote
21 Records (21 excluding Abstracts).
Total impact factor: 74.431 (74.431 excluding Abstracts).
Total 5 year impact factor: 72.527 (72.527 excluding Abstracts).
Total impact factor: 74.431 (74.431 excluding Abstracts).
Total 5 year impact factor: 72.527 (72.527 excluding Abstracts).
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