Synthesis and nucleic acid binding evaluation of a thyminyl L-diaminobutanoic acid-based nucleopeptide (255 views)
Bioorg Chem (ISSN: 0045-2068linking, 1090-2120electronic), 2020 Jul; 100: 103862-103870.
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Paper type: Research Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 4.831, 5-year impact factor: 3.39
Url: https://doi.org/10.1016/j.bioorg.2020.103862
Keywords: Nucleopeptide, Prebiotic, Diaminobutanoic Acid, Synthesis, Rna Binding, Dna Quadruplex, Telomeric Dna, C-Myc,
Affiliations:
*** IBB - CNR ***
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a
Department of Chemical Sciences, Federico II University, Via Cintia 21, 80126 Naples, Italy
References:
Not available.
Bioorg Chem (ISSN: 0045-2068linking, 1090-2120electronic), 2020 Jul; 100: 103862-103870.
Export to BibTeX Export to EndNote
Paper type: Research Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 4.831, 5-year impact factor: 3.39
Url: https://doi.org/10.1016/j.bioorg.2020.103862
Keywords: Nucleopeptide, Prebiotic, Diaminobutanoic Acid, Synthesis, Rna Binding, Dna Quadruplex, Telomeric Dna, C-Myc,
Affiliations:
*** IBB - CNR ***
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- Istituto di Biostrutture e Bioimmagini IBB - CNR, Via Mezzocannone 16, 80134 Naples, Italy
References:
Not available.
Synthesis and nucleic acid binding evaluation of a thyminyl L-diaminobutanoic acid-based nucleopeptide
Herein we present the synthesis of a L-diaminobutanoic acid (DABA) -based nucleopeptide (3), with an oligocationic backbone, realized by solid phase peptide synthesis with thymine-bearing DABA moieties alternating in the sequence with free ones. CD studies evidenced the ability of this oligothymine nucleopeptide, well soluble in aqueous solution, to alter the secondary structure particularly of complementary RNA (poly rA vs poly rU) and inosine-rich RNAs, like poly rI and poly rIC, and showed its preference in binding double vs single-stranded DNAs. Furthermore, ESI mass spectrometry revealed that 3 bound also G-quadruplex (G4) DNAs, with both parallel and antiparallel topologies (adopted in our experimental conditions by c-myc and tel22, respectively). However, it caused detectable changes only in the CD of c-myc (whose parallel G4 structure was also thermally stabilized by ∼3 °C), while leaving unaltered the antiparallel structure of tel22. Interestingly, CD and UV analyses suggested that 3 induced a hybrid mixed parallel/antiparallel G4 DNA structure in a random tel22 DNA obtained under salt-free buffer conditions. Titration of random telomeric DNA with 3 gave a quantitative information on the stoichiometry of the obtained complex (CNH3+/CPO3- =1.5). Overall, the findings of this work suggest that DABA-based nucleopeptides are synthetic nucleic acid analogues potentially useful in antigene and antisense strategies. Nevertheless, the hexathymine DABA-nucleopeptide shows an interesting behaviour as molecular tool itself for its efficacy in provoking G4 induction in disordered G-rich DNA, as well as for the possibility to bind and stabilize c-myc oncogene in a G4 structure.
Herein we present the synthesis of a L-diaminobutanoic acid (DABA) -based nucleopeptide (3), with an oligocationic backbone, realized by solid phase peptide synthesis with thymine-bearing DABA moieties alternating in the sequence with free ones. CD studies evidenced the ability of this oligothymine nucleopeptide, well soluble in aqueous solution, to alter the secondary structure particularly of complementary RNA (poly rA vs poly rU) and inosine-rich RNAs, like poly rI and poly rIC, and showed its preference in binding double vs single-stranded DNAs. Furthermore, ESI mass spectrometry revealed that 3 bound also G-quadruplex (G4) DNAs, with both parallel and antiparallel topologies (adopted in our experimental conditions by c-myc and tel22, respectively). However, it caused detectable changes only in the CD of c-myc (whose parallel G4 structure was also thermally stabilized by ∼3 °C), while leaving unaltered the antiparallel structure of tel22. Interestingly, CD and UV analyses suggested that 3 induced a hybrid mixed parallel/antiparallel G4 DNA structure in a random tel22 DNA obtained under salt-free buffer conditions. Titration of random telomeric DNA with 3 gave a quantitative information on the stoichiometry of the obtained complex (CNH3+/CPO3- =1.5). Overall, the findings of this work suggest that DABA-based nucleopeptides are synthetic nucleic acid analogues potentially useful in antigene and antisense strategies. Nevertheless, the hexathymine DABA-nucleopeptide shows an interesting behaviour as molecular tool itself for its efficacy in provoking G4 induction in disordered G-rich DNA, as well as for the possibility to bind and stabilize c-myc oncogene in a G4 structure.
Synthesis and nucleic acid binding evaluation of a thyminyl L-diaminobutanoic acid-based nucleopeptide
Synthesis and nucleic acid binding evaluation of a thyminyl L-diaminobutanoic acid-based nucleopeptide
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Pirtskhalava M, Egoyan A, Mirtskhulava M, Roviello GN
* A COMPUTER MODELING STUDY OF BINDING PROPERTIES OF CHIRAL NUCLEOPEPTIDE FOR BIOMEDICAL APPLICATIONS (657 views)
Georgian Med News (ISSN: 1512-0112print, 1512-0112linking), 2017 Dec; (273): 1123-1128.
Impact Factor: 0
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Fagoonee S, Picco G, Orso F, Arrigoni A, Longo DL, Forni M, Scarfo I, Cassenti A, Piva R, Cassoni P, Silengo L, Tolosano E, Aime S, Taverna D, Pandolfi PP, Brancaccio M, Medico E, Altruda F
* The RNA-binding protein ESRP1 promotes human colorectal cancer progression (433 views)
Oncotarget (ISSN: 1949-2553electronic, 1949-2553linking), 2016 Dec 28; 8(6): 10007-10024.
Impact Factor: 5.168
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Roviello GN, Musumeci D
* Synthetic approaches to nucleopeptides containing all the four nucleobases, and nucleic acid-binding studies on a mixed-sequence nucleo-oligolysine (633 views)
Rsc Adv (ISSN: 2046-2069, 2046-2069electronic), 2016 Jun; 6: 63578-63585.
Impact Factor: 3.108
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Roviello GN, Vicidomini C, Di Gaetano S, Capasso D, Musumeci D, Roviello V
* Solid phase synthesis and RNA-binding activity of an arginine-containing nucleopeptide (673 views)
Rsc Adv (ISSN: 2046-2069, 2046-2069electronic), 2016; 6(17): 14140-14148.
Impact Factor: 3.108
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Autiero I, Saviano M, Langella E
* Conformational studies of chiral D-Lys-PNA and achiral PNA system in binding with DNA or RNA through a molecular dynamics approach (696 views)
Eur J Med Chem (ISSN: 0223-5234, 1768-3254, 0223-5234linking), 2015 Feb 16; 91: 109-117.
Impact Factor: 3.902
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Roviello GN, Musumeci D, Roviello V, Pirtskhalava M, Egoyan A, Mirtskhulava M
* Natural and artificial binders of polyriboadenylic acid and their effect on RNA structure (538 views)
Beilstein J Nanotech (ISSN: 2190-4286), 2015; 6(1): 1338-1347.
Impact Factor: 2.778
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Roviello GN, Musumeci D, D'Alessandro C, Pedone C
* Binding ability of a thymine-functionalized oligolysine towards nucleic acids (477 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 0968-0896linking), 2014 Feb 1; 22(3): 997-1002.
Impact Factor: 2.793
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Roviello GN, Musumeci D, D'Alessandro C, Pedone C
* Synthesis of a thymine-functionalized nucleoamino acid for the solid phase assembly of cationic nucleopeptides (675 views)
Amino Acids (ISSN: 1438-2199, 0939-4451, 1438-2199electronic), 2013 Oct; 45(4): 779-784.
Impact Factor: 3.653
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Dolga AM, Netter MF, Perocchi F, Doti N, Meissner L, Tobaben S, Grohm J, Zischka H, Plesnila N, Decher N, Culmsee C
* Mitochondrial Small Conductance SK2 Channels Prevent Glutamate-induced Oxytosis and Mitochondrial Dysfunction (719 views)
Jbc Papers (ISSN: 0021-9258, 1083-351x, 0021-9258linking), 2013 Apr 12; 288(15): 10792-10804.
Impact Factor: 4.6
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Roviello GN, Musumeci D, Bucci EM, Pedone C
* Synthesis of a diaminopropanoic acid-based nucleoamino acid and assembly of cationic nucleopeptides for biomedical applications (654 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2012 Dec; 43(6): 2537-2543.
Impact Factor: 3.914
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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 (665 views)
Amino Acids (ISSN: 1438-2199, 0939-4451, 1438-2199electronic), 2012 Oct; 43(4): 1615-1623.
Impact Factor: 3.914
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Roviello GN, Mottola A, Musumeci D, Bucci EM, Pedone C
* Synthesis and aggregation properties of a novel enzymatically resistant nucleoamino acid (585 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2012 Oct; 43(4): 1465-1470.
Impact Factor: 3.914
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Avitabile C, Saviano M, D'Andrea LD, Bianchi N, Fabbri E, Brognara E, Gambari R, Romanelli A
* Targeting pre-miRNA by peptide nucleic acids: a new strategy to interfere in the miRNA maturation (1083 views)
Artif Dna Pna Xnaartificial Dna Pna & Xna (ISSN: 1949-9096, 1949-0968, 1949-095x), 2012 Apr; 3(2): 88-96.
Impact Factor: 0
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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 (759 views)
Int J Pharm (ISSN: 0378-5173, 1873-3476), 2011 Sep 30; 415(1-2): 206-210.
Impact Factor: 3.35
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Haider SM, Autiero I, Neidle S
Surface area accessibility and the preferred topology of telomeric DNA quadruplex-ligand complexes (73 views)
Biochimie (ISSN: 0300-9084linking), 2011 Aug; 93 (8 ): 1275-1279.
Impact Factor:
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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 (771 views)
Mol Biosyst (ISSN: 1742-206x, 1742-2051, 1742-2051electronic), 2011 Apr; 7(4): 1073-1080.
Impact Factor: 3.534
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Fantini D, Vascotto C, Marasco D, D'Ambrosio C, Romanello M, Vitagliano L, Pedone C, Poletto M, Cesaratto L, Quadrifoglio F, Scaloni A, Radicella JP, Tell G
* Critical lysine residues within the overlooked N-terminal domain of human APE1 regulate its biological functions (613 views)
Nucleic Acids Res (ISSN: 1362-4962, 0305-1048, 1362-4962electronic), 2010 Dec; 38(22): 8239-8256.
Impact Factor: 7.836
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Moccia M, Roviello GN, Bucci EM, Pedone C, Saviano M
* Synthesis of a l-lysine-based alternate alpha, epsilon-peptide: A novel linear polycation with nucleic acids-binding ability (706 views)
Int J Pharm (ISSN: 0378-5173, 1873-3476), 2010 Sep 15; 397(1-2): 179-183.
Impact Factor: 3.607
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Roviello GN, Crescenzo C, Capasso D, Di Gaetano S, Franco S, Bucci EM, Pedone C
* 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 (553 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 Sep; 39(3): 795-800.
Impact Factor: 4.106
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Roviello GN, Benedetti E, Pedone C, Bucci EM
* Nucleobase-containing peptides: An overview of their characteristic features and applications (1048 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 Jun; 39(1): 45-57.
Impact Factor: 4.106
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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 (627 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 May; 38(5): 1489-1496.
Impact Factor: 4.106
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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 (760 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 Jan; 38(1): 103-111.
Impact Factor: 4.106
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Roviello GN, Musumeci D, Castiglione M, Bucci EM, Pedone C, Benedetti E
* Solid Phase Synthesis And Rna-Binding Studies Of A Serum-Resistant Nucleo-Epsilon-Peptide (754 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2009 Mar; 15(3): 155-160.
Impact Factor: 1.807
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Marchelli R, Saviano M, Licandro E, Spoto G, Borgatti M, Gambari R
* PNAs targeting the "RNA world": Micro RNA next? (605 views)
Minerva Biotecnol (ISSN: 1120-4826), 2008; 20(4): 183-188.
Impact Factor: 0.1
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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 (549 views)
Nucleosides Nucleotides Nucleic Acids (ISSN: 1525-7770), 2007; 26(10-12): 1307-1310.
Impact Factor: 0.723
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Bucci EM, Valente M, Musumeci D, Sapio R, Anrò V, Roviello GN, Moccia M
* ODN-based drugs for targeting of extracellular proteins (426 views)
Nucleosides Nucleotides Nucleic Acids (ISSN: 1525-7770), 2007; 26(8-9): 1047-1050.
Impact Factor: 0.723
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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 (667 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2006 Dec; 12(12): 829-835.
Impact Factor: 1.801
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Musumeci D, Valente M, Capasso D, Palumbo R, Gorlach M, Schmidtke M, Zell R, Roviello GN, Sapio R, Pedone C, Bucci EM
* A short PNA targeting coxsackievirus B3 5′-nontranslated region prevents virus-induced cytolysis (595 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2006 Mar; 12(3): 161-170.
Impact Factor: 1.801
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Bashan A, Zarivach R, Schluenzen F, Agmon I, Harms J, Auerbach T, Baram D, Berisio R, Bartels H, Hansen HAS, Fucini P, Wilson D, Peretz M, Kessler M, Yonath A
* Ribosomal crystallography: Peptide bond formation and its inhibition (683 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2003 Sep; 70(1): 19-41.
Impact Factor: 2.733
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Zell R, Sidigi K, Bucci E, Stelzner A, Goerlach M
* Determinants of the recognition of enteroviral cloverleaf RNA by coxsackievirus B3 proteinase 3C (595 views)
Rna (ISSN: 1355-8382), 2002; 8(2): 188-201.
Impact Factor: 5.099
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Masullo M, Cantiello P, Paola B, Fiengo A, Vitagliano L, Zagari A, Arcari P
* Valine114 Replacements In The Archaeal Elongation Factor 1a Enhanced Its Ability To Interact With Aminoacyl-Trna And Kirromycin (468 views)
Biochemistry (ISSN: 0006-2960, 1520-4995, 1520-4995electronic), 2002; 41(49): 14482-14488.
Impact Factor: 4.064
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44 Records (44 excluding Abstracts).
Total impact factor: 152.803 (152.803 excluding Abstracts).
Total 5 year impact factor: 148.377 (148.377 excluding Abstracts).
Total impact factor: 152.803 (152.803 excluding Abstracts).
Total 5 year impact factor: 148.377 (148.377 excluding Abstracts).
255 views. Last view on Sunday 01 December 2024, 1:06:12
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