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Biological Chemistry

Editor-in-Chief: Brüne, Bernhard

Editorial Board: Buchner, Johannes / Lei, Ming / Ludwig, Stephan / Thomas, Douglas D. / Turk, Boris / Wittinghofer, Alfred


IMPACT FACTOR 2018: 3.014
5-year IMPACT FACTOR: 3.162

CiteScore 2018: 3.09

SCImago Journal Rank (SJR) 2018: 1.482
Source Normalized Impact per Paper (SNIP) 2018: 0.820

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1437-4315
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Volume 394, Issue 9

Issues

Synthesis of a novel benzodifuran derivative and its molecular recognition of poly rA RNA

Giovanni N. Roviello / Valentina Roviello / Domenica Musumeci
  • Dipartimento di Scienze Chimiche, Università di Napoli “Federico II”, I-80126 Napoli, Italy
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Carlo Pedone
Published Online: 2013-05-29 | DOI: https://doi.org/10.1515/hsz-2013-0154

Abstract

In this manuscript, we describe a synthetic approach to a novel benzodifuran derivative as well as CD studies regarding its ability to interact with DNA and RNA. After the chemical synthesis and ESI-MS and NMR characterization, this heteroaromatic molecule was investigated by CD spectroscopy in order to evaluate it as a potential nucleic acid binder. Interestingly, the benzodifuran compound was found to be able to induce conformational changes in both DNA and RNA homoadenine molecules forming in the latter case a complex with a 6:1 benzodifuran/nucleobase stoichiometric ratio, as evidenced by CD titration experiments.

Keywords: benzodifuran; CD; RNA

References

  • Carella, A., Borbone, F., Roviello, A., Roviello, G., Tuzi, A., Kravinsky, A., Shikler, R., Cantele, G., and Ninno, D. (2012). Benzodifuroxazinones, a new class of heteroacene molecules for possible applications in organic electronics: synthesis, electronic properties and crystal structure. Dyes Pigm. 95, 116–125.Web of ScienceGoogle Scholar

  • Caruso, U., Panunzi, B., Roviello, G.N., Roviello, G., Tingoli, M., and Tuzi, A. (2009). Synthesis, structure and reactivity of amino-benzodifurane derivatives. C. R. Chim. 12, 622–634.CrossrefGoogle Scholar

  • Feng, Z., Mohapatra, S., Klimko, P.G., Hellberg, M.R., May, J.A., Kelly, C., Williams, G., McLaughlin, M.A., and Sharif, N.A. (2007). Novel benzodifuran analogs as potent 5-HT2A receptor agonists with ocular hypotensive activity. Bioorg. Med. Chem. Lett. 17, 2998–3002.CrossrefGoogle Scholar

  • Guiotto, A., Rodighiero, P., Marciani Magno, S., Gia, O., Pastorini, G., Manzini, P., Zucca, M., and Viano, I. (1979). Bis-basic derivatives of planar heterocyclic compounds. Farmaco Sci. 34, 774–788.Google Scholar

  • Krishnamurthy, K.S., Rajitha, B., and Kanakalingeswara Rao, M. (2003). Synthesis of biologically active angularly fused bis aroyl benzodifurans by PTC and solvent free microwave irradiation. Ind. J. Chem. 42B, 425–428.Google Scholar

  • Krzyzanowska, D., Lisowski, M., and Kochman, M. (1998). UV-difference and CD spectroscopy studies on juvenile hormone binding to its carrier protein. J. Pept. Res. 51, 96–102.PubMedGoogle Scholar

  • Li, H., Jiang, P., Yi, C., Li, C., Liu, S., Tan, S., Zhao, B., Braun, J., Meier, W., Wandlowski, T., et al. (2010). Benzodifuran-based π-conjugated copolymers for bulk heterojunction solar cells. Macromolecules 43, 8058–8062.CrossrefGoogle Scholar

  • Nikolaeva, I.S., Adamskaya, E.V., Vozyakova, T.I., Golovanova, E.A., Fomina, A.N., Oleinik, A.F., and Kistenev, B.M. (1989). Synthesis and antiviral activity of tilorone and its analogs. Pharm. Chem. J. 22, 641–644.Google Scholar

  • Piantanida, I., Palm, B.S., Zinic, M., and Schneider, H-J. (2001). A new 4,9-diazapyrenium intercalator for single- and double-stranded nucleic acids: distinct differences from related diazapyrenium compounds and ethidium bromide. J. Chem. Soc., Perkin Trans. 2, 1808–1816.Google Scholar

  • Rocchi, R., Borin, G., Marchiori, F., Moroder, L., Peggion, E., Scoffone, E., Crescenzi, V., and Quadrifoglio, F. (1972). Interaction of S-protein with S-peptide and with synthetic S-peptide analogs. A spectroscopic and calorimetric investigation. Biochemistry 11, 50–57.CrossrefGoogle Scholar

  • Roviello, G.N., Moccia, M., Sapio, R., Valente, M., Bucci, E.M., Castiglione, M., Pedone, C., Perretta, G., Benedetti, E., and Musumeci, D. (2006). Synthesis, characterization and hybridization studies of new nucleo-γ-peptides based on diaminobutyric acid. J. Pept. Sci. 12, 829–835.CrossrefGoogle Scholar

  • Roviello, G.N., Musumeci, D., Moccia, M., Castiglione, M., Sapio, R., Valente, M., Bucci, E.M., Perretta, G., and Pedone, C. (2007). dabPNA: design, synthesis, and DNA binding studies. Nucleos. Nucleot. Nucl. Acids 26, 1307–1310.Web of ScienceCrossrefGoogle Scholar

  • Roviello, G.N., Musumeci, D., Castiglione, M., Bucci, E.M., Pedone, C., and Benedetti, E. (2009a). Solid phase synthesis and RNA-binding studies of a serum-resistant nucleo-ɛ-peptide. J. Pept. Sci. 15, 155–160.CrossrefWeb of ScienceGoogle Scholar

  • Roviello, G.N., Musumeci, D., De Cristofaro, A., Capasso, D., Di Gaetano, S., Bucci, E.M., and Pedone, C. (2009b). Alternate dab-aegPNAs: synthesis, nucleic acid binding studies and biological activity. Mol. BioSyst. 6, 199–205.Web of SciencePubMedGoogle Scholar

  • Roviello, G.N., Musumeci, D., Pedone, C., and Bucci, E.M. (2010). Synthesis, characterization and hybridization studies of an alternate nucleo-ɛ/γ-peptide: complexes formation with natural nucleic acids. Amino Acids 38, 103–111.Web of ScienceCrossrefGoogle Scholar

  • Roviello, G.N., Musumeci, D., Bucci, E.M., and Pedone, C. (2011). Evidences for supramolecular organization of nucleopeptides: synthesis, spectroscopic and biological studies of a novel dithymine L-serine tetrapeptide. Mol. BioSyst. 7, 1073–1080.Web of SciencePubMedCrossrefGoogle Scholar

  • Roviello, G.N., Musumeci, D., Bucci, E.M., and Pedone, C. (2012a). Synthesis of a diaminopropanoic acid-based nucleoamino acid and assembly of cationic nucleopeptides for biomedical applications. Amino Acids 43, 2537–2543.CrossrefWeb of SciencePubMedGoogle Scholar

  • Roviello, G.N., Roviello, G., Musumeci, D., Bucci, E.M., and Pedone, C. (2012b). 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. Amino Acids 43, 1615–1623.Web of ScienceGoogle Scholar

  • Song, G. and Ren, J. (2010). Recognition and regulation of unique nucleic acid structures by small molecules. Chem. Commun. 46, 7283–7294.CrossrefWeb of ScienceGoogle Scholar

  • Topalian, S.L., Kaneko, S., Gonzales, M.I., Bond, G.L., Ward, Y., and Manley, J.L. (2001). Identification and functional characterization of neo-poly(A) polymerase, an RNA processing enzyme overexpressed in human tumors. Mol. Cell. Biol. 21, 5614–5623.CrossrefPubMedGoogle Scholar

  • Tsuji, H., Mitsui, C., Sato, Y., and Nakamura, E. (2009). Bis(carbazolyl)benzodifuran: a high-mobility ambipolar material for homojunction organic light-emitting diode devices. Adv. Mater. 21, 3776–3779.CrossrefWeb of ScienceGoogle Scholar

  • Viano, I., Dianzani, C., Gia, O., Gastaldi, S., and Genazzani, E. (1985). Biological properties of benzodifuran derivatives. Drugs Exp. Clin. Res. 11, 865–867.PubMedGoogle Scholar

About the article

Corresponding author: Giovanni N. Roviello, Istituto di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, I-80134 Napoli, Italy


Received: 2013-03-26

Accepted: 2013-05-28

Published Online: 2013-05-29

Published in Print: 2013-09-01


Citation Information: Biological Chemistry, Volume 394, Issue 9, Pages 1235–1239, ISSN (Online) 1437-4315, ISSN (Print) 1431-6730, DOI: https://doi.org/10.1515/hsz-2013-0154.

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