Istituto di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, I-80134 Napoli, Italy. giovanni.roviello@cnr.it
CNR, Istituto di Biostrutture E Bioimmagini, Via Mezzocannone 16, I-80134 Napoli, Italy
CNR, Istituto per L'Ambiente Marino Costiero, Calata Porta di Massa, I-80133 Napoli, Italy
Dipartimento di Scienze Chimiche, Universita di Napoli Federico II, I-80126 Napoli, Italy
References: Carella, A., Borbone, F., Roviello, A., Roviello, G., Tuzi, A., Kravinsky, A., Shikler, R., Ninno, D., Benzodifuroxazinones, a new class of heteroacene molecules for possible applications in organic electronics: Synthesis, electronic properties and crystal structure (2012) Dyes Pigm, 95, pp. 116-12
Caruso, U., Panunzi, B., Roviello, G.N., Roviello, G., Tingoli, M., Tuzi, A., Synthesis, structure and reactivity of aminobenzodifurane derivatives (2009) C. R. Chim., 12, pp. 622-634
Feng, Z., Mohapatra, S., Klimko, P.G., Hellberg, M.R., May, J.A., Kelly, C., Williams, G., Sharif, N.A., Novel benzodifuran analogs as potent 5-HT2A receptor agonists with ocular hypotensive activity (2007) Bioorg. Med. Chem. Lett., 17, pp. 2998-3002
Guiotto, A., Rodighiero, P., Marciani Magno, S., Gia, O., Pastorini, G., Manzini, P., Zucca, M., Viano, I., Bis-basic derivatives of planar heterocyclic compounds (1979) Farmaco Sci, 34, pp. 774-788
Krishnamurthy, K.S., Rajitha, B., Kanakalingeswara Rao, M., Synthesis of biologically active angularly fused bis aroyl benzodifurans by ptc and solvent free microwave irradiation (2003) Ind. J. Chem., 42 B, pp. 425-428
Krzyzanowska, D., Lisowski, M., Kochman, M., UV-difference and CD spectroscopy studies on juvenile hormone binding to its carrier protein (1998) J. Pept. Res., 51, pp. 96-102
Li, H., Jiang, P., Yi, C., Li, C., Liu, S., Tan, S., Zhao, B., Wandlowski, T., Benzodifuran-based-conjugated copolymers for bulk heterojunction solar cells (2010) Macromolecules, 43, pp. 8058-8062
Nikolaeva, I.S., Adamskaya, E.V., Vozyakova, T.I., Golovanova, E.A., Fomina, A.N., Oleinik, A.F., Kistenev, B.M., Synthesis and antiviral activity of tilorone and its analogs (1989) Pharm. Chem. J., 22, pp. 641-644
Piantanida, I., Palm, B.S., Zinic, M., Schneider, H.-J., A new 4, 9-diazapyrenium intercalator for single- And doublestranded nucleic acids: Distinct differences from related diazapyrenium compounds and ethidium bromide (2001) J. Chem. Soc., Perkin Trans., 2, pp. 1808-1816
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., Moccia, M., Sapio, R., Valente, M., Bucci, E.M., Castiglione, M., Pedone, C., Musumeci, D., Synthesis, characterization and hybridization studies of new nucleo-peptides based on diaminobutyric acid (2006) J. Pept. Sci., 12, pp. 829-835
Roviello, G.N., Musumeci, D., Moccia, M., Castiglione, M., Sapio, R., Valente, M., Bucci, E.M., Pedone, C., DabPNA: Design, synthesis, and DNA binding studies (2007) Nucleos. Nucleot. Nucl. Acids, 26, pp. 1307-1310
Song, G., Ren, J., Recognition and regulation of unique nucleic acid structures by small molecules (2010) Chem. Commun., 46, pp. 7283-7294
Topalian, S.L., Kaneko, S., Gonzales, M.I., Bond, G.L., Ward, Y., Manley, J.L., Identification and functional characterization of neo-poly(A) polymerase, an RNA processing enzyme overexpressed in human tumors (2001) Mol. Cell. Biol., 21, pp. 5614-5623
Tsuji, H., Mitsui, C., Sato, Y., Nakamura, E., Bis(carbazolyl)benzodifuran: A high-mobility ambipolar material for homojunction organic light-emitting diode devices (2009) Adv. Mater., 21, pp. 3776-3779
Viano, I., Dianzani, C., Gia, O., Gastaldi, S., Genazzani, E., Biological properties of benzodifuran derivatives (1985) Drugs Exp. Clin. Res., 11, pp. 865-867
Synthesis of a novel benzodifuran derivative and its molecular recognition of poly rA RNA
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.
Synthesis of a novel benzodifuran derivative and its molecular recognition of poly rA RNA