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

Biological Chemistry

Volumn 394, Issue 9, 2013, Pages 1235-1239

  Roviello, Giovanni N ^a   Roviello, Valentina ^b   Musumeci, Domenica ^c   Pedone, Carlo ^a  

^a CNR   (Italy)

^b CNR   (Italy)

^c UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Benzodifuran; CD; RNA

Indexed keywords

1,4 BENZOQUINONE; AMMONIUM HYDROXIDE; AROMATIC COMPOUND; BENZODIFURAN DERIVATIVE; DNA; RNA; RNA POLYMERASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; CYCLIZATION; ELECTROSPRAY MASS SPECTROMETRY; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE; POLYADENYLATION; PRIORITY JOURNAL; SPECTROSCOPY; STOICHIOMETRY; SYNTHESIS; TAUTOMERIZATION;

BENZOFURANS; MOLECULAR STRUCTURE; POLY A; RNA;

EID: 84881525878     PISSN: 14316730     EISSN: 14374315     Source Type: Journal    
DOI: 10.1515/hsz-2013-0154     Document Type: Article

References (22)

1. 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.
2. Caruso, U., Panunzi, B., Roviello, G.N., Roviello, G., Tingoli, M., and Tuzi, A. (2009). Synthesis, structure and reactivity of aminobenzodifurane derivatives. C. R. Chim. 12, 622 - 634.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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-conjugated copolymers for bulk heterojunction solar cells. Macromolecules 43, 8058 - 8062.
8. 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.
9. Piantanida, I., Palm, B.S., Zinic, M., and Schneider, H-J. (2001). A new 4, 9-diazapyrenium intercalator for single- And doublestranded nucleic acids: distinct differences from related diazapyrenium compounds and ethidium bromide. J. Chem. Soc., Perkin Trans. 2, 1808 - 1816.
10. 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.
11. 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-peptides based on diaminobutyric acid. J. Pept. Sci. 12, 829 - 835.
12. 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.
13. 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- ε -peptide. J. Pept. Sci. 15, 155 - 160.
14. 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.
15. Roviello, G.N., Musumeci, D., Pedone, C., and Bucci, E.M. (2010). Synthesis, characterization and hybridization studies of an alteRNAte nucleo- ε/peptide: complexes formation with natural nucleic acids. Amino Acids 38, 103 - 111.
16. 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.
17. 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.
18. 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.
19. Song, G. and Ren, J. (2010). Recognition and regulation of unique nucleic acid structures by small molecules. Chem. Commun. 46, 7283 - 7294.
20. 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.
21. 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.
22. Viano, I., Dianzani, C., Gia, O., Gastaldi, S., and Genazzani, E. (1985). Biological properties of benzodifuran derivatives. Drugs Exp. Clin. Res. 11, 865 - 867.