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.
We thank Dr. Giuseppe Perretta and Mr. Antonio Liccardo for their technical support, as well as the institutions that supported our laboratory (Consiglio Nazionale delle Ricerche and Università degli Studi di Napoli ‘Federico II’).
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, 116–125.10.1016/j.dyepig.2012.03.033Suche in Google 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, 622–634.10.1016/j.crci.2008.05.015Suche in Google 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, 2998–3002.10.1016/j.bmcl.2007.03.073Suche in Google Scholar PubMed
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.Suche in 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.Suche in 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, 96–102.10.1111/j.1399-3011.1998.tb00625.xSuche in Google Scholar PubMed
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, 8058–8062.10.1021/ma101693dSuche in Google 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, 641–644.10.1007/BF00763632Suche in 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, 1808–1816.10.1039/b103214nSuche in 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, 50–57.10.1021/bi00751a010Suche in Google Scholar PubMed
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, 829–835.10.1002/psc.819Suche in Google Scholar PubMed
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, 1307–1310.10.1080/15257770701530640Suche in Google Scholar PubMed
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, 155–160.10.1002/psc.1072Suche in Google Scholar PubMed
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, 199–205.10.1039/B910278GSuche in Google Scholar PubMed
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, 103–111.10.1007/s00726-008-0214-7Suche in Google Scholar PubMed
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, 1073–1080.10.1039/c0mb00214cSuche in Google Scholar PubMed
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, 2537–2543.10.1007/s00726-012-1335-6Suche in Google Scholar PubMed
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, 1615–1623.10.1007/s00726-012-1237-7Suche in Google Scholar PubMed
Song, G. and Ren, J. (2010). Recognition and regulation of unique nucleic acid structures by small molecules. Chem. Commun. 46, 7283–7294.10.1039/c0cc01312aSuche in Google Scholar PubMed
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, 5614–5623.10.1128/MCB.21.16.5614-5623.2001Suche in Google Scholar PubMed PubMed Central
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, 3776–3779.10.1002/adma.200900634Suche in Google 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.Suche in Google Scholar
©2013 by Walter de Gruyter Berlin Boston
Artikel in diesem Heft
- Masthead
- Masthead
- Reviews
- Imaging the invisible: resolving cellular microcompartments by superresolution microscopy techniques
- Structure and function of MK5/PRAK: the loner among the mitogen-activated protein kinase-activated protein kinases
- Functional ribosome biogenesis is a prerequisite for p53 destabilization: impact of chemotherapy on nucleolar functions and RNA metabolism
- Interleukin-6 and interleukin-11: same same but different
- Cathepsin K: a unique collagenolytic cysteine peptidase
- Research Articles/Short Communications
- Protein Structure and Function
- The active form of goat insulin-like peptide 3 (INSL3) is a single-chain structure comprising three domains B-C-A, constitutively expressed and secreted by testicular Leydig cells
- Molecular Medicine
- Zinc-dependent contact system activation induces vascular leakage and hypotension in rodents
- Cell Biology and Signaling
- ACE inhibition enhances bradykinin relaxations through nitric oxide and B1 receptor activation in bovine coronary arteries
- Changes in COX-2 and oxidative damage factors during differentiation of human mesenchymal stem cells to hepatocyte-like cells is associated with downregulation of P53 gene
- Overexpression of miR-126 promotes the differentiation of mesenchymal stem cells toward endothelial cells via activation of PI3K/Akt and MAPK/ERK pathways and release of paracrine factors
- Novel Techniques
- Synthesis of a novel benzodifuran derivative and its molecular recognition of poly rA RNA
Artikel in diesem Heft
- Masthead
- Masthead
- Reviews
- Imaging the invisible: resolving cellular microcompartments by superresolution microscopy techniques
- Structure and function of MK5/PRAK: the loner among the mitogen-activated protein kinase-activated protein kinases
- Functional ribosome biogenesis is a prerequisite for p53 destabilization: impact of chemotherapy on nucleolar functions and RNA metabolism
- Interleukin-6 and interleukin-11: same same but different
- Cathepsin K: a unique collagenolytic cysteine peptidase
- Research Articles/Short Communications
- Protein Structure and Function
- The active form of goat insulin-like peptide 3 (INSL3) is a single-chain structure comprising three domains B-C-A, constitutively expressed and secreted by testicular Leydig cells
- Molecular Medicine
- Zinc-dependent contact system activation induces vascular leakage and hypotension in rodents
- Cell Biology and Signaling
- ACE inhibition enhances bradykinin relaxations through nitric oxide and B1 receptor activation in bovine coronary arteries
- Changes in COX-2 and oxidative damage factors during differentiation of human mesenchymal stem cells to hepatocyte-like cells is associated with downregulation of P53 gene
- Overexpression of miR-126 promotes the differentiation of mesenchymal stem cells toward endothelial cells via activation of PI3K/Akt and MAPK/ERK pathways and release of paracrine factors
- Novel Techniques
- Synthesis of a novel benzodifuran derivative and its molecular recognition of poly rA RNA