Novel insights into nucleoamino acids: biomolecular recognition and aggregation studies of a thymine-conjugated L-phenyl alanine (379 views)
Amino Acids (ISSN: 1438-2199electronic, 0939-4451linking), 2018 May 15; DOI10.1007/s00726-01: 933-941.
Export to BibTeX Export to EndNote
Paper type: Research Journal Article,
Impact factor: 3.173, 5-year impact factor: 3.541
Url: https://rdcu.be/Oou7
Keywords: Dna And Rna Binding, Nucleoamino Amides, Spectroscopic Properties, Bovine Serum Albumin, Messenger Rna, Nucleic Acid Base, Phenylalanine, Plasma Protein, Polyadenylic Acid, Thymine, Aqueous Solution, Article, Circular Dichroism, Concentration Response, Conjugation, Dna Binding, Drug Delivery System, Enzyme Stability, Molecular Recognition, Photon Correlation Spectroscopy, Priority Journal, Protein Aggregation, Protein Binding, Protein Secondary Structure, Protein Structure, Synthesis, Technology, Temperature Dependence, Ultraviolet Spectroscopy,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini-CNR (UOS Napoli centro), 80134, Naples, Italy. giovanni.roviello@cnr.it.,
References:
Cangelosi, V.M., Zakharov, L.N., Johnson, D.W., Supramolecular “transmetalation” leads to an unusual self-assembled P2L3 cryptand (2010) Angew Chem Int Ed, 49, pp. 1248-125
Dobryszycki, P., Kołodziejczyk, R., Krowarsch, D., Gapiński, J., Ozyhar, A., Kochman, M., Unfolding and refolding of juvenile hormone binding protein (2004) Biophys J, 86, pp. 1138-1148. , PID: 14747348
Dolman, N.P., More, J.C., Alt, A., Knauss, J.L., Troop, H.M., Bleakman, D., Collingridge, G.L., Jane, D.E., Structure-activity relationship studies on N3-substituted willardiine derivatives acting as AMPA or kainate receptor antagonists (2006) J Med Chem, 49, pp. 2579-2592. , PID: 16610801
Du, X., Zhou, J., Guvench, O., Sangiorgi, F.O., Li, X., Zhou, N., Xu, B., Supramolecular assemblies of a conjugate of nucleobase, amino acids, and saccharide act as agonists for proliferation of embryonic stem cells and development of zygotes (2014) Bioconjug Chem, 25, pp. 1031-1035. , PID: 24798034
Esposito, G., Teta, R., Miceli, R., Ceccarelli, L.S., Della Sala, G., Camerlingo, R., Irollo, E., Costantino, V., Isolation and assessment of the in vitro anti-tumor activity of smenothiazole A and B, chlorinated thiazole-containing peptide/polyketides from the Caribbean sponge, Smenospongia aurea (2015) Mar Drugs, 13, pp. 444-459. , PID: 25603342
Giri, P., Kumar, G.S., Molecular recognition of poly(A) targeting by protoberberine alkaloids: in vitro biophysical studies and biological perspectives (2010) Mol BioSyst, 6, pp. 81-88. , PID: 20024069
Goerbitz, C.H., The structure of nanotubes formed by diphenylalanine, the core recognition motif of Alzheimer's â-amyloid polypeptide (2006) Chem Commun, pp. 2332-2334
Gospodarska, E., Kupniewska-Kozak, A., Goch, G., Dadlez, M., The structure of nanotubes formed by diphenylalanine, the core recognition motif of Alzheimer’s beta-amyloid polypeptide (2011) Biochim Biophys Acta, 1814, pp. 592-609. , PID: 21354340
Karst, J.C., Sotomayor Pérez, A.C., Guijarro, J.I., Raynal, B., Chenal, A., Ladant, D., Calmodulin-induced conformational and hydrodynamic changes in the catalytic domain of Bordetella pertussis adenylate cyclase toxin (2010) Biochemistry, 49, pp. 318-328. , PID: 20000337
Katritzky, A.R., Mohapatra, P.P., Singh, S., Clemens, N., Kirichenko, K., Synthesis of α-amino amides via α-amino imidoylbenzotriazoles (2005) J Serb Chem Soc, 70, pp. 319-327
Kitamura, K., Kinsui, E.Z., Abe, F., Critical role of the proton-dependent oligopeptide transporter (POT) in the cellular uptake of the peptidyl nucleoside antibiotic, blasticidin S (2017) Biochim Biophys Acta, 1864, pp. 393-398. , PID: 27916534
Lamberth, C., Naturally occurring amino acid derivatives with herbicidal, fungicidal or insecticidal activity (2016) Amino Acids, 48, pp. 929-940. , PID: 26801938
Lilla, E.A., Yokoyama, K., Carbon extension in peptidylnucleoside biosynthesis by radical SAM enzymes (2016) Nat Chem Biol, 12, pp. 905-907. , PID: 27642865
Lindquist, N.R., Carter, T.G., Cangelosi, V.M., Zakharov, L.N., Johnson, D.W., Three’s company: co-crystallization of a self-assembled S(4) metallacyclophane with two diastereomeric metallacycle intermediates (2010) Chem Commun, 46, pp. 3505-3507
Madonna, S., Scarponi, C., Doti, N., Carbone, T., Cavani, A., Scognamiglio, P.L., Marasco, D., Albanesi, C., Therapeutical potential of a peptide mimicking the SOCS1 kinase inhibitory region in skin immune responses (2013) Eur J Immunol, 43, pp. 1883-1895. , PID: 23592500
Mik, V., Mičková, Z., Doležal, K., Frébort, I., Pospíšil, T., Activity of (+)-Discadenine as a plant cytokinin (2017) J Nat Prod, 80, pp. 2136-2140. , PID: 28665127
Mishra, A., Panda, J.J., Basu, A., Chauhan, V.S., Nanovesicles based on self-assembly of conformationally constrained aromatic residue containing amphiphilic dipeptides (2008) Langmuir, 24, pp. 4571-4576. , PID: 18358051
Miyauchi, K., Kimura, S., Suzuki, T., A cyclic form of N6-threonylcarbamoyladenosine as a widely distributed tRNA hypermodification (2013) Nat Chem Biol, 9, pp. 105-111. , PID: 23242255
Mizutani, M., Jitsukawa, K., Masuda, H., Einaga, H., Synthesis and X-ray structure of a unique multinuclear complex constructed by a nucleobase-amino acid DL-willardiine (1996) Chem Comm, 11, pp. 1389-1390
Musumeci, D., Rozza, L., Merlino, A., Paduano, L., Marzo, T., Massai, L., Messori, L., Montesarchio, D., Interaction of anticancer Ru(III) complexes with single stranded and duplex DNA model systems (2015) Dalton Trans, 44, pp. 13914-13925. , PID: 26154188
Musumeci, D., Roviello, V., Roviello, G.N., DNA- and RNA-binding ability of oligoDapT, a nucleobase-decorated peptide, for biomedical applications (2018) Int J Nanomed, 13, pp. 2613-2629
Pape, V.F., Türk, D., Szabó, P., Wiese, M., Enyedy, E.A., Szakács, G., Synthesis and characterization of the anticancer and metal binding properties of novel pyrimidinylhydrazone derivatives (2015) J Inorg Biochem, 144, pp. 18-30. , PID: 25589012
Pinto, B., Rusciano, G., D’Errico, S., Borbone, N., Sasso, A., Piccialli, V., Mayol, L., Piccialli, G., Synthesis and label free characterization of a bimolecular PNA homo quadruplex (2017) Biochim Biophys Acta, 1861, pp. 1222-1228. , PID: 27913190
Reches, M., Gazit, E., Controlled patterning of aligned self-assembled peptide nanotubes (2006) Nat Nanotechnol, 1, pp. 195-200. , PID: 18654186
Roviello, G.N., Musumeci, D., Synthetic approaches to nucleopeptides containing all four nucleobases, and nucleic acid-binding studies on a mixed-sequence nucleo-oligolysine (2016) RSC Adv, 6, pp. 63578-63585. , PID: 28496969
Roviello, G.N., Di Gaetano, S., Capasso, D., Cesarani, A., Bucci, E.M., Pedone, C., Synthesis, spectroscopic studies and biological activity of a novel nucleopeptide with Moloney murine leukemia virus reverse transcriptase inhibitory activity (2010) Amino Acids, 38, pp. 1489-1496. , PID: 19813074
Roviello, G.N., Crescenzo, C., Capasso, D., Di Gaetano, S., Franco, S., Bucci, E.M., 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 (2010) Amino Acids, 39, pp. 795-800. , PID: 20204432
Roviello, G.N., Ricci, A., Bucci, E.M., Pedone, C., Synthesis, biological evaluation and supramolecular assembly of novel analogues of peptidyl nucleosides (2011) Mol BioSyst, 7, pp. 1773-1778. , PID: 21431179
Roviello, G.N., Vicidomini, C., Di Gaetano, S., Capasso, D., Musumeci, D., Roviello, V., Solid phase synthesis and RNA-binding activity of an arginine-containing nucleopeptide (2016) RSC Adv, 6, pp. 14140-14148. , PID: 29057071
Roviello, G.N., Roviello, V., Autiero, I., Saviano, M., Solid phase synthesis of TyrT, a thymine–tyrosine conjugate with poly(A) RNA-binding ability (2016) RSC Adv, 6, pp. 27607-27613. , PID: 29057072
Roviello, G.N., Oliviero, G., Di Napoli, A., Borbone, N., Piccialli, G., Synthesis, self-assembly-behavior and biomolecular recognition properties of thyminyl dipeptides (2018) Arab J Chem
Rozan, P., Kuo, Y.H., Lambein, F., Amino acids in seeds and seedlings of the genus Lens (2001) Phytochemistry, 58, pp. 281-289. , PID: 11551552
Saghyan, A.S., Simonyan, H.M., Petrosyan, S.G., Geolchanyan, A.V., Roviello, G.N., Musumeci, D., Roviello, V., Thiophenyl-substituted triazolyl-thione l-alanine: asymmetric synthesis, aggregation and biological properties (2014) Amino Acids, 46, pp. 2325-2332. , PID: 24952728
Song, G., Ren, J., Recognition and regulation of unique nucleic acid structures by small molecules (2010) Chem Commun, 46, pp. 7283-7294
Teta, R., Irollo, E., Della Sala, G., Pirozzi, G., Mangoni, A., Costantino, V., Smenamides A and B, chlorinated peptide/polyketide hybrids containing a dolapyrrolidinone unit from the Caribbean sponge Smenospongia aurea. Evaluation of their role as leads in antitumor drug research (2013) Mar Drugs, 11, pp. 4451-4463. , PID: 24217287
Weckenmann, N.M., Nachtsheim, B.J., Enantioselective synthesis of D-α-(Uracil-5-yl)glycine derivatives and their racemization-free incorporation into a Model-Peptide (2015) Eur J Org Chem, 30, pp. 6624-6630
Wu, D., Zhou, J., Shi, J., Du, X., Xu, B., A naphthalene-containing amino acid enables hydrogelation of a conjugate of nucleobase-saccharide-amino acids (2014) Chem Commun, 50, pp. 1992-1994
Yuan, Z.Y., Lu, X., Lei, F., Chai, Y.S., Wang, Y.G., Jiang, J.F., Feng, T.S., Du, L.J., TATA boxes in gene transcription and poly(A) tails in mRNA stability: new perspective on the effects of berberine (2015) Sci Rep., 5, p. 18326
Amino Acids (ISSN: 1438-2199electronic, 0939-4451linking), 2018 May 15; DOI10.1007/s00726-01: 933-941.
Export to BibTeX Export to EndNote
Paper type: Research Journal Article,
Impact factor: 3.173, 5-year impact factor: 3.541
Url: https://rdcu.be/Oou7
Keywords: Dna And Rna Binding, Nucleoamino Amides, Spectroscopic Properties, Bovine Serum Albumin, Messenger Rna, Nucleic Acid Base, Phenylalanine, Plasma Protein, Polyadenylic Acid, Thymine, Aqueous Solution, Article, Circular Dichroism, Concentration Response, Conjugation, Dna Binding, Drug Delivery System, Enzyme Stability, Molecular Recognition, Photon Correlation Spectroscopy, Priority Journal, Protein Aggregation, Protein Binding, Protein Secondary Structure, Protein Structure, Synthesis, Technology, Temperature Dependence, Ultraviolet Spectroscopy,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini-CNR (UOS Napoli centro), 80134, Naples, Italy. giovanni.roviello@cnr.it.,
References:
Cangelosi, V.M., Zakharov, L.N., Johnson, D.W., Supramolecular “transmetalation” leads to an unusual self-assembled P2L3 cryptand (2010) Angew Chem Int Ed, 49, pp. 1248-125
Dobryszycki, P., Kołodziejczyk, R., Krowarsch, D., Gapiński, J., Ozyhar, A., Kochman, M., Unfolding and refolding of juvenile hormone binding protein (2004) Biophys J, 86, pp. 1138-1148. , PID: 14747348
Dolman, N.P., More, J.C., Alt, A., Knauss, J.L., Troop, H.M., Bleakman, D., Collingridge, G.L., Jane, D.E., Structure-activity relationship studies on N3-substituted willardiine derivatives acting as AMPA or kainate receptor antagonists (2006) J Med Chem, 49, pp. 2579-2592. , PID: 16610801
Du, X., Zhou, J., Guvench, O., Sangiorgi, F.O., Li, X., Zhou, N., Xu, B., Supramolecular assemblies of a conjugate of nucleobase, amino acids, and saccharide act as agonists for proliferation of embryonic stem cells and development of zygotes (2014) Bioconjug Chem, 25, pp. 1031-1035. , PID: 24798034
Esposito, G., Teta, R., Miceli, R., Ceccarelli, L.S., Della Sala, G., Camerlingo, R., Irollo, E., Costantino, V., Isolation and assessment of the in vitro anti-tumor activity of smenothiazole A and B, chlorinated thiazole-containing peptide/polyketides from the Caribbean sponge, Smenospongia aurea (2015) Mar Drugs, 13, pp. 444-459. , PID: 25603342
Giri, P., Kumar, G.S., Molecular recognition of poly(A) targeting by protoberberine alkaloids: in vitro biophysical studies and biological perspectives (2010) Mol BioSyst, 6, pp. 81-88. , PID: 20024069
Goerbitz, C.H., The structure of nanotubes formed by diphenylalanine, the core recognition motif of Alzheimer's â-amyloid polypeptide (2006) Chem Commun, pp. 2332-2334
Gospodarska, E., Kupniewska-Kozak, A., Goch, G., Dadlez, M., The structure of nanotubes formed by diphenylalanine, the core recognition motif of Alzheimer’s beta-amyloid polypeptide (2011) Biochim Biophys Acta, 1814, pp. 592-609. , PID: 21354340
Karst, J.C., Sotomayor Pérez, A.C., Guijarro, J.I., Raynal, B., Chenal, A., Ladant, D., Calmodulin-induced conformational and hydrodynamic changes in the catalytic domain of Bordetella pertussis adenylate cyclase toxin (2010) Biochemistry, 49, pp. 318-328. , PID: 20000337
Katritzky, A.R., Mohapatra, P.P., Singh, S., Clemens, N., Kirichenko, K., Synthesis of α-amino amides via α-amino imidoylbenzotriazoles (2005) J Serb Chem Soc, 70, pp. 319-327
Kitamura, K., Kinsui, E.Z., Abe, F., Critical role of the proton-dependent oligopeptide transporter (POT) in the cellular uptake of the peptidyl nucleoside antibiotic, blasticidin S (2017) Biochim Biophys Acta, 1864, pp. 393-398. , PID: 27916534
Lamberth, C., Naturally occurring amino acid derivatives with herbicidal, fungicidal or insecticidal activity (2016) Amino Acids, 48, pp. 929-940. , PID: 26801938
Lilla, E.A., Yokoyama, K., Carbon extension in peptidylnucleoside biosynthesis by radical SAM enzymes (2016) Nat Chem Biol, 12, pp. 905-907. , PID: 27642865
Lindquist, N.R., Carter, T.G., Cangelosi, V.M., Zakharov, L.N., Johnson, D.W., Three’s company: co-crystallization of a self-assembled S(4) metallacyclophane with two diastereomeric metallacycle intermediates (2010) Chem Commun, 46, pp. 3505-3507
Madonna, S., Scarponi, C., Doti, N., Carbone, T., Cavani, A., Scognamiglio, P.L., Marasco, D., Albanesi, C., Therapeutical potential of a peptide mimicking the SOCS1 kinase inhibitory region in skin immune responses (2013) Eur J Immunol, 43, pp. 1883-1895. , PID: 23592500
Mik, V., Mičková, Z., Doležal, K., Frébort, I., Pospíšil, T., Activity of (+)-Discadenine as a plant cytokinin (2017) J Nat Prod, 80, pp. 2136-2140. , PID: 28665127
Mishra, A., Panda, J.J., Basu, A., Chauhan, V.S., Nanovesicles based on self-assembly of conformationally constrained aromatic residue containing amphiphilic dipeptides (2008) Langmuir, 24, pp. 4571-4576. , PID: 18358051
Miyauchi, K., Kimura, S., Suzuki, T., A cyclic form of N6-threonylcarbamoyladenosine as a widely distributed tRNA hypermodification (2013) Nat Chem Biol, 9, pp. 105-111. , PID: 23242255
Mizutani, M., Jitsukawa, K., Masuda, H., Einaga, H., Synthesis and X-ray structure of a unique multinuclear complex constructed by a nucleobase-amino acid DL-willardiine (1996) Chem Comm, 11, pp. 1389-1390
Musumeci, D., Rozza, L., Merlino, A., Paduano, L., Marzo, T., Massai, L., Messori, L., Montesarchio, D., Interaction of anticancer Ru(III) complexes with single stranded and duplex DNA model systems (2015) Dalton Trans, 44, pp. 13914-13925. , PID: 26154188
Musumeci, D., Roviello, V., Roviello, G.N., DNA- and RNA-binding ability of oligoDapT, a nucleobase-decorated peptide, for biomedical applications (2018) Int J Nanomed, 13, pp. 2613-2629
Pape, V.F., Türk, D., Szabó, P., Wiese, M., Enyedy, E.A., Szakács, G., Synthesis and characterization of the anticancer and metal binding properties of novel pyrimidinylhydrazone derivatives (2015) J Inorg Biochem, 144, pp. 18-30. , PID: 25589012
Pinto, B., Rusciano, G., D’Errico, S., Borbone, N., Sasso, A., Piccialli, V., Mayol, L., Piccialli, G., Synthesis and label free characterization of a bimolecular PNA homo quadruplex (2017) Biochim Biophys Acta, 1861, pp. 1222-1228. , PID: 27913190
Reches, M., Gazit, E., Controlled patterning of aligned self-assembled peptide nanotubes (2006) Nat Nanotechnol, 1, pp. 195-200. , PID: 18654186
Roviello, G.N., Musumeci, D., Synthetic approaches to nucleopeptides containing all four nucleobases, and nucleic acid-binding studies on a mixed-sequence nucleo-oligolysine (2016) RSC Adv, 6, pp. 63578-63585. , PID: 28496969
Roviello, G.N., Di Gaetano, S., Capasso, D., Cesarani, A., Bucci, E.M., Pedone, C., Synthesis, spectroscopic studies and biological activity of a novel nucleopeptide with Moloney murine leukemia virus reverse transcriptase inhibitory activity (2010) Amino Acids, 38, pp. 1489-1496. , PID: 19813074
Roviello, G.N., Crescenzo, C., Capasso, D., Di Gaetano, S., Franco, S., Bucci, E.M., 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 (2010) Amino Acids, 39, pp. 795-800. , PID: 20204432
Roviello, G.N., Ricci, A., Bucci, E.M., Pedone, C., Synthesis, biological evaluation and supramolecular assembly of novel analogues of peptidyl nucleosides (2011) Mol BioSyst, 7, pp. 1773-1778. , PID: 21431179
Roviello, G.N., Vicidomini, C., Di Gaetano, S., Capasso, D., Musumeci, D., Roviello, V., Solid phase synthesis and RNA-binding activity of an arginine-containing nucleopeptide (2016) RSC Adv, 6, pp. 14140-14148. , PID: 29057071
Roviello, G.N., Roviello, V., Autiero, I., Saviano, M., Solid phase synthesis of TyrT, a thymine–tyrosine conjugate with poly(A) RNA-binding ability (2016) RSC Adv, 6, pp. 27607-27613. , PID: 29057072
Roviello, G.N., Oliviero, G., Di Napoli, A., Borbone, N., Piccialli, G., Synthesis, self-assembly-behavior and biomolecular recognition properties of thyminyl dipeptides (2018) Arab J Chem
Rozan, P., Kuo, Y.H., Lambein, F., Amino acids in seeds and seedlings of the genus Lens (2001) Phytochemistry, 58, pp. 281-289. , PID: 11551552
Saghyan, A.S., Simonyan, H.M., Petrosyan, S.G., Geolchanyan, A.V., Roviello, G.N., Musumeci, D., Roviello, V., Thiophenyl-substituted triazolyl-thione l-alanine: asymmetric synthesis, aggregation and biological properties (2014) Amino Acids, 46, pp. 2325-2332. , PID: 24952728
Song, G., Ren, J., Recognition and regulation of unique nucleic acid structures by small molecules (2010) Chem Commun, 46, pp. 7283-7294
Teta, R., Irollo, E., Della Sala, G., Pirozzi, G., Mangoni, A., Costantino, V., Smenamides A and B, chlorinated peptide/polyketide hybrids containing a dolapyrrolidinone unit from the Caribbean sponge Smenospongia aurea. Evaluation of their role as leads in antitumor drug research (2013) Mar Drugs, 11, pp. 4451-4463. , PID: 24217287
Weckenmann, N.M., Nachtsheim, B.J., Enantioselective synthesis of D-α-(Uracil-5-yl)glycine derivatives and their racemization-free incorporation into a Model-Peptide (2015) Eur J Org Chem, 30, pp. 6624-6630
Wu, D., Zhou, J., Shi, J., Du, X., Xu, B., A naphthalene-containing amino acid enables hydrogelation of a conjugate of nucleobase-saccharide-amino acids (2014) Chem Commun, 50, pp. 1992-1994
Yuan, Z.Y., Lu, X., Lei, F., Chai, Y.S., Wang, Y.G., Jiang, J.F., Feng, T.S., Du, L.J., TATA boxes in gene transcription and poly(A) tails in mRNA stability: new perspective on the effects of berberine (2015) Sci Rep., 5, p. 18326
Novel insights into nucleoamino acids: biomolecular recognition and aggregation studies of a thymine-conjugated L-phenyl alanine
This article deals with the synthesis in solid phase and characterization of a nucleoamino amide, based on a phenylalaninamide moiety which was N-conjugated to a thymine nucleobase. In analogy to the natural nucleobase–amino acid conjugates, endowed with a wide range of biological properties, the nucleoamino amide interacts with single-stranded nucleic acids as verified in DNA- and RNA-binding assays conducted by CD and UV spectroscopies. These technologies were used to show also that this conjugate binds serum proteins altering significantly their secondary structure, as evidenced by CD and UV using BSA as a model. The biomolecular recognition seems to rely on the ability of the novel compound to bind aromatic and heteroaromatic moieties in protein and nucleic acids, not hindered by its propensity to self-assemble in aqueous solution, behavior suggested by dynamic light scattering (DLS) and CD spectroscopy in concentration- and temperature-dependent experiments. Finally, the high stability in human serum concurs to define the picture of the nucleoamino amide: this enzymatically stable drug candidate could interfere with protein and single-stranded nucleic acid-driven biological processes, particularly those associated with mRNA poly(A) tail, and its self-assembling nature, in analogy to other l-Phe-based systems, discloses new scenarios in drug delivery technology. © 2018, Springer-Verlag GmbH Austria, part of Springer Nature.
This article deals with the synthesis in solid phase and characterization of a nucleoamino amide, based on a phenylalaninamide moiety which was N-conjugated to a thymine nucleobase. In analogy to the natural nucleobase–amino acid conjugates, endowed with a wide range of biological properties, the nucleoamino amide interacts with single-stranded nucleic acids as verified in DNA- and RNA-binding assays conducted by CD and UV spectroscopies. These technologies were used to show also that this conjugate binds serum proteins altering significantly their secondary structure, as evidenced by CD and UV using BSA as a model. The biomolecular recognition seems to rely on the ability of the novel compound to bind aromatic and heteroaromatic moieties in protein and nucleic acids, not hindered by its propensity to self-assemble in aqueous solution, behavior suggested by dynamic light scattering (DLS) and CD spectroscopy in concentration- and temperature-dependent experiments. Finally, the high stability in human serum concurs to define the picture of the nucleoamino amide: this enzymatically stable drug candidate could interfere with protein and single-stranded nucleic acid-driven biological processes, particularly those associated with mRNA poly(A) tail, and its self-assembling nature, in analogy to other l-Phe-based systems, discloses new scenarios in drug delivery technology. © 2018, Springer-Verlag GmbH Austria, part of Springer Nature.
Novel insights into nucleoamino acids: biomolecular recognition and aggregation studies of a thymine-conjugated L-phenyl alanine
| ▼ Structural characterization of self-assembling systems of biomedical and biotechnological interest |
Novel insights into nucleoamino acids: biomolecular recognition and aggregation studies of a thymine-conjugated L-phenyl alanine
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Pensato S, Saviano M, Bianchi N, Borgatti M, Fabbri E, Gambari R, Romanelli A
* Gamma-Hydroxymethyl Pnas: Synthesis, Interaction With Dna And Inhibition Of Protein/Dna Interactions (377 views)
Bioorg Chem, 2010 Sep; 38(5): 196-201.
Impact Factor: 2.141
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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 (464 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 Sep; 39(3): 795-800.
Impact Factor: 4.106
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Del Vecchio S, Zannetti A, Iommelli F, Lettieri A, Brunetti A, Salvatore M
* Molecular imaging of tumor microenvironment (504 views)
Q J Nucl Med Mol Im (ISSN: 1824-4785, 1824-4478, 1824-4785linking), 2010 Jun; 54(3): 243-258.
Impact Factor: 1.724
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Del Vecchio S, Zannetti A, Iommelli F, Lettieri A, Brunetti A, Salvatore M
* Molecular imaging of tumor microenvironment: Challenges and perspectives (597 views)
Q J Nucl Med Mol Im (ISSN: 1824-4785, 1824-4478, 1824-4785linking), 2010 Jun; 54(3): 249-258.
Impact Factor: 1.724
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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 (443 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 May; 38(5): 1489-1496.
Impact Factor: 4.106
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Galasso G, De Rosa R, Piscione F, Iaccarino G, Vosa C, Sorriento D, Piccolo R, Rapacciuolo A, Walsh K, Chiariello M
* Myocardial expression of FOXO3a-Atrogin-1 pathway in human heart failure (304 views)
Eur J Heart Fail European Journal Of Heart Failure (ISSN: 1388-9842), 2010; 12(12): 1290-1296.
Impact Factor: 4.512
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Criscuolo C, Filla A, Coppola G, Rinaldi C, Carbone R, Pinto S, Wang Q, De Leva MF, Salvatore E, Banfi S, Brunetti A, Quarantelli M, Geschwind DH, Pappata S, De Michele G
* Two novel CYP7B1 mutations in Italian families with SPG5: A clinical and genetic study (359 views)
J Neurol (ISSN: 0340-5354, 1432-1459, 1432-1459electronic), 2009 Sep; 256(8): 1252-1257.
Impact Factor: 2.903
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Calabrese V, Cornelius C, Mancuso C, Pennisi G, Calafato S, Bellia F, Bates TE, Giuffrida Stella AM, Schapira T, Dinkova Kostova AT, Rizzarelli E
* Cellular stress response: a novel target for chemoprevention and nutritional neuroprotection in aging, neurodegenerative disorders and longevity (1387 views)
Neurochemical Research (ISSN: 1573-6903, 0364-3190), 2008 Dec; 33(12): 2444-2471.
Impact Factor: 2.26
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Breveglieri G, Pensato S, Salvatori F, Saviano M, Pedone C, Romanelli A, Gambari R
* PNA-mediated alteration of mRNA splicing (349 views)
Minerva Biotecnol (ISSN: 1120-4826), 2008; 20(4): 175-181.
Impact Factor: 0.1
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Marchelli R, Saviano M, Licandro E, Spoto G, Borgatti M, Gambari R
* PNAs targeting the "RNA world": Micro RNA next? (401 views)
Minerva Biotecnol (ISSN: 1120-4826), 2008; 20(4): 183-188.
Impact Factor: 0.1
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Saporito A, Marasco D, Chambery A, Botti P, Monti SM, Pedone C, Ruvo M
* The chemical synthesis of the GstI protein by NCL on a X-Met site (645 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2006 Dec 5; 83(5): 508-518.
Impact Factor: 2.48
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Cittadini A, Monti MG, Iaccarino G, Di Rella F, Tsichlis PN, Di Gianni A, Strömer H, Sorriento D, Peschle C, Trimarco B, Saccà L, Condorelli G
* Adenoviral gene transfer of Akt enhances myocardial contractility and intracellular calcium handling (582 views)
Gene Ther (ISSN: 0969-7128, 0969-7128linking), 2006; 13(1): 8-19.
Impact Factor: 4.782
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Zielenkiewicz W, Swierzewski R, Attanasio F, Rialdi G
* Thermochemical, volumetric and spectroscopic properties of lysozyme-poly(ethylene) glycol system (214 views)
Journal Of Thermal Analysis And Calorimetry (ISSN: 1388-6150), 2006; 83(3): 587-595.
Impact Factor: 1.438
View Export to BibTeX Export to EndNote
Agmon I, Amit M, Auerbach T, Bashan A, Baram D, Bartels H, Berisio R, Greenberg I, Harms J, Hansen HAS, Kessler M, Pyetan E, Schluenzen F, Sittner A, Yonath A, Zarivach R
* Ribosomal crystallography: A flexible nucleotide anchoring tRNA translocation, facilitates peptide-bond formation, chirality discrimination and antibiotics synergism (312 views)
Febs Lett (ISSN: 0014-5793, 0014-5793print, 1873-3468electronic), 2004 Jun 1; 567(1): 20-26.
Impact Factor: 3.843
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Pasquali D, Bellastella A, Valente A, Botti G, Capasso I, del Vecchio S, Salvatore M, Colantuoni V, Sinisi AA
Retinoic acid receptors α, β and γ, and cellular retinol binding protein-I expression in breast fibrocystic disease and cancer (572 views)
Eur J Endocrinol (ISSN: 0804-4643), 1997 Oct; 137(4): 410-414.
Impact Factor: 1.968
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Fogliano V, Monti SM, Ritieni A, Marchisano C, Peluso G, Randazzo G
An immunological approach to monitor protein lactosylation of heated food model systems (348 views)
Food Chem (ISSN: 0308-8146, 0308-8146print), 1997; 58(1-2): 53-58.
Impact Factor: 0.812
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FRITTITTA L, VIGNERI R, PAPA V, GOLDFINE I, GRASSO G, TRISCHITTA V
Structural and functional studies of insulin receptors in human breast cancer (446 views)
Breast Cancer Res Tr Kluwer Academic Publishers (ISSN: 0167-6806), 1993; 25(1): 73-82.
Impact Factor: 2.43
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Papa V, Reese CC, Brunetti A, Vigneri R, Siiteri PK, Goldfine ID
Progestins increase insulin receptor content and insulin stimulation of growth in human breast carcinoma cells (442 views)
Cancer Res (ISSN: 0008-5472, 1538-7445, 1538-7445electronic), 1990 Dec 15; 50(24): 7858-7862.
Impact Factor: 8.426
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Marchetti P, Benzi L, Trischitta V, Brunetti A, Cecchetti P, Ciccarone AM, Pezzino V, Vigneri R, Navalesi R
Complementary use of gel permeation and reversed-phase liquid chromatography for the analysis of A14-[125I]insulin and its degradation products in isolated human monocytes (1719 views)
J Chromatogr B Biomed Sci Appl (ISSN: 0378-4347), 1986 Apr 25; 377(C): 339-344.
Impact Factor: 1.588
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* Biochemical, structural, and computational studies of a γ-carbonic anhydrase from the pathogenic bacterium Burkholderia pseudomallei (10 views)
Comput Struct Biotechnol J (ISSN: 2001-0370linking), 2022 Jul 27; 20: 4185-4194.
Impact Factor: 6.155
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Giacomelli C, Trincavelli ML, Satriano C, Hansson O, La Mendola D, Rizzarelli E, Martini C
* Copper (II) ions modulate Angiogenin activity in human endothelial cells (424 views)
Int J Biochem Cell B (ISSN: 1357-2725), 2015 Mar; 60: 185-196.
Impact Factor: 3.905
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Bisconte MG, Caldora M, Musollino G, Cardiero G, Flagiello A, La Porta G, Lagona L, Prezioso R, Qualtieri G, Gaudiano C, Medulla E, Merlino A, Pucci P, Lacerra G
* α-thalassemia associated with Hb instability: A tale of two features. The case of Hb Rogliano or α1 Cod 108(G15)Thr→Asn and Hb Policoro or α2 Cod 124(H7)Ser→Pro (421 views)
Plosone (ISSN: 1932-6203, 1932-6203electronic, 1932-6203linking), 2015; 10(3): N/D-N/D.
Impact Factor: 3.057
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Neve Polimeno M, Ierano C, D'Alterio C, Simona Losito N, Napolitano M, Portella L, Scognamiglio G, Tatangelo F, Maria Trotta A, Curley S, Costantini S, Liuzzi R, Izzo F, Scala S
* CXCR4 expression affects overall survival of HCC patients whereas CXCR7 expression does not (655 views)
Cell Mol Immunol (ISSN: 1672-7681), 2014 Nov 3; 12(4): 474-482.
Impact Factor: 4.112
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D'Agata R, Spoto G
* Artificial DNA and surface plasmon resonance (536 views)
Artificial Dna Pna & Xna (ISSN: 1949-095x), 2012 Apr; 3(2): N/D-N/D.
Impact Factor: 0
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Russo Krauss I, Sica F, Mattia CA, Merlino A
* Increasing the X-ray diffraction power of protein crystals by dehydration: the case of bovine serum albumin and a survey of literature data (533 views)
Int J Mol Sc (ISSN: 1422-0067, 1661-6596, 1422-0067electronic), 2012 Mar; 13(3): 3782-3800.
Impact Factor: 2.464
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Pilla P, Sandomenico A, Malachovsk V, Borriello A, Giordano M, Cutolo A, Ruvo M, Cusano A
* A protein-based biointerfacing route toward label-free immunoassays with long period gratings in transition mode (428 views)
Biosens Bioelectron (ISSN: 0956-5663, 1873-4235electronic, 0956-5663linking), 2012 Jan 15; 31(1): 486-491.
Impact Factor: 5.437
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Esposito G, De Falco F, Tinto N, Testa F, Vitagliano L, Tandurella IC, Iannone L, Rossi S, Rinaldi E, Simonelli F, Zagari A, Salvatore F
* Comprehensive mutation analysis (20 families) of the choroideremia gene reveals a missense variant that prevents the binding of REP1 with Rab geranylgeranyl transferase (819 views)
Hum Mutat (ISSN: 1059-7794, 1098-1004, 1098-1004electronic), 2011 Dec; 32(12): 1460-1469.
Impact Factor: 5.686
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Pensato S, Saviano M, Bianchi N, Borgatti M, Fabbri E, Gambari R, Romanelli A
* Gamma-Hydroxymethyl Pnas: Synthesis, Interaction With Dna And Inhibition Of Protein/Dna Interactions (377 views)
Bioorg Chem, 2010 Sep; 38(5): 196-201.
Impact Factor: 2.141
View Export to BibTeX Export to EndNote
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 (464 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 Sep; 39(3): 795-800.
Impact Factor: 4.106
View Export to BibTeX Export to EndNote
Del Vecchio S, Zannetti A, Iommelli F, Lettieri A, Brunetti A, Salvatore M
* Molecular imaging of tumor microenvironment (504 views)
Q J Nucl Med Mol Im (ISSN: 1824-4785, 1824-4478, 1824-4785linking), 2010 Jun; 54(3): 243-258.
Impact Factor: 1.724
View Export to BibTeX Export to EndNote
Del Vecchio S, Zannetti A, Iommelli F, Lettieri A, Brunetti A, Salvatore M
* Molecular imaging of tumor microenvironment: Challenges and perspectives (597 views)
Q J Nucl Med Mol Im (ISSN: 1824-4785, 1824-4478, 1824-4785linking), 2010 Jun; 54(3): 249-258.
Impact Factor: 1.724
View Export to BibTeX Export to EndNote
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 (443 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 May; 38(5): 1489-1496.
Impact Factor: 4.106
View Export to BibTeX Export to EndNote
Galasso G, De Rosa R, Piscione F, Iaccarino G, Vosa C, Sorriento D, Piccolo R, Rapacciuolo A, Walsh K, Chiariello M
* Myocardial expression of FOXO3a-Atrogin-1 pathway in human heart failure (304 views)
Eur J Heart Fail European Journal Of Heart Failure (ISSN: 1388-9842), 2010; 12(12): 1290-1296.
Impact Factor: 4.512
View Export to BibTeX Export to EndNote
Criscuolo C, Filla A, Coppola G, Rinaldi C, Carbone R, Pinto S, Wang Q, De Leva MF, Salvatore E, Banfi S, Brunetti A, Quarantelli M, Geschwind DH, Pappata S, De Michele G
* Two novel CYP7B1 mutations in Italian families with SPG5: A clinical and genetic study (359 views)
J Neurol (ISSN: 0340-5354, 1432-1459, 1432-1459electronic), 2009 Sep; 256(8): 1252-1257.
Impact Factor: 2.903
View Export to BibTeX Export to EndNote
Calabrese V, Cornelius C, Mancuso C, Pennisi G, Calafato S, Bellia F, Bates TE, Giuffrida Stella AM, Schapira T, Dinkova Kostova AT, Rizzarelli E
* Cellular stress response: a novel target for chemoprevention and nutritional neuroprotection in aging, neurodegenerative disorders and longevity (1387 views)
Neurochemical Research (ISSN: 1573-6903, 0364-3190), 2008 Dec; 33(12): 2444-2471.
Impact Factor: 2.26
View Export to BibTeX Export to EndNote
Breveglieri G, Pensato S, Salvatori F, Saviano M, Pedone C, Romanelli A, Gambari R
* PNA-mediated alteration of mRNA splicing (349 views)
Minerva Biotecnol (ISSN: 1120-4826), 2008; 20(4): 175-181.
Impact Factor: 0.1
View Export to BibTeX Export to EndNote
Marchelli R, Saviano M, Licandro E, Spoto G, Borgatti M, Gambari R
* PNAs targeting the "RNA world": Micro RNA next? (401 views)
Minerva Biotecnol (ISSN: 1120-4826), 2008; 20(4): 183-188.
Impact Factor: 0.1
View Export to BibTeX Export to EndNote
Saporito A, Marasco D, Chambery A, Botti P, Monti SM, Pedone C, Ruvo M
* The chemical synthesis of the GstI protein by NCL on a X-Met site (645 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2006 Dec 5; 83(5): 508-518.
Impact Factor: 2.48
View Export to BibTeX Export to EndNote
Cittadini A, Monti MG, Iaccarino G, Di Rella F, Tsichlis PN, Di Gianni A, Strömer H, Sorriento D, Peschle C, Trimarco B, Saccà L, Condorelli G
* Adenoviral gene transfer of Akt enhances myocardial contractility and intracellular calcium handling (582 views)
Gene Ther (ISSN: 0969-7128, 0969-7128linking), 2006; 13(1): 8-19.
Impact Factor: 4.782
View Export to BibTeX Export to EndNote
Zielenkiewicz W, Swierzewski R, Attanasio F, Rialdi G
* Thermochemical, volumetric and spectroscopic properties of lysozyme-poly(ethylene) glycol system (214 views)
Journal Of Thermal Analysis And Calorimetry (ISSN: 1388-6150), 2006; 83(3): 587-595.
Impact Factor: 1.438
View Export to BibTeX Export to EndNote
Agmon I, Amit M, Auerbach T, Bashan A, Baram D, Bartels H, Berisio R, Greenberg I, Harms J, Hansen HAS, Kessler M, Pyetan E, Schluenzen F, Sittner A, Yonath A, Zarivach R
* Ribosomal crystallography: A flexible nucleotide anchoring tRNA translocation, facilitates peptide-bond formation, chirality discrimination and antibiotics synergism (312 views)
Febs Lett (ISSN: 0014-5793, 0014-5793print, 1873-3468electronic), 2004 Jun 1; 567(1): 20-26.
Impact Factor: 3.843
View Export to BibTeX Export to EndNote
Pasquali D, Bellastella A, Valente A, Botti G, Capasso I, del Vecchio S, Salvatore M, Colantuoni V, Sinisi AA
Retinoic acid receptors α, β and γ, and cellular retinol binding protein-I expression in breast fibrocystic disease and cancer (572 views)
Eur J Endocrinol (ISSN: 0804-4643), 1997 Oct; 137(4): 410-414.
Impact Factor: 1.968
View Export to BibTeX Export to EndNote
Fogliano V, Monti SM, Ritieni A, Marchisano C, Peluso G, Randazzo G
An immunological approach to monitor protein lactosylation of heated food model systems (348 views)
Food Chem (ISSN: 0308-8146, 0308-8146print), 1997; 58(1-2): 53-58.
Impact Factor: 0.812
View Export to BibTeX Export to EndNote
FRITTITTA L, VIGNERI R, PAPA V, GOLDFINE I, GRASSO G, TRISCHITTA V
Structural and functional studies of insulin receptors in human breast cancer (446 views)
Breast Cancer Res Tr Kluwer Academic Publishers (ISSN: 0167-6806), 1993; 25(1): 73-82.
Impact Factor: 2.43
View Export to BibTeX Export to EndNote
Papa V, Reese CC, Brunetti A, Vigneri R, Siiteri PK, Goldfine ID
Progestins increase insulin receptor content and insulin stimulation of growth in human breast carcinoma cells (442 views)
Cancer Res (ISSN: 0008-5472, 1538-7445, 1538-7445electronic), 1990 Dec 15; 50(24): 7858-7862.
Impact Factor: 8.426
View Export to BibTeX Export to EndNote
Marchetti P, Benzi L, Trischitta V, Brunetti A, Cecchetti P, Ciccarone AM, Pezzino V, Vigneri R, Navalesi R
Complementary use of gel permeation and reversed-phase liquid chromatography for the analysis of A14-[125I]insulin and its degradation products in isolated human monocytes (1719 views)
J Chromatogr B Biomed Sci Appl (ISSN: 0378-4347), 1986 Apr 25; 377(C): 339-344.
Impact Factor: 1.588
View Export to BibTeX Export to EndNote
27 Records (26 excluding Abstracts).
Total impact factor: 82.259 (82.259 excluding Abstracts).
Total 5 year impact factor: 78.121 (78.121 excluding Abstracts).
Total impact factor: 82.259 (82.259 excluding Abstracts).
Total 5 year impact factor: 78.121 (78.121 excluding Abstracts).
379 views. Last view on Friday 24 March 2023, 7:11:16
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