Synthesis, Characterization And Hybridization Studies Of An Alternate Nucleo-Epsilon/Gamma-Peptide: Complexes Formation With Natural Nucleic Acids (494 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 Jan; 38(1): 103-111.
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Paper type: Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 4.106, 5-year impact factor: 3.541
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-76449093612&partnerID=40&md5=8ad4e1b430c1bbb718d26fa2ea44d19f
Keywords: ε-Lys γ-Dabpnas, Binding Studies, Nucleopeptides, Odn Analogs, Serum Stability, Diaminobutyric Acid, Lysine, Oligodeoxyribonucleotide, Peptide Derivative, Peptide Nucleic Acid, Article, Circular Dichroism, Complex Formation, Dna Binding, Drug Stability, Human, Peptide Synthesis, Priority Journal, Rna Binding, Ultraviolet Spectroscopy, Molecular Structure, Nucleic Acid Hybridization, -Lys-Dabpnas,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, Napoli 80134, Italy
Bioindustry Park Del Canavese SpA, Via Ribes 5, Colleretto Giacosa, Turin 10010, Italy
References:
Altenbrunn, F., Seitz, O., O-Allyl protection in the Fmoc-based synthesis of difficult PNA (2008) Organic and Biomolecular Chemistry, 6 (14), pp. 2493-2498. , DOI 10.1039/b805165
Briones, C., Martin-Gago, J.A., Nucleic acids and their analogs as nanomaterials for biosensor development (2006) Curr Nanosci, 2, pp. 257-273
Foster, J.G., Cress, W.D., Wright, S.F., Hess, J.L., Intracellular localization of the neurotoxin 2, 4-diaminobutyric acid in Lathyrus sylvestris L. leaf tissue (1987) Plant Physiol, 83 (4), pp. 900-904. , 10.1104/pp.83.4.900
Gangamani, B.P., Kumar, V.A., Ganesh, K.N., Chiral analogues of peptide nucleic acids: Synthesis of 4-aminoprolyl nucleic acids and DNA complementation studies using UV/CD spectroscopy (1999) Tetrahedron, 55 (1), pp. 177-192. , DOI 10.1016/S0040-4020(98)01024-2, PII S0040402098010242
Glavin, D.P., Bada, J.L., Isolation of purines and pyrimidines from the Murchison meteorite (2004) 35th Lunar and Planetary Science Conference, , Houston, Abstract 1022
Haimaa, G., Lohse, A., Buchardt, O., Nielsen, P.E., Peptide nucleic acids (PNAs) containing thymine monomers derived from chiral amino acids: Hybridization and solubility properties of D-lysine PNA (1996) Angew Chem Int Ed Engl, 35, pp. 1939-1942. , 10.1002/anie.199619391
Helene, C., Le Doan, T., Oligonucleotides: Problems and frontiers of practical applications (1991) Trends Biotechnol, 9, pp. 339-340. , 10.1016/0167-7799(91)90115-X
Hiraki, J., Ichikawa, T., Ninomiya, S.-I., Seki, H., Uohama, K., Seki, H., Kimura, S., Barnett Jr., J.W., Use of ADME studies to confirm the safety of ε-polylysine as a preservative in food (2003) Regulatory Toxicology and Pharmacology, 37 (2), pp. 328-340. , DOI 10.1016/S0273-2300(03)00029-1
Iwashita, Y., Goto, S., Tominaga, M., Sasaki, A., Ohmori, N., Goto, T., Sato, S., Kitano, S., Dendritic cell immunotherapy with poly(D,L-2,4-diaminobutyric acid)-mediated intratumoral delivery of the interleukin-12 gene suppresses tumor growth significantly (2005) Cancer Science, 96 (5), pp. 303-307. , DOI 10.1111/j.1349-7006.2005.00049.x
Kito, M., Takimoto, R., Onji, Y., Yoshida, T., Nagasawa, T., Purification and characterization of an ε-poly-l-lysine-degrading enzyme from the ε-poly-l-lysine-tolerant Chryseobacterium sp. OJ7 (2003) J Biosci Bioeng, 96 (1), pp. 92-94
Knudsen, H., Nielsen, P.E., Antisense properties of duplex- and triplex-forming PNAs (1996) Nucleic Acids Research, 24 (3), pp. 494-500. , DOI 10.1093/nar/24.3.494
Kurreck, J., Antisense technologies: Improvement through novel chemical modifications (2003) European Journal of Biochemistry, 270 (8), pp. 1628-1644. , DOI 10.1046/j.1432-1033.2003.03555.x
Lagriffoule, P., Wittung, P., Jensen, K., Eriksson, M., Norden, B., Buchardt, O., Nielsen, P.E., Peptide nucleic acids with a conformationally constrained chiral cyclohexyl-derived backbone (1997) Chem Eur J, 3, pp. 912-919. , 10.1002/chem.19970030613
Meierhenrich, U.J., Munoz Caro, G.M., Bredehoft, J.H., Jessberger, E.K., Thiemann, W.H.-P., Identification of diamino acid in the Murchison meteorite (2004) Proceedings of the National Academy of Sciences of the United States of America, 101 (25), pp. 9182-9186. , DOI 10.1073/pnas.0403043101
Nelson, K.E., Levy, M., Miller, S.L., Peptide nucleic acids rather than RNA may have been the first genetic molecule (2000) Proceedings of the National Academy of Sciences of the United States of America, 97 (8), pp. 3868-3871. , DOI 10.1073/pnas.97.8.3868
Nielsen, P.E., Egholm, M., Berg, R.M., Buchardt, O., Sequence-selective recognition of DNA by strand displacement with thymine-substituted polyamide (1991) Science, 254, pp. 1497-1500. , 10.1126/science.1962210
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-γ-peptides based on diaminobutyric acid (2006) Journal of Peptide Science, 12 (12), pp. 829-835. , DOI 10.1002/psc.819
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) Nucleosides, Nucleotides and Nucleic Acids, 26 (10-12), pp. 1307-1310. , DOI 10.1080/15257770701530640, PII 788145344
Saimura, M., Takehara, M., Mizukami, S., Kataoka, K., Hirohara, H., Biosynthesis of nearly monodispersed poly(epsilon-l-lysine) in Streptomyces species (2008) Biotechnol Lett, 30 (3), pp. 377-385. , 10.1007/s10529-007-9563-7
Schmidt, J.G., Nielsen, P.E., Orgel, L.E., Information transfer from peptide nucleic acids to RNA by template-directed syntheses (1997) Nucleic Acids Res, 25, pp. 4797-4802. , 10.1093/nar/25.23.4797
Sforza, S., Haaima, G., Marchelli, R., Nielsen, P.E., Chiral peptide nucleic acids (PNAs): Helix handedness and DNA recognition (1999) Eur J Org Chem, 1999, pp. 197-204. , 10.1002/(SICI)1099-0690(199901)1999:1<197::AID-EJOC197> 3.0.CO
Sforza, S., Galaverna, G., Dossena, A., Corradini, R., Marchelli, R., Role of chirality and optical purity in nucleic acid recognition by PNA and PNA analogs (2002) Chirality, 14 (7), pp. 591-598. , DOI 10.1002/chir.10087
Strasdeit, H., New studies on the Murchison meteorite shed light on the pre-RNA world (2005) ChemBioChem, 6 (5), pp. 801-803. , DOI 10.1002/cbic.200400435
Takehara, M., Saimura, M., Inaba, H., Hirohara, H., Poly(γ-L-diaminobutanoic acid), a novel poly(amino acid), coproduced with poly(ε-L-lysine) by two strains of Streptomyces celluloflavus (2008) FEMS Microbiology Letters, 286 (1), pp. 110-117. , DOI 10.1111/j.1574-6968.2008.01261.x
Temussi, P.A., Paolillo, L., Ferrara, L., Benedetti, L., Andini, S., Structural characterization of thermal prebiotic polypeptides (1976) J Mol Evol, 7, pp. 105-110. , 10.1007/BF01732469
Uhlmann, E., Peyman, A., Breipohl, G., Will, D.W., PNA: Synthetic polyamide nucleic acids with unusual binding properties (1998) Angewandte Chemie - International Edition, 37 (20), pp. 2796-2823. , DOI 10.1002/(SICI)1521-3773(19981102)37:20<2796::AID-ANIE2796> 3.0. CO
Wolman, Y., Haverland, W.J., Miller, S.L., Nonprotein amino acids from spark discharges and their comparison with the Murchison meteorite amino acids (1972) Proc Natl Acad Sci USA, 69, pp. 809-811. , 10.1073/pnas.69.4.809
Foster, J. G., Cress, W. D., Wright, S. F., Hess, J. L., Intracellular localization of the neurotoxin 2, 4-diaminobutyric acid in Lathyrus sylvestris L. leaf tissue (1987) Plant Physiol, 83 (4), pp. 900-904. , 10. 1104/pp. 83. 4. 900
Gangamani, B. P., Kumar, V. A., Ganesh, K. N., Chiral analogues of peptide nucleic acids: Synthesis of 4-aminoprolyl nucleic acids and DNA complementation studies using UV/CD spectroscopy (1999) Tetrahedron, 55 (1), pp. 177-192. , DOI 10. 1016/S0040-4020 (98) 01024-2, PII S0040402098010242
Glavin, D. P., Bada, J. L., Isolation of purines and pyrimidines from the Murchison meteorite (2004) 35th Lunar and Planetary Science Conference, , Houston, Abstract 1022
Meierhenrich, U. J., Munoz Caro, G. M., Bredehoft, J. H., Jessberger, E. K., Thiemann, W. H. -P., Identification of diamino acid in the Murchison meteorite (2004) Proceedings of the National Academy of Sciences of the United States of America, 101 (25), pp. 9182-9186. , DOI 10. 1073/pnas. 0403043101
Nelson, K. E., Levy, M., Miller, S. L., Peptide nucleic acids rather than RNA may have been the first genetic molecule (2000) Proceedings of the National Academy of Sciences of the United States of America, 97 (8), pp. 3868-3871. , DOI 10. 1073/pnas. 97. 8. 3868
Nielsen, P. E., Egholm, M., Berg, R. M., Buchardt, O., Sequence-selective recognition of DNA by strand displacement with thymine-substituted polyamide (1991) Science, 254, pp. 1497-1500. , 10. 1126/science. 1962210
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) Journal of Peptide Science, 12 (12), pp. 829-835. , DOI 10. 1002/psc. 819
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) Nucleosides, Nucleotides and Nucleic Acids, 26 (10-12), pp. 1307-1310. , DOI 10. 1080/15257770701530640, PII 788145344
Schmidt, J. G., Nielsen, P. E., Orgel, L. E., Information transfer from peptide nucleic acids to RNA by template-directed syntheses (1997) Nucleic Acids Res, 25, pp. 4797-4802. , 10. 1093/nar/25. 23. 4797
Temussi, P. A., Paolillo, L., Ferrara, L., Benedetti, L., Andini, S., Structural characterization of thermal prebiotic polypeptides (1976) J Mol Evol, 7, pp. 105-110. , 10. 1007/BF01732469
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 Jan; 38(1): 103-111.
Export to BibTeX Export to EndNote
Paper type: Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 4.106, 5-year impact factor: 3.541
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-76449093612&partnerID=40&md5=8ad4e1b430c1bbb718d26fa2ea44d19f
Keywords: ε-Lys γ-Dabpnas, Binding Studies, Nucleopeptides, Odn Analogs, Serum Stability, Diaminobutyric Acid, Lysine, Oligodeoxyribonucleotide, Peptide Derivative, Peptide Nucleic Acid, Article, Circular Dichroism, Complex Formation, Dna Binding, Drug Stability, Human, Peptide Synthesis, Priority Journal, Rna Binding, Ultraviolet Spectroscopy, Molecular Structure, Nucleic Acid Hybridization, -Lys-Dabpnas,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, Napoli 80134, Italy
Bioindustry Park Del Canavese SpA, Via Ribes 5, Colleretto Giacosa, Turin 10010, Italy
References:
Altenbrunn, F., Seitz, O., O-Allyl protection in the Fmoc-based synthesis of difficult PNA (2008) Organic and Biomolecular Chemistry, 6 (14), pp. 2493-2498. , DOI 10.1039/b805165
Briones, C., Martin-Gago, J.A., Nucleic acids and their analogs as nanomaterials for biosensor development (2006) Curr Nanosci, 2, pp. 257-273
Foster, J.G., Cress, W.D., Wright, S.F., Hess, J.L., Intracellular localization of the neurotoxin 2, 4-diaminobutyric acid in Lathyrus sylvestris L. leaf tissue (1987) Plant Physiol, 83 (4), pp. 900-904. , 10.1104/pp.83.4.900
Gangamani, B.P., Kumar, V.A., Ganesh, K.N., Chiral analogues of peptide nucleic acids: Synthesis of 4-aminoprolyl nucleic acids and DNA complementation studies using UV/CD spectroscopy (1999) Tetrahedron, 55 (1), pp. 177-192. , DOI 10.1016/S0040-4020(98)01024-2, PII S0040402098010242
Glavin, D.P., Bada, J.L., Isolation of purines and pyrimidines from the Murchison meteorite (2004) 35th Lunar and Planetary Science Conference, , Houston, Abstract 1022
Haimaa, G., Lohse, A., Buchardt, O., Nielsen, P.E., Peptide nucleic acids (PNAs) containing thymine monomers derived from chiral amino acids: Hybridization and solubility properties of D-lysine PNA (1996) Angew Chem Int Ed Engl, 35, pp. 1939-1942. , 10.1002/anie.199619391
Helene, C., Le Doan, T., Oligonucleotides: Problems and frontiers of practical applications (1991) Trends Biotechnol, 9, pp. 339-340. , 10.1016/0167-7799(91)90115-X
Hiraki, J., Ichikawa, T., Ninomiya, S.-I., Seki, H., Uohama, K., Seki, H., Kimura, S., Barnett Jr., J.W., Use of ADME studies to confirm the safety of ε-polylysine as a preservative in food (2003) Regulatory Toxicology and Pharmacology, 37 (2), pp. 328-340. , DOI 10.1016/S0273-2300(03)00029-1
Iwashita, Y., Goto, S., Tominaga, M., Sasaki, A., Ohmori, N., Goto, T., Sato, S., Kitano, S., Dendritic cell immunotherapy with poly(D,L-2,4-diaminobutyric acid)-mediated intratumoral delivery of the interleukin-12 gene suppresses tumor growth significantly (2005) Cancer Science, 96 (5), pp. 303-307. , DOI 10.1111/j.1349-7006.2005.00049.x
Kito, M., Takimoto, R., Onji, Y., Yoshida, T., Nagasawa, T., Purification and characterization of an ε-poly-l-lysine-degrading enzyme from the ε-poly-l-lysine-tolerant Chryseobacterium sp. OJ7 (2003) J Biosci Bioeng, 96 (1), pp. 92-94
Knudsen, H., Nielsen, P.E., Antisense properties of duplex- and triplex-forming PNAs (1996) Nucleic Acids Research, 24 (3), pp. 494-500. , DOI 10.1093/nar/24.3.494
Kurreck, J., Antisense technologies: Improvement through novel chemical modifications (2003) European Journal of Biochemistry, 270 (8), pp. 1628-1644. , DOI 10.1046/j.1432-1033.2003.03555.x
Lagriffoule, P., Wittung, P., Jensen, K., Eriksson, M., Norden, B., Buchardt, O., Nielsen, P.E., Peptide nucleic acids with a conformationally constrained chiral cyclohexyl-derived backbone (1997) Chem Eur J, 3, pp. 912-919. , 10.1002/chem.19970030613
Meierhenrich, U.J., Munoz Caro, G.M., Bredehoft, J.H., Jessberger, E.K., Thiemann, W.H.-P., Identification of diamino acid in the Murchison meteorite (2004) Proceedings of the National Academy of Sciences of the United States of America, 101 (25), pp. 9182-9186. , DOI 10.1073/pnas.0403043101
Nelson, K.E., Levy, M., Miller, S.L., Peptide nucleic acids rather than RNA may have been the first genetic molecule (2000) Proceedings of the National Academy of Sciences of the United States of America, 97 (8), pp. 3868-3871. , DOI 10.1073/pnas.97.8.3868
Nielsen, P.E., Egholm, M., Berg, R.M., Buchardt, O., Sequence-selective recognition of DNA by strand displacement with thymine-substituted polyamide (1991) Science, 254, pp. 1497-1500. , 10.1126/science.1962210
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-γ-peptides based on diaminobutyric acid (2006) Journal of Peptide Science, 12 (12), pp. 829-835. , DOI 10.1002/psc.819
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) Nucleosides, Nucleotides and Nucleic Acids, 26 (10-12), pp. 1307-1310. , DOI 10.1080/15257770701530640, PII 788145344
Saimura, M., Takehara, M., Mizukami, S., Kataoka, K., Hirohara, H., Biosynthesis of nearly monodispersed poly(epsilon-l-lysine) in Streptomyces species (2008) Biotechnol Lett, 30 (3), pp. 377-385. , 10.1007/s10529-007-9563-7
Schmidt, J.G., Nielsen, P.E., Orgel, L.E., Information transfer from peptide nucleic acids to RNA by template-directed syntheses (1997) Nucleic Acids Res, 25, pp. 4797-4802. , 10.1093/nar/25.23.4797
Sforza, S., Haaima, G., Marchelli, R., Nielsen, P.E., Chiral peptide nucleic acids (PNAs): Helix handedness and DNA recognition (1999) Eur J Org Chem, 1999, pp. 197-204. , 10.1002/(SICI)1099-0690(199901)1999:1<197::AID-EJOC197> 3.0.CO
Sforza, S., Galaverna, G., Dossena, A., Corradini, R., Marchelli, R., Role of chirality and optical purity in nucleic acid recognition by PNA and PNA analogs (2002) Chirality, 14 (7), pp. 591-598. , DOI 10.1002/chir.10087
Strasdeit, H., New studies on the Murchison meteorite shed light on the pre-RNA world (2005) ChemBioChem, 6 (5), pp. 801-803. , DOI 10.1002/cbic.200400435
Takehara, M., Saimura, M., Inaba, H., Hirohara, H., Poly(γ-L-diaminobutanoic acid), a novel poly(amino acid), coproduced with poly(ε-L-lysine) by two strains of Streptomyces celluloflavus (2008) FEMS Microbiology Letters, 286 (1), pp. 110-117. , DOI 10.1111/j.1574-6968.2008.01261.x
Temussi, P.A., Paolillo, L., Ferrara, L., Benedetti, L., Andini, S., Structural characterization of thermal prebiotic polypeptides (1976) J Mol Evol, 7, pp. 105-110. , 10.1007/BF01732469
Uhlmann, E., Peyman, A., Breipohl, G., Will, D.W., PNA: Synthetic polyamide nucleic acids with unusual binding properties (1998) Angewandte Chemie - International Edition, 37 (20), pp. 2796-2823. , DOI 10.1002/(SICI)1521-3773(19981102)37:20<2796::AID-ANIE2796> 3.0. CO
Wolman, Y., Haverland, W.J., Miller, S.L., Nonprotein amino acids from spark discharges and their comparison with the Murchison meteorite amino acids (1972) Proc Natl Acad Sci USA, 69, pp. 809-811. , 10.1073/pnas.69.4.809
Foster, J. G., Cress, W. D., Wright, S. F., Hess, J. L., Intracellular localization of the neurotoxin 2, 4-diaminobutyric acid in Lathyrus sylvestris L. leaf tissue (1987) Plant Physiol, 83 (4), pp. 900-904. , 10. 1104/pp. 83. 4. 900
Gangamani, B. P., Kumar, V. A., Ganesh, K. N., Chiral analogues of peptide nucleic acids: Synthesis of 4-aminoprolyl nucleic acids and DNA complementation studies using UV/CD spectroscopy (1999) Tetrahedron, 55 (1), pp. 177-192. , DOI 10. 1016/S0040-4020 (98) 01024-2, PII S0040402098010242
Glavin, D. P., Bada, J. L., Isolation of purines and pyrimidines from the Murchison meteorite (2004) 35th Lunar and Planetary Science Conference, , Houston, Abstract 1022
Meierhenrich, U. J., Munoz Caro, G. M., Bredehoft, J. H., Jessberger, E. K., Thiemann, W. H. -P., Identification of diamino acid in the Murchison meteorite (2004) Proceedings of the National Academy of Sciences of the United States of America, 101 (25), pp. 9182-9186. , DOI 10. 1073/pnas. 0403043101
Nelson, K. E., Levy, M., Miller, S. L., Peptide nucleic acids rather than RNA may have been the first genetic molecule (2000) Proceedings of the National Academy of Sciences of the United States of America, 97 (8), pp. 3868-3871. , DOI 10. 1073/pnas. 97. 8. 3868
Nielsen, P. E., Egholm, M., Berg, R. M., Buchardt, O., Sequence-selective recognition of DNA by strand displacement with thymine-substituted polyamide (1991) Science, 254, pp. 1497-1500. , 10. 1126/science. 1962210
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) Journal of Peptide Science, 12 (12), pp. 829-835. , DOI 10. 1002/psc. 819
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) Nucleosides, Nucleotides and Nucleic Acids, 26 (10-12), pp. 1307-1310. , DOI 10. 1080/15257770701530640, PII 788145344
Schmidt, J. G., Nielsen, P. E., Orgel, L. E., Information transfer from peptide nucleic acids to RNA by template-directed syntheses (1997) Nucleic Acids Res, 25, pp. 4797-4802. , 10. 1093/nar/25. 23. 4797
Temussi, P. A., Paolillo, L., Ferrara, L., Benedetti, L., Andini, S., Structural characterization of thermal prebiotic polypeptides (1976) J Mol Evol, 7, pp. 105-110. , 10. 1007/BF01732469
Synthesis, Characterization And Hybridization Studies Of An Alternate Nucleo-Epsilon/Gamma-Peptide: Complexes Formation With Natural Nucleic Acids
In order to develop new oligodeoxyribonucleotide (ODN) analogs to be used in biotechnological applications, we report here the synthesis, characterization and nucleic acid binding studies of novel nucleopeptides, that we called ε-lys/γ-dabPNAs, containing a backbone of alternated l-diaminobutyric acid and l-lysine moieties. Exploring the hybridization properties of the new ODN analog, we found, by circular dichroism and UV spectroscopies, that a homothymine ε-lys/γ-dabPNA hexamer binds both DNA and RNA of complementary sequence. Furthermore, human serum stability assays on the alternate nucleopeptide evidenced a noteworthy degradation resistance. These results encourage us to deepen the knowledge of this analog, in order to evaluate its possible use in antigene/antisense or diagnostic applications. © 2008 Springer-Verlag.
In order to develop new oligodeoxyribonucleotide (ODN) analogs to be used in biotechnological applications, we report here the synthesis, characterization and nucleic acid binding studies of novel nucleopeptides, that we called ε-lys/γ-dabPNAs, containing a backbone of alternated l-diaminobutyric acid and l-lysine moieties. Exploring the hybridization properties of the new ODN analog, we found, by circular dichroism and UV spectroscopies, that a homothymine ε-lys/γ-dabPNA hexamer binds both DNA and RNA of complementary sequence. Furthermore, human serum stability assays on the alternate nucleopeptide evidenced a noteworthy degradation resistance. These results encourage us to deepen the knowledge of this analog, in order to evaluate its possible use in antigene/antisense or diagnostic applications. © 2008 Springer-Verlag.
Synthesis, Characterization And Hybridization Studies Of An Alternate Nucleo-Epsilon/Gamma-Peptide: Complexes Formation With Natural Nucleic Acids
Synthesis, Characterization And Hybridization Studies Of An Alternate Nucleo-Epsilon/Gamma-Peptide: Complexes Formation With Natural Nucleic Acids
Other filter: ([btitle,keywords] "ε-Lys γ-Dabpnas" O ...
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Roviello GN, Musumeci D, Roviello V, Pirtskhalava M, Egoyan A, Mirtskhulava M
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Beilstein J Nanotech (ISSN: 2190-4286), 2015; 6(1): 1338-1347.
Impact Factor: 2.778
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Basile L, Pappalardo M, Guccione S, Milardi D, Ramsay RR
* Computational comparison of imidazoline association with the I2 binding site in human monoamine oxidases (359 views)
J Chem Inf Model (ISSN: 1549-9596), 2014 Apr 28; 54(4): 1200-1207.
Impact Factor: 3.738
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Roviello GN, Musumeci D, D'Alessandro C, Pedone C
* Synthesis of a thymine-functionalized nucleoamino acid for the solid phase assembly of cationic nucleopeptides (486 views)
Amino Acids (ISSN: 1438-2199, 0939-4451, 1438-2199electronic), 2013 Oct; 45(4): 779-784.
Impact Factor: 3.653
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Roviello GN, Musumeci D, Bucci EM, Pedone C
* Synthesis of a diaminopropanoic acid-based nucleoamino acid and assembly of cationic nucleopeptides for biomedical applications (444 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2012 Dec; 43(6): 2537-2543.
Impact Factor: 3.914
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Mercurio FA, Marasco D, Pirone L, Pedone E, Pellecchia M, Leone M
* Solution Structure of the First Sam Domain of Odin and Binding Studies with the EphA2 Receptor (469 views)
Biochemistry (ISSN: 0006-2960, 1520-4995, 1520-4995electronic), 2012 Mar 13; 51(10): 2136-2145.
Impact Factor: 3.377
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Roviello GN, Musumeci D, Bucci EM, Pedone C
* Synthesis and characterization of a novel ester-based nucleoamino acid for the assembly of aromatic nucleopeptides for biomedical applications (531 views)
Int J Pharm (ISSN: 0378-5173, 1873-3476), 2011 Sep 30; 415(1-2): 206-210.
Impact Factor: 3.35
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Roviello GN, Musumeci D, Bucci EM, Pedone C
* Evidences for supramolecular organization of nucleopeptides: Synthesis, spectroscopic and biological studies of a novel dithymine l-serine tetrapeptide (578 views)
Mol Biosyst (ISSN: 1742-206x, 1742-2051, 1742-2051electronic), 2011 Apr; 7(4): 1073-1080.
Impact Factor: 3.534
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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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Di Fiore A, Monti SM, Innocenti A, Winum J-Y, De Simone G, Supuran CT
* Carbonic anhydrase inhibitors: Crystallographic and solution binding studies for the interaction of a boron-containing aromatic sulfamide with mammalian isoforms I-XV (352 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2010 Jun 15; 20(12): 3601-3605.
Impact Factor: 2.661
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Roviello GN, Musumeci D, De Cristofaro A, Capasso D, Di Gaetano S, Bucci EM, Pedone C
* Alternate dab-aegPNAs: synthesis, nucleic acid binding studies and biological activity (526 views)
Mol Biosyst (ISSN: 1742-2051, 1742-206x, 1742-2051electronic), 2010 Jan; 6(1): 199-205.
Impact Factor: 3.825
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Roviello GN, Musumeci D, Castiglione M, Bucci EM, Pedone C, Benedetti E
* Solid Phase Synthesis And Rna-Binding Studies Of A Serum-Resistant Nucleo-Epsilon-Peptide (435 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2009 Mar; 15(3): 155-160.
Impact Factor: 1.807
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Roviello GN, Musumeci D, Moccia M, Castiglione M, Sapio R, Valente M, Bucci EM, Perretta G, Pedone C
* Dabpna: Design, Synthesis And Nucleic Acids Binding Studies (430 views)
Nucleosides Nucleotides Nucleic Acids (ISSN: 1525-7770), 2007; 26(10-12): 1307-1310.
Impact Factor: 0.723
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De Luca S, Ragone R, Bracco C, Digilio G, Aloj L, Tesauro D, Saviano M, Pedone C, Morelli G
* A cyclic CCK8 analogue selective for the cholecystokinin type A receptor: design, synthesis, NMR structure and binding measurements (472 views)
Chembiochem (ISSN: 1439-7633, 1439-4227, 1439-7633electronic), 2003 Nov 7; 4(11): 1176-1187.
Impact Factor: 3.992
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* From Prebiotic Chemistry to Supramolecular Biomedical Materials: Exploring the Properties of Self-Assembling Nucleobase-Containing Peptides (28 views)
Molecules (ISSN: 1420-3049linking, 1420-3049electronic), 2021 Jun 10; 26(12): 3558-3558.
Impact Factor: 4.411
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Riccardi C, Capasso D, Coppola A, Platella C, Montesarchio D, Di Gaetano S, Roviello GN, Musumeci D
* Synthesis, Antiproliferative Activity, and DNA Binding Studies of Nucleoamino Acid-Containing Pt(II) Complexes (150 views)
Pharmaceuticals (ISSN: 1424-8247linking, 1424-8247print), 2020 Sep 30; 13(10): 284-284.
Impact Factor: 4.421
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Riccardi C, Capasso D, Rozza GM, Platella C, Montesarchio D, Di Gaetano S, Marzo T, Pratesi A, Messori L, Roviello GN, Musumeci D
* Synthesis, DNA binding studies, and antiproliferative activity of novel Pt(II)- complexes with an L-alanyl-based ligand (261 views)
J Chem Res (ISSN: 0162-0134linking, 0162-0134print), 2020 Feb; 203: 110868-110868.
Impact Factor: 3.224
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Musumeci D, Roviello V, Roviello GN
* DNA- and RNA-binding ability of oligoDapT, a nucleobase-decorated peptide, for biomedical applications (1942 views)
Int J Nanomed (ISSN: 1176-9114linking, 1178-2013electronic), 2018 May 1; 2018:13: 2613-2629.
Impact Factor: 4.3
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Avitabile C, D'Andrea LD, Saviano M, Olivieri M, Cimmino A, Romanelli A
* Binding studies of antimicrobial peptides to Escherichia coli cells (389 views)
Biochem Bioph Res Co (ISSN: 0006-291x), 2016 Sep 09; 478(1): 149-153.
Impact Factor: 2.466
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Roviello GN, Musumeci D
* Synthetic approaches to nucleopeptides containing all the four nucleobases, and nucleic acid-binding studies on a mixed-sequence nucleo-oligolysine (435 views)
Rsc Adv (ISSN: 2046-2069), 2016 Jun; 6: 63578-63585.
Impact Factor: 3.108
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Roviello GN, Musumeci D, Roviello V, Pirtskhalava M, Egoyan A, Mirtskhulava M
* Natural and artificial binders of polyriboadenylic acid and their effect on RNA structure (380 views)
Beilstein J Nanotech (ISSN: 2190-4286), 2015; 6(1): 1338-1347.
Impact Factor: 2.778
View Export to BibTeX Export to EndNote
Basile L, Pappalardo M, Guccione S, Milardi D, Ramsay RR
* Computational comparison of imidazoline association with the I2 binding site in human monoamine oxidases (359 views)
J Chem Inf Model (ISSN: 1549-9596), 2014 Apr 28; 54(4): 1200-1207.
Impact Factor: 3.738
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, D'Alessandro C, Pedone C
* Synthesis of a thymine-functionalized nucleoamino acid for the solid phase assembly of cationic nucleopeptides (486 views)
Amino Acids (ISSN: 1438-2199, 0939-4451, 1438-2199electronic), 2013 Oct; 45(4): 779-784.
Impact Factor: 3.653
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, Bucci EM, Pedone C
* Synthesis of a diaminopropanoic acid-based nucleoamino acid and assembly of cationic nucleopeptides for biomedical applications (444 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2012 Dec; 43(6): 2537-2543.
Impact Factor: 3.914
View Export to BibTeX Export to EndNote
Mercurio FA, Marasco D, Pirone L, Pedone E, Pellecchia M, Leone M
* Solution Structure of the First Sam Domain of Odin and Binding Studies with the EphA2 Receptor (469 views)
Biochemistry (ISSN: 0006-2960, 1520-4995, 1520-4995electronic), 2012 Mar 13; 51(10): 2136-2145.
Impact Factor: 3.377
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, Bucci EM, Pedone C
* Synthesis and characterization of a novel ester-based nucleoamino acid for the assembly of aromatic nucleopeptides for biomedical applications (531 views)
Int J Pharm (ISSN: 0378-5173, 1873-3476), 2011 Sep 30; 415(1-2): 206-210.
Impact Factor: 3.35
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, Bucci EM, Pedone C
* Evidences for supramolecular organization of nucleopeptides: Synthesis, spectroscopic and biological studies of a novel dithymine l-serine tetrapeptide (578 views)
Mol Biosyst (ISSN: 1742-206x, 1742-2051, 1742-2051electronic), 2011 Apr; 7(4): 1073-1080.
Impact Factor: 3.534
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
Di Fiore A, Monti SM, Innocenti A, Winum J-Y, De Simone G, Supuran CT
* Carbonic anhydrase inhibitors: Crystallographic and solution binding studies for the interaction of a boron-containing aromatic sulfamide with mammalian isoforms I-XV (352 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2010 Jun 15; 20(12): 3601-3605.
Impact Factor: 2.661
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, De Cristofaro A, Capasso D, Di Gaetano S, Bucci EM, Pedone C
* Alternate dab-aegPNAs: synthesis, nucleic acid binding studies and biological activity (526 views)
Mol Biosyst (ISSN: 1742-2051, 1742-206x, 1742-2051electronic), 2010 Jan; 6(1): 199-205.
Impact Factor: 3.825
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, Castiglione M, Bucci EM, Pedone C, Benedetti E
* Solid Phase Synthesis And Rna-Binding Studies Of A Serum-Resistant Nucleo-Epsilon-Peptide (435 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2009 Mar; 15(3): 155-160.
Impact Factor: 1.807
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, Moccia M, Castiglione M, Sapio R, Valente M, Bucci EM, Perretta G, Pedone C
* Dabpna: Design, Synthesis And Nucleic Acids Binding Studies (430 views)
Nucleosides Nucleotides Nucleic Acids (ISSN: 1525-7770), 2007; 26(10-12): 1307-1310.
Impact Factor: 0.723
View Export to BibTeX Export to EndNote
De Luca S, Ragone R, Bracco C, Digilio G, Aloj L, Tesauro D, Saviano M, Pedone C, Morelli G
* A cyclic CCK8 analogue selective for the cholecystokinin type A receptor: design, synthesis, NMR structure and binding measurements (472 views)
Chembiochem (ISSN: 1439-7633, 1439-4227, 1439-7633electronic), 2003 Nov 7; 4(11): 1176-1187.
Impact Factor: 3.992
View Export to BibTeX Export to EndNote
19 Records (19 excluding Abstracts).
Total impact factor: 63.388 (63.388 excluding Abstracts).
Total 5 year impact factor: 58.931 (58.931 excluding Abstracts).
Total impact factor: 63.388 (63.388 excluding Abstracts).
Total 5 year impact factor: 58.931 (58.931 excluding Abstracts).
494 views. Last view on Monday 22 May 2023, 16:02:14
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