title: Synthesis and biological properties of caffeic acid-PNA dimers containing guanine.
abstract: Caffeic acid (CA; 3,4-dihydroxycinnamic acid) is endowed with high antioxidant activity. CA derivatives (such as amides) have gained a lot of attention due to their antioxidative, antitumor and antimicrobial properties as well as stable characteristics. Caffeoyl-peptide derivatives showed different antioxidant activity depending on the type and the sequence of amino acid used. For these reasons, we decided to combine CA with Peptide Nucleic Acid (PNA) to test whether the new PNA-CA amide derivatives would result in an improvement or gain of CA's biological (i.e., antioxidant, cytotoxic, cytoprotective) properties. We performed the synthesis and characterization of seven dimer conjugates with various combinations of nucleic acid bases and focused NMR studies on the model compound ga-CA dimer. We demonstrate that PNA dimers containing guanine conjugated to CA exhibited different biological activities depending on composition and sequence of the nucleobases. The dimer ag-CA protected HepG2, SK-B-NE(2), and C6 cells from a cytotoxic dose of hydrogen peroxide (H₂O₂).
authors.affiliation: Department of Environmental, Biological and Pharmaceutical Sciences and Technologies, Second University of Studies of Naples, Via Vivaldi 43, 81100 Caserta, Italy.
authors.forename: Maria
authors.initials: M
authors.lastname: Gaglione
authors.forename: Gaetano
authors.initials: G
authors.lastname: Malgieri
authors.forename: Severina
authors.initials: S
authors.lastname: Pacifico
authors.forename: Valeria
authors.initials: V
authors.lastname: Severino
authors.forename: Brigida
authors.initials: B
authors.lastname: D'Abrosca
authors.forename: Luigi
authors.initials: L
authors.lastname: Russo
authors.forename: Antonio
authors.initials: A
authors.lastname: Fiorentino
authors.forename: Anna
authors.initials: A
authors.lastname: Messere
mesh_terms: D000975:Antioxidants / Q000737:chemistry; D001087:Arabinonucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D002109:Caffeic Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D019281:Dimerization; D006147:Guanine / Q000737:chemistry* / Q000494:pharmacology; D056945:Hep G2 Cells; D006801:Humans; D006861:Hydrogen Peroxide / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C585590:2-amino-9-(2,3-dideoxy-2,3-dihydro-beta-D-arabinofuranosyl)-6-methoxy-9H-purine; D000975:Antioxidants; D001087:Arabinonucleosides; D002109:Caffeic Acids; D020135:Peptide Nucleic Acids; D006147:Guanine; D006861:Hydrogen Peroxide; C040048:caffeic acid
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