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Molecules 2013, 18(8), 9147-9162; doi:10.3390/molecules18089147

Synthesis and Biological Properties of Caffeic Acid-PNA Dimers Containing Guanine

Department of Environmental, Biological and Pharmaceutical Sciences and Technologies, Second University of Studies of Naples, Via Vivaldi, 43, 81100 Caserta, Italy
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Received: 24 June 2013 / Revised: 18 July 2013 / Accepted: 29 July 2013 / Published: 31 July 2013
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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).
Keywords: caffeic acid; PNAs; caffeic acid-amide derivatives; biological properties; cytoprotective activity caffeic acid; PNAs; caffeic acid-amide derivatives; biological properties; cytoprotective activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Gaglione, M.; Malgieri, G.; Pacifico, S.; Severino, V.; D'Abrosca, B.; Russo, L.; Fiorentino, A.; Messere, A. Synthesis and Biological Properties of Caffeic Acid-PNA Dimers Containing Guanine. Molecules 2013, 18, 9147-9162.

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