Synthesis and Biological Properties of Caffeic Acid-PNA Dimers Containing Guanine
Abstract
:1. Introduction
Compounds | Crude yield (%) | Theoretical molecular mass | Experimental molecular mass [M+H]+ | Δ (Da) |
---|---|---|---|---|
CA-ag-NH2 (1) | 45 | 745.27 | 746.28 | 0.01 |
CA-ga-NH2 (2) | 50 | 745.27 | 746.28 | 0.01 |
CA-cg-NH2 (3) | 55 | 721.27 | 722.27 | 0.00 |
CA-gc-NH2 (4) | 50 | 721.27 | 722.27 | 0.00 |
CA-tg-NH2 (5) | 45 | 736.27 | 737.27 | 0.00 |
CA-gt-NH2 (6) | 55 | 736.27 | 737.27 | 0.00 |
CA-gg-NH2 (7) | 40 | 761.27 | 762.27 | 0.00 |
2. Results and Discussion
2.1. Synthesis of Dimers 1–7
Compounds | CLog P a | CLog S b |
---|---|---|
Caffeic acid (CA) | 0.97 | −1.41 |
CA-ag-NH2 (1) | −2.24 | −1.73 |
CA-ga-NH2 (2) | −2.24 | −1.73 |
CA-cg-NH2 (3) | −2.52 | −1.12 |
CA-gc-NH2 (4) | −2.52 | −1.12 |
CA-tg-NH2 (5) | −2.0 | −1.10 |
CA-gt-NH2 (6) | −2.0 | −1.10 |
CA-gg-NH2 (7) | −3.23 | −1.12 |
2.2. Chemical Characterization of Dimer 1
2.3. Biological Characterization
Compounds | DPPH IC50 | ABTS IC50 | TBARS IC50 |
---|---|---|---|
CA-ag-NH2 (1) | >100 | >100 | 85.34 |
CA-ga-NH2 (2) | 51.36 | 13.91 | 41.38 |
2.4. In Silico Conformational Study
3. Experimental
3.1. Synthetic Procedure for CA-PNA Dimers
3.2. NMR Characterization of CA-PNA Dimer 1
3.3. Conformation Sampling Method
3.4. Cytoprotection Assay
4. Conclusions
Supplementary Materials
Acknowledgments
Conflicts of Interest
References
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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. https://doi.org/10.3390/molecules18089147
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(8):9147-9162. https://doi.org/10.3390/molecules18089147
Chicago/Turabian StyleGaglione, Maria, Gaetano Malgieri, Severina Pacifico, Valeria Severino, Brigida D'Abrosca, Luigi Russo, Antonio Fiorentino, and Anna Messere. 2013. "Synthesis and Biological Properties of Caffeic Acid-PNA Dimers Containing Guanine" Molecules 18, no. 8: 9147-9162. https://doi.org/10.3390/molecules18089147