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Synthesis, protonation constants and biological activity determination of amino acid-salicylaldehyde-derived Schiff bases. | LitMetric

Synthesis, protonation constants and biological activity determination of amino acid-salicylaldehyde-derived Schiff bases.

Amino Acids

Department of Chemical and Geological Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, 09042, Cagliari, Italy.

Published: March 2020

AI Article Synopsis

  • Schiff bases, important in organic and coordination chemistry, have been extensively studied, yet varied experimental conditions have hindered effective comparisons of their chemical and biological properties.
  • Six Schiff bases derived from salicylaldehyde and natural amino acids were fully characterized using nuclear magnetic resonance and infrared spectroscopy, focusing on maintaining consistent experimental conditions for better insight into their structure-activity correlation.
  • The synthesized Schiff bases exhibited DNA binding constants around 10-10 M, influenced by the amino acid side-chain, but showed limited cytotoxicity with IC50 values over 100 µM in human tumor cell lines.

Article Abstract

Schiff bases represent a class of molecules widely studied for their importance in organic and coordination chemistry. Despite the large amount of studies on the chemical and biological properties of the Schiff bases, the different experimental conditions prevent a useful comparison to search for a correlation structure-activity. Moreover, literature is lacking in comprehensive data on the spectroscopic characterization of these compounds. For this reason, six Schiff bases, derived from salicylaldehyde and natural amino acids were fully characterized by nuclear magnetic resonance and infrared spectroscopy, and their aqueous solution equilibria, antiproliferative activity and DNA-binding activity were examined. All experimental conditions were kept constants to achieve comparable information and useful insights about their structure-activity correlation. The synthesized compounds showed DNA binding constants in the 10-10 M range, depending on the substituent present in the amino acid side-chain, and resulted devoid of significant cytotoxic activity against the different human tumor cell lines showing IC50 values higher than 100 µM.

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Source
http://dx.doi.org/10.1007/s00726-019-02816-0DOI Listing

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