Lac-l-TTA, a novel lactose-based amino acid–sugar conjugate for anti-metastatic applications
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Here we describe the synthesis, chromatographic purification, MS and NMR characterization of a new lactosyl-derivative, i.e. a lactosyl thiophenyl-substituted triazolyl-thione l-alanine (Lac-L-TTA). This amino acid–sugar conjugate was prepared by solution synthesis in analogy to the natural fructosyl-amino acids. Furthermore, we investigated the inhibition of PC-3 prostate cancer cell colony formation by this lactose derivative in comparison with the less polar fructose-based derivative, Fru-L-TTA. This let us to compare the properties of the artificial derivative, object of the present work, with the monosaccharide-based counterpart and to obtain a preliminary information on the influence of polarity on such biological activity. A significantly higher anticancer effect of Lac-L-TTA with respect to the fructose analogue emerged from our study suggesting that the anti-metastatic potential of fructosyl-amino acids can be enhanced by increasing the polarity of the compounds, for example by introducing disaccharide moieties in place of fructose.
KeywordsGlycated amino acid Anti-metastatic Fructosyl-amino acid Lactose
- Esposito G, Teta R, Miceli R, Ceccarelli LS, Della Sala G, Camerlingo R, Irollo E, Mangoni A, Pirozzi G, Costantino V (2015) Isolation and assessment of the in vitro anti-tumor activity of smenothiazole A and B, chlorinated thiazole containing peptide/polyketides from the Caribbean sponge, Smenospongia aurea. Mar Drugs 13:444–459CrossRefPubMedPubMedCentralGoogle Scholar
- Mottram DS (1994) Flavor compounds formed during the Maillard reaction: thermally generated flavors. Maillard Microw Extrus Process 543:104–126Google Scholar
- Teta R, Irollo E, Della Sala G, Pirozzi G, Mangoni A, Costantino V (2013) Smenamides A and B, chlorinated peptide/polyketide hybrids containing a dolapyrrolidinone unit from the Caribbean sponge Smenospongia aurea. Evaluation of their role as leads in antitumor drug research. Mar Drugs 11:4451–4463CrossRefPubMedPubMedCentralGoogle Scholar