Lac-l-TTA, a novel lactose-based amino acid–sugar conjugate for anti-metastatic applications
| Autor: | Hayarpi M. Simonyan, Roberta Iannitti, Valentina Roviello, Caterina Vicidomini, Giovanni N. Roviello, Rosanna Palumbo |
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| Přispěvatelé: | Roviello, G. N., Iannitti, R., Palumbo, R., Simonyan, H., Vicidomini, C., Roviello, V. |
| Rok vydání: | 2017 |
| Předmět: |
Male
0301 basic medicine Clinical Biochemistry Disaccharide Antineoplastic Agents Lactose Anti-metastatic 01 natural sciences Biochemistry Antineoplastic Agent Colony-Forming Units Assay 03 medical and health sciences chemistry.chemical_compound Tumor Cells Cultured Humans Organic chemistry Monosaccharide Sugar Amino Acids Neoplasm Metastasis Glycated amino acid Cell Proliferation Fructosyl-amino acid Alanine chemistry.chemical_classification 010405 organic chemistry Organic Chemistry Prostatic Neoplasms Fructose Combinatorial chemistry 0104 chemical sciences Amino acid Neoplasm Metastasi Amino Acid 030104 developmental biology chemistry Prostatic Neoplasm Sugars Derivative (chemistry) Human Conjugate |
| Zdroj: | Amino Acids. 49:1347-1353 |
| ISSN: | 1438-2199 0939-4451 |
| DOI: | 10.1007/s00726-017-2433-2 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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