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Synthesis and biological evaluation of a novel Amadori compound

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Abstract

Here, we report the synthesis, purification, ESI MS and NMR characterization, as well as the SEM analysis of a fructosyl thiophenyl-substituted triazolyl-thione l-alanine (denominated Fru-l-TTA). This novel fructosyl derivative was obtained by solution synthesis using the Amadori reaction, in analogy to other natural fructosyl-amino acids, and fully characterized. In particular, we report an accurate NMR/MS/SEM characterization of Fru-l-TTA alongside some biological properties, and investigated to compare the properties of the artificial derivative of this work with the natural counterparts. In particular, Fru-l-TTA shares with natural fructosyl-amino acids the possibility to inhibit the colony formation of prostate cancer cells and additionally decreases their migration.

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Acknowledgements

We thank Prof. Antonio Roviello for his precious suggestions and Mr. Leopoldo Zona for his invaluable technical assistance. We also thank Regione Campania for the research grant received for the research project “Nuovi sistemi nucleopeptidici per applicazioni diagnostiche” under the research program Legge Regionale n. 5 (annualità 2007).

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Authors and Affiliations

  1. CNR, Istituto di Biostrutture e Bioimmagini, Via Mezzocannone site and Headquarters, 80134, Naples, Italy

    Giovanni N. Roviello, Roberta Iannitti, Rosanna Palumbo & Caterina Vicidomini

  2. Centro Regionale di Competenza (CRdC) Tecnologie, Via Nuova Agnano, 11, 80125, Naples, Italy

    Valentina Roviello

  3. Department of Pharmacy, Yerevan State University, 1 A. Manoogian Str., 0025, Yerevan, Armenia

    Hayarpi Simonyan

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  1. Giovanni N. Roviello
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  2. Roberta Iannitti
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  4. Rosanna Palumbo
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  5. Hayarpi Simonyan
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  6. Caterina Vicidomini
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Correspondence to Giovanni N. Roviello.

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This article does not contain any study with human participants or animals performed by any of the authors.

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Handling Editor: J. Bode.

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726_2016_2363_MOESM1_ESM.doc

This supporting information provides a possible mechanistic explanation of some MS signals, as well as the HRMS characterization of Fru-L-TTA. (DOC 63 kb)

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Roviello, G.N., Iannitti, R., Roviello, V. et al. Synthesis and biological evaluation of a novel Amadori compound. Amino Acids 49, 327–335 (2017). https://doi.org/10.1007/s00726-016-2363-4

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  • DOI: https://doi.org/10.1007/s00726-016-2363-4

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