title: Synthesis and biological evaluation of a novel Amadori compound.
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.
authors.affiliation: CNR, Istituto di Biostrutture e Bioimmagini, Via Mezzocannone site and Headquarters, 80134, Naples, Italy. giovanni.roviello@cnr.it.
authors.forename: Giovanni N
authors.initials: GN
authors.lastname: Roviello
authors.affiliation: CNR, Istituto di Biostrutture e Bioimmagini, Via Mezzocannone site and Headquarters, 80134, Naples, Italy.
authors.forename: Roberta
authors.initials: R
authors.lastname: Iannitti
authors.affiliation: Centro Regionale di Competenza (CRdC) Tecnologie, Via Nuova Agnano, 11, 80125, Naples, Italy.
authors.forename: Valentina
authors.initials: V
authors.lastname: Roviello
authors.affiliation: CNR, Istituto di Biostrutture e Bioimmagini, Via Mezzocannone site and Headquarters, 80134, Naples, Italy.
authors.forename: Rosanna
authors.initials: R
authors.lastname: Palumbo
authors.affiliation: Department of Pharmacy, Yerevan State University, 1 A. Manoogian Str., 0025, Yerevan, Armenia.
authors.forename: Hayarpi
authors.initials: H
authors.lastname: Simonyan
authors.affiliation: CNR, Istituto di Biostrutture e Bioimmagini, Via Mezzocannone site and Headquarters, 80134, Naples, Italy.
authors.forename: Caterina
authors.initials: C
authors.lastname: Vicidomini
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002465:Cell Movement / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D003300:Copper / Q000378:metabolism; D004354:Drug Screening Assays, Antitumor / Q000379:methods; D005632:Fructose / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008855:Microscopy, Electron, Scanning; D011471:Prostatic Neoplasms / Q000188:drug therapy; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: C000625773:3-(4-propyl-3-(2-thienyl)-5-thioxo-1,2,4-triazol-1-yl)-2-((2,3,4,5-tetrahydroxytetrahydropyran-2-yl)methylamino)propanoic acid; D000970:Antineoplastic Agents; D005632:Fructose; D003300:Copper; D000409:Alanine
keywords: Amadori compound; ESI MS; Glycated amino acid; SEM