title: Thiophenyl-substituted triazolyl-thione L-alanine: asymmetric synthesis, aggregation and biological properties.
abstract: In this work, we report the asymmetric synthesis and characterization of an artificial amino acid based on triazolyl-thione L-alanine, which was modified with a thiophenyl-substituted moiety, as well as in vitro studies of its nucleic acid-binding ability. We found, by dynamic light scattering studies, that the synthetic amino acid was able to form supramolecular aggregates having a hydrodynamic diameter higher than 200 nm. Furthermore, we demonstrated, by UV and CD experiments, that the heteroaromatic amino acid, whose enzymatic stability was demonstrated by HPLC analysis also after 24 h of incubation in human serum, was able to bind a RNA complex, which is a feature of biomedical interest in view of innovative antiviral strategies based on modulation of RNA-RNA molecular recognition.
authors: Department of Pharmaceutical Chemistry, Yerevan State University, 1 A. Manoogian Str., 0025, Yerevan, Armenia.
authors: Ashot S
authors: AS
authors: Saghyan
authors: Hayarpi M
authors: HM
authors: Simonyan
authors: Satenik G
authors: SG
authors: Petrosyan
authors: Arpine V
authors: AV
authors: Geolchanyan
authors: Giovanni N
authors: GN
authors: Roviello
authors: Domenica
authors: D
authors: Musumeci
authors: Valentina
authors: V
authors: Roviello
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D024322:Amino Acids, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D002942:Circular Dichroism; D015195:Drug Design; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009391:Nephelometry and Turbidimetry; D012313:RNA / Q000737:chemistry / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism
chemical_list: D024322:Amino Acids, Aromatic; D000998:Antiviral Agents; D013876:Thiophenes; D014230:Triazoles; D012313:RNA; D000409:Alanine