New antitumor cyclic astin analogues: Synthesis, conformation and bioactivity (Articolo in rivista)

Type
Label
  • New antitumor cyclic astin analogues: Synthesis, conformation and bioactivity (Articolo in rivista) (literal)
Anno
  • 2004-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/psc.506 (literal)
Alternative label
  • Rossi Filomena; Zanotti Giancarlo; Saviano Michele; Iacovino Rosa; Palladino Pasquale; Saviano Gabriella; Amodeo Pietro; Tancredi Teodorico; Laccetti Paolo; Corbier Catherine; Benedetti Ettore (2004)
    New antitumor cyclic astin analogues: Synthesis, conformation and bioactivity
    in Journal of peptide science (Print); John Wiley & Sons Ltd., Chichester (Regno Unito)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Rossi Filomena; Zanotti Giancarlo; Saviano Michele; Iacovino Rosa; Palladino Pasquale; Saviano Gabriella; Amodeo Pietro; Tancredi Teodorico; Laccetti Paolo; Corbier Catherine; Benedetti Ettore (literal)
Pagina inizio
  • 92 (literal)
Pagina fine
  • 102 (literal)
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  • 10 (literal)
Rivista
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  • 2 (literal)
Note
  • ISI Web of Science (WOS) (literal)
  • Scopu (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipartimento di Chimica Biologica, Universit `a di Napoli ''Federico II'', 80134 Napoli, Italy b Istituto di Chimica Biomolecolare, CNR, Sezione di Roma, Universit `a di Roma ''La Sapienza'', 00185 Roma, Italy c Istituto di Biostrutture e Bioimmagini, C.N.R., 80134 Napoli, Italy d Dipartimento di Scienze e Tecnologie per l'Ambiente e il Territorio, Universit `a degli Studi del Molise, 86170 Isernia, Italy e Istituto di Chimica Biomolecolare, CNR, 80078 Pozzuoli (NA), Italy f LCM3B, Groupe de Biocristallographie, UHP Nancy I, UMR 7036, 54506 Vandoeuvre l ` es Nancy, France (literal)
Titolo
  • New antitumor cyclic astin analogues: Synthesis, conformation and bioactivity (literal)
Abstract
  • Astins, antitumor cyclic pentapeptides, were isolated from the Aster tataricus. Their chem. structures, consist of a 16-membered ring system contg. a unique b,g-dichlorinated proline [Pro(Cl)2], other non-coded amino acid residues and a cis conformation in one of the peptide bonds. The astin backbone conformation, along with the cis peptide bond in which the b,g-dichlorinated proline residue is involved, was considered to play an important role in their antineoplastic activities on sarcoma 180A and P388 lymphocytic leukemia in mice, but the scope and potential applications of this activity remain unclear. With the aim at improving our knowledge of the conformational properties influencing the bioactivity in this class of compds., new astin-related cyclopeptides were synthesized differing from the natural products by the presence of some non-proteinogenic amino acid residues: Aib (aminoisobutyric acid), Abu (aminobutanoic acid), -(S)b3-hPhe and a peptide bond surrogate (-SO2-NH-). The analogs prepd. c(-Pro-Thr-Aib-b3-Phe-Abu-), c[Pro-Thr-Aib-(S)b3-hPhe-Abu], c[Pro-Abu-Ser-(S)b3-hPhey(CH2-SO2-NH)-Abu] and c[Pro-Thr-Aib-(S)b3-hPhey(CH2-SO2-NH)-Abu] were synthesized by classical methods in soln. and tested for their antitumor effect. These mols. were studied by crystal-state X-ray diffraction anal. and/or soln. NMR and MD techniques. (literal)
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