Synthesis of Bicyclic Molecular Scaffolds (BTAa). An Investigation Towards New Selective MMP-12 Inhibitors (Articolo in rivista)

Type
Label
  • Synthesis of Bicyclic Molecular Scaffolds (BTAa). An Investigation Towards New Selective MMP-12 Inhibitors (Articolo in rivista) (literal)
Anno
  • 2006-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.bmc.2006.07.028 (literal)
Alternative label
  • Mannino, Claudia; Nievo, Marco; Machetti,Fabrizio; Papakyriakou, A.; Calderone, V.: Fragai, Marco; Guarna, Antonio (2006)
    Synthesis of Bicyclic Molecular Scaffolds (BTAa). An Investigation Towards New Selective MMP-12 Inhibitors
    in Bioorganic & medicinal chemistry (Print); Pergamon-Elsevier Science Ltd., Oxford (Regno Unito)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Mannino, Claudia; Nievo, Marco; Machetti,Fabrizio; Papakyriakou, A.; Calderone, V.: Fragai, Marco; Guarna, Antonio (literal)
Pagina inizio
  • 7392 (literal)
Pagina fine
  • 7403 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://www.sciencedirect.com/science/article/pii/S0968089606005827 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 14 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 12 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 22 (literal)
Note
  • Scopu (literal)
  • ISI Web of Science (WOS) (literal)
  • PubMe (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Istituto di chimica dei composti organometallici del CNR Dipartimento di chimica Organica 'Ugo Schiff' dell'Università di Firenze (literal)
Titolo
  • Synthesis of Bicyclic Molecular Scaffolds (BTAa). An Investigation Towards New Selective MMP-12 Inhibitors (literal)
Abstract
  • Starting from 3-aza-6,8-dioxa-bicyclo[3.2.1]octane scaffold (BTAa) a virtual library of molecules was generated and screened in silico against the crystal structure of the Human Macrophage Metalloelastase (MMP-12). The molecules obtaining high score were synthesized and the affinity for the catalytic domain of MMP-12 was experimentally proved by NMR experiments. A BTAa scaffold 20 having a N-hydroxyurea group in position 3 and a p-phenylbenzylcarboxy amide in position 7 showed a fair inhibition potency (IC50 = 149 lM) for MMP-12 and some selectivity towards five different MMPs. These results, taken together with the X-ray structure of the adduct between MMP-12, the inhibitor 20 and the acetohydroxamic acid (AHA), suggest that bicyclic scaffold derivatives may be exploited for the design of new selective matrix metalloproteinase inhibitors (MMPIs). (literal)
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