Design, synthesis and in vitro evaluation of new naphthylnitrobutadienes with potential antiproliferative activity: towards a structure/activity correlation. (Articolo in rivista)

Type
Label
  • Design, synthesis and in vitro evaluation of new naphthylnitrobutadienes with potential antiproliferative activity: towards a structure/activity correlation. (Articolo in rivista) (literal)
Anno
  • 2008-01-01T00:00:00+01:00 (literal)
Alternative label
  • Petrillo G, Mariggio' MA, Aiello C, Cordazzo C, Fenoglio C, Morganti S, Croce M, Rizzato E, Spinelli D, Maccagno M, Bianchi L, Prevosto C, Tavani C, Viale M. (2008)
    Design, synthesis and in vitro evaluation of new naphthylnitrobutadienes with potential antiproliferative activity: towards a structure/activity correlation.
    in Bioorganic & medicinal chemistry (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Petrillo G, Mariggio' MA, Aiello C, Cordazzo C, Fenoglio C, Morganti S, Croce M, Rizzato E, Spinelli D, Maccagno M, Bianchi L, Prevosto C, Tavani C, Viale M. (literal)
Pagina inizio
  • 240 (literal)
Pagina fine
  • 247 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 16 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • (PG; MM; BL; TC) Dipartimento di Chimica e Chimica Industriale, Università di Genova, Via Dodecaneso 31, 16146 Genova; (MAM) Dipartimento di Scienze Biomediche e Oncologia Umana, Università di Bari, Osp. Policlinico, P.za G. Cesare 11, 70124 Bari; (AC; CC; CM; VM) Istituto Nazionale per la Ricerca sul Cancro, S. C. Terapia Immunologica, L.go R. Benzi 10, 16132 Genova; (MS; RE; SD) Dipartimento di Chimica Organica “A. Mangini”, Università di Bologna, Via San Giacomo 11, 40126, Bologna; (PC) Istituto Nazionale per la Ricerca sul Cancro, S. C. Oncologia Sperimentale D, L.go R. Benzi 10, 16132 Genova; (FC) Dipartimento di Biologia Animale, Laboratorio di Anatomia Comparata, Università degli Studi di Pavia, Pavia, Italy, and Istochemistry and Cytometry section, Institute of Molecular Genetics, Consiglio Nazionale delle Ricerche, 27100 Pavia, Italy (literal)
Titolo
  • Design, synthesis and in vitro evaluation of new naphthylnitrobutadienes with potential antiproliferative activity: towards a structure/activity correlation. (literal)
Abstract
  • On the grounds of previous encouraging results on the antitumor activity of (1E,3E)-1,4-bis(1-naphthyl)-2,3-dinitro-1,3-butadiene (1), we have designed and synthesized two new molecules [(1E,3E)-1,4-bis(4-carboxy-1-naphthyl)-2,3-dinitro-1,3-butadiene (2) and methyl (2Z,4E)-2-methylsulfanyl-5-(1-naphthyl)-4-nitro-2,4-pentadienoate (3)] characterized by a common naphthylnitrobutadiene array but with different structural properties, with the aim of approaching to some structure-activity correlation. When 2 and 3 were analyzed in vitro for their inhibition of cell proliferation and pro-apoptotic properties, the carboxyderivative 2 did not furnish appreciable results. In contrast, 3 (which contains only one of the two naphthylnitroethenyl moieties of the original compound 1) showed remarkable activities in the range of micromolar concentrations (in six over eight cell lines its IC(50)s are in the 1-3muM range), with a significant improvement compared to 1. In particular, 3 proved able to bind to DNA, to upregulate p53, to block cells in the G2/M phase of their cycle, and to induce apoptosis. Thus, very interestingly, the performance of 3 with respect to 1 shows that a single 1-(1-naphthyl)-2-nitroethene moiety is able to ensure better (on four out of eight of the cell lines tested) or comparable levels of activity. This result suggests that the 'molecular-simplification strategy' could furnish a useful instrument for future design in our antitumor research. (literal)
Prodotto di
Autore CNR
Insieme di parole chiave

Incoming links:


Prodotto
Autore CNR di
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi
Insieme di parole chiave di
data.CNR.it