The present study describes the synthesis, the characterization and the evaluation of some derivatives of N-6-isopentenyladenosine on T24 human bladder carcinoma cells. In particular we have modified the hydroxyl groups in the ribose moiety, the position of the isopentenyl chain in the purine ring and the base moiety. The structures of the compounds were confirmed by standard studies of NMR, MS and elemental analysis. We here show that only two derivatives, 1-(3-methyl-2-butenylamino)-9-(3'-deoxy-beta-D-ribofuranosyl)- purine hydrobromide and 2-amino-6-(3-methyl-2-butenylamino)-9-(beta-D-ribofuranosyl)-purine, inhibit the growth of T24 cells, although to a lower extent than N-6-isopentenyladenosine. We conclude that the integrity of ribosidic and purine moiety and the N-6 position of the chain are essential for maintaining the antiproliferative activity.

Synthesis and evaluation of in vitro anticancer activity of some novel isopentenyladenosine derivatives / R. Ottria, S. Casati, A. Manzocchi, E. Baldoli, M. Mariotti, J.A.M. Maier, P. Ciuffreda. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - 18:12(2010 Jun 15), pp. 4249-4254.

Synthesis and evaluation of in vitro anticancer activity of some novel isopentenyladenosine derivatives

R. Ottria;S. Casati;A. Manzocchi;E. Baldoli;M. Mariotti;J.A.M. Maier;P. Ciuffreda
2010-06-15

Abstract

The present study describes the synthesis, the characterization and the evaluation of some derivatives of N-6-isopentenyladenosine on T24 human bladder carcinoma cells. In particular we have modified the hydroxyl groups in the ribose moiety, the position of the isopentenyl chain in the purine ring and the base moiety. The structures of the compounds were confirmed by standard studies of NMR, MS and elemental analysis. We here show that only two derivatives, 1-(3-methyl-2-butenylamino)-9-(3'-deoxy-beta-D-ribofuranosyl)- purine hydrobromide and 2-amino-6-(3-methyl-2-butenylamino)-9-(beta-D-ribofuranosyl)-purine, inhibit the growth of T24 cells, although to a lower extent than N-6-isopentenyladenosine. We conclude that the integrity of ribosidic and purine moiety and the N-6 position of the chain are essential for maintaining the antiproliferative activity.
Antitumor agents; Bladder carcinoma cells; Isopentenyladenosine; Modified nucleosides
Settore BIO/10 - Biochimica
Settore MED/04 - Patologia Generale
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/143997
Citazioni
  • ???jsp.display-item.citation.pmc??? 2
  • Scopus 22
  • ???jsp.display-item.citation.isi??? 22
social impact