Strategies for improving the water solubility of new antitumour nitronaphthylbutadiene derivatives.

Abstract

Different nitronaphthylbutadienes have been previously proved to have antitumour activity. The main drawback of these derivatives is their low water solubility. With the aim of facilitating the administration of these new drugs we have synthesized the hexyl (2Z,4E)-2-methylsulfanyl-5-(1-naphthyl)-4-nitro-2,4-pentadienoate analogue (1-Naph-NHCB) which is demonstrated to be easily included into cyclodextrins and/or entrapped into liposomes. Its antitumour activity was revealed to be almost comparable with that of the previously studied methyl analogue ester (1-Naph-NMCB). On the other hand, in vitro studies with different cancer cell lines showed that the cytotoxic activity of both 1-Naph-NMCB and 1-Naph-NHCB were fully preserved and in some cases also enhanced when entrapped into liposomal carriers.

• Authors: Antonella Fontana, Maurizio Viale, Susanna Guernelli, Carla Gasbarri, Egon Rizzato, Massimo Maccagno, Giovanni Petrillo, Cinzia Aiello, Silvano Ferrini, Domenico Spinelli
• Journal: Organic & biomolecular chemistry (Org Biomol Chem) Vol. 8 Issue 24 Pg. 5674-81 (Dec 21 2010) ISSN: 1477-0539 [Electronic] England
• PMID: 20936232 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Butadienes
• Nitro Compounds
• Water

Topics

• Antineoplastic Agents (chemistry, pharmacology)
• Butadienes (chemistry, pharmacology)
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Humans
• Molecular Structure
• Nitro Compounds (chemistry, pharmacology)
• Solubility
• Water (chemistry)