Strategies for improving the water solubility of new antitumour nitronaphthylbutadiene derivatives

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-...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2010-12, Vol.8 (24), p.5674-5681
Main Authors: Fontana, Antonella, Viale, Maurizio, Guernelli, Susanna, Gasbarri, Carla, Rizzato, Egon, Maccagno, Massimo, Petrillo, Giovanni, Aiello, Cinzia, Ferrini, Silvano, Spinelli, Domenico
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Butadienes - chemistry
Butadienes - pharmacology
Cancer
Cell Line, Tumor
Cell Proliferation - drug effects
cyclodextrin
Cytotoxicity
Drugs
Esters
Humans
Liposomes
Molecular Structure
Nitro Compounds - chemistry
Nitro Compounds - pharmacology
Solubility
Tumor cell lines
Water - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c0ob00493f