1,3-Dinitrobenzene induces apoptosis in TM4 mouse Sertoli cells: Involvement of the c-Jun N-terminal kinase (JNK) MAPK pathway

A new route to thiopyran S,S-dioxide derivatives via an overall ring-enlargement protocol from 3-nitrothiophene

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.

Strategies for improving the water solubility of new antitumour nitronaphthylbutadiene derivatives

Riviste censite dal Science Citation Index (ed. 2007)

Breast cancer is still considered a high-incidence disease, and numerous are the research efforts for the development of new useful and effective therapies. Among anticancer drugs, carbazole compounds are largely studied for their anticancer properties and their ability to interfere with specific targets, such as microtubule components. The latter are involved in vital cellular functions, and the perturbation of their dynamics leads to cell cycle arrest and subsequent apoptosis. In this context, we report the anticancer activity of a series of carbazole analogues 1–8. Among them, 2-nitrocarbazole 1 exhibited the best cytotoxic profile, showing good anticancer activity against two breast cancer cell lines, namely MCF-7 and MDA-MB-231, with IC50 values of 7 ± 1.0 and 11.6 ± 0.8 μM, respectively. Furthermore, compound 1 did not interfere with the growth of the normal cell line MCF-10A, contrarily to Ellipticine, a well-known carbazole derivative used as a reference molecule. Finally, in vitro immunofluorescence analysis and in silico studies allowed us to demonstrate the ability of compound 1 to interfere with tubulin organization, similarly to vinblastine: a feature that results in triggering MCF-7 cell death by apoptosis, as demonstrated using a TUNEL assay.

A Nitrocarbazole as a New Microtubule-Targeting Agent in Breast Cancer Treatment

Two new molecules (1E,3E)-1,4-bis(1-naphthyl)- 2,3-dinitro-1,3-butadiene (1-Naph-DNB) and (2Z,4E)-2- methylsulfanyl-5-(1-naphthyl)-4-nitro-2,4-pentadienoate (1- Naph-NMCB) in previous studies showed interesting antiproliferative activity in vitro. Furthermore, toxicological tests and histological analysis provided promising results, in particular for 1-Naph-NMCB that displayed lower toxic activity both in terms of lethal effect and tissue damage of the main organs. Finally, studies of the antitumour activity in vivo confirmed the efficacy of both molecules, though with some differences in tumour selectivity and levels of activity. In this investigation the activities of some specific enzymes, acid phosphatase (AcPase), alkaline phosphatase (AlkPase), catalase (Cat), succinic dehydrogenase (SDH), glucose-6- phosphatase (G6Pase) and K + p-nitrophenyl phosphatase (K + pNPPase) were studied in the liver and kidney as histopathological biomarkers, to assess the effects of the two compounds in organs generally involved in the metabolism and excretion of different drugs. As oxidative stress may also develop as a consequence of the toxic effect of chemicals, reactive oxygen species (ROS) production was evaluated by a histochemical method. The results indicated that some enzyme activities and ROS expression changed in a dose-related manner. Nevertheless, neither in the liver nor in the kidney were dramatic toxic effects evident. By contrast, the variations of some enzyme activities (AlkPase, AcPase, Cat, K + pNPPase) were interpreted as possible defensive mechanisms

A Histochemical Approach to the Evaluation of the In Vivo Cytotoxicity of the Nitrobutadienes (1E,3E)-1,4-bis(1-naphthyl)- 2,3-dinitro-1,3-butadiene and Methyl (2Z,4E)-2-Methylsulfanyl-5- (1-naphthyl)-4-nitro-2,4-pentadienoate in Mice Liver and Kidney

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A Histochemical Approach to the Evaluation of the In Vivo Cytotoxicity of the Nitrobutadienes (1E,3E)-1,4-bis(1-naphthyl)- 2,3-dinitro-1,3-butadiene and Methyl (2Z,4E)-2-Methylsulfanyl-5- (1-naphthyl)-4-nitro-2,4-pentadienoate in Mice Liver and Kidney