Abstract
BackgroundA large number of studies are attempting to identify alternative products from natural sources or synthesized compounds that effectively interact with cancer cells without causing adverse effects on healthy cells. Resorcinolic lipids are a class of bioactive compounds that possess anticancer activity and are able to interact with the lipid bilayer. Therefore, the objective of this study was to synthesize a novel resorcinolic lipid and test its biological proprieties.MethodsWe aimed to synthesize a novel resorcinolic lipid belonging to the class of cytosporones, AMS049 (3-Heptyl-4,6-dihydroxy-3H-isobenzofuran-1-one) and to evaluate the toxicity of two concentrations of this lipid (7.5 and 10 mg/kg) by determining its genotoxic, mutagenic, immunomodulatory, and apoptotic effects, as well as any biochemical and histopathological alterations in mice treated with cyclophosphamide. The results were analyzed by ANOVA followed by the Tukey test A . level of significance of p < 0.05 was adopted.ResultsThe new cytosporone AMS049 was synthesized in only three steps and in satisfactory yields. The results indicate that the compound is neither genotoxic nor mutagenic and does not alter biochemical parameters. The histological alterations observed in the liver and kidneys did not compromise the function of these organs. Histology of the spleen suggested immunomodulation, although no changes were observed in splenic phagocytosis or differential blood cell count. The results also show that AMS049 potentiates the mutagenic effect of the chemotherapy drug cyclophosphamide and that the combination induces apoptosis.ConclusionThese facts indicate a potential therapeutic application of this novel cytosporone as an important chemotherapeutic adjuvant.Electronic supplementary materialThe online version of this article (doi:10.1186/s12885-015-1532-2) contains supplementary material, which is available to authorized users.
Highlights
A large number of studies are attempting to identify alternative products from natural sources or synthesized compounds that effectively interact with cancer cells without causing adverse effects on healthy cells [1] or that potentiate the effects of chemotherapy drugs and reduce their side effects [2]
Interesting are phenolic lipids of the cytosporone class, which present allelopathic activity [14] and can interact with the orphan nuclear receptor Nur77, triggering apoptosis [15]. This observation is supported by a study from our research group showing that the synthetic resorcinolic lipid 3-heptyl-3,4,6-trimethoxy3H-isobenzofuran-1-one (AMS35AA) has anti-genotoxic and immunostimulatory activities, potentiates the mutagenic effect of the chemotherapy drug cyclophosphamide and increases the rate of apoptosis induced by this drug [2]
The target compound is achieved by the keyintermediate after hydrogenation followed by demethylation reactions
Summary
A large number of studies are attempting to identify alternative products from natural sources or synthesized compounds that effectively interact with cancer cells without causing adverse effects on healthy cells. A large number of studies are attempting to identify alternative products from natural sources or synthesized compounds that effectively interact with cancer cells without causing adverse effects on healthy cells [1] or that potentiate the effects of chemotherapy drugs and reduce their side effects [2]. Interesting are phenolic lipids of the cytosporone class, which present allelopathic activity [14] and can interact with the orphan nuclear receptor Nur, triggering apoptosis [15] This observation is supported by a study from our research group showing that the synthetic resorcinolic lipid 3-heptyl-3,4,6-trimethoxy3H-isobenzofuran-1-one (AMS35AA) has anti-genotoxic and immunostimulatory activities, potentiates the mutagenic effect of the chemotherapy drug cyclophosphamide and increases the rate of apoptosis induced by this drug [2]
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