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Synthesis and Bioactivity of Secondary Metabolites from Marine Sponges Containing Dibrominated Indolic Systems
Via dei Vestini 31, Department of Pharmaceutical Sciences, Faculty of Pharmacy, University “G. d’ Annunzio” of Chieti-Pescara, Chieti 66100, Italy
Piazzale Aldo Moro 5, Department of Organic Chemistry, Faculty of Chemistry, University of Rome “La Sapienza”, Roma 00197, Italy
* Author to whom correspondence should be addressed.
Received: 20 April 2012; in revised form: 14 May 2012 / Accepted: 15 May 2012 / Published: 21 May 2012
Abstract: Marine sponges. (e.g., Hyrtios sp., Dragmacidin sp., Aglophenia pleuma, Aplidium cyaneum, Aplidium meridianum.) produce bioactive secondary metabolites involved in their defence mechanisms. Recently it was demonstrated that several of those compounds show a large variety of biological activities against different human diseases with possible applications in medicinal chemistry and in pharmaceutical fields, especially related to the new drug development process. Researchers have focused their attention principally on secondary metabolites with anti-cancer and cytotoxic activities. A common target for these molecules is the cytoskeleton, which has a central role in cellular proliferation, motility, and profusion involved in the metastatic process associate with tumors. In particular, many substances containing brominated indolic rings such as 5,6-dibromotryptamine, 5,6-dibromo-N-methyltryptamine, 5,6-dibromo-N-methyltryptophan (dibromoabrine), 5,6-dibromo-N,N-dimethyltryptamine and 5,6-dibromo-L-hypaphorine isolated from different marine sources, have shown anti-cancer activity, as well as antibiotic and anti-inflammatory properties. Considering the structural correlation between endogenous monoamine serotonin with marine indolic alkaloids 5,6-dibromoabrine and 5,6-dibromotryptamine, a potential use of some dibrominated indolic metabolites in the treatment of depression-related pathologies has also been hypothesized. Due to the potential applications in the treatment of various diseases and the increasing demand of these compounds for biological assays and the difficult of their isolation from marine sources, we report in this review a series of recent syntheses of marine dibrominated indole-containing products.
Keywords: dibrominated indole; marine secondary metabolites; anticancer; natural products; alkaloids
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Mollica, A.; Locatelli, M.; Stefanucci, A.; Pinnen, F. Synthesis and Bioactivity of Secondary Metabolites from Marine Sponges Containing Dibrominated Indolic Systems. Molecules 2012, 17, 6083-6099.
Mollica A, Locatelli M, Stefanucci A, Pinnen F. Synthesis and Bioactivity of Secondary Metabolites from Marine Sponges Containing Dibrominated Indolic Systems. Molecules. 2012; 17(5):6083-6099.
Mollica, Adriano; Locatelli, Marcello; Stefanucci, Azzurra; Pinnen, Francesco. 2012. "Synthesis and Bioactivity of Secondary Metabolites from Marine Sponges Containing Dibrominated Indolic Systems." Molecules 17, no. 5: 6083-6099.