The present invention relates to a process of prepn. of marmycine A and its analogs, new analogs of marmycine A, as well as the use as a marker of organoids and in pharmacy of these compds., in particular as antibiotics, anti-cancer and antipaludic.  The present invention relates to a method for prepg. marmycin A and analogs I, wherein R1-R11 are independently an atom or group of atoms via copper-catalyzed coupling reaction of anthracene-9,16-diones with aminoglycosides; as an organelle marker and in pharmacy, in particular as antibiotics, anticancer, and antimalarial agents.  Here, we report the chem. synthesis of marmycin A and the study of its cellular activity.  The arom. core was constructed by means of a one-pot multistep reaction comprising a regioselective Diels-Alder cycloaddn., and the complex sugar backbone was introduced through a copper-catalyzed Ullmann cross-coupling, followed by a challenging Friedel-Crafts cyclization.  Remarkably, fluorescence microscopy revealed that marmycin A does not target the nucleus but instead accumulates in lysosomes, thereby promoting cell death independently of genome targeting.  Furthermore, a synthetic dimer of marmycin A and the lysosome-targeting agent artesunate exhibited a synergistic activity against the invasive MDA-MB-231 cancer cell line.  These findings shed light on the elusive pathways through which anthraquinone derivs. act in cells, pointing towards unanticipated biol. and therapeutic applications.

Method for preparing marmycin A and analogs thereof, and also uses thereof as antibiotics, anticancer, and antimalarials agents / Rodriguez, Raphael; Caneque, Tatiana; Gomes da Cruz, Filipe; Mai, Trang; Malacria, Max; Maestri, Giovanni. - (2016).

Method for preparing marmycin A and analogs thereof, and also uses thereof as antibiotics, anticancer, and antimalarials agents

MAESTRI, Giovanni
2016

Abstract

The present invention relates to a process of prepn. of marmycine A and its analogs, new analogs of marmycine A, as well as the use as a marker of organoids and in pharmacy of these compds., in particular as antibiotics, anti-cancer and antipaludic.  The present invention relates to a method for prepg. marmycin A and analogs I, wherein R1-R11 are independently an atom or group of atoms via copper-catalyzed coupling reaction of anthracene-9,16-diones with aminoglycosides; as an organelle marker and in pharmacy, in particular as antibiotics, anticancer, and antimalarial agents.  Here, we report the chem. synthesis of marmycin A and the study of its cellular activity.  The arom. core was constructed by means of a one-pot multistep reaction comprising a regioselective Diels-Alder cycloaddn., and the complex sugar backbone was introduced through a copper-catalyzed Ullmann cross-coupling, followed by a challenging Friedel-Crafts cyclization.  Remarkably, fluorescence microscopy revealed that marmycin A does not target the nucleus but instead accumulates in lysosomes, thereby promoting cell death independently of genome targeting.  Furthermore, a synthetic dimer of marmycin A and the lysosome-targeting agent artesunate exhibited a synergistic activity against the invasive MDA-MB-231 cancer cell line.  These findings shed light on the elusive pathways through which anthraquinone derivs. act in cells, pointing towards unanticipated biol. and therapeutic applications.
Method for preparing marmycin A and analogs thereof, and also uses thereof as antibiotics, anticancer, and antimalarials agents / Rodriguez, Raphael; Caneque, Tatiana; Gomes da Cruz, Filipe; Mai, Trang; Malacria, Max; Maestri, Giovanni. - (2016).
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11381/2807700
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