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The material consists of nanometric mesoporous MCM\u201041\u2010like supports loaded with Rhodamine B and capped with an azopyridine derivative. The material was designed to show \u201czero delivery\u201d and to display a cargo release in the presence of reductases and esterases, which are usually present in the colon, mainly due to intestinal microflora. The opening and cargo release of <jats:bold>Rh\u2010Azo\u2010S<\/jats:bold> in vitro studies were assessed and seen to occur in the presence of these enzymes, whereas no delivery was noted in the presence of pepsine. Moreover, <jats:bold>Rh\u2010Azo\u2010S<\/jats:bold> nanoparticles were used to study controlled Rhodamine\u2005B dye delivery in intracellular media. HeLa cells were employed for testing the \u201cnon\u201d\u2010toxicity of nanoparticles. Moreover, delivery of the dye in these cells, through internalization and enzyme\u2010mediated gate opening, was confirmed by confocal microscopy. Furthermore, the nanoparticles capped with the <jats:bold>Azo<\/jats:bold> group and loaded with a cytotoxic camptothecin (<jats:bold>CPT<\/jats:bold>) were also prepared (solid <jats:bold>CPT\u2010Azo\u2010S<\/jats:bold>) and used as delivery nanodevices in HeLa cells. 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