Nucleotide delivery is enhanced by removal of negative charge and/or by addition of net positive charge to the molecule. Positively charged delivery systems can rely on, for example, polyamidoamine (PAMAM) dendrons and guanidinium-rich molecular transporters (GRTs). Both approaches are extensively investigated for molecule delivery. The surface primary amines of dendrons and guanidine groups from GRTs are partially protonated at physiological pH, providing positive charges. Of note, lower generation PAMAM dendrons are less cytotoxic and more biocompatible than those of higher generations. In an alternative design, oligonucleotide delivery has also been described relying on thiol-mediated exchange, representing a novel delivery paradigm. To enable a more precise control over molecule delivery and release, one strategy is to use photocages. Photocages are a great boon to study functions of biomolecules by first rendering them biologically inert and subsequently activating them by irradiation. Using light as an external trigger allows us to manipulate a certain biological process induced by the active molecule spatially, temporally, and in precise dosage. Among the numerous known photocages, those based on a coumarin scaffold have several advantages for their use in living systems, such as single cells or even whole organisms. For instance, coumarins have a high biocompatibility, relatively high uncaging efficiency, flexibility of structural modifications with tunable photophysical and photochemical properties and a well-studied mechanism of photocleavage. A broad variety of functional groups have been released from their coumarin-caged precursors including phosphates. Importantly, Ellis-Davies has previously shown that the coumarin scaffold, specifically 7diethylaminocoumarin 450 (DEAC450), can be functionalized with PEG-Dendrons using click chemistry. This modification led to largely reduced interactions of the caged molecule (γ-amino butyric acid, GABA) with its receptor prior to uncaging due to steric crowding. They also applied the same strategy to introduce other larger dendrons derived from 2, 2bis(methylol)propionic acid. This further reduced the antagonistic effects. Also the group of Nadler has designed related clickable cages and applied them to lipids. Based on these promising results, we envisioned to use DEAC450 with polycationic modifications to achieve organismal delivery of NTPs. In this approach, dendronized DEAC450 would be responsible for (sub)cellular delivery of the cargo and, due to the covalent binding of the delivery/transport vehicle, might enable deep tissue penetration of the probe. After delivery, one could remove the combined cage and delivery substructure in a traceless way by photouncaging.