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Dye synthesis in the Pechmann reaction: catalytic behaviour of samarium oxide nanoparticles studied using single molecule fluorescence microscopy.

ABSTRACT: Photochemically prepared samarium oxide nanoparticles (Sm₂O₃NP) efficiently catalyze the formation of coumarin 153 via the Pechmann trans-esterification and condensation process. The formation of the fluorescent coumarin allowed the catalytic process to be monitored in real time at the single molecule level using Total Internal Reflection Fluorescence Microscopy (TIRFM). Benchtop experiments conducted in parallel demonstrated that the observed catalysis occurred in solution rather than by pure heterogeneous catalysis and is due to a mobile population of small Sm₂O₃NP released from a polydisperse original sample containing larger particles. TIRFM provided unique insights by demonstrating that catalysis by these smaller colloidal particles is in fact a surface process, while the larger particles are merely suppliers of the small catalytic nanostructures. We refer to this behaviour as a semi-heterogeneous catalytic system. This work showcases the opportunity that single molecule fluorescence techniques can offer in terms of understanding and ultimately improving benchtop and scaled-up synthesis. This specific example highlights the general applicability of this approach to the study of widely-utilized chemical reactions and lays the groundwork for researchers to adopt similar strategies in other systems.

SUBMITTER: Hodgson GK

PROVIDER: S-EPMC5975723 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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Dye synthesis in the Pechmann reaction: catalytic behaviour of samarium oxide nanoparticles studied using single molecule fluorescence microscopy.

Hodgson Gregory K GK Impellizzeri Stefania S Scaiano Juan C JC

Chemical science 20151109 2

Photochemically prepared samarium oxide nanoparticles (Sm2O3NP) efficiently catalyze the formation of coumarin 153 via the Pechmann trans-esterification and condensation process. The formation of the fluorescent coumarin allowed the catalytic process to be monitored in real time at the single molecule level using Total Internal Reflection Fluorescence Microscopy (TIRFM). Benchtop experiments conducted in parallel demonstrated that the observed catalysis occurred in s ...[more]

PMID: 29910889

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Project description:While the in vivo efficacy of Sn-2 phosphatidylcholine prodrugs incorporated into targeted, non-pegylated lipid-encapsulated nanoparticles was demonstrated in prior preclinical studies, the microscopic details of cell prodrug internalization and trafficking events are unknown. Classic fluorescence microscopy, fluorescence lifetime imaging microscopy, and single-molecule super-resolution microscopy were used to investigate the cellular handling of doxorubicin-prodrug and AlexaFluor™-488-prodrug. Sn-2 phosphatidylcholine prodrugs delivered by hemifusion of nanoparticle and cell phospholipid membranes functioned as phosphatidylcholine mimics, circumventing the challenges of endosome sequestration and release. Phosphatidylcholine prodrugs in the outer cell membrane leaflet translocated to the inner membrane leaflet by ATP-dependent and ATP-independent mechanisms and distributed broadly within the cytosolic membranes over the next 12 h. A portion of the phosphatidylcholine prodrug populated vesicle membranes trafficked to the perinuclear Golgi/ER region, where the drug was enzymatically liberated and activated. Native doxorubicin entered the cells, passed rapidly to the nucleus, and bound to dsDNA, whereas DOX was first enzymatically liberated from DOX-prodrug within the cytosol, particularly in the perinuclear region, before binding nuclear dsDNA. Much of DOX-prodrug was initially retained within intracellular membranes. In vitro anti-proliferation effectiveness of the two drug delivery approaches was equivalent at 48 h, suggesting that residual intracellular DOX-prodrug may constitute a slow-release drug reservoir that enhances effectiveness. We have demonstrated that Sn-2 phosphatidylcholine prodrugs function as phosphatidylcholine mimics following reported pathways of phosphatidylcholine distribution and metabolism. Drug complexed to the Sn-2 fatty acid is enzymatically liberated and reactivated over many hours, which may enhance efficacy overtime.

Dataset Information

Dye synthesis in the Pechmann reaction: catalytic behaviour of samarium oxide nanoparticles studied using single molecule fluorescence microscopy.

Publications

Dye synthesis in the Pechmann reaction: catalytic behaviour of samarium oxide nanoparticles studied using single molecule fluorescence microscopy.

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