Establishing meso-methyl BODIPYs as viable visible-light excitable photocages

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• Roy Weinstain - Tel-Aviv University
• Tuesday 12 March 2019, 16:00-17:00
• Wolfson Lecture Theatre.

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Photocaging facilitates non-invasive and precise spatio-temporal user control over the release of biologically relevant small- and macro-molecules using light. We, and others, have recently introduced meso-methyl BODIPY as visible light excitable photovages that can overcome the traditional limitations associated with the ubiquitous UV excitable ones, i.e., phototoxicity, sample heating and light penetration. Further SAR studies revealed two key structural modification that, when combined, lead to photocages with uncaging cross sections over 10 000 M–1 cm–1, values that surpass cross sections of any other photocage absorbing visible light. To tune meso-methyl BODIPY photocages for biological applications, we aimed to overcome basic, prevalent difficulties including water solubility, cell permeability and sub-cellular specificity. Toward this end, we developed a general method for chemical functionalization of BODIP Ys at large, which enables introducing reactive functional groups post-synthetically and without the need for protecting groups. We first applied this chemistry for functionalization and further conjugation of meso–methyl BODIPY photocages to generate ER-, lysosome- and mitochondria-targeted derivatives. We find that not only that photocaging introduces unprecedented spatio-temporal specificity to organelle targeting, it additionally leads to higher efficacy of the released bioactive molecule, most probably due to a localized and abrupt release. Finally, we show that a similar chemistry can be applied to control the cellular permeability of meso-methyl BODIPY photocages through strategic introduction of sulfonates. By controlling the number of introduced sulfonates, the water solubility of meso-methyl BODIPY photocages can be dramatically increased and their cellular permeability can be pre-determined.

This talk is part of the Biological Chemistry Research Interest Group series.

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