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SUMMARY:Establishing meso-methyl BODIPYs as viable visible-light excitable
  photocages - Roy Weinstain - Tel-Aviv University
DTSTART:20190312T160000Z
DTEND:20190312T170000Z
UID:TALK116155@talks.cam.ac.uk
CONTACT:48618
DESCRIPTION:Photocaging facilitates non-invasive and precise spatio-tempor
 al user control over the release of biologically relevant small- and macro
 -molecules using light. We\, and others\, have recently introduced meso-me
 thyl BODIPY as visible light excitable photovages that can overcome the tr
 aditional limitations associated with the ubiquitous UV excitable ones\, i
 .e.\, phototoxicity\, sample heating and light penetration. Further SAR st
 udies 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 visibl
 e light. To tune meso-methyl BODIPY photocages for biological applications
 \, we aimed to overcome basic\, prevalent difficulties including water sol
 ubility\, cell permeability and sub-cellular specificity. Toward this end\
 , we developed a general method for chemical functionalization of BODIPYs 
 at large\, which enables introducing reactive functional groups post-synth
 etically 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 de
 rivatives. We find that not only that photocaging introduces unprecedented
  spatio-temporal specificity to organelle targeting\, it additionally lead
 s to higher efficacy of the released bioactive molecule\, most probably du
 e to a localized and abrupt release. Finally\, we show that a similar chem
 istry can be applied to control the cellular permeability of meso-methyl B
 ODIPY photocages through strategic introduction of sulfonates. By controll
 ing the number of introduced sulfonates\, the water solubility of meso-met
 hyl BODIPY photocages can be dramatically increased and their cellular per
 meability can be pre-determined. \n
LOCATION:Wolfson Lecture Theatre
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