ja5125308_si_004.avi (45 MB)
Photoactivatable BODIPYs Designed To Monitor the Dynamics of Supramolecular Nanocarriers
media
posted on 2015-04-15, 00:00 authored by Yang Zhang, Subramani Swaminathan, Sicheng Tang, Jaume Garcia-Amorós, Marcia Boulina, Burjor Captain, James D. Baker, Françisco M. RaymoSelf-assembling
nanoparticles of amphiphilic polymers can transport
hydrophobic molecules across hydrophilic media and, as a result, can
be valuable delivery vehicles for a diversity of biomedical applications.
Strategies to monitor their dynamics noninvasively and in real time
are, therefore, essential to investigate their translocation within
soft matrices and, possibly, rationalize the mechanisms responsible
for their diffusion in biological media. In this context, we designed
molecular guests with photoactivatable fluorescence for these supramolecular
hosts and demonstrated that the activation of the fluorescent cargo,
under optical control, permits the tracking of the nanocarrier translocation
across hydrogel matrices with the sequential acquisition of fluorescence
images. In addition, the mild illumination conditions sufficient to
implement these operating principles permit fluorescence activation
within developing Drosophila melanogaster embryos
and enable the monitoring of the loaded nanocarriers for long periods
of time with no cytotoxic effects and no noticeable influence on embryogenesis.
These photoresponsive compounds combine a borondipyrromethene (BODIPY)
chromophore and a photocleavable oxazine within their covalent skeleton.
Under illumination at an appropriate activation wavelength, the oxazine
ring cleaves irreversibly to bring the adjacent BODIPY fragment in
conjugation with an indole heterocycle. This structural transformation
shifts bathochromically the BODIPY absorption and permits the selective
excitation of the photochemical product with concomitant fluorescence.
In fact, these operating principles allow the photoactivation of BODIPY
fluorescence with large brightness and infinite contrast. Thus, our
innovative structural design translates into activatable fluorophores
with excellent photochemical and photophysical properties as well
as provides access to a general mechanism for the real-time tracking
of supramolecular nanocarriers in hydrophilic matrices.
History
Usage metrics
Categories
Keywords
photoresponsive compoundsPhotoactivatable BODIPYsBODIPY fragmentnanocarrier translocationoxazine ring cleavesphotophysical propertiessequential acquisitionfluorescence imagesdynamics noninvasivelysupramolecular hostsBODIPY fluorescencecovalent skeletonDrosophila melanogaster embryosamphiphilic polymersphotoactivatable fluorescenceactivatable fluorophorestransformation shifts bathochromicallyphotocleavable oxazinehydrogel matricesindole heterocyclesupramolecular nanocarriersmediamechanismfluorescence activationBODIPY absorptionillumination conditionsdelivery vehiclescytotoxic effectsactivation wavelengthprinciple
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC