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Abstract
Light-triggered molecular tools releasing bioactive actuators with high spatial and temporal control have prompted significant advances in optobiology. Such probes however require high levels of photosensitivity at biocompatible wavelengths to trigger a biological response safely and efficiently. Here, we propose synergistic, multi-chromophoric, water-soluble systems in which quadrupolar antennas sensitize a coumarinyl photocage, delivering a carboxylic acid payload upon one-photon (visible) or two-photon excitation in the biological transparency near-infrared (NIR) window. Strikingly, the molecular design promotes a 50 % increase in photo-cleavage quantum yield, leading to record photosensitivity for NIR-triggered release of acetic acid. We further demonstrated that these molecular tools efficiently rescue impaired lysosomal pH in a genetic cellular model of Parkinson’s disease. These photoactivated tools are therefore promising candidates for the phototherapeutic management of neurodegenerative diseases
Supplementary materials
Title
Electronic Supplementary Information
Description
I. Synthesis1
1. Materials and methods 1
2. Synthetic procedures and characterization 2
a. Synthesis of the graftable DEAC450 derivative 2
b. Synthesis of the antennas 7
c. Synthesis of the triads 12
d. Synthesis of the reference compounds for photolysis 17
II. One- and two-photon photophysical studies 19
1. Materials and Methods 19
2. Optical properties of the lipophilic compounds 20
3. Optical properties of the hydrophilic compounds 21
4. Förster radius 23
5. FRET efficiency 24
III. Comparative photolysis experiments 25
1. Materials & methods 25
2. 1H NMR Follow-up 26
IV. Dark stability experiments 27
V. In vitro lysosomal photo-acidification experiment 28
1. Cell culture and Cell viability Assay 28
2. Lysosomal pH Measurement 28
3. Statistics 28
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