Effect of Short PEG on Near-Infrared BODIPY-Based
Activatable Optical Probes
Posted on 2020-06-17 - 03:46
Targeted near-infrared
(NIR) fluorescence probes are playing a
significant role in biomedical imaging because NIR penetrates deeper
into tissues and is associated with reduced autofluorescence compared
to visible light fluorescence probes. Long-wavelength emitting 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) is an attractive platform for synthesizing
NIR fluorophores because of its high photostability, high molar absorption
coefficient, and sharp absorption and emission spectra. However, its
lipophilicity hampers the conjugation chemistry necessary to add targeting
moieties. In this study, we synthesized a novel NIR BODIPY derivative, NMP14. Substitutions of ethylene-bridged pyrrole units at
the 3- or 5-position of the parent BODIPY chromophore result in a
red shift of more than 200 nm. However, NMP14 cannot
be conjugated to antibodies because of its hydrophobicity. Therefore,
we synthesized NMP13 by adding short poly(ethylene glycol)
to NMP14 and successfully conjugated NMP13 to cetuximab and trastuzumab. In vitro microscopic
studies showed that NMP13 conjugated antibodies were
activated after internalization and lysosomal processing, which means
that NMP13 acts as an activatable probe only turning
on after cellular internalization. After the administration of NMP13 conjugated antibodies, mice tumors were detected with
high tumor to background ratios for a long period. These results suggest
that NMP13 has potential as an activatable fluorescence
probe for further clinical applications.
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Inagaki, Fuyuki
F.; Fujimura, Daiki; Ansteatt, Sara; Okada, Ryuhei; Furusawa, Aki; Choyke, Peter L.; et al. (1753). Effect of Short PEG on Near-Infrared BODIPY-Based
Activatable Optical Probes. ACS Publications. Collection. https://doi.org/10.1021/acsomega.0c01869