A Photoactivatable Far-Red/Near-Infrared BODIPY to Monitor Cellular Dynamics in Vivo

Lorenzo Sansalone, Sicheng Tang, Jaume Garcia-Amorós, Yang Zhang, Santi Nonell, James D. Baker, Burjor Captain, Françisco M. Raymo*

*Corresponding author for this work

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

A mechanism to photoactivate far-red/near-infrared fluorescence with infinite contrast and under mild visible illumination was designed around the photophysical properties of borondipyrromethene (BODIPY) dyes and the photochemical behavior of oxazine heterocycles. Specifically, the photoinduced and irreversible cleavage of an oxazine ring with a laser line at 405 nm extends the electronic conjugation of a BODIPY chromophore over a 3H-indole auxochrome with a 2-(4-methoxyphenyl)ethenyl substituent in position 5. This structural transformation shifts bathochromically the main absorption band of the BODIPY component to allow the selective excitation of the photochemical product with a laser line of 633 nm and produce fluorescence between 600 and 850 nm. This combination of activation, excitation, and emission wavelengths permits the visualization of the cellular blastoderm of developing Drosophila melanogaster embryos with optimal contrast and essentially no autofluorescence from the biological specimen. Furthermore, the sequential acquisition of images, after the photoactivation event, enables the tracking of individual cells within the embryos in real time. Thus, our structural design and operating principles for the photoactivation of far-red/near-infrared fluorescence can evolve into invaluable probes to monitor cellular dynamics in vivo.

Original languageEnglish (US)
Pages (from-to)1347-1353
Number of pages7
JournalACS Sensors
Volume3
Issue number7
DOIs
StatePublished - Jul 27 2018

Keywords

  • BODIPY
  • Drosophila melanogaster
  • NIR dyes
  • TICT
  • fluorescence
  • imaging
  • photoactivatable fluorophores
  • photocages

ASJC Scopus subject areas

  • Bioengineering
  • Instrumentation
  • Process Chemistry and Technology
  • Fluid Flow and Transfer Processes

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  • Cite this

    Sansalone, L., Tang, S., Garcia-Amorós, J., Zhang, Y., Nonell, S., Baker, J. D., Captain, B., & Raymo, F. M. (2018). A Photoactivatable Far-Red/Near-Infrared BODIPY to Monitor Cellular Dynamics in Vivo. ACS Sensors, 3(7), 1347-1353. https://doi.org/10.1021/acssensors.8b00262