DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: A Photoactivatable BODIPY Probe for Localization-based Super-Resolution Cellular Imaging

Abstract

Abstract The synthesis and application of a photoactivatable boron‐alkylated BODIPY probe for localization‐based super‐resolution microscopy is reported. Photoactivation and excitation of the probe is achieved by a previously unknown boron‐photodealkylation reaction with a single low‐power visible laser and without requiring the addition of reducing agents or oxygen scavengers in the imaging buffer. These features lead to a versatile probe for localization‐based microscopy of biological systems. The probe can be easily linked to nucleophile‐containing molecules to target specific cellular organelles. By attaching paclitaxel to the photoactivatable BODIPY, in vitro and in vivo super‐resolution imaging of microtubules is demonstrated. This is the first example of single‐molecule localization‐based super‐resolution microscopy using a visible‐light‐activated BODIPY compound as a fluorescent probe.

Authors:
 [1];  [1];  [1];  [1];  [1];  [1]
  1. Iowa State Univ. of Science and Technology, Ames, IA (United States)
Publication Date:
Research Org.:
Ames Laboratory (AMES), Ames, IA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1464487
Alternate Identifier(s):
OSTI ID: 1468373
Report Number(s):
IS-J-9578
Journal ID: ISSN 1433-7851
Grant/Contract Number:  
AC02-07CH11358
Resource Type:
Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
Journal Name: Angewandte Chemie (International Edition); Journal Volume: 57; Journal Issue: 39; Journal ID: ISSN 1433-7851
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; bodipy; fluorescence; imaging agents; photoactivation; super-resolution microscopy

Citation Formats

Wijesooriya, Chamari S., Peterson, Julie A., Shrestha, Pradeep, Gehrmann, Elizabeth J., Winter, Arthur H., and Smith, Emily. A Photoactivatable BODIPY Probe for Localization-based Super-Resolution Cellular Imaging. United States: N. p., 2018. Web. doi:10.1002/anie.201805827.
Wijesooriya, Chamari S., Peterson, Julie A., Shrestha, Pradeep, Gehrmann, Elizabeth J., Winter, Arthur H., & Smith, Emily. A Photoactivatable BODIPY Probe for Localization-based Super-Resolution Cellular Imaging. United States. https://doi.org/10.1002/anie.201805827
Wijesooriya, Chamari S., Peterson, Julie A., Shrestha, Pradeep, Gehrmann, Elizabeth J., Winter, Arthur H., and Smith, Emily. Wed . "A Photoactivatable BODIPY Probe for Localization-based Super-Resolution Cellular Imaging". United States. https://doi.org/10.1002/anie.201805827. https://www.osti.gov/servlets/purl/1464487.
@article{osti_1464487,
title = {A Photoactivatable BODIPY Probe for Localization-based Super-Resolution Cellular Imaging},
author = {Wijesooriya, Chamari S. and Peterson, Julie A. and Shrestha, Pradeep and Gehrmann, Elizabeth J. and Winter, Arthur H. and Smith, Emily},
abstractNote = {Abstract The synthesis and application of a photoactivatable boron‐alkylated BODIPY probe for localization‐based super‐resolution microscopy is reported. Photoactivation and excitation of the probe is achieved by a previously unknown boron‐photodealkylation reaction with a single low‐power visible laser and without requiring the addition of reducing agents or oxygen scavengers in the imaging buffer. These features lead to a versatile probe for localization‐based microscopy of biological systems. The probe can be easily linked to nucleophile‐containing molecules to target specific cellular organelles. By attaching paclitaxel to the photoactivatable BODIPY, in vitro and in vivo super‐resolution imaging of microtubules is demonstrated. This is the first example of single‐molecule localization‐based super‐resolution microscopy using a visible‐light‐activated BODIPY compound as a fluorescent probe.},
doi = {10.1002/anie.201805827},
journal = {Angewandte Chemie (International Edition)},
number = 39,
volume = 57,
place = {United States},
year = {Wed Jul 18 00:00:00 EDT 2018},
month = {Wed Jul 18 00:00:00 EDT 2018}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 71 works
Citation information provided by
Web of Science

Figures / Tables:

Table 1 Table 1: Photophysical properties of compounds 1-3

Save / Share:

Works referenced in this record:

Super-Resolution Imaging with Small Organic Fluorophores
journal, September 2009

  • Heilemann, Mike; van de Linde, Sebastian; Mukherjee, Anindita
  • Angewandte Chemie International Edition, Vol. 48, Issue 37
  • DOI: 10.1002/anie.200902073

Fluoreszenzmikroskopie unterhalb der optischen Auflösungsgrenze mit konventionellen Fluoreszenzsonden
journal, August 2008

  • Heilemann, Mike; van de Linde, Sebastian; Schüttpelz, Mark
  • Angewandte Chemie, Vol. 120, Issue 33
  • DOI: 10.1002/ange.200802376

Fluorescent Photoswitchable Diarylethenes for Biolabeling and Single-Molecule Localization Microscopies with Optical Superresolution
journal, May 2017

  • Roubinet, Benoît; Weber, Michael; Shojaei, Heydar
  • Journal of the American Chemical Society, Vol. 139, Issue 19
  • DOI: 10.1021/jacs.7b00274

Fluorescent taxoids
journal, December 1996


Twinkle, twinkle little star: Photoswitchable fluorophores for super-resolution imaging
journal, July 2014


Three-dimensional, single-molecule fluorescence imaging beyond the diffraction limit by using a double-helix point spread function
journal, February 2009

  • Pavani, S. R. P.; Thompson, M. A.; Biteen, J. S.
  • Proceedings of the National Academy of Sciences, Vol. 106, Issue 9
  • DOI: 10.1073/pnas.0900245106

Ultra-High Resolution Imaging by Fluorescence Photoactivation Localization Microscopy
journal, December 2006


Phosphine Quenching of Cyanine Dyes as a Versatile Tool for Fluorescence Microscopy
journal, January 2013

  • Vaughan, Joshua C.; Dempsey, Graham T.; Sun, Eileen
  • Journal of the American Chemical Society, Vol. 135, Issue 4
  • DOI: 10.1021/ja3105279

Imaging Intracellular Fluorescent Proteins at Nanometer Resolution
journal, September 2006


Fluorogenic probes for live-cell imaging of the cytoskeleton
journal, May 2014

  • Lukinavičius, Gražvydas; Reymond, Luc; D'Este, Elisa
  • Nature Methods, Vol. 11, Issue 7
  • DOI: 10.1038/nmeth.2972

Toward fluorescence nanoscopy
journal, October 2003

  • Hell, Stefan W.
  • Nature Biotechnology, Vol. 21, Issue 11
  • DOI: 10.1038/nbt895

Masked Rhodamine Dyes of Five Principal Colors Revealed by Photolysis of a 2-Diazo-1-Indanone Caging Group: Synthesis, Photophysics, and Light Microscopy Applications
journal, September 2014

  • Belov, Vladimir N.; Mitronova, Gyuzel Yu.; Bossi, Mariano L.
  • Chemistry - A European Journal, Vol. 20, Issue 41
  • DOI: 10.1002/chem.201403316

Synthesis of a Fluorescent Analogue of Paclitaxel That Selectively Binds Microtubules and Sensitively Detects Efflux by P-Glycoprotein
journal, May 2017

  • Lee, Molly M.; Gao, Zhe; Peterson, Blake R.
  • Angewandte Chemie, Vol. 129, Issue 24
  • DOI: 10.1002/ange.201703298

In Search of the Perfect Photocage: Structure–Reactivity Relationships in meso -Methyl BODIPY Photoremovable Protecting Groups
journal, October 2017

  • Slanina, Tomáš; Shrestha, Pradeep; Palao, Eduardo
  • Journal of the American Chemical Society, Vol. 139, Issue 42
  • DOI: 10.1021/jacs.7b08532

Super-resolution imaging of lysosomes with a nitroso-caged rhodamine
journal, January 2018

  • He, Haihong; Ye, Zhiwei; Zheng, Ying
  • Chemical Communications, Vol. 54, Issue 23
  • DOI: 10.1039/C7CC08886H

Direct stochastic optical reconstruction microscopy with standard fluorescent probes
journal, June 2011

  • van de Linde, Sebastian; Löschberger, Anna; Klein, Teresa
  • Nature Protocols, Vol. 6, Issue 7
  • DOI: 10.1038/nprot.2011.336

Photoactivatable fluorophores and techniques for biological imaging applications
journal, January 2012

  • Li, Wen-hong; Zheng, Genhua
  • Photochemical & Photobiological Sciences, Vol. 11, Issue 3
  • DOI: 10.1039/c2pp05342j

When Push Comes to Shove: Unravelling the Mechanism and Scope of Nonemissive meso -Unsaturated BODIPY Dyes
journal, March 2015

  • Lincoln, Richard; Greene, Lana E.; Bain, Cheryl
  • The Journal of Physical Chemistry B, Vol. 119, Issue 13
  • DOI: 10.1021/acs.jpcb.5b02080

Synthesis of a Far-Red Photoactivatable Silicon-Containing Rhodamine for Super-Resolution Microscopy
journal, December 2015

  • Grimm, Jonathan B.; Klein, Teresa; Kopek, Benjamin G.
  • Angewandte Chemie, Vol. 128, Issue 5
  • DOI: 10.1002/ange.201509649

Photochromic Rhodamines Provide Nanoscopy with Optical Sectioning
journal, July 2007

  • Fölling, J.; Belov, V.; Kunetsky, R.
  • Angewandte Chemie International Edition, Vol. 46, Issue 33
  • DOI: 10.1002/anie.200702167

Evaluation of fluorophores for optimal performance in localization-based super-resolution imaging
journal, November 2011

  • Dempsey, Graham T.; Vaughan, Joshua C.; Chen, Kok Hao
  • Nature Methods, Vol. 8, Issue 12
  • DOI: 10.1038/nmeth.1768

Photoactivatable Fluorophores for Super-Resolution Imaging Based on Oxazine Auxochromes
journal, February 2012

  • Deniz, Erhan; Tomasulo, Massimiliano; Cusido, Janet
  • The Journal of Physical Chemistry C, Vol. 116, Issue 10
  • DOI: 10.1021/jp211796p

Photoswitching Mechanism of Cyanine Dyes
journal, December 2009

  • Dempsey, Graham T.; Bates, Mark; Kowtoniuk, Walter E.
  • Journal of the American Chemical Society, Vol. 131, Issue 51
  • DOI: 10.1021/ja904588g

Transition-Metal-Free CO-Releasing BODIPY Derivatives Activatable by Visible to NIR Light as Promising Bioactive Molecules
journal, December 2015

  • Palao, Eduardo; Slanina, Tomáš; Muchová, Lucie
  • Journal of the American Chemical Society, Vol. 138, Issue 1
  • DOI: 10.1021/jacs.5b10800

Sub-diffraction-limit imaging by stochastic optical reconstruction microscopy (STORM)
journal, August 2006

  • Rust, Michael J.; Bates, Mark; Zhuang, Xiaowei
  • Nature Methods, Vol. 3, Issue 10
  • DOI: 10.1038/nmeth929

Highly Activatable and Environment-Insensitive Optical Highlighters for Selective Spatiotemporal Imaging of Target Proteins
journal, June 2012

  • Kobayashi, Tomonori; Komatsu, Toru; Kamiya, Mako
  • Journal of the American Chemical Society, Vol. 134, Issue 27
  • DOI: 10.1021/ja212125w

ThunderSTORM: a comprehensive ImageJ plug-in for PALM and STORM data analysis and super-resolution imaging
journal, May 2014


Photoactivatable Rhodamine Spiroamides and Diazoketones Decorated with “Universal Hydrophilizer” or Hydroxyl Groups
journal, May 2018

  • Roubinet, Benôit; Bischoff, Matthias; Nizamov, Shamil
  • The Journal of Organic Chemistry, Vol. 83, Issue 12
  • DOI: 10.1021/acs.joc.8b00756

Complementarity of PALM and SOFI for super-resolution live-cell imaging of focal adhesions
journal, December 2016

  • Deschout, Hendrik; Lukes, Tomas; Sharipov, Azat
  • Nature Communications, Vol. 7, Issue 1
  • DOI: 10.1038/ncomms13693

A new photoactivatable near-infrared-emitting QCy7 fluorophore for single-molecule super-resolution microscopy
journal, January 2017

  • Klötzner, Dean-Paulos; Klehs, Kathrin; Heilemann, Mike
  • Chemical Communications, Vol. 53, Issue 71
  • DOI: 10.1039/C7CC04996J

Subdiffraction-Resolution Fluorescence Imaging with Conventional Fluorescent Probes
journal, August 2008

  • Heilemann, Mike; van de Linde, Sebastian; Schüttpelz, Mark
  • Angewandte Chemie International Edition, Vol. 47, Issue 33
  • DOI: 10.1002/anie.200802376

A Caged, Localizable Rhodamine Derivative for Superresolution Microscopy
journal, November 2011

  • Banala, Sambashiva; Maurel, Damien; Manley, Suliana
  • ACS Chemical Biology, Vol. 7, Issue 2
  • DOI: 10.1021/cb2002889

Small-Molecule Labeling of Live Cell Surfaces for Three-Dimensional Super-Resolution Microscopy
journal, August 2014

  • Lee, Marissa K.; Rai, Prabin; Williams, Jarrod
  • Journal of the American Chemical Society, Vol. 136, Issue 40
  • DOI: 10.1021/ja508028h

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy
journal, November 2012

  • Klán, Petr; Šolomek, Tomáš; Bochet, Christian G.
  • Chemical Reviews, Vol. 113, Issue 1
  • DOI: 10.1021/cr300177k

Specific protein labeling with caged fluorophores for dual-color imaging and super-resolution microscopy in living cells
journal, January 2017

  • Hauke, Sebastian; von Appen, Alexander; Quidwai, Tooba
  • Chemical Science, Vol. 8, Issue 1
  • DOI: 10.1039/C6SC02088G

Photochromic Rhodamines Provide Nanoscopy with Optical Sectioning
journal, August 2007


meso-Methylhydroxy BODIPY: a scaffold for photo-labile protecting groups
journal, January 2015

  • Rubinstein, Naama; Liu, Pei; Miller, Evan W.
  • Chemical Communications, Vol. 51, Issue 29
  • DOI: 10.1039/C5CC00550G

Chemical tags: inspiration for advanced imaging techniques
journal, August 2013

  • Chen, Zhixing; Cornish, Virginia W.; Min, Wei
  • Current Opinion in Chemical Biology, Vol. 17, Issue 4
  • DOI: 10.1016/j.cbpa.2013.05.018

Synthesis of a Fluorescent Analogue of Paclitaxel That Selectively Binds Microtubules and Sensitively Detects Efflux by P-Glycoprotein
journal, May 2017

  • Lee, Molly M.; Gao, Zhe; Peterson, Blake R.
  • Angewandte Chemie International Edition, Vol. 56, Issue 24
  • DOI: 10.1002/anie.201703298

Synthesis of a Far-Red Photoactivatable Silicon-Containing Rhodamine for Super-Resolution Microscopy
journal, December 2015

  • Grimm, Jonathan B.; Klein, Teresa; Kopek, Benjamin G.
  • Angewandte Chemie International Edition, Vol. 55, Issue 5
  • DOI: 10.1002/anie.201509649

BODIPY-Derived Photoremovable Protecting Groups Unmasked with Green Light
journal, March 2015

  • Goswami, Pratik P.; Syed, Aleem; Beck, Christie L.
  • Journal of the American Chemical Society, Vol. 137, Issue 11
  • DOI: 10.1021/jacs.5b01297

A general strategy for developing cell-permeable photo-modulatable organic fluorescent probes for live-cell super-resolution imaging
journal, November 2014

  • Pan, Deng; Hu, Zhe; Qiu, Fengwu
  • Nature Communications, Vol. 5, Issue 1
  • DOI: 10.1038/ncomms6573

Hochauflösende Mikroskopie mit kleinen organischen Farbstoffen
journal, September 2009

  • Heilemann, Mike; van de Linde, Sebastian; Mukherjee, Anindita
  • Angewandte Chemie, Vol. 121, Issue 37
  • DOI: 10.1002/ange.200902073

Masked Rhodamine Dyes of Five Principal Colors Revealed by Photolysis of a 2-Diazo-1-Indanone Caging Group: Synthesis, Photophysics, and Light Microscopy Applications
journal, August 2014

  • Belov, Vladimir N.; Mitronova, Gyuzel Yu; Bossi, Mariano L.
  • Chemistry - A European Journal, Vol. 20, Issue 41
  • DOI: 10.1002/chem.201404826

Photoswitching Mechanism of Cyanine Dyes
journal, January 2010


Three-dimensional total-internal reflection fluorescence nanoscopy with nanometric axial resolution by photometric localization of single molecules
journal, January 2021


Microtubules and Microscopes: How the Development of Light Microscopic Imaging Technologies Has Contributed to Discoveries about Microtubule Dynamics in Living Cells
text, January 1998

  • M., Waterman-Storer, Clare
  • The University of North Carolina at Chapel Hill University Libraries
  • DOI: 10.17615/kr5w-jm31

Complementarity of PALM and SOFI for super-resolution live cell imaging of focal adhesions
text, January 2016


Works referencing / citing this record:

The Role of Photochemical Reactions in the Development of Advanced Soft Materials for Biomedical Applications
journal, April 2019

  • Fernandez‐Villamarin, Marcos; Brooks, Laura; Mendes, Paula M.
  • Advanced Optical Materials, Vol. 7, Issue 16
  • DOI: 10.1002/adom.201900215

Optoelectronic, Aggregation, and Redox Properties of Double‐Rotor Boron Difluoride Hydrazone Dyes
journal, March 2019

  • Cappello, Daniela; Therien, Denis A. B.; Staroverov, Viktor N.
  • Chemistry – A European Journal, Vol. 25, Issue 23
  • DOI: 10.1002/chem.201900383

A Synthetic Strategy for the Structural Modification of Photoactivatable BODIPY‐Oxazine Dyads
journal, February 2020

  • Thapaliya, Ek Raj; Mazza, Mercedes M. A.; Cusido, Janet
  • ChemPhotoChem, Vol. 4, Issue 5
  • DOI: 10.1002/cptc.201900276

Single-molecule localization microscopy and tracking with red-shifted states of conventional BODIPY conjugates in living cells
journal, July 2019


Single-molecule localization microscopy and tracking with red-shifted states of conventional BODIPY conjugates in living cells
journal, July 2019


Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.