Tuning BODIPY molecular rotors into the red: sensitivity to viscosity vs. temperature

Viscosity variations in the microscopic world are of paramount importance for diffusion and reactions. In the last decade a new class of fluorescent probes for measuring viscosity has emerged termed ‘molecular rotors’, which allows quantitative mapping of viscosity in microscopically heterogeneous environments. Here we attempt to tune the absorption and emission of one such ‘molecular rotor’ based on the BODIPY fluorescent core into the red region of the spectrum, to allow better compatibility with the ‘tissue optical window’ and imaging of cells and tissues. We consequently find that our red-emitting BODIPY fluorophores are sensitive to environmental temperature rather than to viscosity, thus suggesting a new prototype for a ‘molecular thermometer’.

[1]  Jonathan M Cooper,et al.  Imaging phase separation in model lipid membranes through the use of BODIPY based molecular rotors. , 2015, Physical chemistry chemical physics : PCCP.

[2]  M. Kuimova,et al.  Unravelling the effect of temperature on viscosity-sensitive fluorescent molecular rotors† †Electronic supplementary information (ESI) available: Additional spectroscopic and imaging data. See DOI: 10.1039/c5sc02248g Click here for additional data file. , 2015, Chemical science.

[3]  M. Kuimova,et al.  Dual mode quantitative imaging of microscopic viscosity using a conjugated porphyrin dimer. , 2015, Physical chemistry chemical physics : PCCP.

[4]  Z. Gryczynski,et al.  BODIPY–BODIPY dyad: assessing the potential as a viscometer for molecular and ionic liquids , 2015, RSC advances.

[5]  Ismael López-Duarte,et al.  A molecular rotor for measuring viscosity in plasma membranes of live cells. , 2014, Chemical communications.

[6]  A. Zumbusch,et al.  Monitoring of viscosity changes during free radical polymerization using fluorescence lifetime measurements , 2014 .

[7]  Junle Qu,et al.  Dual mode monitoring probe for mitochondrial viscosity in single cell , 2014 .

[8]  Markus Kalberer,et al.  Fluorescent lifetime imaging of atmospheric aerosols: a direct probe of aerosol viscosity. , 2013, Faraday discussions.

[9]  O. Ces,et al.  Molecular rheometry: direct determination of viscosity in Lo and Ld lipid phases via fluorescence lifetime imaging. , 2013, Physical chemistry chemical physics : PCCP.

[10]  Chulhun Kang,et al.  A self-calibrating bipartite viscosity sensor for mitochondria. , 2013, Journal of the American Chemical Society.

[11]  Meng-Xing Tang,et al.  Mapping microbubble viscosity using fluorescence lifetime imaging of molecular rotors , 2013, Proceedings of the National Academy of Sciences.

[12]  Yi Xiao,et al.  Activatable rotor for quantifying lysosomal viscosity in living cells. , 2013, Journal of the American Chemical Society.

[13]  M. Kuimova.  Mapping viscosity in cells using molecular rotors. , 2012, Physical chemistry chemical physics : PCCP.

[14]  Wei Min,et al.  Mapping protein-specific micro-environments in live cells by fluorescence lifetime imaging of a hybrid genetic-chemical molecular rotor tag. , 2012, Chemical communications.

[15]  J. Qu,et al.  Fluorescence ratiometry and fluorescence lifetime imaging: using a single molecular sensor for dual mode imaging of cellular viscosity. , 2011, Journal of the American Chemical Society.

[16]  B. Trofimov,et al.  A general synthetic strategy for the design of new BODIPY fluorophores based on pyrroles with polycondensed aromatic and metallocene substituents. , 2011, Chemistry.

[17]  M. Kuimova,et al.  Membrane-Bound Molecular Rotors Measure Viscosity in Live Cells via Fluorescence Lifetime Imaging , 2009 .

[18]  J. Catalán.  Toward a generalized treatment of the solvent effect based on four empirical scales: dipolarity (SdP, a new scale), polarizability (SP), acidity (SA), and basicity (SB) of the medium. , 2009, The journal of physical chemistry. B.

[19]  M. Kuimova,et al.  Molecular rotor measures viscosity of live cells via fluorescence lifetime imaging. , 2008, Journal of the American Chemical Society.

[20]  W. Dehaen,et al.  Boron dipyrromethene analogs with phenyl, styryl, and ethynylphenyl substituents: synthesis, photophysics, electrochemistry, and quantum-chemical calculations. , 2007, The journal of physical chemistry. A.

[21]  Mark A Haidekker,et al.  Molecular rotors--fluorescent biosensors for viscosity and flow. , 2007, Organic & biomolecular chemistry.

[22]  W. Dehaen,et al.  Palladium‐Catalyzed Coupling Reactions for the Functionalization of BODIPY Dyes with Fluorescence Spanning the Visible Spectrum , 2006 .

[23]  Koji Yamada,et al.  Preparation of BODIPY probes for multicolor fluorescence imaging studies of membrane dynamics , 2001 .

[24]  K. Kobs,et al.  Rhodamine B and rhodamine 101 as reference substances for fluorescence quantum yield measurements , 1980 .

[25]  H Lenz,et al.  Measurements on the depth of penetration of light (0.35–1.0 µm) in tissue , 1977, Radiation and environmental biophysics.