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Light-responsive compounds and photo-uncaging.

ORAL

Abstract

Light-responsive protecting groups enable scientists to regulate activities of bioactive molecules in living cells upon light irradiation. The basic idea behind this technique is that molecules of interest can be inactive with photo-responsive groups, after light-triggered photo-cleavage the molecules of interest can be freed and act in an intact form. This approach has been used for drug delivery and exhibited pinpoint accuracy with light guidance as well as low off-target toxicity. However, most of the light-responsive groups show absorbability in the UV-to-blue region (300 -- 450 nm), in which the high energy radiant leads to unwanted photo-toxicity. Thus, there is a strong need to develop photo-responsive groups that can absorb light in longer wavelengths. Boron-dipyrromethene (BODIPY) derivatives were identified as one of the potential chromophores to sense light, they absorb at the visible region with high molar extinction coefficients. A new class of BODIPY-based oxime ester light-responsive compound was designed to sense green light and photo-uncage carboxylic acids. The mechanism and kinetics of the light-responsive procedure were studied. Further, we constructed a photo-uncaging drug delivery system to release valproic acid, which can inhibit the histone deacetylases and induce apoptosis in tumor cells.

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Authors

  • Yuanwei Zhang

    New Jersey Inst of Tech, NJIT

  • Anuradha Gupta

    New Jersey Inst of Tech, Pennsylvania State University, Bard College, University of Mississippi, Drexel Univ, Collaborator, University of Dayton, Morgan State University, Louisiana State University, University of Geneva, Instituto Superior Tecnico - Lisboa, Department of Biochemistry and Molecular Biology, Rutgers University, Institute for Quantitative Biomedicine, Rutgers University, Pennsylvania State University, and University of Illinois at Urbana-Champaign, University of Illinois at Urbana-Champaign, Department of Chemical Engineering, New Jersey Institute of Technology, Department of Physics and Astronomy, Rutgers University-New Brunswick, Department of Physics, Rutgers University, Max-Planck-Institut für Festkörperforschung, Heisenbergstrasse 1, 70569 Stuttgart, Germany, Department of Physics and Fribourg Center for Nanomaterials, University of Fribourg, Chemin du Musée 3, CH-1700 Fribourg, Switzerland, The MacDiarmid Institute for Advanced Materials and Nanotechnology, 1010 Auckland, New Zealand, Department of Physics, College of William & Mary, Williamsburg, VA 23187-8795, USA, New Jersey Institute of Technology, Newark, NJ, USA, University of California, Los Angeles, CA, USA, University of California, Berkeley, CA, USA, Space Research Institute of RAS, Moscow, Russia, Georgetown University, Institut Polytechnique de Paris, University of Delaware, Brookhaven National Laboratory, San Diego State University, University of Chicago, University of Illinois at Chicago, Argonne National Laboratory, Department of Physics and Astronomy, Rutgers University, Piscataway, NJ 08854, USA, University of Washington

  • Anuradha Gupta

    New Jersey Inst of Tech, Pennsylvania State University, Bard College, University of Mississippi, Drexel Univ, Collaborator, University of Dayton, Morgan State University, Louisiana State University, University of Geneva, Instituto Superior Tecnico - Lisboa, Department of Biochemistry and Molecular Biology, Rutgers University, Institute for Quantitative Biomedicine, Rutgers University, Pennsylvania State University, and University of Illinois at Urbana-Champaign, University of Illinois at Urbana-Champaign, Department of Chemical Engineering, New Jersey Institute of Technology, Department of Physics and Astronomy, Rutgers University-New Brunswick, Department of Physics, Rutgers University, Max-Planck-Institut für Festkörperforschung, Heisenbergstrasse 1, 70569 Stuttgart, Germany, Department of Physics and Fribourg Center for Nanomaterials, University of Fribourg, Chemin du Musée 3, CH-1700 Fribourg, Switzerland, The MacDiarmid Institute for Advanced Materials and Nanotechnology, 1010 Auckland, New Zealand, Department of Physics, College of William & Mary, Williamsburg, VA 23187-8795, USA, New Jersey Institute of Technology, Newark, NJ, USA, University of California, Los Angeles, CA, USA, University of California, Berkeley, CA, USA, Space Research Institute of RAS, Moscow, Russia, Georgetown University, Institut Polytechnique de Paris, University of Delaware, Brookhaven National Laboratory, San Diego State University, University of Chicago, University of Illinois at Chicago, Argonne National Laboratory, Department of Physics and Astronomy, Rutgers University, Piscataway, NJ 08854, USA, University of Washington