Two-photon uncaging, from neuroscience to materials

The use of photolabile protecting groups has been growing in emphasis for decades, in particular because of their numerous applications ranging from organic synthesis to neurosciences. More recently, two-photon sensitive photolabile protecting groups were developed, bringing the advantages (e.g. finer spatial resolution with a deeper tissue penetration) of this nonlinear excitation technique to a photostimulation method. However, the widespread photolabile protecting groups developed for classical one-photon excitation exhibited low two-photon sensitivity. Therefore, the rules of molecular engineering pointed out for the optimization of nonlinear properties of molecular systems for material sciences were applied to this specific field. Consequently, efficient two-photon photolabile protecting groups have been developed. We describe here the recent developments in molecular engineering of two-photon sensitive photolabile protecting groups as well as their application in neurobiology, physiology and biomaterials.

[1]  M. Jin,et al.  Long conjugated 2-nitrobenzyl derivative caged anticancer prodrugs with visible light regulated release: preparation and functionalizations. , 2012, Organic & biomolecular chemistry.

[2]  H. Javot,et al.  Synthesis and Characterization of Cell‐Permeable Caged Phosphates that Can Be Photolyzed by Visible Light or 800 nm Two‐Photon Photolysis , 2013, Chembiochem : a European journal of chemical biology.

[3]  D. Ogden,et al.  Two-photon "caging" groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups. , 2015, Organic letters.

[4]  G. Ellis‐Davies,et al.  Caged compounds: photorelease technology for control of cellular chemistry and physiology , 2007, Nature Methods.

[5]  V. Pillai Photoremovable Protecting Groups in Organic Synthesis , 1980 .

[6]  A. Dreuw,et al.  Emission turn-on and solubility turn-off in conjugated polymers: one- and two-photon-induced removal of fluorescence-quenching solubilizing groups. , 2015, Macromolecular rapid communications.

[7]  David Ogden,et al.  From one-photon to two-photon probes: "caged" compounds, actuators, and photoswitches. , 2013, Angewandte Chemie.

[8]  Alexandre Specht,et al.  Photochemical tools to study dynamic biological processes , 2009, HFSP journal.

[9]  N. Abbott,et al.  Using Light to Control Dynamic Surface Tensions of Aqueous Solutions of Water Soluble Surfactants , 1999 .

[10]  Yang Jiao,et al.  Near-infrared light-controlled drug release and cancer therapy with polymer-caged upconversion nanoparticles , 2015 .

[11]  Emily A. Smith,et al.  BODIPY-derived photoremovable protecting groups unmasked with green light. , 2015, Journal of the American Chemical Society.

[12]  E M Callaway,et al.  Brominated 7-hydroxycoumarin-4-ylmethyls: photolabile protecting groups with biologically useful cross-sections for two photon photolysis. , 1999, Proceedings of the National Academy of Sciences of the United States of America.

[13]  M. Blanchard‐Desce,et al.  Cooperative dyads for two-photon uncaging. , 2015, Organic letters.

[14]  Kristi S. Anseth,et al.  Photodegradable Hydrogels for Dynamic Tuning of Physical and Chemical Properties , 2009, Science.

[15]  P. Dunkel,et al.  Quinoline-derived two-photon sensitive quadrupolar probes. , 2014, Organic & biomolecular chemistry.

[16]  Shanshan Huang,et al.  Near-infrared light-triggered micelles for fast controlled drug release in deep tissue. , 2013, Biomaterials.

[17]  A. Heckel,et al.  Light-controlled tools. , 2012, Angewandte Chemie.

[18]  G. Ellis‐Davies,et al.  Caged compounds for multichromic optical interrogation of neural systems , 2015, The European journal of neuroscience.

[19]  A. Almutairi,et al.  Increasing materials' response to two-photon NIR light via self-immolative dendritic scaffolds. , 2012, Chemical communications.

[20]  Mathieu L. Viger,et al.  Highest Efficiency Two-Photon Degradable Copolymer for Remote Controlled Release. , 2013, ACS macro letters.

[21]  Adah Almutairi,et al.  In vivo visible light-triggered drug release from an implanted depot , 2014, Chemical science.

[22]  D. Ogden,et al.  New Photoremovable Protecting Groups for Carboxylic Acids with High Photolytic Efficiencies at Near‐UV Irradiation. Application to the Photocontrolled Release of L‐Glutamate , 2006, Chembiochem : a European journal of chemical biology.

[23]  J. Nicoud,et al.  Molecular engineering of photoremovable protecting groups for two-photon uncaging. , 2008, Angewandte Chemie.

[24]  P. Neveu,et al.  Two-photon uncaging with the efficient 3,5-dibromo-2,4-dihydroxycinnamic caging group. , 2007, Angewandte Chemie.

[25]  André Nadler,et al.  Caged lipids as tools for investigating cellular signaling. , 2014, Biochimica et biophysica acta.

[26]  A. del Campo,et al.  A Polyurethane-Based Positive Photoresist. , 2014, Macromolecular rapid communications.

[27]  Philip M Bennett,et al.  Model dyads for 2PA uncaging of a protecting group via photoinduced electron transfer. , 2015, Physical chemistry chemical physics : PCCP.

[28]  Fuyou Li,et al.  Spatiotemporally Controllable and Cytocompatible Approach Builds 3D Cell Culture Matrix by Photo‐Uncaged‐Thiol Michael Addition Reaction , 2014, Advanced materials.

[29]  T. M. Dore,et al.  Brominated hydroxyquinoline as a photolabile protecting group with sensitivity to multiphoton excitation. , 2002, Organic letters.

[30]  S. P. Fodor,et al.  Light-directed, spatially addressable parallel chemical synthesis. , 1991, Science.

[31]  D. Wan,et al.  Micropatterning of polymethacrylates by single- or two-photon irradiation using π-conjugated o-nitrobenzyl ester phototrigger as side chains , 2013 .

[32]  R. Tampé,et al.  Three-dimensional protein networks assembled by two-photon activation. , 2014, Angewandte Chemie.

[33]  R. Givens,et al.  Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy , 2012, Chemical reviews.

[34]  H. Kasai,et al.  Caged glutamates with π-extended 1,2-dihydronaphthalene chromophore: design, synthesis, two-photon absorption property, and photochemical reactivity. , 2014, The Journal of organic chemistry.

[35]  R. Wombacher,et al.  Light-induced protein dimerization by one- and two-photon activation of gibberellic acid derivatives in living cells. , 2015, Angewandte Chemie.

[36]  Maria Goeppert-Mayer Über Elementarakte mit zwei Quantensprüngen , 1931 .

[37]  P. Neveu,et al.  Two-photon uncaging with fluorescence reporting: evaluation of the o-hydroxycinnamic platform. , 2007, Journal of the American Chemical Society.

[38]  R. Etchenique,et al.  Multiphoton reactive surfaces using ruthenium(II) photocleavable cages. , 2012, Langmuir : the ACS journal of surfaces and colloids.

[39]  Linyong Zhu,et al.  Styryl conjugated coumarin caged alcohol: efficient photorelease by either one-photon long wavelength or two-photon NIR excitation. , 2012, Organic letters.

[40]  Sylvie Maurin,et al.  Coumarinylmethyl caging groups with redshifted absorption. , 2013, Chemistry.

[41]  Fuyou Li,et al.  Anticancer drug release from a mesoporous silica based nanophotocage regulated by either a one- or two-photon process. , 2010, Journal of the American Chemical Society.

[42]  Min Suk Shim,et al.  Engineered photo-responsive materials for near-infrared-triggered drug delivery , 2015 .

[43]  C. Katan,et al.  Synthesis and photochemical reactivity of caged glutamates with a π-extended coumarin chromophore as a photolabile protecting group , 2013 .

[44]  John-Christopher Boyer,et al.  Near-infrared light-triggered dissociation of block copolymer micelles using upconverting nanoparticles. , 2011, Journal of the American Chemical Society.

[45]  Sébastien Charon,et al.  The donor–acceptor biphenyl platform: A versatile chromophore for the engineering of highly efficient two-photon sensitive photoremovable protecting groups , 2012, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[46]  G. Ellis‐Davies,et al.  Optically selective two-photon uncaging of glutamate at 900 nm. , 2013, Journal of the American Chemical Society.

[47]  E. Schlaeger,et al.  Synthesis, structure, and reactivity of adenosine cyclic 3',5'-phosphate-benzyltriesters , 1977 .

[48]  Yasushi Miyashita,et al.  Dendritic spine geometry is critical for AMPA receptor expression in hippocampal CA1 pyramidal neurons , 2001, Nature Neuroscience.

[49]  M. Blanchard‐Desce,et al.  Octupolar chimeric compounds built from quinoline caged acetate moieties: a novel approach for 2-photon uncaging of biomolecules , 2013 .

[50]  A. del Campo,et al.  Dual Photosensitive Polymers with Wavelength‐Selective Photoresponse , 2014, Advanced materials.

[51]  J. Kaplan,et al.  Rapid photolytic release of adenosine 5'-triphosphate from a protected analogue: utilization by the Na:K pump of human red blood cell ghosts. , 1978, Biochemistry.

[52]  Christopher M. Pavlos,et al.  8-Bromo-7-hydroxyquinoline as a photoremovable protecting group for physiological use: mechanism and scope. , 2006, Journal of the American Chemical Society.

[53]  Yue Zhao,et al.  Light-Responsive Block Copolymer Micelles , 2012 .

[54]  Water-soluble, donor-acceptor biphenyl derivatives in the 2-(o-nitrophenyl)propyl series: highly efficient two-photon uncaging of the neurotransmitter γ-aminobutyric acid at λ = 800 nm. , 2012, Angewandte Chemie.

[55]  J. Allard,et al.  A new two-photon-sensitive block copolymer nanocarrier. , 2009, Angewandte Chemie.

[56]  Ludovic Jullien,et al.  How to control proteins with light in living systems. , 2014, Nature chemical biology.

[57]  Masamitsu Shirai,et al.  Photobase generators: Recent progress and application trend in polymer systems , 2009 .

[58]  Yang Jiao,et al.  Coumarin-containing photo-responsive nanocomposites for NIR light-triggered controlled drug release via a two-photon process. , 2013, Journal of materials chemistry. B.

[59]  Jiaxi Cui,et al.  Light-triggered multifunctionality at surfaces mediated by photolabile protecting groups. , 2013, Macromolecular rapid communications.

[60]  H. Adesnik,et al.  Optogenetic pharmacology for control of native neuronal signaling proteins , 2013, Nature Neuroscience.

[61]  H. Tian,et al.  Building Biomedical Materials using Photochemical Bond Cleavage , 2015, Advanced materials.

[62]  K. Ruud,et al.  Chemical control of channel interference in two-photon absorption processes. , 2014, Accounts of chemical research.

[63]  W. Denk,et al.  Deep tissue two-photon microscopy , 2005, Nature Methods.