Photocontrolled release using one-photon absorption of visible or NIR light.

Light is an excellent means to externally control the properties of materials and small molecules for many applications. Light's ability to initiate chemistries largely independent of a material's local environment makes it particularly useful as a bio-orthogonal and on-demand trigger in living systems. Materials responsive to UV light are widely reported in the literature; however, UV light has substantial limitations for in vitro and in vivo applications. Many biological molecules absorb these energetic wavelengths directly, not only preventing substantial tissue penetration but also causing detrimental photochemical reactions. The more innocuous nature of long-wavelength light (>400nm) and its ability at longer wavelengths (600-950nm) to effectively penetrate tissues is ideal for biological applications. Multi-photon processes (e.g. two-photon excitation and upconversion) using longer wavelength light, often in the near-infrared (NIR) range, have been proposed as a means of avoiding the negative characteristics of UV light. However, high-power focused laser light and long irradiation times are often required to initiate photorelease using these inefficient non-linear optical methods, limiting their in vivo use in mammalian tissues where NIR light is readily scattered. The development of materials that efficiently convert a single photon of long-wavelength light to chemical change is a viable solution to achieve in vivo photorelease. However, to date only a few such materials have been reported. Here we review current technologies for photo-regulated release using photoactive organic materials that directly absorb visible and NIR light.

[1]  S. Mukhopadhyay,et al.  1-Acetylpyrene-salicylic acid: photoresponsive fluorescent organic nanoparticles for the regulated release of a natural antimicrobial compound, salicylic acid. , 2014, ACS applied materials & interfaces.

[2]  Pengcheng Zhu,et al.  Perylene-derived single-component organic nanoparticles with tunable emission: efficient anticancer drug carriers with real-time monitoring of drug release. , 2014, ACS nano.

[3]  Yue Zhao,et al.  Fast Photodegradable Block Copolymer Micelles for Burst Release , 2011 .

[4]  Robert H Pierce,et al.  Polyketal copolymers: a new acid-sensitive delivery vehicle for treating acute inflammatory diseases. , 2008, Bioconjugate chemistry.

[5]  Xinjing Tang,et al.  Synthesis of Light-Induced Expandable Photoresponsive Polymeric Nanoparticles for Triggered Release. , 2013, ChemPlusChem.

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

[7]  Moses Bio,et al.  Click and photo-unclick chemistry of aminoacrylate for visible light-triggered drug release. , 2012, Chemical communications.

[8]  Frank A. Leibfarth,et al.  Photoswitching using visible light: a new class of organic photochromic molecules. , 2014, Journal of the American Chemical Society.

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

[10]  Linyong Zhu,et al.  Highly Discriminating Photorelease of Anticancer Drugs Based on Hypoxia Activatable Phototrigger Conjugated Chitosan Nanoparticles , 2013, Advanced materials.

[11]  A. N. Bashkatov,et al.  Optical properties of human skin, subcutaneous and mucous tissues in the wavelength range from 400 to 2000 nm , 2005 .

[12]  Robert Langer,et al.  pH-Responsive Polymer Microspheres: Rapid Release of Encapsulated Material within the Range of Intracellular pH** , 2001 .

[13]  A. Mueller,et al.  Visible-Light-Stimulated Destabilization of PEG-Liposomes , 2000 .

[14]  Yi Li,et al.  Stabilized vesicles consisting of small amphiphiles for stepwise photorelease via UV light. , 2012, Langmuir : the ACS journal of surfaces and colloids.

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

[16]  Kristi S. Anseth,et al.  Photocontrolled Nanoparticles for On-Demand Release of Proteins , 2012, Biomacromolecules.

[17]  V. Ahsen,et al.  Light-triggered liposomal release: membrane permeabilization by photodynamic action. , 2010, Langmuir : the ACS journal of surfaces and colloids.

[18]  Vincent M Rotello,et al.  Gold nanoparticles in delivery applications. , 2008, Advanced drug delivery reviews.

[19]  D. Kohane,et al.  Shedding light on nanomedicine. , 2012, Wiley interdisciplinary reviews. Nanomedicine and nanobiotechnology.

[20]  Toyoichi Tanaka,et al.  Phase transition in polymer gels induced by visible light , 1990, Nature.

[21]  A. C. Mitchell,et al.  Fast laser-induced solute release from liposomes sensitized with photochromic lipid: effects of temperature, lipid host, and sensitizer concentration. , 1999, Biochemical and biophysical research communications.

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

[23]  A. Mourot,et al.  Two-photon uncaging: New prospects in neuroscience and cellular biology. , 2010, Bioorganic & medicinal chemistry.

[24]  Ying Li,et al.  Dual redox responsive assemblies formed from diselenide block copolymers. , 2010, Journal of the American Chemical Society.

[25]  Roberto Etchenique,et al.  A New Inorganic Photolabile Protecting Group for Highly Efficient Visible Light GABA Uncaging , 2007, Chembiochem : a European journal of chemical biology.

[26]  Adah Almutairi,et al.  UV and near-IR triggered release from polymeric nanoparticles. , 2010, Journal of the American Chemical Society.

[27]  S. Ghosh,et al.  1-(Hydroxyacetyl)pyrene a new fluorescent phototrigger for cell imaging and caging of alcohols, phenol and adenosine , 2012, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[28]  Kyle E Broaders,et al.  Acetal-derivatized dextran: an acid-responsive biodegradable material for therapeutic applications. , 2008, Journal of the American Chemical Society.

[29]  E. Gillies,et al.  Dendrimersomes with photodegradable membranes for triggered release of hydrophilic and hydrophobic cargo. , 2014, Chemical communications.

[30]  M. Steinmetz,et al.  Photochemical cyclization with release of carboxylic acids and phenol from pyrrolidino-substituted 1,4-benzoquinones using visible light. , 2005, Organic letters.

[31]  Michael E. Hahn,et al.  Enzyme-directed assembly and manipulation of organic nanomaterials. , 2011, Chemical communications.

[32]  Mostafa A. El-Sayed,et al.  The golden age: gold nanoparticles for biomedicine. , 2012, Chemical Society reviews.

[33]  P. Neveu,et al.  o-nitrobenzyl photolabile protecting groups with red-shifted absorption: syntheses and uncaging cross-sections for one- and two-photon excitation. , 2006, Chemistry.

[34]  D. Hammer,et al.  Caging Metal Ions with Visible Light-Responsive Nanopolymersomes , 2014, Langmuir : the ACS journal of surfaces and colloids.

[35]  C. Miller,et al.  Visible light‐induced destabilization of endocytosed liposomes , 2000, FEBS letters.

[36]  P. Prasad,et al.  Upconversion Nanoparticles: Design, Nanochemistry, and Applications in Theranostics , 2014, Chemical reviews.

[37]  A. G. Bosanquet,et al.  Chlorambucil: stability of solutions during preparation and storage , 2004, Cancer Chemotherapy and Pharmacology.

[38]  N. Gagey-Eilstein,et al.  A blue-absorbing photolabile protecting group for in vivo chromatically orthogonal photoactivation. , 2013, ACS chemical biology.

[39]  Victor S-Y Lin,et al.  Functionalized mesoporous silica nanoparticle-based visible light responsive controlled release delivery system. , 2011, Chemical communications.

[40]  T. K. Maiti,et al.  Perylene-3-ylmethanol: fluorescent organic nanoparticles as a single-component photoresponsive nanocarrier with real-time monitoring of anticancer drug release. , 2012, Journal of the American Chemical Society.

[41]  Youngjae You,et al.  Far-Red Light Activatable, Multifunctional Prodrug for Fluorescence Optical Imaging and Combinational Treatment , 2014, Journal of medicinal chemistry.

[42]  Adah Almutairi,et al.  Photochemical mechanisms of light-triggered release from nanocarriers. , 2012, Advanced drug delivery reviews.

[43]  G. Fleming,et al.  Synthetic micelle sensitive to IR light via a two-photon process. , 2005, Journal of the American Chemical Society.

[44]  J. Sunamoto,et al.  Liposomal membranes. 13. Transport of an amino acid across liposomal bilayers as mediated by a photoresponsive carrier , 1982 .

[45]  M. Saraste,et al.  FEBS Lett , 2000 .

[46]  Masahiro Irie,et al.  Diarylethenes for Memories and Switches. , 2000, Chemical reviews.

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

[48]  Andrew A. Beharry,et al.  Azobenzene photoswitching without ultraviolet light. , 2011, Journal of the American Chemical Society.

[49]  D. Valenzeno,et al.  THE ROLE OF SINGLET OXYGEN IN PHOTOOXIDATION OF EXCITABLE CELL MEMBRANES , 1979, Photochemistry and photobiology.

[50]  Moses Bio,et al.  Low energy light-triggered oxidative cleavage of olefins , 2009 .

[51]  Daniel T Chiu,et al.  Laser photolysis of dye-sensitized nanocapsules occurs via a photothermal pathway. , 2009, Journal of the American Chemical Society.

[52]  Liang Yan,et al.  Recent Advances in Design and Fabrication of Upconversion Nanoparticles and Their Safe Theranostic Applications , 2013, Advanced materials.

[53]  K. Gee,et al.  Toward the development of new photolabile protecting groups that can rapidly release bioactive compounds upon photolysis with visible light. , 2003, The Journal of organic chemistry.

[54]  S. Samanta,et al.  Photoswitching of ortho-substituted azonium ions by red light in whole blood. , 2013, Angewandte Chemie.

[55]  Lisa Pakstis,et al.  Stimuli-responsive polypeptide vesicles by conformation-specific assembly , 2004, Nature materials.

[56]  N. Branda,et al.  Two colors of light are needed to break bonds and release small molecules from the surface of SiO2-Au core-shell nanoparticles. , 2015, Journal of the American Chemical Society.

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

[58]  K. Landfester,et al.  Patchy nanocapsules of poly(vinylferrocene)-based block copolymers for redox-responsive release. , 2012, ACS nano.

[59]  Samuel G. Awuah,et al.  Site-specific and far-red-light-activatable prodrug of combretastatin A-4 using photo-unclick chemistry. , 2013, Journal of medicinal chemistry.

[60]  Karen L Wooley,et al.  Design of polymeric nanoparticles for biomedical delivery applications. , 2012, Chemical Society reviews.

[61]  Rein V. Ulijn,et al.  Enzyme responsive materials: design strategies and future developments. , 2013, Biomaterials science.

[62]  D. Dolphin,et al.  Site-specific prodrug release using visible light. , 2008, Journal of the American Chemical Society.

[63]  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.

[64]  David H. Thompson,et al.  Cascade liposomal triggering: light-induced Ca2+ release from diplasmenylcholine liposomes triggers PLA2-catalyzed hydrolysis and contents leakage from DPPC liposomes. , 1998, Bioconjugate chemistry.

[65]  Samuel G. Awuah,et al.  Visible Light Controlled Release of Anticancer Drug through Double Activation of Prodrug. , 2013, ACS medicinal chemistry letters.

[66]  J. Ji,et al.  Near-infrared light-sensitive micelles for enhanced intracellular drug delivery , 2012 .

[67]  P. Klán,et al.  Fluorescein analogues as photoremovable protecting groups absorbing at ∼520 nm. , 2013, The Journal of organic chemistry.

[68]  Samuel G. Awuah,et al.  Folate Receptor-Mediated Enhanced and Specific Delivery of Far-Red Light-Activatable Prodrugs of Combretastatin A-4 to FR-Positive Tumor , 2014, Bioconjugate chemistry.

[69]  David S Lawrence,et al.  Illuminating the chemistry of life: design, synthesis, and applications of "caged" and related photoresponsive compounds. , 2009, ACS chemical biology.

[70]  Carmen Alvarez-Lorenzo,et al.  Light‐sensitive Intelligent Drug Delivery Systems † , 2009, Photochemistry and photobiology.

[71]  Kyle E Broaders,et al.  A biocompatible oxidation-triggered carrier polymer with potential in therapeutics. , 2011, Journal of the American Chemical Society.

[72]  V. Hagen,et al.  Deactivation behavior and excited-state properties of (coumarin-4-yl)methyl derivatives. 2. Photocleavage of selected (coumarin-4-yl)methyl-caged adenosine cyclic 3',5'-monophosphates with fluorescence enhancement. , 2002, The Journal of organic chemistry.

[73]  Weiling Fu,et al.  Visible light mediated killing of multidrug-resistant bacteria using photoacids. , 2013, Journal of materials chemistry. B.

[74]  D. Thompson,et al.  Triggerable plasmalogen liposomes: improvement of system efficiency. , 1996, Biochimica et biophysica acta.

[75]  R. Martínez‐Máñez,et al.  Photochemical and Chemical Two‐Channel Control of Functional Nanogated Hybrid Architectures , 2007 .

[76]  D. Strohecker,et al.  Negative photochromism of a TCF chromophore. , 2011, Chemical communications.

[77]  Mako Kamiya,et al.  Boron dipyrromethene as a fluorescent caging group for single-photon uncaging with long-wavelength visible light. , 2014, ACS chemical biology.

[78]  Guoying Zhang,et al.  Self-immolative polymersomes for high-efficiency triggered release and programmed enzymatic reactions. , 2014, Journal of the American Chemical Society.

[79]  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.

[80]  R. Haag,et al.  Photoresponsive amphiphiles based on azobenzene-dendritic glycerol conjugates show switchable transport behavior. , 2011, Chemical communications.

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

[82]  J. Stenhouse Ueber die Oele, die bei der Einwirkung der Schwefelsäure auf verschiedene Vegetabilien entstehen , 1850 .

[83]  H. Nishihara,et al.  Extremely efficient and reversible visible-light photochromism and accompanying switch of electronic communication in N-phenylcarbazole-appended diethynylethene. , 2012, Chemistry.

[84]  Dakrong Pissuwan,et al.  Therapeutic possibilities of plasmonically heated gold nanoparticles. , 2006, Trends in biotechnology.

[85]  R. Jain,et al.  Photodynamic therapy for cancer , 2003, Nature Reviews Cancer.

[86]  Günter Mayer,et al.  Biologically active molecules with a "light switch". , 2006, Angewandte Chemie.

[87]  J. Fréchet,et al.  pH-Responsive copolymer assemblies for controlled release of doxorubicin. , 2005, Bioconjugate chemistry.

[88]  Krzysztof Matyjaszewski,et al.  Light-induced reversible formation of polymeric micelles. , 2007, Angewandte Chemie.

[89]  Jean-François Gohy,et al.  Synthesis and self-assembly of diblock copolymers bearing 2-nitrobenzyl photocleavable side groups† , 2012 .

[90]  R. S. Foote,et al.  Photolabile protecting groups for nucleosides: Synthesis and photodeprotection rates , 1997 .

[91]  C. Näther,et al.  Highly efficient reversible Z-E photoisomerization of a bridged azobenzene with visible light through resolved S(1)(n pi*) absorption bands. , 2009, Journal of the American Chemical Society.

[92]  Peng Wang,et al.  Photodegradable polyurethane self-assembled nanoparticles for photocontrollable release. , 2012, Langmuir : the ACS journal of surfaces and colloids.

[93]  Avijit Jana,et al.  Perylen-3-ylmethyl: fluorescent photoremovable protecting group (FPRPG) for carboxylic acids and alcohols , 2012 .

[94]  N. Branda,et al.  From slow to fast--the user controls the rate of the release of molecules from masked forms using a photoswitch and different types of light. , 2015, Chemical communications.

[95]  D. Strohecker,et al.  Long-lived photoacid based upon a photochromic reaction. , 2011, Journal of the American Chemical Society.

[96]  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.

[97]  Yuichi Ohya,et al.  Photo-sensitive lipid membrane perturbation by a single chain lipid having terminal spiropyran group , 1998 .

[98]  Petras Juzenas,et al.  Noninvasive fluorescence excitation spectroscopy during application of 5-aminolevulinic acid in vivo , 2002, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[99]  Avijit Jana,et al.  1-Acetylpyrene with dual functions as an environment-sensitive fluorophore and fluorescent photoremovable protecting group , 2010 .

[100]  U. Steiner,et al.  Intramolecular sensitization of photocleavage of the photolabile 2-(2-nitrophenyl)propoxycarbonyl (NPPOC) protecting group: photoproducts and photokinetics of the release of nucleosides. , 2008, Chemistry.

[101]  G. Ellis‐Davies Two-photon microscopy for chemical neuroscience. , 2011, ACS chemical neuroscience.

[102]  G. G. Stokes "J." , 1890, The New Yale Book of Quotations.

[103]  M. Steinmetz,et al.  Photoactivation of amino-substituted 1,4-benzoquinones for release of carboxylate and phenolate leaving groups using visible light. , 2006, The Journal of organic chemistry.

[104]  Jinming Hu,et al.  Enzyme-responsive polymeric assemblies, nanoparticles and hydrogels. , 2012, Chemical Society reviews.

[105]  Naoto Tamai,et al.  Ultrafast Dynamics of Photochromic Systems. , 2000, Chemical reviews.

[106]  N. Branda,et al.  Selective and sequential photorelease using molecular switches. , 2006, Angewandte Chemie.

[107]  Didier Merlin,et al.  Orally delivered thioketal nanoparticles loaded with TNF-α-siRNA target inflammation and inhibit gene expression in the intestines. , 2010, Nature materials.

[108]  Jingwen He,et al.  Photo-responsive reversible micelles based on azobenzene-modified poly(carbonate)s via azide–alkyne click chemistry , 2014 .

[109]  V. Tropepe,et al.  Photoswitching azo compounds in vivo with red light. , 2013, Journal of the American Chemical Society.

[110]  Yingchun Zhu,et al.  Installing dynamic molecular photomechanics in mesopores: a multifunctional controlled-release nanosystem. , 2007, Angewandte Chemie.

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

[112]  Dongyun Chen,et al.  Light-triggered reversible assemblies of azobenzene-containing amphiphilic copolymer with β-cyclodextrin-modified hollow mesoporous silica nanoparticles for controlled drug release. , 2012, Chemical communications.

[113]  J. Pooler PHOTOOXIDATION OF CELL MEMBRANES USING EOSIN DERIVATIVES THAT LOCATE IN LIPID OR PROTEIN TO STUDY THE ROLE OF DIFFUSIBLE INTERMEDIATES , 1989, Photochemistry and photobiology.

[114]  Evan W. Miller,et al.  meso-Methylhydroxy BODIPY: a scaffold for photo-labile protecting groups. , 2015, Chemical communications.

[115]  Wei Liu,et al.  UV- and NIR-responsive polymeric nanomedicines for on-demand drug delivery , 2013 .

[116]  Omid C Farokhzad,et al.  pH-Responsive nanoparticles for drug delivery. , 2010, Molecular pharmaceutics.

[117]  Xiaobing Zhang,et al.  Photon-manipulated drug release from a mesoporous nanocontainer controlled by azobenzene-modified nucleic acid. , 2012, ACS nano.

[118]  Miss A.O. Penney (b) , 1974, The New Yale Book of Quotations.

[119]  Valentine K. Johns,et al.  Visible-light-responsive reversible photoacid based on a metastable carbanion. , 2014, Chemistry.

[120]  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.

[121]  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.

[122]  Linyong Zhu,et al.  Photocleavable coumarin crosslinkers based polystyrene microgels: phototriggered swelling and release , 2012 .

[123]  S. Nie,et al.  Therapeutic Nanoparticles for Drug Delivery in Cancer Types of Nanoparticles Used as Drug Delivery Systems , 2022 .

[124]  H. Sung,et al.  Current Progress in Reactive Oxygen Species (ROS)‐Responsive Materials for Biomedical Applications , 2013, Advanced healthcare materials.

[125]  D. Thompson,et al.  Triggered release of hydrophilic agents from plasmalogen liposomes using visible light or acid. , 1992, Biochimica et biophysica acta.

[126]  Jeffrey I Zink,et al.  Light-activated nanoimpeller-controlled drug release in cancer cells. , 2008, Small.

[127]  Dirk Trauner,et al.  Photochemical tools for remote control of ion channels in excitable cells , 2005, Nature chemical biology.

[128]  Jayanth Panyam,et al.  Biodegradable nanoparticles for drug and gene delivery to cells and tissue. , 2003, Advanced drug delivery reviews.

[129]  T. Kunitake,et al.  PHOTORESPONSIVE MEMBRANES. REGULATION OF MEMBRANE PROPERTIES BY PHOTOREVERSIBLE cis–trans ISOMERIZATION OF AZOBENZENES , 1980 .

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

[131]  Daniel T Chiu,et al.  Spectrally tunable uncaging of biological stimuli from nanocapsules. , 2008, Chemical communications.

[132]  S. Sortino Photoactivated nanomaterials for biomedical release applications , 2012 .

[133]  N. Branda,et al.  Controlling a polymer adhesive using light and a molecular switch. , 2014, Journal of the American Chemical Society.

[134]  S. Hecht,et al.  o-Fluoroazobenzenes as readily synthesized photoswitches offering nearly quantitative two-way isomerization with visible light. , 2012, Journal of the American Chemical Society.

[135]  Yong Zhang,et al.  Photocontrolled nanoparticle delivery systems for biomedical applications. , 2014, Accounts of chemical research.

[136]  Jyothi U. Menon,et al.  Nanomaterials for Photo-Based Diagnostic and Therapeutic Applications , 2013, Theranostics.

[137]  Jeffrey I. Zink,et al.  Photo-Driven Expulsion of Molecules from Mesostructured Silica Nanoparticles , 2007 .

[138]  S. Mackem,et al.  A Near-IR Uncaging Strategy Based on Cyanine Photochemistry , 2014, Journal of the American Chemical Society.

[139]  A photo-degradable gene delivery system for enhanced nuclear gene transcription. , 2014, Biomaterials.