Abstract

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.

© 2016 Optical Society of America

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2015 (12)

P. P. Goswami, A. Syed, C. L. Beck, T. R. Albright, K. M. Mahoney, R. Unash, E. A. Smith, and A. H. Winter, “BODIPY-Derived Photoremovable Protecting Groups Unmasked with Green Light,” J. Am. Chem. Soc. 137(11), 3783–3786 (2015).
[Crossref] [PubMed]

C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-Photon “Caging” Groups: Effect of Position Isomery on the Photorelease Properties of Aminoquinoline-Derived Photolabile Protecting Groups,” Org. Lett. 17(3), 402–405 (2015).
[Crossref] [PubMed]

E. J. Cueto Díaz, S. Picard, V. Chevasson, J. Daniel, V. Hugues, O. Mongin, E. Genin, and M. Blanchard-Desce, “Cooperative Dyads for Two-Photon Uncaging,” Org. Lett. 17(1), 102–105 (2015).
[Crossref] [PubMed]

A. I. Ciuciu, K. A. Korzycka, W. J. M. Lewis, P. M. Bennett, H. L. Anderson, and L. Flamigni, “Model dyads for 2PA uncaging of a protecting group via photoinduced electron transfer,” Phys. Chem. Chem. Phys. 17(9), 6554–6564 (2015).
[Crossref] [PubMed]

K. A. Korzycka, P. M. Bennett, E. J. Cueto-Diaz, G. Wicks, M. Drobizhev, M. Blanchard-Desce, A. Rebane, and H. L. Anderson, “Two-photon sensitive protecting groups operating via intramolecular electron transfer: uncaging of GABA and tryptophan,” Chem. Sci. (Camb.) 6(4), 2419–2426 (2015).
[Crossref]

J. M. Amatrudo, J. P. Olson, H. K. Agarwal, and G. C. R. Ellis-Davies, “Caged compounds for multichromic optical interrogation of neural systems,” Eur. J. Neurosci. 41(1), 5–16 (2015).
[Crossref] [PubMed]

K. M. Schelkle, T. Griesbaum, D. Ollech, S. Becht, T. Buckup, M. Hamburger, and R. Wombacher, “Light-Induced Protein Dimerization by One- and Two-Photon Activation of Gibberellic Acid Derivatives in Living Cells,” Angew. Chem. Int. Ed. Engl. 54(9), 2825–2829 (2015).
[Crossref] [PubMed]

H. J. Cho, M. Chung, and M. S. Shim, “Engineered photo-responsive materials for near-infrared-triggered drug delivery,” J. Ind. Eng. Chem. 31, 15–25 (2015).
[Crossref]

C. Bao, L. Zhu, Q. Lin, and H. Tian, “Building biomedical materials using photochemical bond cleavage,” Adv. Mater. 27(10), 1647–1662 (2015).
[Crossref] [PubMed]

Q. Xing, N. Li, Y. Jiao, D. Chen, J. Xu, Q. Xu, and J. Lu, “Near-infrared light-controlled drug release and cancer therapy with polymer-caged upconversion nanoparticles,” RSC Advances 5(7), 5269–5276 (2015).
[Crossref]

C.-J. Carling, M. L. Viger, V. A. Huu, A. V. Garcia, and A. Almutairi, “In vivo visible light-triggered drug release from an implanted depot,” Chem. Sci. (Camb.) 6(1), 335–341 (2015).
[Crossref] [PubMed]

K. M. Schelkle, S. Becht, S. Faraji, M. Petzoldt, K. Müllen, T. Buckup, A. Dreuw, M. Motzkus, and M. Hamburger, “Emission turn-on and solubility turn-off in conjugated polymers: one- and two-photon-induced removal of fluorescence-quenching solubilizing groups,” Macromol. Rapid Commun. 36(1), 31–37 (2015).
[Crossref] [PubMed]

2014 (9)

Z. Liu, Q. Lin, Y. Sun, T. Liu, C. Bao, F. Li, and L. Zhu, “Spatiotemporally Controllable and Cytocompatible Approach Builds 3D Cell Culture Matrix by Photo-Uncaged-Thiol Michael Addition Reaction,” Adv. Mater. 26(23), 3912–3917 (2014).
[Crossref] [PubMed]

V. Gatterdam, R. Ramadass, T. Stoess, M. A. H. Fichte, J. Wachtveitl, A. Heckel, and R. Tampé, “Three-dimensional protein networks assembled by two-photon activation,” Angew. Chem. Int. Ed. Engl. 53(22), 5680–5684 (2014).
[Crossref] [PubMed]

D. Höglinger, A. Nadler, and C. Schultz, “Caged lipids as tools for investigating cellular signaling,” Biochim. Biophys. Acta 1841(8), 1085–1096 (2014).
[Crossref] [PubMed]

L. García-Fernández, C. Herbivo, V. S. M. Arranz, D. Warther, L. Donato, A. Specht, and A. del Campo, “Dual photosensitive polymers with wavelength-selective photoresponse,” Adv. Mater. 26(29), 5012–5017 (2014).
[Crossref] [PubMed]

L. García-Fernández, A. Specht, and A. Del Campo, “A Polyurethane-Based Positive Photoresist,” Macromol. Rapid Commun. 35(20), 1801–1807 (2014).
[Crossref] [PubMed]

M. M. Alam, M. Chattopadhyaya, S. Chakrabarti, and K. Ruud, “Chemical Control of Channel Interference in Two-Photon Absorption Processes,” Acc. Chem. Res. 47(5), 1604–1612 (2014).
[Crossref] [PubMed]

P. Dunkel, C. Tran, T. Gallavardin, H. Dhimane, D. Ogden, and P. I. Dalko, “Quinoline-derived two-photon sensitive quadrupolar probes,” Org. Biomol. Chem. 12(48), 9899–9908 (2014).
[Crossref] [PubMed]

S. Boinapally, B. Huang, M. Abe, C. Katan, J. Noguchi, S. Watanabe, H. Kasai, B. Xue, and T. Kobayashi, “Caged Glutamates with π-Extended 1,2-Dihydronaphthalene Chromophore: Design, Synthesis, Two-Photon Absorption Property, and Photochemical Reactivity,” J. Org. Chem. 79(17), 7822–7830 (2014).
[Crossref] [PubMed]

A. Gautier, C. Gauron, M. Volovitch, D. Bensimon, L. Jullien, and S. Vriz, “How to control proteins with light in living systems,” Nat. Chem. Biol. 10(7), 533–541 (2014).
[Crossref] [PubMed]

2013 (13)

R. H. Kramer, A. Mourot, and H. Adesnik, “Optogenetic pharmacology for control of native neuronal signaling proteins,” Nat. Neurosci. 16(7), 816–823 (2013).
[Crossref] [PubMed]

G. Bort, T. Gallavardin, D. Ogden, and P. I. Dalko, “From one-photon to two-photon probes: “caged” compounds, actuators, and photoswitches,” Angew. Chem. Int. Ed. Engl. 52(17), 4526–4537 (2013).
[Crossref] [PubMed]

P. Klán, T. Šolomek, C. G. Bochet, A. Blanc, R. Givens, M. Rubina, V. Popik, A. Kostikov, and J. Wirz, “Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy,” Chem. Rev. 113(1), 119–191 (2013).
[Crossref] [PubMed]

L. Fournier, I. Aujard, T. Le Saux, S. Maurin, S. Beaupierre, J.-B. Baudin, and L. Jullien, “Coumarinylmethyl Caging Groups with Redshifted Absorption,” Chemistry 19(51), 17494–17507 (2013).
[Crossref] [PubMed]

Y. Sakamoto, S. Boinapally, C. Katan, and M. Abe, “Synthesis and photochemical reactivity of caged glutamates with a π-extended coumarin chromophore as a photolabile protecting group,” Tetrahedron Lett. 54(52), 7171–7174 (2013).
[Crossref]

S. Picard, E. Genin, G. Clermont, V. Hugues, O. Mongin, and M. Blanchard-Desce, “Octupolar chimeric compounds built from quinoline caged acetate moieties: a novel approach for 2-photon uncaging of biomolecules,” New J. Chem. 37(12), 3899 (2013).
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W. Ji, N. Li, D. Chen, X. Qi, W. Sha, Y. Jiao, Q. Xu, and J. Lu, “Coumarin-containing photo-responsive nanocomposites for NIR light-triggered controlled drug release via a two-photon process,” J. Mater. Chem. B Mater. Biol. Med. 1(43), 5942 (2013).
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M. Jin, H. Xu, H. Hong, C. Bao, H. Pu, D. Wan, and L. Zhu, “Micropatterning of polymethacrylates by single- or two-photon irradiation using π-conjugated o -nitrobenzyl ester phototrigger as side chains,” J. Appl. Polym. Sci. 130, 4099–4106 (2013).

J. Cui, V. S. Miguel, and A. del Campo, “Light-Triggered Multifunctionality at Surfaces Mediated by Photolabile Protecting Groups,” Macromol. Rapid Commun. 34(4), 310–329 (2013).
[Crossref] [PubMed]

J. Olejniczak, J. Sankaranarayanan, M. L. Viger, and A. Almutairi, “Highest Efficiency Two-Photon Degradable Copolymer for Remote Controlled Release,” ACS Macro Lett. 2(8), 683–687 (2013).
[Crossref] [PubMed]

J. Cao, S. Huang, Y. Chen, S. Li, X. Li, D. Deng, Z. Qian, L. Tang, and Y. Gu, “Near-infrared light-triggered micelles for fast controlled drug release in deep tissue,” Biomaterials 34(26), 6272–6283 (2013).
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J. P. Olson, H.-B. Kwon, K. T. Takasaki, C. Q. Chiu, M. J. Higley, B. L. Sabatini, and G. C. R. Ellis-Davies, “Optically Selective Two-Photon Uncaging of Glutamate at 900 nm,” J. Am. Chem. Soc. 135(16), 5954–5957 (2013).
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C. Herbivo, Z. Omran, J. Revol, H. Javot, and A. Specht, “Synthesis and Characterization of Cell-Permeable Caged Phosphates that Can Be Photolyzed by Visible Light Or 800 nm Two-Photon Photolysis,” ChemBioChem 14(17), 2277–2283 (2013).
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2012 (8)

V. San Miguel, M. Álvarez, O. Filevich, R. Etchenique, and A. del Campo, “Multiphoton Reactive Surfaces Using Ruthenium(II) Photocleavable Cages,” Langmuir 28(2), 1217–1221 (2012).
[Crossref] [PubMed]

A. Specht, F. Bolze, L. Donato, C. Herbivo, S. Charon, D. Warther, S. Gug, J.-F. Nicoud, and M. Goeldner, “The donor-acceptor biphenyl platform: a versatile chromophore for the engineering of highly efficient two-photon sensitive photoremovable protecting groups,” Photochem. Photobiol. Sci. 11(3), 578–586 (2012).
[Crossref] [PubMed]

C. Bao, G. Fan, Q. Lin, B. Li, S. Cheng, Q. Huang, and L. Zhu, “Styryl Conjugated Coumarin Caged Alcohol: Efficient Photorelease by Either One-Photon Long Wavelength or Two-Photon NIR Excitation,” Org. Lett. 14(2), 572–575 (2012).
[Crossref] [PubMed]

C. Bao, M. Jin, B. Li, Y. Xu, J. Jin, and L. Zhu, “Long conjugated 2-nitrobenzyl derivative caged anticancer prodrugs with visible light regulated release: preparation and functionalizations,” Org. Biomol. Chem. 10(27), 5238–5244 (2012).
[Crossref] [PubMed]

N. Fomina, C. L. McFearin, and A. Almutairi, “Increasing materials’ response to two-photon NIR light via self-immolative dendritic scaffolds,” Chem. Commun. (Camb.) 48(73), 9138–9140 (2012).
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L. Donato, A. Mourot, C. M. Davenport, C. Herbivo, D. Warther, J. Léonard, F. Bolze, J.-F. Nicoud, R. H. Kramer, M. Goeldner, and A. Specht, “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,” Angew. Chem. Int. Ed. Engl. 51(8), 1840–1843 (2012).
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Y. Zhao, “Light-Responsive Block Copolymer Micelles,” Macromolecules 45(9), 3647–3657 (2012).
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C. Brieke, F. Rohrbach, A. Gottschalk, G. Mayer, and A. Heckel, “Light-Controlled Tools,” Angew. Chem. Int. Ed. Engl. 51(34), 8446–8476 (2012).
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2011 (1)

B. Yan, J.-C. Boyer, N. R. Branda, and Y. Zhao, “Near-Infrared Light-Triggered Dissociation of Block Copolymer Micelles Using Upconverting Nanoparticles,” J. Am. Chem. Soc. 133(49), 19714–19717 (2011).
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2010 (1)

Q. Lin, Q. Huang, C. Li, C. Bao, Z. Liu, F. Li, and L. Zhu, “Anticancer Drug Release from a Mesoporous Silica Based Nanophotocage Regulated by Either a One- or Two-Photon Process,” J. Am. Chem. Soc. 132(31), 10645–10647 (2010).
[Crossref] [PubMed]

2009 (4)

K. Suyama and M. Shirai, “Photobase generators: Recent progress and application trend in polymer systems,” Prog. Polym. Sci. 34(2), 194–209 (2009).
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A. M. Kloxin, A. M. Kasko, C. N. Salinas, and K. S. Anseth, “Photodegradable Hydrogels for Dynamic Tuning of Physical And Chemical Properties,” Science 324(5923), 59–63 (2009).
[Crossref] [PubMed]

J. Babin, M. Pelletier, M. Lepage, J.-F. Allard, D. Morris, and Y. Zhao, “A New Two-Photon-Sensitive Block Copolymer Nanocarrier,” Angew. Chem. Int. Ed. Engl. 48(18), 3329–3332 (2009).
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A. Specht, F. Bolze, Z. Omran, J. F. Nicoud, and M. Goeldner, “Photochemical tools to study dynamic biological processes,” HFSP J. 3(4), 255–264 (2009).
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2008 (1)

S. Gug, F. Bolze, A. Specht, C. Bourgogne, M. Goeldner, and J.-F. Nicoud, “Molecular Engineering of Photoremovable Protecting Groups for Two-Photon Uncaging,” Angew. Chem. Int. Ed. Engl. 47(49), 9525–9529 (2008).
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2007 (3)

N. Gagey, P. Neveu, C. Benbrahim, B. Goetz, I. Aujard, J.-B. Baudin, and L. Jullien, “Two-Photon Uncaging with Fluorescence Reporting: Evaluation of the o-Hydroxycinnamic Platform,” J. Am. Chem. Soc. 129(32), 9986–9998 (2007).
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N. Gagey, P. Neveu, and L. Jullien, “Two-Photon Uncaging with the Efficient 3,5-Dibromo-2,4-dihydroxycinnamic Caging Group,” Angew. Chem. Int. Ed. Engl. 46(14), 2467–2469 (2007).
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G. C. R. Ellis-Davies, “Caged compounds: photorelease technology for control of cellular chemistry and physiology,” Nat. Methods 4(8), 619–628 (2007).
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2006 (2)

A. Specht, J.-S. Thomann, K. Alarcon, W. Wittayanan, D. Ogden, T. Furuta, Y. Kurakawa, and M. Goeldner, “New Photoremovable Protecting Groups for Carboxylic Acids with High Photolytic Efficiencies at Near-UV Irradiation. Application to the Photocontrolled Release of L-Glutamate,” ChemBioChem 7(11), 1690–1695 (2006).
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Y. Zhu, C. M. Pavlos, J. P. Toscano, and T. M. Dore, “8-Bromo-7-hydroxyquinoline as a Photoremovable Protecting Group for Physiological Use: Mechanism and Scope,” J. Am. Chem. Soc. 128(13), 4267–4276 (2006).
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2005 (1)

F. Helmchen and W. Denk, “Deep tissue two-photon microscopy,” Nat. Methods 2(12), 932–940 (2005).
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2002 (1)

O. D. Fedoryak and T. M. Dore, “Brominated hydroxyquinoline as a photolabile protecting group with sensitivity to multiphoton excitation,” Org. Lett. 4(20), 3419–3422 (2002).
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2001 (1)

M. Matsuzaki, G. C. R. Ellis-Davies, T. Nemoto, Y. Miyashita, M. Iino, and H. Kasai, “Dendritic spine geometry is critical for AMPA receptor expression in hippocampal CA1 pyramidal neurons,” Nat. Neurosci. 4(11), 1086–1092 (2001).
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1999 (2)

T. Furuta, S. S.-H. Wang, J. L. Dantzker, T. M. Dore, W. J. Bybee, E. M. Callaway, W. Denk, and R. Y. Tsien, “Brominated 7-hydroxycoumarin-4-ylmethyls: Photolabile protecting groups with biologically useful cross-sections for two photon photolysis,” Proc. Natl. Acad. Sci. U.S.A. 96(4), 1193–1200 (1999).
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J. Y. Shin and N. L. Abbott, “Using Light to Control Dynamic Surface Tensions of Aqueous Solutions of Water Soluble Surfactants,” Langmuir 15(13), 4404–4410 (1999).
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1991 (1)

S. P. Fodor, J. L. Read, M. C. Pirrung, L. Stryer, A. T. Lu, and D. Solas, “Light-directed, spatially addressable parallel chemical synthesis,” Science 251(4995), 767–773 (1991).
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1980 (1)

V. N. Rajasekharan Pillai, “Photoremovable Protecting Groups in Organic Synthesis,” Synthesis 1980(01), 1–26 (1980).
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1978 (1)

J. H. Kaplan, B. Forbush, and J. F. Hoffman, “Rapid photolytic release of adenosine 5′-triphosphate from a protected analog: utilization by the sodium:potassium pump of human red blood cell ghosts,” Biochemistry (Mosc.) 17(10), 1929–1935 (1978).
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1977 (1)

J. Engels and E. J. Schlaeger, “Synthesis, structure, and reactivity of adenosine cyclic 3′,5′-phosphate benzyltriesters,” J. Med. Chem. 20(7), 907–911 (1977).
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1931 (1)

M. Göppert-Mayer, “Über Elementarakte mit zwei Quantensprüngen,” Ann. Phys. 401(3), 273–294 (1931).
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Abbott, N. L.

J. Y. Shin and N. L. Abbott, “Using Light to Control Dynamic Surface Tensions of Aqueous Solutions of Water Soluble Surfactants,” Langmuir 15(13), 4404–4410 (1999).
[Crossref]

Abe, M.

S. Boinapally, B. Huang, M. Abe, C. Katan, J. Noguchi, S. Watanabe, H. Kasai, B. Xue, and T. Kobayashi, “Caged Glutamates with π-Extended 1,2-Dihydronaphthalene Chromophore: Design, Synthesis, Two-Photon Absorption Property, and Photochemical Reactivity,” J. Org. Chem. 79(17), 7822–7830 (2014).
[Crossref] [PubMed]

Y. Sakamoto, S. Boinapally, C. Katan, and M. Abe, “Synthesis and photochemical reactivity of caged glutamates with a π-extended coumarin chromophore as a photolabile protecting group,” Tetrahedron Lett. 54(52), 7171–7174 (2013).
[Crossref]

Acher, F. C.

C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-Photon “Caging” Groups: Effect of Position Isomery on the Photorelease Properties of Aminoquinoline-Derived Photolabile Protecting Groups,” Org. Lett. 17(3), 402–405 (2015).
[Crossref] [PubMed]

Adesnik, H.

R. H. Kramer, A. Mourot, and H. Adesnik, “Optogenetic pharmacology for control of native neuronal signaling proteins,” Nat. Neurosci. 16(7), 816–823 (2013).
[Crossref] [PubMed]

Agarwal, H. K.

J. M. Amatrudo, J. P. Olson, H. K. Agarwal, and G. C. R. Ellis-Davies, “Caged compounds for multichromic optical interrogation of neural systems,” Eur. J. Neurosci. 41(1), 5–16 (2015).
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Alam, M. M.

M. M. Alam, M. Chattopadhyaya, S. Chakrabarti, and K. Ruud, “Chemical Control of Channel Interference in Two-Photon Absorption Processes,” Acc. Chem. Res. 47(5), 1604–1612 (2014).
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Alarcon, K.

A. Specht, J.-S. Thomann, K. Alarcon, W. Wittayanan, D. Ogden, T. Furuta, Y. Kurakawa, and M. Goeldner, “New Photoremovable Protecting Groups for Carboxylic Acids with High Photolytic Efficiencies at Near-UV Irradiation. Application to the Photocontrolled Release of L-Glutamate,” ChemBioChem 7(11), 1690–1695 (2006).
[Crossref] [PubMed]

Albright, T. R.

P. P. Goswami, A. Syed, C. L. Beck, T. R. Albright, K. M. Mahoney, R. Unash, E. A. Smith, and A. H. Winter, “BODIPY-Derived Photoremovable Protecting Groups Unmasked with Green Light,” J. Am. Chem. Soc. 137(11), 3783–3786 (2015).
[Crossref] [PubMed]

Allard, J.-F.

J. Babin, M. Pelletier, M. Lepage, J.-F. Allard, D. Morris, and Y. Zhao, “A New Two-Photon-Sensitive Block Copolymer Nanocarrier,” Angew. Chem. Int. Ed. Engl. 48(18), 3329–3332 (2009).
[Crossref] [PubMed]

Almutairi, A.

C.-J. Carling, M. L. Viger, V. A. Huu, A. V. Garcia, and A. Almutairi, “In vivo visible light-triggered drug release from an implanted depot,” Chem. Sci. (Camb.) 6(1), 335–341 (2015).
[Crossref] [PubMed]

J. Olejniczak, J. Sankaranarayanan, M. L. Viger, and A. Almutairi, “Highest Efficiency Two-Photon Degradable Copolymer for Remote Controlled Release,” ACS Macro Lett. 2(8), 683–687 (2013).
[Crossref] [PubMed]

N. Fomina, C. L. McFearin, and A. Almutairi, “Increasing materials’ response to two-photon NIR light via self-immolative dendritic scaffolds,” Chem. Commun. (Camb.) 48(73), 9138–9140 (2012).
[Crossref] [PubMed]

Álvarez, M.

V. San Miguel, M. Álvarez, O. Filevich, R. Etchenique, and A. del Campo, “Multiphoton Reactive Surfaces Using Ruthenium(II) Photocleavable Cages,” Langmuir 28(2), 1217–1221 (2012).
[Crossref] [PubMed]

Amatrudo, J. M.

J. M. Amatrudo, J. P. Olson, H. K. Agarwal, and G. C. R. Ellis-Davies, “Caged compounds for multichromic optical interrogation of neural systems,” Eur. J. Neurosci. 41(1), 5–16 (2015).
[Crossref] [PubMed]

Anderson, H. L.

K. A. Korzycka, P. M. Bennett, E. J. Cueto-Diaz, G. Wicks, M. Drobizhev, M. Blanchard-Desce, A. Rebane, and H. L. Anderson, “Two-photon sensitive protecting groups operating via intramolecular electron transfer: uncaging of GABA and tryptophan,” Chem. Sci. (Camb.) 6(4), 2419–2426 (2015).
[Crossref]

A. I. Ciuciu, K. A. Korzycka, W. J. M. Lewis, P. M. Bennett, H. L. Anderson, and L. Flamigni, “Model dyads for 2PA uncaging of a protecting group via photoinduced electron transfer,” Phys. Chem. Chem. Phys. 17(9), 6554–6564 (2015).
[Crossref] [PubMed]

Anseth, K. S.

A. M. Kloxin, A. M. Kasko, C. N. Salinas, and K. S. Anseth, “Photodegradable Hydrogels for Dynamic Tuning of Physical And Chemical Properties,” Science 324(5923), 59–63 (2009).
[Crossref] [PubMed]

Arranz, V. S. M.

L. García-Fernández, C. Herbivo, V. S. M. Arranz, D. Warther, L. Donato, A. Specht, and A. del Campo, “Dual photosensitive polymers with wavelength-selective photoresponse,” Adv. Mater. 26(29), 5012–5017 (2014).
[Crossref] [PubMed]

Aujard, I.

L. Fournier, I. Aujard, T. Le Saux, S. Maurin, S. Beaupierre, J.-B. Baudin, and L. Jullien, “Coumarinylmethyl Caging Groups with Redshifted Absorption,” Chemistry 19(51), 17494–17507 (2013).
[Crossref] [PubMed]

N. Gagey, P. Neveu, C. Benbrahim, B. Goetz, I. Aujard, J.-B. Baudin, and L. Jullien, “Two-Photon Uncaging with Fluorescence Reporting: Evaluation of the o-Hydroxycinnamic Platform,” J. Am. Chem. Soc. 129(32), 9986–9998 (2007).
[Crossref] [PubMed]

Babin, J.

J. Babin, M. Pelletier, M. Lepage, J.-F. Allard, D. Morris, and Y. Zhao, “A New Two-Photon-Sensitive Block Copolymer Nanocarrier,” Angew. Chem. Int. Ed. Engl. 48(18), 3329–3332 (2009).
[Crossref] [PubMed]

Bao, C.

C. Bao, L. Zhu, Q. Lin, and H. Tian, “Building biomedical materials using photochemical bond cleavage,” Adv. Mater. 27(10), 1647–1662 (2015).
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Z. Liu, Q. Lin, Y. Sun, T. Liu, C. Bao, F. Li, and L. Zhu, “Spatiotemporally Controllable and Cytocompatible Approach Builds 3D Cell Culture Matrix by Photo-Uncaged-Thiol Michael Addition Reaction,” Adv. Mater. 26(23), 3912–3917 (2014).
[Crossref] [PubMed]

M. Jin, H. Xu, H. Hong, C. Bao, H. Pu, D. Wan, and L. Zhu, “Micropatterning of polymethacrylates by single- or two-photon irradiation using π-conjugated o -nitrobenzyl ester phototrigger as side chains,” J. Appl. Polym. Sci. 130, 4099–4106 (2013).

C. Bao, G. Fan, Q. Lin, B. Li, S. Cheng, Q. Huang, and L. Zhu, “Styryl Conjugated Coumarin Caged Alcohol: Efficient Photorelease by Either One-Photon Long Wavelength or Two-Photon NIR Excitation,” Org. Lett. 14(2), 572–575 (2012).
[Crossref] [PubMed]

C. Bao, M. Jin, B. Li, Y. Xu, J. Jin, and L. Zhu, “Long conjugated 2-nitrobenzyl derivative caged anticancer prodrugs with visible light regulated release: preparation and functionalizations,” Org. Biomol. Chem. 10(27), 5238–5244 (2012).
[Crossref] [PubMed]

Q. Lin, Q. Huang, C. Li, C. Bao, Z. Liu, F. Li, and L. Zhu, “Anticancer Drug Release from a Mesoporous Silica Based Nanophotocage Regulated by Either a One- or Two-Photon Process,” J. Am. Chem. Soc. 132(31), 10645–10647 (2010).
[Crossref] [PubMed]

Baudin, J.-B.

L. Fournier, I. Aujard, T. Le Saux, S. Maurin, S. Beaupierre, J.-B. Baudin, and L. Jullien, “Coumarinylmethyl Caging Groups with Redshifted Absorption,” Chemistry 19(51), 17494–17507 (2013).
[Crossref] [PubMed]

N. Gagey, P. Neveu, C. Benbrahim, B. Goetz, I. Aujard, J.-B. Baudin, and L. Jullien, “Two-Photon Uncaging with Fluorescence Reporting: Evaluation of the o-Hydroxycinnamic Platform,” J. Am. Chem. Soc. 129(32), 9986–9998 (2007).
[Crossref] [PubMed]

Beaupierre, S.

L. Fournier, I. Aujard, T. Le Saux, S. Maurin, S. Beaupierre, J.-B. Baudin, and L. Jullien, “Coumarinylmethyl Caging Groups with Redshifted Absorption,” Chemistry 19(51), 17494–17507 (2013).
[Crossref] [PubMed]

Becht, S.

K. M. Schelkle, T. Griesbaum, D. Ollech, S. Becht, T. Buckup, M. Hamburger, and R. Wombacher, “Light-Induced Protein Dimerization by One- and Two-Photon Activation of Gibberellic Acid Derivatives in Living Cells,” Angew. Chem. Int. Ed. Engl. 54(9), 2825–2829 (2015).
[Crossref] [PubMed]

K. M. Schelkle, S. Becht, S. Faraji, M. Petzoldt, K. Müllen, T. Buckup, A. Dreuw, M. Motzkus, and M. Hamburger, “Emission turn-on and solubility turn-off in conjugated polymers: one- and two-photon-induced removal of fluorescence-quenching solubilizing groups,” Macromol. Rapid Commun. 36(1), 31–37 (2015).
[Crossref] [PubMed]

Beck, C. L.

P. P. Goswami, A. Syed, C. L. Beck, T. R. Albright, K. M. Mahoney, R. Unash, E. A. Smith, and A. H. Winter, “BODIPY-Derived Photoremovable Protecting Groups Unmasked with Green Light,” J. Am. Chem. Soc. 137(11), 3783–3786 (2015).
[Crossref] [PubMed]

Benbrahim, C.

N. Gagey, P. Neveu, C. Benbrahim, B. Goetz, I. Aujard, J.-B. Baudin, and L. Jullien, “Two-Photon Uncaging with Fluorescence Reporting: Evaluation of the o-Hydroxycinnamic Platform,” J. Am. Chem. Soc. 129(32), 9986–9998 (2007).
[Crossref] [PubMed]

Bennett, P. M.

K. A. Korzycka, P. M. Bennett, E. J. Cueto-Diaz, G. Wicks, M. Drobizhev, M. Blanchard-Desce, A. Rebane, and H. L. Anderson, “Two-photon sensitive protecting groups operating via intramolecular electron transfer: uncaging of GABA and tryptophan,” Chem. Sci. (Camb.) 6(4), 2419–2426 (2015).
[Crossref]

A. I. Ciuciu, K. A. Korzycka, W. J. M. Lewis, P. M. Bennett, H. L. Anderson, and L. Flamigni, “Model dyads for 2PA uncaging of a protecting group via photoinduced electron transfer,” Phys. Chem. Chem. Phys. 17(9), 6554–6564 (2015).
[Crossref] [PubMed]

Bensimon, D.

A. Gautier, C. Gauron, M. Volovitch, D. Bensimon, L. Jullien, and S. Vriz, “How to control proteins with light in living systems,” Nat. Chem. Biol. 10(7), 533–541 (2014).
[Crossref] [PubMed]

Blanc, A.

P. Klán, T. Šolomek, C. G. Bochet, A. Blanc, R. Givens, M. Rubina, V. Popik, A. Kostikov, and J. Wirz, “Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy,” Chem. Rev. 113(1), 119–191 (2013).
[Crossref] [PubMed]

Blanchard-Desce, M.

C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-Photon “Caging” Groups: Effect of Position Isomery on the Photorelease Properties of Aminoquinoline-Derived Photolabile Protecting Groups,” Org. Lett. 17(3), 402–405 (2015).
[Crossref] [PubMed]

K. A. Korzycka, P. M. Bennett, E. J. Cueto-Diaz, G. Wicks, M. Drobizhev, M. Blanchard-Desce, A. Rebane, and H. L. Anderson, “Two-photon sensitive protecting groups operating via intramolecular electron transfer: uncaging of GABA and tryptophan,” Chem. Sci. (Camb.) 6(4), 2419–2426 (2015).
[Crossref]

E. J. Cueto Díaz, S. Picard, V. Chevasson, J. Daniel, V. Hugues, O. Mongin, E. Genin, and M. Blanchard-Desce, “Cooperative Dyads for Two-Photon Uncaging,” Org. Lett. 17(1), 102–105 (2015).
[Crossref] [PubMed]

S. Picard, E. Genin, G. Clermont, V. Hugues, O. Mongin, and M. Blanchard-Desce, “Octupolar chimeric compounds built from quinoline caged acetate moieties: a novel approach for 2-photon uncaging of biomolecules,” New J. Chem. 37(12), 3899 (2013).
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C. Bao, M. Jin, B. Li, Y. Xu, J. Jin, and L. Zhu, “Long conjugated 2-nitrobenzyl derivative caged anticancer prodrugs with visible light regulated release: preparation and functionalizations,” Org. Biomol. Chem. 10(27), 5238–5244 (2012).
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C. Bao, M. Jin, B. Li, Y. Xu, J. Jin, and L. Zhu, “Long conjugated 2-nitrobenzyl derivative caged anticancer prodrugs with visible light regulated release: preparation and functionalizations,” Org. Biomol. Chem. 10(27), 5238–5244 (2012).
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Figures (9)

Fig. 1
Fig. 1 General principle of uncaging.
Fig. 2
Fig. 2 Most popular platforms for the development of photolabile protecting group.
Fig. 3
Fig. 3 Fluorescent compound upon one (up) and two-photon (down) excitation showing fluorescence upon the whole optical pathway in the case of one-photon excitation which is restricted to the focal point in the case of two-photon excitation.
Fig. 4
Fig. 4 Example of significant two-photon sensitive protecting groups.
Fig. 5
Fig. 5 Recently described two-photon sensitive photolabile protecting groups.
Fig. 6
Fig. 6 (a) Uncaging of CANBP-GABA activates GABA receptors in brain slices. L2/3 pyramidal cell were filled with an Alexa 488 fluorophore in order to visualize neurons. Two-photon photoactivation is located within the white box. The puffer pipette containing CANBP-GABA is visible as a shadow (arrow). (b) Outward current evoked obtained by patch clamp technique by λ = 800 nm uncaging flash (blue line) in the presence of CANBP-GABA (black), which is blocked by picrotoxin (red). Scale bar = 2 pA/200 ms (Reproduced from [38]. with permission from John Wiley and Sons). (c) Self-immolative principle for Generation 0, 1 and 2 glutamate release (Reproduced from [37]. with permission from The Royal Society of Chemistry). (d) molecular formula of the second generation (G2) of [37] dendrimer for glutamate uncaging.
Fig. 7
Fig. 7 New “caged” neurotransmitters applied in neuroscience and physiology.
Fig. 8
Fig. 8 (a) Light sensitive Block CoPolymer with co-encapsulated hydrophobic drug and upconverting nanoparticle (Reprinted with permission from [47]. Copyright (2011) American Chemical Society.” (b) Mesoporous silica nanoparticle coated by light sensitive BCP and hydrophobic drug loading (Reproduced from [50]. with permission from The Royal Society of Chemistry).
Fig. 9
Fig. 9 Caging systems used in micelles, nanoparticles, polymers for drug release and micropatterning.

Equations (2)

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P = 1 2 σ 2 I 2
δ u = δ a Φ u

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