[1] Brieke C, Rohrbach F, Gottschalk A, Mayer G, Heckel A. Light-controlled tools[J]. Angewandte Chemie International Edition, 2012, 51(34): 8446-8476.
[2] Pelliccioli A P, Wirz J. Photoremovable protecting groups: reaction mechanisms and applications[J]. Photochemical & Photobiological Sciences, 2002, 1(7): 441-458.
[3] Patchornik A, Amit B, Woodward R B. Photosensitive protecting groups[J]. Journal of the American Chemical Society, 1970, 92(21): 6333-6335.
[4] Walker J W, Reid G P, Mccray J A, Trentham D R. Photolabile 1-(2-nitrophenyl)ethyl phosphate-esters of adenine-nucleotide analogs-synthesis and mechanism of photolysis[J]. Journal of the American Chemical Society,1988, 110(21): 7170-7177.
[5] Barth A, Corrie J E T, Gradwell M J, Maeda Y, Mntele W, Meier T, Trentham D R. Time-resolved infrared spectroscopy of intermediates and products from photolysis of 1-(2-nitrophenyl)ethyl phosphates: reaction of the 2-nitrosoacetophenone byproduct with thiols[J]. Journal of the American Chemical Society, 1997, 119(18): 4149-4159.
[6] Holmes C P. Model studies for new o-nitrobenzyl photolabile linkers: substituent effects on the rates of photochemical cleavage[J]. The Journal of Organic Chemistry, 1997, 62(8): 2370-2380.
[7] Pease A C, Solas D, Sullivan E J, Cronin M T, Holmes C P, Fodor S P. Light-generated oligonucleotide arrays for rapid DNA sequence analysis[J]. Proceedings of the National Academy of Sciences, 1994, 91(11): 5022-5026.
[8] Wieboldt R, Ramesh D, Jabri E, Karplus P A, Carpenter B K, Hess G P. Synthesis and characterization of photolabile o-nitrobenzyl derivatives of urea[J]. The Journal of Organic Chemistry, 2002, 67(25): 8827-8831.
[9] Russell A G, Ragoussi M E, Ramalho R, Wharton C W, Carteau D, Bassani D M, Snaith J S. α-Carboxy-6-nitroveratryl: a photolabile protecting group for carboxylic acids[J]. The Journal of Organic Chemistry, 2010, 75(13): 4648-4651.
[10] Schaper K, Mobarekeh S, Abdollah M, Grewer C. Synthesis and photophysical characterization of a new highly hydrophilic caging group[J]. European Journal of Organic Chemistry, 2002, 2002(6): 1037-1046.
[11] Pirrung M C, Lee Y R, Park K, Springer J B. Pentadienylnitrobenzyl and pentadienylnitropiperonyl photochemically removable protecting groups[J]. The Journal of Organic Chemistry, 1999, 64(14): 5042-5047.
[12] Singh A K, Khade P K. 7-Methoxy-3-nitro-2-naphthalenemethanol: a new phototrigger for caging applications[J]. Tetrahedron Letters, 2011, 52(38): 4899-4902.
[13] Momotake A, Lindegger N, Niggli E, Barsotti R J, Ellis-Davies G C R. The nitrodibenzofuran chromophore: a new caging group for ultra-efficient photolysis in living cells[J]. Nature Methods, 2006, 3(1): 35-40.
[14] Givens R S, Park C H. p-Hydroxyphenacyl ATP1: a new phototrigger[J]. Tetrahedron Letters, 1996, 37(35): 6259-6262.
[15] Givens R S, Jung A, Park C H, Weber J, Bartlett W. New photoactivated protecting groups .7. p-Hydroxyphenacyl: a phototrigger for excitatory amino acids and peptides[J]. Journal of the American Chemical Society, 1997, 119(35): 8369-8370.
[16] Givens R S, Weber J F W, Conrad P G, Orosz G, Donahue S L, Thayer S A. New phototriggers 9: p-Hydroxyphenacyl as a C-terminal photoremovable protecting group for oligopeptides[J]. Journal of the American Chemical Society, 2000, 122(12): 2687-2697.
[17] Zhang K, Corrie J E T, Munasinghe V R N, Wan P. Mechanism of photosolvolytic rearrangement of p-hydroxyphenacyl esters: evidence for excited-state intramolecular proton transfer as the primary photochemical step[J]. Journal of the American Chemical Society, 1999, 121(24): 5625-5632.
[18] Conrad P G, Givens R S, Weber J F W, Kandler K. New phototriggers: 1extending the p-hydroxyphenacyl π-π* absorption range[J]. Organic Letters, 2000, 2(11): 1545-1547.
[19] Barltrop J, Schofield P. Photosensitive protecting groups[J]. Tetrahedron Letters, 1962, 3(16): 697-699.
[20] Misetic A, Boyd M K. The pixyl (Px) group: a novel photocleavable protecting group for primary alcohols[J]. Tetrahedron Letters, 1998, 39(13): 1653-1656.
[21] Coleman M P, Boyd M K. S-pixyl analogues as photocleavable protecting groups for nucleosides[J]. The Journal of Organic Chemistry, 2002, 67(22): 7641-7648.
[22] Furuta T, Torigai H, Osawa T, Iwamura M. New photochemically labile protecting group for phosphates[J]. Chemistry Letters, 1993, 22(7): 1179-1182.
[23] Furuta T, Hirayama Y, Iwamura M. Anthraquinon-2-ylmethoxycarbonyl (aqmoc): a new photochemically removable protecting group for alcohols[J]. Organic Letters, 2001, 3(12): 1809-1812.
[24] Arumugam S, Popik V V. Photochemical generation and the reactivity of o-naphthoquinone methides in aqueous solutions[J]. Journal of the American Chemical Society, 2009, 131(33): 11892-11899.
[25] Arumugam S, Popik V V. Attach, remove, or replace: reversible surface functionalization using thiol-quinone methide photoclick chemistry[J]. Journal of the American Chemical Society, 2012, 134(20): 8408-8411.
[26] Fedoryak O D, Dore T M. Brominated hydroxyquinoline as a photolabile protecting group with sensitivity to multiphoton excitation[J]. Organic Letters, 2002, 4(20): 3419-3422.
[27] Zhu Y, Pavlos C M, Toscano J P, Dore T M. 8-Bromo-7-hydroxyquinoline as a photoremovable protecting group for physiological use: mechanism and scope[J]. Journal of the American Chemical Society, 2006, 128(13): 4267-4276.
[28] Davis M J, Kragor C H, Reddie K G, Wilson H C, Zhu Y, Dore T M. Substituent effects on the sensitivity of a quinoline photoremovable protecting group to one-and two-photon excitation[J]. The Journal of Organic Chemistry, 2009, 74(4): 1721-1729.
[29] Givens R S, Matuszewski B. Photochemistry of phosphate esters: an efficient method for the generation of electrophiles[J]. Journal of the American Chemical Society, 1984, 106(22): 6860-6861.
[30] Schultz C. Molecular tools for cell and systems biology[J]. HFSP Journal, 2007, 1(4): 230-248.
[31] Givens R S, Rubina M, Wirz J. Applications of p-hydroxyphenacyl (pHP) and coumarin-4-ylmethyl photoremovable protecting groups[J]. Photochemical & Photobiological Sciences, 2012, 11(3): 472-488.
[32] Schmidt R, Geissler D, Hagen V, Bendig J. Mechanism of photocleavage of (coumarin-4-yl) methyl esters[J]. The Journal of Physical Chemistry A, 2007, 111(26): 5768-5774.
[33] Schmidt R, Geissler D, Hagen V, Bendig J. Kinetics study of the photocleavage of (coumarin-4-yl) methyl esters[J]. The Journal of Physical Chemistry A, 2005, 109(23): 5000-5004.
[34] Senda N, Momotake A, Nishimura Y, Arai T. Synthesis and photochemical properties of a new water-soluble coumarin, designed as a chromophore for highly water-soluble and photolabile protecting group[J]. Bulletin of the Chemical Society of Japan, 2006, 79(11): 1753-1757.
[35] Schade B, Hagen V, Schmidt R, Herbrich R, Krause E, Eckardt T, Bendig J. Deactivation behavior and excited-state properties of (coumarin-4-yl) methyl derivatives. 1. Photocleavage of (7-methoxycoumarin-4-yl) methyl-caged acids with fluorescence enhancement[J]. The Journal of Organic Chemistry, 1999, 64(25): 9109-9117.
[36] Furuta T, Watanabe T, Tanabe S, Sakyo J, Matsuba C. Phototriggers for nucleobases with improved photochemical properties[J]. Organic Letters, 2007, 9(23): 4717-4720.
[37] Kotzur N, Briand B T, Beyermann M, Hagen V. Wavelength-selective photoactivatable protecting groups for thiols[J]. Journal of the American Chemical Society, 2009, 131(46): 16927-16931.
[38] Fonseca A S, Gonalves M S T, Costa S P. Photocleavage studies of fluorescent amino acid conjugates bearing different types of linkages[J]. Tetrahedron, 2007, 63(6): 1353-1359.
[39] Suzuki A Z, Watanabe T, Kawamoto M, Nishiyama K, Yamashita H, Ishii M, Iwamura M, Furuta T. Coumarin-4-ylmethoxycarbonyls as phototriggers for alcohols and phenols[J]. Organic Letters, 2003, 5(25): 4867-4870.
[40] Hagen V, Kilic F, Schaal J, Dekowski B, Schmidt R, Kotzur N. [8-\-6-bromo-7-hydroxycoumarin-4-yl\]methyl moieties as photoremovable protecting groups for compounds with COOH, NH2, OH, and C=O functions[J]. The Journal of Organic Chemistry, 2010, 75(9): 2790-2797.
[41] Subramaniam R, Xiao Y, Li Y, Qian S Y, Sun W, Mallik S. Light-mediated and H-bond facilitated liposomal release: the role of lipid head groups in release efficiency[J]. Tetrahedron Letters, 2010, 51(3): 529-532.
[42] Wylie R G, Shoichet M S. Two-photon micropatterning of amines within an agarose hydrogel[J]. Journal of Materials Chemistry, 2008, 18(23): 2716-2721.
[43] Klan P, olomek T S, Bochet C G, Blanc A L, Givens R, Rubina M, Popik V, Kostikov A, Wirz J. Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy[J]. Chemical Reviews, 2013, 113(1): 119-191.
[44] Eckardt T, Hagen V, Schade B, Schmidt R, Schweitzer C, Bendig J. 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[J]. The Journal of Organic Chemistry, 2002, 67(3): 703-710.
[45] Geiler D, Kresse W, Wiesner B, Bendig J, Kettenmann H, Hagen V. DMACM-caged adenosine nucleotides: ultrafast phototriggers for ATP, ADP, and AMP activated by long-wavelength irradiation[J]. ChemBioChem, 2003, 4(2-3): 162-170.
[46] Cürten B, Kullmann P H, Bier M E, Kandler K, Schmidt B F. Synthesis, photophysical, photochemical and biological properties of caged GABA, 4-[\ amino\] butanoic acid[J].Photochemistry and Photobiology, 2005, 81(3): 641-648.
[47] Fernandes M J, Gonalves M S T, Costa S P. Comparative study of polyaromatic and polyheteroaromatic fluorescent photocleavable protecting groups[J]. Tetrahedron, 2008, 64(13): 3032-3038.
[48] Takaoka K, Tatsu Y, Yumoto N, Nakajima T, Shimamoto K. Synthesis of carbamate-type caged derivatives of a novel glutamate transporter blocker[J]. Bioorganic & Medicinal Chemistry, 2004, 12(13): 3687-3694.
[49] Hagen V, Frings S, Bendig J, Lorenz D, Wiesner B, Kaupp U B. Fluorescence spectroscopic quantification of the release of cyclic nucleotides from photocleavable methyl esters inside cells[J]. Angewandte Chemie International Edition, 2002, 41(19): 3625-3628.
[50] Piloto A M, Rovira D, Costa S P, Gonalves M S T. Oxobenzo benzopyrans as new fluorescent photolabile protecting groups for the carboxylic function[J]. Tetrahedron, 2006, 62(51): 11955-11962.
[51] Fernandes M J, Gonalves M S T, Costa S P. Neurotransmitter amino acid-oxobenzo benzopyran conjugates: synthesis and photorelease studies[J]. Tetrahedron, 2008, 64(49): 11175-11179.
[52] Fernandes M J G, Costa S P, Gonalves M S T. Phototriggering of neuroactive amino acids from 5, 6-benzocoumarinyl conjugates[J]. Tetrahedron, 2011, 67(13): 2422-2426.
[53] Lin Q, Bao C, Fan G, Cheng S, Liu H, Liu Z and Zhu L. 7-Amino coumarin based fluorescent phototriggers coupled with nano/bio-conjugated bonds: synthesis, labeling and photorelease[J]. Journal of Material Chemistry, 2012, 22: 6680-6688.
[54] Vogel A, Venugopalan V. Mechanisms of pulsed laser ablation of biological tissues[J]. Chemical Reviews, 2003, 103(2): 577-644.
[55] Dougherty T J. Photochemistry in the treatment of cancer[J]. Advances in Photochemistry, 1992, 17: 275-311.
[56] Weissleder R, Ntziachristos V. Shedding light onto live molecular targets[J]. Nature Medicine, 2003, 9(1): 123-128.
[57] Juzenas P, Juzeniene A, Kaalhus O, Iani V, Moan J. Noninvasive fluorescence excitation spectroscopy during application of 5-aminolevulinic acid in vivo[J]. Photochemical & Photobiological Sciences, 2002, 1(10): 745-748.
[58] Furuta T, Wang S S H, Dantzker J L, Dore T M, Bybee W J, Callaway E M, Denk W, Tsien R Y. Brominated 7-hydroxycoumarin-4-ylmethyls: photolabile protecting groups with biologically useful cross-sections for two photon photolysis[J]. Proceedings of the National Academy of Sciences, 1999, 96(4): 1193-1200.
[59] Denk W. Two-photon Molecular Excitation in Laser-scanning Microscopy[M]. Handbook of Biological Confocal Microscopy. 1995. 445-458.
[60] LaFratta C N, Fourkas J T, Baldacchini T, Farrer R A. Multiphoton fabrication[J]. Angewandte Chemie International Edition, 2007, 46(33): 6238-6258.
[61] Specht A, Thomann J S, Alarcon K, Wittayanan W, Ogden D, Furuta T, Kurakawa Y, Goeldner M. New photoremovable protecting groups for carboxylic acids with high photolytic efficiencies at near-UV irradiation: application to the photocontrolled release of L-glutamate[J]. ChemBioChem, 2006, 7(11): 1690-1695.
[62] Gug S, Charon S, Specht A, Alarcon K, Ogden D, Zietz B, Léonard J, Haacke S, Bolze F, Nicoud J F. Photolabile glutamate protecting group with high one- and two-photon uncaging efficiencies[J]. ChemBioChem, 2008, 9(8): 1303-1307.
[63] Gug S, Bolze F, Specht A, Bourgogne C, Goeldner M, Nicoud J F. Molecular engineering of photoremovable protecting groups for two-photon uncaging[J]. Angewandte Chemie, 2008, 120(49): 9667-9671.
[64] Warther D, Bolze F D R, Leéonard J R M, Gug S, Specht A, Puliti D, Sun X H, Kessler P, Lutz Y, Vonesch J L. Live-cell one-and two-photon uncaging of a far-red emitting acridinone fluorophore[J]. Journal of the American Chemical Society, 2010, 132(8): 2585-2590.
[65] Lu M, Fedoryak O D, Moister B R, Dore T M. Bhc-diol as a photolabile protecting group for aldehydes and ketones[J]. Organic Letters, 2003, 5(12): 2119-2122.
[66] Bao C, Fan G, Lin Q, Li B, Cheng S, Huang Q, Zhu L. Styryl conjugated coumarin caged alcohol: efficient photorelease by either one-photon long wavelength or two-photon NIR excitation[J]. Organic Letters, 2011, 14(2): 572-575.
[67] Gagey N, Neveu P, Benbrahim C, Goetz B, Aujard I, Baudin J B, Jullien L. Two-photon uncaging with fluorescence reporting: evaluation of the o-hydroxycinnamic platform[J]. Journal of the American Chemical Society, 2007, 129(32): 9986-9998.
[68] Lin Q, Huang Q, Li C, Bao C, Liu Z, Li F and Zhu L. Anticancer drug release from a mesoporous silica based nanophotocage regulated by either a one- or two-photon process[J]. Journal of the American Chemical Society, 2010, 132: 10645-10647.
[69] Zhao Y, Zheng Q, Dakin K, Xu K, Martinez M L, Li W H. New caged coumarin fluorophores with extraordinary uncaging cross sections suitable for biological imaging applications[J]. Journal of the American Chemical Society, 2004, 126(14): 4653-4663.
[70] Zheng G, Guo Y M, Li W H. Photoactivatable and water soluble FRET dyes with high uncaging cross section[J]. Journal of the American Chemical Society, 2007, 129(35): 10616-10617.
[71] Kobayashi T, Urano Y, Kamiya M, Ueno T, Kojima H, Nagano T. Highly activatable and rapidly releasable caged fluorescein derivatives[J]. Journal of the American Chemical Society, 2007, 129(21): 6696-6697.
[72] Mitchison T, Sawin K, Theriot J, Gee K, Mallavarapu A. Caged fluorescent probes[J]. Methods in Enzymology, 1998, 291: 63-78.
[73] Ottl J, Gabriel D, Marriott G. Preparation and photoactivation of caged fluorophores and caged proteins using a new class of heterobifunctional, photocleavable cross-linking reagents[J]. Bioconjugate Chemistry, 1998, 9(2): 143-151.
[74] Tang X, Dmochowski I J. Phototriggering of caged fluorescent oligodeoxynucleotides[J]. Organic Letters, 2005, 7(2): 279-282.
[75] Pellois J-P, Hahn M E, Muir T W. Simultaneous triggering of protein activity and fluorescence[J]. Journal of the American Chemical Society, 2004, 126(23): 7170-7171.
[76] Maurel D, Banala S, Laroche T, Johnsson K. Photoactivatable and photoconvertible fluorescent probes for protein labeling[J]. ACS Chemical Biology, 2010, 5(5): 507-516.
[77] Dakin K, Zhao Y, Li W-H. LAMP, a new imaging assay of gap junctional communication unveils that Ca2+ influx inhibits cell coupling[J]. Nature Methods, 2004, 2(1): 55-62.
[78] Guo Y M, Chen S, Shetty P, Zheng G, Lin R, Li W H. Imaging dynamic cell-cell junctional coupling in vivo using trojan-LAMP[J]. Nature Methods, 2008, 5(9): 835-841.
[79] Rust M J, Bates M, Zhuang X. Sub-diffraction-limit imaging by stochastic optical reconstruction microscopy (STORM) [J]. Nature Methods, 2006, 3(10): 793-796.
[80] Zhang M, Chang H, Zhang Y, Yu J, Wu L, Ji W, Chen J, Liu B, Lu J, Liu Y. Rational design of true monomeric and bright photoactivatable fluorescent proteins[J]. Nature Methods, 2012,9(7): 727-729.
[81] Subach F V, Patterson G H, Manley S, Gillette J M, Lippincott-Schwartz J, Verkhusha V V. Photoactivatable mCherry for high-resolution two-color fluorescence microscopy[J]. Nature Methods, 2009, 6(2): 153-159.
[82] Biteen J S, Thompson M A, Tselentis N K, Bowman G R, Shapiro L, Moerner W. Super-resolution imaging in live caulobacter crescentus cells using photoswitchable EYFP[J]. Nature Methods, 2008, 5(11): 947-949.
[83] Gurskaya N G, Verkhusha V V, Shcheglov A S, Staroverov D B, Chepurnykh T V, Fradkov A F, Lukyanov S, Lukyanov K A. Engineering of a monomeric green-to-red photoactivatable fluorescent protein induced by blue light[J]. Nature Biotechnology, 2006, 24(4): 461-465.
[84] Bates M, Huang B, Dempsey G T, Zhuang X. Multicolor super-resolution imaging with photo-switchable fluorescent probes[J]. Science, 2007, 317(5845): 1749-1753.
[85] Bates M, Blosser T R, Zhuang X. Short-range spectroscopic ruler based on a single-molecule optical switch[J]. Physical Review Letters, 2005, 94(10): 108101
[86] Flling J, Belov V, Kunetsky R, Medda R, Schnle A, Egner A, Eggeling C, Bossi M, Hell S E W. Photochromic rhodamines provide nanoscopy with optical sectioning[J]. Angewandte Chemie International Edition, 2007, 46(33): 6266-6270.
[87] Kaplan J H, Forbush III B, Hoffman J F. Rapid photolytic release of adenosine 5'-triphosphate from a protected analog: utilization by the sodium: potassium pump of human red blood cell ghosts[J]. Biochemistry, 1978, 17(10): 1929-1935.
[88] Strünker T, Weyand I, Bnigk W, Van Q, Loogen A, Brown J E, Kashikar N, Hagen V, Krause E, Kaupp U B. A K+-selective cGMP-gated ion channel controls chemosensation of sperm[J]. Nature Cell Biology, 2006, 8(10): 1149-1154.
[89] Ellis-Davies G C R. Neurobiology with caged calcium[J]. Chemical Reviews, 2008, 108(5): 1603-1613.
[90] Matsuzaki M, Hayama T, Kasai H, Ellis-Davies G C. Two-photon uncaging of γ-aminobutyric acid in intact brain tissue[J]. Nature Chemical Biology, 2010, 6(4): 255-257.
[91] Kantevari S, Matsuzaki M, Kanemoto Y, Kasai H, Ellis-Davies G C. Two-color, two-photon uncaging of glutamate and GABA[J]. Nature Methods, 2009, 7(2): 123-125.
[92] Kantevari S, Buskila Y, Ellis-Davies G C. Synthesis and characterization of cell-permeant 6-nitrodibenzofuranyl-caged IP3[J]. Photochemical & Photobiological Sciences, 2012, 11(3): 508-513.
[93] Subramanian D, Laketa V, Müller R, Tischer C, Zarbakhsh S, Pepperkok R, Schultz C. Activation of membrane-permeant caged PtdIns (3) P induces endosomal fusion in cells[J]. Nature Chemical Biology, 2010, 6(5): 324-326.
[94] Mentel M, Laketa V, Subramanian D, Gillandt H, Schultz C. Photoactivatable and cell-membrane-permeable phosphatidylinositol 3, 4, 5-trisphosphate[J]. Angewandte Chemie International Edition, 2011, 50(16): 3811-3814.
[95] Hishikawa K, Nakagawa H, Furuta T, Fukuhara K, Tsumoto H, Suzuki T, Miyata N. Photoinduced nitric oxide release from a hindered nitrobenzene derivative by two-photon excitation[J]. Journal of the American Chemical Society, 2009, 131(22): 7488-7489.
[96] Zhao J, Gover T D, Muralidharan S, Auston D A, Weinreich D, Kao J P. Caged vanilloid ligands for activation of TRPV1 receptors by 1-and 2-photon excitation[J]. Biochemistry, 2006, 45(15): 4915-4926.
[97] Karginov A V, Zou Y, Shirvanyants D, Kota P, Dokholyan N V, Young D D, Hahn K M, Deiters A. Light regulation of protein dimerization and kinase activity in living cells using photocaged rapamycin and engineered FKBP[J]. Journal of the American Chemical Society, 2011, 133(3): 420-423.
[98] Cruz F G, Koh J T, Link K H. Light-activated gene expression[J]. Journal of the American Chemical Society, 2000, 122(36): 8777-8778.
[99] Kristian H, Shi Y, Koh J T. Light activated recombination[J]. Journal of the American Chemical Society, 2005, 127(38): 13088-13089.
[100] Sauers D J, Temburni M K, Biggins J B, Ceo L M, Galileo D S, Koh J T. Light-activated gene expression directs segregation of co-cultured cells in vitro[J]. ACS Chemical Biology, 2010, 5(3): 313-320. |