Phototriggers：Work Mechanisms and Applications

doi:10.7517/j.issn.1674-0475.2014.01.003

Abstract

Abstract:

The advantage of non-invasive manipulating with high spatiotemporal resolution of light-control technology make it favourable in bio-applications. Phototrigger with three major functions of photoactivation, photocleavge and photorelease is one important class of the photoresponsive molecules to construct materials with photo-controllability. However, with the expansion of the application of light-control technology in the bio-medicine field, new requirements and challenges are proposed for photoresponsive molecules especially for phototriggers. This review summarizes the typical types of phototriggers, their basic working principles, and their applications in the field of biology and material research in recent years.

Key words: phototrigger, coumarin, light-control, photocleavage

LIN Qiuning, YANG Yunlong, FANG Qian, BAO Chunyan, ZHU Linyong. Phototriggers：Work Mechanisms and Applications[J]. Imaging Science and Photochemistry, 2014, 32(1): 3-27.

References

[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, Mntele 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, Gonalves 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] Klan 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] Geiler 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, Gonalves 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, Gonalves 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, Gonalves 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, Gonalves 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] Flling J, Belov V, Kunetsky R, Medda R, Schnle 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, Bnigk 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.