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Volumn 21, Issue , 2014, Pages 89-95

Photoclick chemistry: A fluorogenic light-triggered in vivo ligation reaction

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDE; ALKENE DERIVATIVE; AMINOACYL TRANSFER RNA; CHLORIDE; FLUORESCENT DYE; IMINE; NITRILE; PROTEIN; TETRAZOLE DERIVATIVE; TYROSINE TRANSFER RNA LIGASE; HYDROGEL;

EID: 84904254320     PISSN: 13675931     EISSN: 18790402     Source Type: Journal    
DOI: 10.1016/j.cbpa.2014.05.024     Document Type: Review
Times cited : (108)

References (42)
  • 1
    • 84887044199 scopus 로고    scopus 로고
    • Bioorthogonal chemistry: strategies and recent developments
    • Ramil C.P., Lin Q. Bioorthogonal chemistry: strategies and recent developments. Chem Commun 2013, 49:11007-11022.
    • (2013) Chem Commun , vol.49 , pp. 11007-11022
    • Ramil, C.P.1    Lin, Q.2
  • 2
    • 84878393371 scopus 로고    scopus 로고
    • Light-induced click reactions
    • Tasdelen M.A., Yagci Y. Light-induced click reactions. Angew Chem Int Ed 2013, 52:5930-5938.
    • (2013) Angew Chem Int Ed , vol.52 , pp. 5930-5938
    • Tasdelen, M.A.1    Yagci, Y.2
  • 3
    • 84943108795 scopus 로고
    • 1.3-Dipolare cycloadditionen, xxv. Der nachweis des freien diphenylnitrilimins als zwischenstufe bei cycloadditionen
    • Clovis J.S., Eckell A., Huisgen R., Sustmann R. 1.3-Dipolare cycloadditionen, xxv. Der nachweis des freien diphenylnitrilimins als zwischenstufe bei cycloadditionen. Chem Ber 1967, 100:60-70.
    • (1967) Chem Ber , vol.100 , pp. 60-70
    • Clovis, J.S.1    Eckell, A.2    Huisgen, R.3    Sustmann, R.4
  • 4
    • 42249110717 scopus 로고    scopus 로고
    • A photoinducible 1,3-dipolar cycloaddition reaction for rapid, selective modification of tetrazole-containing proteins
    • Song W., Wang Y., Qu J., Madden M.M., Lin Q. A photoinducible 1,3-dipolar cycloaddition reaction for rapid, selective modification of tetrazole-containing proteins. Angew Chem Int Ed 2008, 47:2832-2835.
    • (2008) Angew Chem Int Ed , vol.47 , pp. 2832-2835
    • Song, W.1    Wang, Y.2    Qu, J.3    Madden, M.M.4    Lin, Q.5
  • 5
    • 48249141055 scopus 로고    scopus 로고
    • Selective functionalization of a genetically encoded alkene-containing protein via "photoclick chemistry" in bacterial cells
    • Song W., Wang Y., Qu J., Lin Q. Selective functionalization of a genetically encoded alkene-containing protein via "photoclick chemistry" in bacterial cells. J Am Chem Soc 2008, 130:9654-9655.
    • (2008) J Am Chem Soc , vol.130 , pp. 9654-9655
    • Song, W.1    Wang, Y.2    Qu, J.3    Lin, Q.4
  • 6
    • 0000096835 scopus 로고    scopus 로고
    • Click chemistry: diverse chemical function from a few good reactions
    • Kolb H.C., Finn M.G., Sharpless K.B. Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 2001, 40:2004-2021.
    • (2001) Angew Chem Int Ed , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 7
    • 80053028238 scopus 로고    scopus 로고
    • Photoinducible bioorthogonal chemistry: a spatiotemporally controllable tool to visualize and perturb proteins in live cells
    • Lim R.K.V., Lin Q. Photoinducible bioorthogonal chemistry: a spatiotemporally controllable tool to visualize and perturb proteins in live cells. Acc Chem Res 2011, 44:828-839.
    • (2011) Acc Chem Res , vol.44 , pp. 828-839
    • Lim, R.K.V.1    Lin, Q.2
  • 8
    • 0037022571 scopus 로고    scopus 로고
    • Analysis of the ultraviolet b response in primary human keratinocytes using oligonucleotide microarrays
    • Sesto A., Navarro M., Burslem F., Jorcano J.L. Analysis of the ultraviolet b response in primary human keratinocytes using oligonucleotide microarrays. Proc Natl Acad Sci U S A 2002, 99:2965-2970.
    • (2002) Proc Natl Acad Sci U S A , vol.99 , pp. 2965-2970
    • Sesto, A.1    Navarro, M.2    Burslem, F.3    Jorcano, J.L.4
  • 9
    • 84885165332 scopus 로고    scopus 로고
    • Design of oligothiophene-based tetrazoles for laser-triggered photoclick chemistry in living cells
    • An P., Yu Z., Lin Q. Design of oligothiophene-based tetrazoles for laser-triggered photoclick chemistry in living cells. Chem Commun 2013, 49:9920-9922.
    • (2013) Chem Commun , vol.49 , pp. 9920-9922
    • An, P.1    Yu, Z.2    Lin, Q.3
  • 10
    • 53349098596 scopus 로고    scopus 로고
    • Discovery of long-wavelength photoactivatable diaryltetrazoles for bioorthogonal 1,3-dipolar cycloaddition reactions
    • Wang Y., Hu W.J., Song W., Lim R.K.V., Lin Q. Discovery of long-wavelength photoactivatable diaryltetrazoles for bioorthogonal 1,3-dipolar cycloaddition reactions. Org Lett 2008, 10:3725-3728.
    • (2008) Org Lett , vol.10 , pp. 3725-3728
    • Wang, Y.1    Hu, W.J.2    Song, W.3    Lim, R.K.V.4    Lin, Q.5
  • 11
    • 80051789999 scopus 로고    scopus 로고
    • Discovery of new photoactivatable diaryltetrazoles for photoclick chemistry via 'scaffold hopping'
    • Yu Z., Ho L.Y., Wang Z., Lin Q. Discovery of new photoactivatable diaryltetrazoles for photoclick chemistry via 'scaffold hopping'. Bioorg Med Chem Lett 2011, 21:5033-5036.
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 5033-5036
    • Yu, Z.1    Ho, L.Y.2    Wang, Z.3    Lin, Q.4
  • 12
    • 70349786296 scopus 로고    scopus 로고
    • Fast alkene functionalization in vivo by photoclick chemistry: homo lifting of nitrile imine dipoles
    • Wang Y., Song W., Hu W.J., Lin Q. Fast alkene functionalization in vivo by photoclick chemistry: homo lifting of nitrile imine dipoles. Angew Chem Int Ed Engl 2009, 48:5330-5333.
    • (2009) Angew Chem Int Ed Engl , vol.48 , pp. 5330-5333
    • Wang, Y.1    Song, W.2    Hu, W.J.3    Lin, Q.4
  • 13
    • 84887061479 scopus 로고    scopus 로고
    • Design and synthesis of laser-activatable tetrazoles for a fast and fluorogenic red-emitting 1,3-dipolar cycloaddition reaction
    • An P., Yu Z., Lin Q. Design and synthesis of laser-activatable tetrazoles for a fast and fluorogenic red-emitting 1,3-dipolar cycloaddition reaction. Org Lett 2013, 15:5496-5499.
    • (2013) Org Lett , vol.15 , pp. 5496-5499
    • An, P.1    Yu, Z.2    Lin, Q.3
  • 14
    • 84887735332 scopus 로고    scopus 로고
    • Fluorogenic, two-photon-triggered photoclick chemistry in live mammalian cells
    • Yu Z., Ohulchanskyy T.Y., An P., Prasad P.N., Lin Q. Fluorogenic, two-photon-triggered photoclick chemistry in live mammalian cells. J Am Chem Soc 2013, 135:16766-16769.
    • (2013) J Am Chem Soc , vol.135 , pp. 16766-16769
    • Yu, Z.1    Ohulchanskyy, T.Y.2    An, P.3    Prasad, P.N.4    Lin, Q.5
  • 15
    • 0033574057 scopus 로고    scopus 로고
    • Brominated 7-hydroxycoumarin-4-ylmethyls: photolabile protecting groups with biologically useful cross-sections for two photon photolysis
    • Furuta T., Wang S.S., 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. Proc Natl Acad Sci U S A 1999, 96:1193-1200.
    • (1999) Proc Natl Acad Sci U S A , vol.96 , pp. 1193-1200
    • Furuta, T.1    Wang, S.S.2    Dantzker, J.L.3    Dore, T.M.4    Bybee, W.J.5    Callaway, E.M.6    Denk, W.7    Tsien, R.Y.8
  • 16
    • 84860174738 scopus 로고    scopus 로고
    • A genetically encoded norbornene amino acid for the mild and selective modification of proteins in a copper-free click reaction
    • Kaya E., Vrabel M., Deiml C., Prill S., Fluxa V.S., Carell T. A genetically encoded norbornene amino acid for the mild and selective modification of proteins in a copper-free click reaction. Angew Chem Int Ed 2012, 51:4466-4469.
    • (2012) Angew Chem Int Ed , vol.51 , pp. 4466-4469
    • Kaya, E.1    Vrabel, M.2    Deiml, C.3    Prill, S.4    Fluxa, V.S.5    Carell, T.6
  • 17
    • 84896689964 scopus 로고    scopus 로고
    • The nitrilimine-alkene cycloaddition is an ultra rapid click reaction
    • Wang X.S., Lee Y.-J., Liu W.R. The nitrilimine-alkene cycloaddition is an ultra rapid click reaction. Chem Commun 2014, 50:3176-3179.
    • (2014) Chem Commun , vol.50 , pp. 3176-3179
    • Wang, X.S.1    Lee, Y.-J.2    Liu, W.R.3
  • 18
    • 84887131438 scopus 로고    scopus 로고
    • Trans-Cylooctene-a stable, voracious dienophile for bioorthogonal labeling
    • Selvaraj R., Fox J.M. trans-Cylooctene-a stable, voracious dienophile for bioorthogonal labeling. Curr Opin Chem Biol 2013, 17:753-760.
    • (2013) Curr Opin Chem Biol , vol.17 , pp. 753-760
    • Selvaraj, R.1    Fox, J.M.2
  • 19
    • 84896513115 scopus 로고    scopus 로고
    • Design of spiro[2.3]hex-1-ene, a genetically encodable double-strained alkene for superfast photoclick chemistry
    • Yu Z., Lin Q. Design of spiro[2.3]hex-1-ene, a genetically encodable double-strained alkene for superfast photoclick chemistry. J Am Chem Soc 2014, 136:4153-4156.
    • (2014) J Am Chem Soc , vol.136 , pp. 4153-4156
    • Yu, Z.1    Lin, Q.2
  • 21
    • 84898072114 scopus 로고    scopus 로고
    • Bioorthogonal reactions for labeling proteins
    • Lang K., Chin J.W. Bioorthogonal reactions for labeling proteins. ACS Chem Biol 2014, 9:16-20.
    • (2014) ACS Chem Biol , vol.9 , pp. 16-20
    • Lang, K.1    Chin, J.W.2
  • 22
    • 77953643054 scopus 로고    scopus 로고
    • Adding new chemistries to the genetic code
    • Liu C.C., Schultz P.G. Adding new chemistries to the genetic code. Annu Rev Biochem 2010, 79:413-444.
    • (2010) Annu Rev Biochem , vol.79 , pp. 413-444
    • Liu, C.C.1    Schultz, P.G.2
  • 23
    • 68949086189 scopus 로고    scopus 로고
    • Synthesis and evaluation of photoreactive tetrazole amino acids
    • Wang Y., Lin Q. Synthesis and evaluation of photoreactive tetrazole amino acids. Org Lett 2009, 11:3570-3573.
    • (2009) Org Lett , vol.11 , pp. 3570-3573
    • Wang, Y.1    Lin, Q.2
  • 26
    • 84883519264 scopus 로고    scopus 로고
    • Expanding the genetic code for photoclick chemistry in E. coli, mammalian cells, and A. thaliana
    • Li F., Zhang H., Sun Y., Pan Y., Zhou J., Wang J. Expanding the genetic code for photoclick chemistry in E. coli, mammalian cells, and A. thaliana. Angew Chem Int Ed 2013, 52:9700-9704.
    • (2013) Angew Chem Int Ed , vol.52 , pp. 9700-9704
    • Li, F.1    Zhang, H.2    Sun, Y.3    Pan, Y.4    Zhou, J.5    Wang, J.6
  • 27
    • 78649894174 scopus 로고    scopus 로고
    • Synthesis of macrocyclic tetrazoles for rapid photoinduced bioorthogonal 1,3-dipolar cycloaddition reactions
    • Yu Z., Lim R.K.V., Lin Q. Synthesis of macrocyclic tetrazoles for rapid photoinduced bioorthogonal 1,3-dipolar cycloaddition reactions. Chem Eur J 2010, 16:13325-13329.
    • (2010) Chem Eur J , vol.16 , pp. 13325-13329
    • Yu, Z.1    Lim, R.K.V.2    Lin, Q.3
  • 28
    • 84857445877 scopus 로고    scopus 로고
    • Genetically encoded norbornene directs site-specific cellular protein labelling via a rapid bioorthogonal reaction
    • Lang K., Davis L., Torres-Kolbus J., Chou C., Deiters A., Chin J.W. Genetically encoded norbornene directs site-specific cellular protein labelling via a rapid bioorthogonal reaction. Nat Chem 2012, 4:298-304.
    • (2012) Nat Chem , vol.4 , pp. 298-304
    • Lang, K.1    Davis, L.2    Torres-Kolbus, J.3    Chou, C.4    Deiters, A.5    Chin, J.W.6
  • 31
    • 84867527159 scopus 로고    scopus 로고
    • Genetically encoded cyclopropene directs rapid, photoclick-chemistry-mediated protein labeling in mammalian cells
    • Yu Z., Pan Y., Wang Z., Wang J., Lin Q. Genetically encoded cyclopropene directs rapid, photoclick-chemistry-mediated protein labeling in mammalian cells. Angew Chem Int Ed 2012, 51:10600-10604.
    • (2012) Angew Chem Int Ed , vol.51 , pp. 10600-10604
    • Yu, Z.1    Pan, Y.2    Wang, Z.3    Wang, J.4    Lin, Q.5
  • 33
    • 84864202913 scopus 로고    scopus 로고
    • Live-cell imaging of cyclopropene tags with fluorogenic tetrazine cycloadditions
    • Yang J., Seckute J., Cole C.M., Devaraj N.K. Live-cell imaging of cyclopropene tags with fluorogenic tetrazine cycloadditions. Angew Chem Int Ed 2012, 51:7476-7479.
    • (2012) Angew Chem Int Ed , vol.51 , pp. 7476-7479
    • Yang, J.1    Seckute, J.2    Cole, C.M.3    Devaraj, N.K.4
  • 35
    • 71249129936 scopus 로고    scopus 로고
    • Synthesis and applications of biomedical and pharmaceutical polymers via click chemistry methodologies
    • van Dijk M., Rijkers D.T.S., Liskamp R.M.J., van Nostrum C.F., Hennink W.E. Synthesis and applications of biomedical and pharmaceutical polymers via click chemistry methodologies. Bioconjugate Chem 2009, 20:2001-2016.
    • (2009) Bioconjugate Chem , vol.20 , pp. 2001-2016
    • van Dijk, M.1    Rijkers, D.T.S.2    Liskamp, R.M.J.3    van Nostrum, C.F.4    Hennink, W.E.5
  • 36
    • 84881604498 scopus 로고    scopus 로고
    • In situ forming hydrogels via catalyst-free and bioorthogonal "tetrazole-alkene" photo-click chemistry
    • Fan Y., Deng C., Cheng R., Meng F., Zhong Z. In situ forming hydrogels via catalyst-free and bioorthogonal "tetrazole-alkene" photo-click chemistry. Biomacromolecules 2013, 14:2814-2821.
    • (2013) Biomacromolecules , vol.14 , pp. 2814-2821
    • Fan, Y.1    Deng, C.2    Cheng, R.3    Meng, F.4    Zhong, Z.5
  • 37
    • 84886245689 scopus 로고    scopus 로고
    • Bioactive hydrogels: lighting the way
    • Alge D.L., Anseth K.S. Bioactive hydrogels: lighting the way. Nat Mater 2013, 12:950-952.
    • (2013) Nat Mater , vol.12 , pp. 950-952
    • Alge, D.L.1    Anseth, K.S.2
  • 38
    • 79961132112 scopus 로고    scopus 로고
    • Rapid, photoactivatable turn-on fluorescent probes based on an intramolecular photoclick reaction
    • Yu Z., Ho L.Y., Lin Q. Rapid, photoactivatable turn-on fluorescent probes based on an intramolecular photoclick reaction. J Am Chem Soc 2011, 133:11912-11915.
    • (2011) J Am Chem Soc , vol.133 , pp. 11912-11915
    • Yu, Z.1    Ho, L.Y.2    Lin, Q.3
  • 39
    • 84890657488 scopus 로고    scopus 로고
    • Photodegradable supramolecular hydrogels with fluorescence turn-on reporter for photomodulation of cellular microenvironments
    • He M., Li J., Tan S., Wang R., Zhang Y. Photodegradable supramolecular hydrogels with fluorescence turn-on reporter for photomodulation of cellular microenvironments. J Am Chem Soc 2013, 135:18718-18721.
    • (2013) J Am Chem Soc , vol.135 , pp. 18718-18721
    • He, M.1    Li, J.2    Tan, S.3    Wang, R.4    Zhang, Y.5
  • 40
    • 84882441298 scopus 로고    scopus 로고
    • Design and synthesis of minimalist terminal alkyne-containing diazirine photo-crosslinkers and their incorporation into kinase inhibitors for cell- and tissue-based proteome profiling
    • Li Z., Hao P., Li L., Tan C.Y., Cheng X., Chen G.Y., Sze S.K., Shen H.M., Yao S.Q. Design and synthesis of minimalist terminal alkyne-containing diazirine photo-crosslinkers and their incorporation into kinase inhibitors for cell- and tissue-based proteome profiling. Angew Chem Int Ed 2013, 52:8551-8556.
    • (2013) Angew Chem Int Ed , vol.52 , pp. 8551-8556
    • Li, Z.1    Hao, P.2    Li, L.3    Tan, C.Y.4    Cheng, X.5    Chen, G.Y.6    Sze, S.K.7    Shen, H.M.8    Yao, S.Q.9
  • 41
    • 84856252572 scopus 로고    scopus 로고
    • No-wash protein labeling with designed fluorogenic probes and application to real-time pulse-chase analysis
    • Mizukami S., Watanabe S., Akimoto Y., Kikuchi K. No-wash protein labeling with designed fluorogenic probes and application to real-time pulse-chase analysis. J Am Chem Soc 2012, 134:1623-1629.
    • (2012) J Am Chem Soc , vol.134 , pp. 1623-1629
    • Mizukami, S.1    Watanabe, S.2    Akimoto, Y.3    Kikuchi, K.4
  • 42
    • 80052570495 scopus 로고    scopus 로고
    • Expanding the genetic code of an animal
    • Greiss S., Chin J.W. Expanding the genetic code of an animal. J Am Chem Soc 2011, 133:14196-14199.
    • (2011) J Am Chem Soc , vol.133 , pp. 14196-14199
    • Greiss, S.1    Chin, J.W.2


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