A Blue-Absorbing Photolabile Protecting Group for in Vivo Chromatically Orthogonal Photoactivation

被引：97

作者：

Fournier, Ludovic ^{[1
]}

Gauron, Carole ^{[2
]}

Xu, Lijun ^{[3
,4
]}

Aujard, Isabelle ^{[1
]}

Le Saux, Thomas ^{[1
,5
]}

Gagey-Eilstein, Nathalie ^{[1
]}

Maurin, Sylvie ^{[1
]}

Dubruille, Sylvie ^{[6
]}

Baudin, Jean-Bernard ^{[1
]}

Bensimon, David ^{[3
,4
,7
]}

Volovitch, Michel ^{[2
]}

Vriz, Sophie ^{[2
]}

Jullien, Ludovic ^{[1
]}

机构：

[1] Ecole Normale Super, Dept Chim, UMR CNRSENSUPMC PASTEUR 8640, F-75231 Paris 05, France

[2] CIRB, Coll France, CNRS UMR 7241, INSERM,U1050, F-75231 Paris 05, France

[3] Ecole Normale Super, Dept Phys, F-75231 Paris, France

[4] UMR CNRS ENS 8550, Dept Biol, Lab Phys Stat, F-75231 Paris, France

[5] UPMC, F-75232 Paris 05, France

[6] CNRS, Ctr Rech, Inst Curie, UMR 176, F-75248 Paris, France

[7] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90024 USA

来源：

ACS CHEMICAL BIOLOGY | 2013年 / 8卷 / 07期

关键词：

SITE-SPECIFIC RECOMBINATION; CARBOXYLIC-ACIDS; SUBSTITUTED 1,4-BENZOQUINONES; PHOTOCHEMICAL CONTROL; LONG-WAVELENGTH; SINGLET OXYGEN; RETINOIC ACID; ONE-PHOTON; ZEBRAFISH; PHOTOPHYSICS;

D O I：

10.1021/cb400178m

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The small and synthetically easily accessible 7-diethylamino4-thiocoumarinylmethyl photolabile protecting group has been validated for uncaging with blue light. It exhibits a significant action cross-section for uncaging in the 470-500 nm wavelength range and a low light absorption between 350 and 400 nm. These attractive features have been implemented in living zebrafish embryos to perform chromatic orthogonal photoactivation of two biologically active species controlling biological development with UV and blue-cyan light sources, respectively.

引用

页码：1528 / 1536

页数：9

共 70 条

[1] Photo-mediated gene activation using caged RNA/DNA in zebrafish embryos [J].

Ando, H ;

Furuta, T ;

Tsien, RY ;

Okamoto, H .

NATURE GENETICS, 2001, 28 (04) :317-325

[2] o-Nitrobenzyl photolabile protecting groups with red-shifted absorption:: Syntheses and uncaging cross-sections for one- and two-photon excitation [J].

Aujard, Isabelle ;

Benbrahim, Chouaha ;

Gouget, Marine ;

Ruel, Odile ;

Baudin, Jean-Bernard ;

Neveu, Pierre ;

Jullien, Ludovic .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (26) :6865-6879

[3]

Ausubel FM, 1995, CURRENT PROTOCOLS MO

[4] Singlet oxygen generation by UVA light exposure of endogenous photosensitizers [J].

Baier, Juergen ;

Maisch, Tim ;

Maier, Max ;

Engel, Eva ;

Landthaler, Michael ;

Baeumler, Wolfgang .

BIOPHYSICAL JOURNAL, 2006, 91 (04) :1452-1459

[5] Styryl Conjugated Coumarin Caged Alcohol: Efficient Photorelease by Either One-Photon Long Wavelength or Two-Photon NIR Excitation [J].

Bao, Chunyan ;

Fan, Guanshui ;

Lin, Qiuning ;

Li, Bo ;

Cheng, Shuiyu ;

Huang, Qi ;

Zhu, Linyong .

ORGANIC LETTERS, 2012, 14 (02) :572-575

[6] PHOTOSENSITIZERS - COMPREHENSIVE PHOTOPHYSICS PHOTOCHEMISTRY AND THEORY OF COUMARINS, CHROMONES, THEIR HOMOLOGS AND THIONE ANALOGS [J].

BECKER, RS ;

CHAKRAVORTI, S ;

GARTNER, CA ;

MIGUEL, MD .

JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1993, 89 (07) :1007-1019

[7] TRIPLET-STATE PHOTOPHYSICS AND TRANSIENT PHOTOCHEMISTRY OF CYCLIC ENETHIONES - A LASER FLASH-PHOTOLYSIS STUDY [J].

BHATTACHARYYA, K ;

DAS, PK ;

RAMAMURTHY, V ;

RAO, VP .

JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS II, 1986, 82 :135-147

[8]

Bochet CG, 2001, ANGEW CHEM INT EDIT, V40, P2071, DOI 10.1002/1521-3773(20010601)40:11<2071::AID-ANIE2071>3.0.CO

[9]

2-9

[10] Photorelease of carboxylic acids mediated by visible-light-absorbing gold-nanoparticles [J].

Borak, J. Brian ;

Lopez-Sola, Susana ;

Falvey, Daniel E. .

ORGANIC LETTERS, 2008, 10 (03) :457-460

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