DNA labelling in live cells via visible light-induced [2+2] photocycloaddition

被引：10

作者：

Michenfelder, Rita T. ^{[1
,2
]}

Delafresnaye, Laura ^{[2
]}

Truong, Vinh X. ^{[2
,3
]}

Barner-Kowollik, Christopher ^{[2
,4
]}

Wagenknecht, Hans-Achim ^{[1
]}

机构：

[1] Karlsruhe Inst Technol KIT, Inst Organ Chem, Fritz Haber Weg 6, D-76131 Karlsruhe, Germany

[2] Queensland Univ Technol QUT, Ctr Mat Sci, Sch Chem & Phys, 2 George St, Brisbane, QLD 4000, Australia

[3] ASTAR, Inst Mat Res & Engn, 2 Fusionopolis Way, Singapore 138634, Singapore

[4] Karlsruhe Inst Technol KIT, Inst Nanotechnol, Hermann von Helmholtz Pl 1, D-76344 Eggenstein Leopoldshafen, Germany

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 27期

关键词：

PHOTOCLICK CHEMISTRY; CLICK CHEMISTRY; NITRILE IMINE; TETRAZOLES;

D O I：

10.1039/d3cc00817g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We introduce a visible light-driven (lambda(max) = 451 nm) photo-chemical strategy for labelling of DNA in living HeLa cells via the [2+2] cycloaddition of a styrylquinoxaline moiety, which we incorporate into both the DNA and the fluorescent label. Our methodology offers advanced opportunities for the mild remote labelling of DNA in water while avoiding UV light activation.

引用

收藏

页码：4012 / 4015

页数：4

相关论文

共 45 条

[1] Sterically Shielded, Stabilized Nitrile Imine for Rapid Bioorthogonal Protein Labeling in Live Cells [J].

An, Peng ;

Lewandowski, Tracey M. ;

Erbay, Tugce G. ;

Liu, Peng ;

Lin, Qing .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (14) :4860-4868

[2] Design of oligothiophene-based tetrazoles for laser-triggered photoclick chemistry in living cells [J].

An, Peng ;

Yu, Zhipeng ;

Lin, Qing .

CHEMICAL COMMUNICATIONS, 2013, 49 (85) :9920-9922

[3] Solubility of acenaphthene, anthracene, and pyrene in water at 50 °C to 300 °C [J].

Andersson, TA ;

Hartonen, KM ;

Riekkola, ML .

JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2005, 50 (04) :1177-1183

[4] "Photoclick" Postsynthetic Modification of DNA [J].

Arndt, Stefanie ;

Wagenknecht, Hans-Achim .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (52) :14580-14582

[5] Spatial and temporal control of chemical processes [J].

Aubert, Sidonie ;

Bezagu, Marine ;

Spivey, Alan C. ;

Arseniyadis, Stellios .

NATURE REVIEWS CHEMISTRY, 2019, 3 (12) :706-722

[6] Recent Advances in Bioorthogonal Click Chemistry for Biomedical Applications [J].

Battigelli, Alessia ;

Almeida, Bethany ;

Shukla, Anita .

BIOCONJUGATE CHEMISTRY, 2022, 33 (02) :263-271

[7] Amino-functionalized DNA:: the properties of C5-amino-alkyl substituted 2′-deoxyuridines and their application in DNA triplex formation [J].

Brazier, JA ;

Shibata, T ;

Townsley, J ;

Taylor, BF ;

Frary, E ;

Williams, NH ;

Williams, DM .

NUCLEIC ACIDS RESEARCH, 2005, 33 (04) :1362-1371

[8] Imaging cell surface glycans with bioorthogonal chemical reporters [J].

Chang, Pamela V. ;

Prescher, Jennifer A. ;

Hangauer, Matthew J. ;

Bertozzi, Carolyn R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (27) :8400-+

[9] Clicking 1,2,4,5-tetrazine and cyclooctynes with tunable reaction rates [J].

Chen, Weixuan ;

Wang, Danzhu ;

Dai, Chaofeng ;

Hamelberg, Donald ;

Wang, Binghe .

CHEMICAL COMMUNICATIONS, 2012, 48 (12) :1736-1738

[10] 1.3-DIPOLARE CYCLOADDITIONEN .28. DIPHENYLNITRILIMIN UND ARYLKONJUGIERTE ALKENE [J].

CLOVIS, JS ;

ECKELL, A ;

HUISGEN, R ;

SUSTMANN, R ;

WALLBILL.G ;

WEBERNDO.V .

CHEMISCHE BERICHTE-RECUEIL, 1967, 100 (05) :1593-&

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