A Water-Soluble Warped Nanographene: Synthesis and Applications for Photoinduced Cell Death

被引:104
|
作者
Lin, Hsing-An [1 ,2 ]
Sato, Yoshikatsu [3 ]
Segawa, Yasutomo [1 ,2 ]
Nishihara, Taishi [1 ,2 ]
Sugimoto, Nagisa [3 ]
Scott, Lawrence T. [4 ]
Higashiyama, Tetsuya [2 ,3 ]
Itami, Kenichiro [1 ,2 ,3 ]
机构
[1] Nagoya Univ, Itami Mol Nanocarbon Project, JST ERATO, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Grad Sch Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[3] Nagoya Univ, Inst Transformat Bio Mol WPI ITbM, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[4] Boston Coll, Merkert Chem Ctr, Chestunt Hill, MA 02467 USA
基金
美国国家科学基金会;
关键词
arenes; cell death; chromophores; fluorescence; polycycles; warped nanographenes; CATALYZED BORYLATION; PHOTODYNAMIC THERAPY; AROMATIC SADDLES; GRAPHENE;
D O I
10.1002/anie.201713387
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Nanographene, a small piece of graphene, has attracted unprecedented interest across diverse scientific disciplines particularly in organic electronics. The biological applications of nanographenes, such as bioimaging, cancer therapies and drug delivery, provide significant opportunities for breakthroughs in the field. However, the intrinsic aggregation behavior and low solubility of nanographenes, which stem from their flat structures, hamper their development for bioapplications. Herein, we report a water-soluble warped nanographene (WNG) that can be easily synthesized by sequential regioselective C-H borylation and cross-coupling reactions of the saddle-shaped WNG core structure. The saddle-shaped structure and hydrophilic tetraethylene glycol chains impart high water solubility to the WNG. The watersoluble WNG possesses a range of promising properties including good photostability and low cytotoxicity. Moreover, the water-soluble WNG was successfully internalized into HeLa cells and promoted photoinduced cell death.
引用
收藏
页码:2874 / 2878
页数:5
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