Assessment of water-soluble π-extended squaraines as one- and two-photon singlet oxygen photosensitizers:: Design, synthesis, and characterization

被引：152

作者：

Beverina, Luca ^{[1
,2
]}

Crippa, Maurizio ^{[1
,2
]}

Landenna, Mirko ^{[1
,2
]}

Ruffo, Riccardo ^{[1
,2
]}

Salice, Patrizio ^{[1
,2
]}

Silvestri, Fabio ^{[1
,2
]}

Versari, Silvia ^{[5
,6
]}

Villa, Alessandro ^{[5
,6
]}

Ciaffoni, Luca

Collini, Elisabetta ^{[3
,4
]}

Ferrante, Camilla ^{[3
,4
]}

Bradamante, Silvia

Mari, Claudio M. ^{[1
,2
]}

Bozio, Renato ^{[3
,4
]}

Pagani, Giorgio A. ^{[1
,2
]}

机构：

[1] Univ Milano Bicocca, Dept Mat Sci, I-20125 Milan, Italy

[2] Univ Milano Bicocca, INSTM, I-20125 Milan, Italy

[3] Univ Padua, Dept Chem, I-35131 Padua, Italy

[4] Univ Padua, INSTM, I-35131 Padua, Italy

[5] CNR, ISTM, Inst Mol Sci & Technol, I-20133 Milan, Italy

[6] CNR, ISTM, Inst Mol Sci & Technol, I-20133 Milan, Italy

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 06期

关键词：

D O I：

10.1021/ja075933a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Singlet oxygen sensitization by organic molecules is a topic of major interest in the development of both efficient photodynamic therapy (PDT) and aerobic oxidations under complete green chemistry conditions. We report on the design, synthesis, biology, and complete spectroscopic characterization (vis-NIR linear and two-photon absorption spectroscopy, singlet oxygen generation efficiencies for both one-and two-photon excitation, electrochemistry, intrinsic dark toxicity, cellular uptake, and subcellular localization) of three classes of innovative singlet oxygen sensitizers pertaining to the family of symmetric squaraine derivatives originating from pi-excessive heterocycles. The main advantage of pi-extended squaraine photosensitizers over the large number of other known photosensitizers is their exceedingly strong two-photon absorption enabling, together with sizable singlet oxygen sensitization capabilities, for their use at the clinical application relevant wavelength of 806 nm. We finally show encouraging results about the dark toxicity and cellular uptake capabilities of water-soluble squaraine photosensitizers, opening the way for clinical small animal PDT trials.

引用

页码：1894 / 1902

页数：9

共 75 条

[1] 1H NMR spectral evidence for a specific host-guest complexation induced charge localization in squaraine dyes [J].