Flavylium Polymethine Fluorophores for Near- and Shortwave Infrared Imaging

被引：348

作者：

Cosco, Emily D. ^{[1
]}

Caram, Justin R. ^{[2
]}

Bruns, Oliver T. ^{[2
]}

Franke, Daniel ^{[2
]}

Day, Rachael A. ^{[1
]}

Farr, Erik P. ^{[1
]}

Bawendi, Moungi G. ^{[2
]}

Sletten, Ellen M. ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[2] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 42期

关键词：

fluorescent dyes; imaging agents; near-infrared; polymethines; shortwave infrared; HEPTAMETHINE CYANINE DYES; FLUORESCENT LABELS; QUANTUM DOTS; PHOTOLUMINESCENCE; PHOTOSTABILITY;

D O I：

10.1002/anie.201706974

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Bright fluorophores in the near-infrared and shortwave infrared (SWIR) regions of the electromagnetic spectrum are essential for optical imaging invivo. In this work, we utilized a 7-dimethylamino flavylium heterocycle to construct a panel of novel red-shifted polymethine dyes, with emission wavelengths from 680 to 1045nm. Photophysical characterization revealed that the 1- and 3-methine dyes display enhanced photostability and the 5- and 7-methine dyes exhibit exceptional brightness for their respective spectral regions. A micelle formulation of the 7-methine facilitated SWIR imaging in mice. This report presents the first polymethine dye designed and synthesized for SWIR invivo imaging.

引用

页码：13126 / 13129

页数：4

共 33 条

[11] Layer-by-layer assembled fluorescent probes in the second near-infrared window for systemic delivery and detection of ovarian cancer [J].

Dang, Xiangnan ;

Gu, Li ;

Qi, Jifa ;

Correa, Santiago ;

Zhang, Geran ;

Belcher, Angela M. ;

Hammond, Paula T. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2016, 113 (19) :5179-5184

[12] TELLUROPYRYLIUM DYES .1. 2,6-DIPHENYLTELLUROPYRYLIUM DYES [J].

DETTY, MR ;

MURRAY, BJ .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (27) :5235-5239

[13] A Bright Future for Precision Medicine: Advances in Fluorescent Chemical Probe Design and Their Clinical Application [J].

Garland, Megan ;

Yim, Joshua J. ;

Bogyo, Matthew .

CELL CHEMICAL BIOLOGY, 2016, 23 (01) :122-136

[14] Cyanine polyene reactivity: scope and biomedical applications [J].

Gorka, Alexander P. ;

Nani, Roger R. ;

Schnermann, Martin J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (28) :7584-7598

[15] BODIPY-Derived Photoremovable Protecting Groups Unmasked with Green Light [J].

Goswami, Pratik P. ;

Syed, Aleem ;

Beck, Christie L. ;

Albright, Toshia R. ;

Mahoney, Kaitlyn M. ;

Unash, Ryan ;

Smith, Emily A. ;

Winter, Arthur H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (11) :3783-3786

[16] Absolute photoluminescence quantum yields of IR26 and IR-emissive Cd1-xHgxTe and PbS quantum dots - method- and material-inherent challenges [J].

Hatami, Soheil ;

Wuerth, Christian ;

Kaiser, Martin ;

Leubner, Susanne ;

Gabriel, Stefanie ;

Bahrig, Lydia ;

Lesnyak, Vladimir ;

Pauli, Jutta ;

Gaponik, Nikolai ;

Eychmueller, Alexander ;

Resch-Genger, Ute .

NANOSCALE, 2015, 7 (01) :133-143

[17] Near-infrared fluorescence: application to in vivo molecular imaging [J].

Hilderbrand, Scott A. ;

Weissleder, Ralph .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2010, 14 (01) :71-79

[18] Multifunctional in vivo vascular imaging using near-infrared II fluorescence [J].

Hong, Guosong ;

Lee, Jerry C. ;

Robinson, Joshua T. ;

Raaz, Uwe ;

Xie, Liming ;

Huang, Ngan F. ;

Cooke, John P. ;

Dai, Hongjie .

NATURE MEDICINE, 2012, 18 (12) :1841-+

[19] In Vivo Fluorescence Imaging with Ag2S Quantum Dots in the Second Near-Infrared Region [J].

Hong, Guosong ;

Robinson, Joshua T. ;

Zhang, Yejun ;

Diao, Shuo ;

Antaris, Alexander L. ;

Wang, Qiangbin ;

Dai, Hongjie .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (39) :9818-9821

[20]

Ishchenko A.A., 1991, Russ. Chem, V60, P865, DOI 10.1070/RC1991v060n08ABEH001116

← 1 2 3 4 →