Flavylium Polymethine Fluorophores for Near‐ and Shortwave Infrared Imaging

Cosco, Emily D.; Caram, Justin R.; Bruns, Oliver T.; Franke, Daniel; Day, Rachael A.; Farr, Erik P.; Bawendi, Moungi G.; Sletten, Ellen M.

doi:10.1002/ange.201706974

Title: Flavylium Polymethine Fluorophores for Near‐ and Shortwave Infrared Imaging

Journal Article · Thu Sep 14 00:00:00 EDT 2017 · Angewandte Chemie

DOI:https://doi.org/10.1002/ange.201706974· OSTI ID:1390340

Cosco, Emily D. ^[1]; Caram, Justin R. ^[2];

^[2]; Franke, Daniel ^[2]; Day, Rachael A. ^[1]; Farr, Erik P. ^[1]; Bawendi, Moungi G. ^[2];

^[1]

Department of Chemistry and Biochemistry University of California, Los Angeles Los Angeles CA 90095 USA
Department of Chemistry Massachusetts Institute of Technology Cambridge MA 02139 USA

Abstract Bright fluorophores in the near‐infrared and shortwave infrared (SWIR) regions of the electromagnetic spectrum are essential for optical imaging in vivo. 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 1045 nm. 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 in vivo imaging.

View Accepted Manuscript (Publisher)

Cite

Export

Save

Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0001088

OSTI ID:: 1390340

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Vol. 129 Journal Issue: 42; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

References (32)

Lifetime, photostability, and chemical structure of IR heptamethine cyanine dyes absorbing beyond 1 ?m Kopainsky, B.; Qiu, P.; Kaiser, W. Applied Physics B Photophysics and Laser Chemistry, Vol. 29, Issue 1 https://doi.org/10.1007/BF00694363	journal	September 1982
Telluropyrylium dyes. 1. 2,6-Diphenyltelluropyrylium dyes Detty, Michael R.; Murray, Bruce J. The Journal of Organic Chemistry, Vol. 47, Issue 27 https://doi.org/10.1021/jo00148a001	journal	December 1982
Biological Imaging Using Nanoparticles of Small Organic Molecules with Fluorescence Emission at Wavelengths Longer than 1000 nm Tao, Zhimin; Hong, Guosong; Shinji, Chihiro Angewandte Chemie, Vol. 125, Issue 49 https://doi.org/10.1002/ange.201307346	journal	October 2013
Near-infrared fluorescence: application to in vivo molecular imaging Hilderbrand, Scott A.; Weissleder, Ralph Current Opinion in Chemical Biology, Vol. 14, Issue 1 https://doi.org/10.1016/j.cbpa.2009.09.029	journal	February 2010
A high quantum yield molecule-protein complex fluorophore for near-infrared II imaging Antaris, Alexander L.; Chen, Hao; Diao, Shuo Nature Communications, Vol. 8, Issue 1 https://doi.org/10.1038/ncomms15269	journal	May 2017
Selection of Quantum Dot Wavelengths for Biomedical Assays and Imaging Lim, Yong Taik; Kim, Sungjee; Nakayama, Akira Molecular Imaging, Vol. 2, Issue 1 https://doi.org/10.1162/153535003765276282	journal	January 2003
Synthesis and Characterization of Coumarin-Based Spiropyran Photochromic Colorants Chen, Jhih-Rong; Wong, Jen-Bing; Kuo, Pei-Yu Organic Letters, Vol. 10, Issue 21 https://doi.org/10.1021/ol8018902	journal	November 2008
Absolute Photoluminescence Quantum Yields of IR-26 Dye, PbS, and PbSe Quantum Dots Semonin, Octavi E.; Johnson, Justin C.; Luther, Joseph M. The Journal of Physical Chemistry Letters, Vol. 1, Issue 16 https://doi.org/10.1021/jz100830r	journal	July 2010
A new infrared laser dye of superior photostability tunable to 1.24 μm with picosecond excitation Kranitzky, W.; Kopainsky, B.; Kaiser, W. Optics Communications, Vol. 36, Issue 2 https://doi.org/10.1016/0030-4018(81)90158-9	journal	January 1981
Layer-by-layer assembled fluorescent probes in the second near-infrared window for systemic delivery and detection of ovarian cancer Dang, Xiangnan; Gu, Li; Qi, Jifa Proceedings of the National Academy of Sciences, Vol. 113, Issue 19 https://doi.org/10.1073/pnas.1521175113	journal	April 2016
Fluorescent labels for proteomics and genomics Waggoner, A. Current Opinion in Chemical Biology, Vol. 10, Issue 1 https://doi.org/10.1016/j.cbpa.2006.01.005	journal	February 2006
Cyanine polyene reactivity: scope and biomedical applications Gorka, Alexander P.; Nani, Roger R.; Schnermann, Martin J. Organic & Biomolecular Chemistry, Vol. 13, Issue 28 https://doi.org/10.1039/C5OB00788G	journal	January 2015
Absolute photoluminescence quantum yields of IR26 and IR-emissive Cd _1−x Hg _x Te and PbS quantum dots – method- and material-inherent challenges Hatami, Soheil; Würth, Christian; Kaiser, Martin Nanoscale, Vol. 7, Issue 1 https://doi.org/10.1039/C4NR04608K	journal	January 2015
Core/Shell NaGdF ₄ :Nd ³⁺ /NaGdF ₄ Nanocrystals with Efficient Near-Infrared to Near-Infrared Downconversion Photoluminescence for Bioimaging Applications Chen, Guanying; Ohulchanskyy, Tymish Y.; Liu, Sha ACS Nano, Vol. 6, Issue 4 https://doi.org/10.1021/nn2042362	journal	March 2012
Near-Infrared Fluorescence Imaging in Humans with Indocyanine Green: A Review and Update~!2009-12-07~!2009-12-23~!2010-05-26~! Marshall, Milton V.; Rasmussen, John C.; Tan, I-Chih The Open Surgical Oncology Journal, Vol. 2, Issue 2 https://doi.org/10.2174/1876504101002020012	journal	June 2010
Rare-earth-doped biological composites as in vivo shortwave infrared reporters Naczynski, D. J.; Tan, M. C.; Zevon, M. Nature Communications, Vol. 4, Issue 1 https://doi.org/10.1038/ncomms3199	journal	July 2013
In Vivo Fluorescence Imaging with Ag ₂ S Quantum Dots in the Second Near-Infrared Region Hong, Guosong; Robinson, Joshua T.; Zhang, Yejun Angewandte Chemie, Vol. 124, Issue 39 https://doi.org/10.1002/ange.201206059	journal	September 2012
Structure and spectral-luminescent properties of polymethine dyes Ishchenko, Aleksandr A. Russian Chemical Reviews, Vol. 60, Issue 8 https://doi.org/10.1070/RC1991v060n08ABEH001116	journal	August 1991
A small-molecule dye for NIR-II imaging Antaris, Alexander L.; Chen, Hao; Cheng, Kai Nature Materials, Vol. 15, Issue 2 https://doi.org/10.1038/nmat4476	journal	November 2015
Bright Ideas for Chemical Biology Lavis, Luke D.; Raines, Ronald T. ACS Chemical Biology, Vol. 3, Issue 3 https://doi.org/10.1021/cb700248m	journal	March 2008
Biological Imaging Using Nanoparticles of Small Organic Molecules with Fluorescence Emission at Wavelengths Longer than 1000 nm Tao, Zhimin; Hong, Guosong; Shinji, Chihiro Angewandte Chemie International Edition, Vol. 52, Issue 49 https://doi.org/10.1002/anie.201307346	journal	October 2013
Shortwave-infrared (SWIR) emitters for biological imaging: a review of challenges and opportunities Thimsen, Elijah; Sadtler, Bryce; Berezin, Mikhail Y. Nanophotonics, Vol. 6, Issue 5 https://doi.org/10.1515/nanoph-2017-0039	journal	June 2017
Rational Design of Molecular Fluorophores for Biological Imaging in the NIR-II Window Yang, Qinglai; Ma, Zhuoran; Wang, Huasen Advanced Materials, Vol. 29, Issue 12 https://doi.org/10.1002/adma.201605497	journal	January 2017
Next-generation in vivo optical imaging with short-wave infrared quantum dots Bruns, Oliver T.; Bischof, Thomas S.; Harris, Daniel K. Nature Biomedical Engineering, Vol. 1, Issue 4 https://doi.org/10.1038/s41551-017-0056	journal	April 2017
A route to brightly fluorescent carbon nanotubes for near-infrared imaging in mice Welsher, Kevin; Liu, Zhuang; Sherlock, Sarah P. Nature Nanotechnology, Vol. 4, Issue 11 https://doi.org/10.1038/nnano.2009.294	journal	October 2009
A Bright Future for Precision Medicine: Advances in Fluorescent Chemical Probe Design and Their Clinical Application Garland, Megan; Yim, Joshua J.; Bogyo, Matthew Cell Chemical Biology, Vol. 23, Issue 1 https://doi.org/10.1016/j.chembiol.2015.12.003	journal	January 2016
Molecular design of near infrared polymethine dyes: A review Bricks, Julia L.; Kachkovskii, Alexei D.; Slominskii, Yurii L. Dyes and Pigments, Vol. 121 https://doi.org/10.1016/j.dyepig.2015.05.016	journal	October 2015
Multifunctional in vivo vascular imaging using near-infrared II fluorescence Hong, Guosong; Lee, Jerry C.; Robinson, Joshua T. Nature Medicine, Vol. 18, Issue 12 https://doi.org/10.1038/nm.2995	journal	November 2012
In Vivo Fluorescence Imaging with Ag ₂ S Quantum Dots in the Second Near-Infrared Region Hong, Guosong; Robinson, Joshua T.; Zhang, Yejun Angewandte Chemie International Edition, Vol. 51, Issue 39 https://doi.org/10.1002/anie.201206059	journal	September 2012
Fluorescence efficiency of four infrared polymethine dyes Casalboni, M.; De Matteis, F.; Prosposito, P. Chemical Physics Letters, Vol. 373, Issue 3-4 https://doi.org/10.1016/S0009-2614(03)00608-0	journal	May 2003
BODIPY-Derived Photoremovable Protecting Groups Unmasked with Green Light Goswami, Pratik P.; Syed, Aleem; Beck, Christie L. Journal of the American Chemical Society, Vol. 137, Issue 11 https://doi.org/10.1021/jacs.5b01297	journal	March 2015
A New Method for the Synthesis of Heptamethine Cyanine Dyes: Synthesis of New Near-Infrared Fluorescent Labels Narayanan, Narasimhachari; Patonay, Gabor The Journal of Organic Chemistry, Vol. 60, Issue 8 https://doi.org/10.1021/jo00113a018	journal	April 1995

Similar Records

Flavylium Polymethine Fluorophores for Near‐ and Shortwave Infrared Imaging

Journal Article · Thu Sep 14 00:00:00 EDT 2017 · Angewandte Chemie (International Edition) · OSTI ID:1390340

Cosco, Emily D.; Caram, Justin R.; Bruns, Oliver T.; +5 more

Bright Chromenylium Polymethine Dyes Enable Fast, Four-Color In Vivo Imaging with Shortwave Infrared Detection

Journal Article · Mon May 03 00:00:00 EDT 2021 · Journal of the American Chemical Society · OSTI ID:1390340

Cosco, Emily D.; Arús, Bernardo A.; Spearman, Anthony L.; +7 more

Polymethine Thiopyrylium Fluorophores with Absorption beyond 1000 nm for Biological Imaging in the Second Near-infrared Sub-window

Journal Article · Sun Dec 02 00:00:00 EST 2018 · Journal of Medicinal Chemistry · OSTI ID:1390340

Ding, Bingbing; Xiao, Yuling; Zhou, Hui; +6 more

Title: Flavylium Polymethine Fluorophores for Near‐ and Shortwave Infrared Imaging

Citation Formats

References (32)

Similar Records

Related Subjects