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

Ding, Bingbing; Xiao, Yuling; Zhou, Hui; Zhang, Xiao; Qu, Chunrong; Xu, Fuchun; Deng, Zixin; Cheng, Zhen; Hong, Xuechuan

doi:10.1021/acs.jmedchem.8b01682

Title: 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

DOI:https://doi.org/10.1021/acs.jmedchem.8b01682· OSTI ID:1485259

Ding, Bingbing ^[1]; Xiao, Yuling ^[2]; Zhou, Hui ^[2]; Zhang, Xiao ^[3]; Qu, Chunrong ^[3]; Xu, Fuchun ^[4]; Deng, Zixin ^[2]; Cheng, Zhen ^[3]; Hong, Xuechuan ^[5]

Wuhan Univ. School of Pharmaceutical Sciences, Wuhan (China); Stanford Univ., Stanford, CA (United States)
Wuhan Univ. School of Pharmaceutical Sciences, Wuhan (China)
Stanford Univ., Stanford, CA (United States)
Tibet Univ., Lasa (China)
Wuhan Univ. School of Pharmaceutical Sciences, Wuhan (China); Tibet Univ., Lasa (China); Shenzhen Institute of Wuhan Univ., Shenzhen (China)

Small-molecule fluorescence imaging in the second near-infrared (NIR-II, 1000-1700 nm) window has gained increasing interest in clinical application. Till now, very few studies have been exploited in the small-molecule fluorophores with both excitation and emission in the NIR-II window. Inspired by indocyanine green structure, a series of polymethine dyes with both absorption and emission in NIR-II window have been developed for NIR-II imaging, providing the feasibility to directly compare optical imaging in NIR-IIa (1300-1400 nm) sub-window under 1064 nm excitation with that in NIR-II window under 808 nm excitation. The signal-background ratio (SBR) and tumor to normal tissue ratio (T/NT) achieved great improvement under 1064 nm excitation in the imaging of mouse blood pool and U87 glioma tumors. Furthermore, our study not only introduces a broadband emission fluorophore for both NIR-II and NIR-IIa imaging, but also reveals the advantages of NIR-II excitation over NIR-I in in vivo imaging.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: The Leland Stanford Junior Univ., Palo Alto, CA (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0008397

OSTI ID:: 1485259

Journal Information:: Journal of Medicinal Chemistry, Vol. 62, Issue 4; ISSN 0022-2623

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 114 works

Citation information provided by
Web of Science

References (38)

Carbon Nanomaterials for Biological Imaging and Nanomedicinal Therapy Hong, Guosong; Diao, Shuo; Antaris, Alexander L. Chemical Reviews, Vol. 115, Issue 19 https://doi.org/10.1021/acs.chemrev.5b00008	journal	April 2015
Diketopyrrolopyrrole-based semiconducting polymer nanoparticles for in vivo second near-infrared window imaging and image-guided tumor surgery Shou, Kangquan; Tang, Yufu; Chen, Hao Chemical Science, Vol. 9, Issue 12 https://doi.org/10.1039/c8sc00206a	journal	January 2018
Molecular imaging of biological systems with a clickable dye in the broad 800- to 1,700-nm near-infrared window Zhu, Shoujun; Yang, Qinglai; Antaris, Alexander L. Proceedings of the National Academy of Sciences, Vol. 114, Issue 5 https://doi.org/10.1073/pnas.1617990114	journal	January 2017
Non-invasive through-skull brain vascular imaging and small tumor diagnosis based on NIR-II emissive lanthanide nanoprobes beyond 1500 nm Xue, Zhenluan; Zeng, Songjun; Hao, Jianhua Biomaterials, Vol. 171 https://doi.org/10.1016/j.biomaterials.2018.04.037	journal	July 2018
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
Biological imaging without autofluorescence in the second near-infrared region Diao, Shuo; Hong, Guosong; Antaris, Alexander L. Nano Research, Vol. 8, Issue 9 https://doi.org/10.1007/s12274-015-0808-9	journal	August 2015
Proteomic Analysis and NIR-II Imaging of MCM2 Protein in Hepatocellular Carcinoma Yang, Jing; Xie, Qi; Zhou, Hui Journal of Proteome Research, Vol. 17, Issue 7 https://doi.org/10.1021/acs.jproteome.8b00181	journal	May 2018
New NIR-II dyes without a benzobisthiadiazole core Zhou, Hui; Xiao, Yuling; Hong, Xuechuan Chinese Chemical Letters, Vol. 29, Issue 10 https://doi.org/10.1016/j.cclet.2018.08.009	journal	October 2018
An Efficient 1064 nm NIR-II Excitation Fluorescent Molecular Dye for Deep-Tissue High-Resolution Dynamic Bioimaging Li, Benhao; Lu, Lingfei; Zhao, Mengyao Angewandte Chemie, Vol. 130, Issue 25 https://doi.org/10.1002/ange.201801226	journal	March 2018
Real-Time Monitoring Surface Chemistry-Dependent In Vivo Behaviors of Protein Nanocages via Encapsulating an NIR-II Ag ₂ S Quantum Dot Li, Chunyan; Li, Feng; Zhang, Yejun ACS Nano, Vol. 9, Issue 12 https://doi.org/10.1021/acsnano.5b05503	journal	October 2015
Flavylium Polymethine Fluorophores for Near- and Shortwave Infrared Imaging Cosco, Emily D.; Caram, Justin R.; Bruns, Oliver T. Angewandte Chemie International Edition, Vol. 56, Issue 42 https://doi.org/10.1002/anie.201706974	journal	September 2017
Synthesis, Characterization, and Biomedical Applications of a Targeted Dual-Modal Near-Infrared-II Fluorescence and Photoacoustic Imaging Nanoprobe Cheng, Kai; Chen, Hao; Jenkins, Cesare H. ACS Nano, Vol. 11, Issue 12 https://doi.org/10.1021/acsnano.7b05966	journal	October 2016
Computational Thermochemistry: Scale Factor Databases and Scale Factors for Vibrational Frequencies Obtained from Electronic Model Chemistries Alecu, I. M.; Zheng, Jingjing; Zhao, Yan Journal of Chemical Theory and Computation, Vol. 6, Issue 9 https://doi.org/10.1021/ct100326h	journal	August 2010
Pyrazolopyrimidines as Potent Stimulators for Transient Receptor Potential Canonical 3/6/7 Channels Qu, Chunrong; Ding, Mingmin; Zhu, Yingmin Journal of Medicinal Chemistry, Vol. 60, Issue 11 https://doi.org/10.1021/acs.jmedchem.7b00304	journal	April 2017
Donor Engineering for NIR-II Molecular Fluorophores with Enhanced Fluorescent Performance Yang, Qinglai; Hu, Zhubin; Zhu, Shoujun Journal of the American Chemical Society, Vol. 140, Issue 5 https://doi.org/10.1021/jacs.7b10334	journal	January 2018
New glowing dyes in vivo imaging with wavelengths beyond 1500 nm Yang, Jing; Hong, Xuechuan Science China Chemistry, Vol. 62, Issue 1 https://doi.org/10.1007/s11426-018-9341-7	journal	September 2018
Near-infrared fluorophores for biomedical imaging Hong, Guosong; Antaris, Alexander L.; Dai, Hongjie Nature Biomedical Engineering, Vol. 1, Issue 1 https://doi.org/10.1038/s41551-016-0010	journal	January 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
Pyrazolo[1,5-a]pyrimidine TRPC6 antagonists for the treatment of gastric cancer Ding, Mingmin; Wang, Hongbo; Qu, Chunrong Cancer Letters, Vol. 432 https://doi.org/10.1016/j.canlet.2018.05.041	journal	September 2018
Fluorescence Imaging In Vivo at Wavelengths beyond 1500 nm Diao, Shuo; Blackburn, Jeffrey L.; Hong, Guosong Angewandte Chemie, Vol. 127, Issue 49 https://doi.org/10.1002/ange.201507473	journal	October 2015
Deep-tissue anatomical imaging of mice using carbon nanotube fluorophores in the second near-infrared window Welsher, K.; Sherlock, S. P.; Dai, H. Proceedings of the National Academy of Sciences, Vol. 108, Issue 22 https://doi.org/10.1073/pnas.1014501108	journal	May 2011
Through-skull fluorescence imaging of the brain in a new near-infrared window Hong, Guosong; Diao, Shuo; Chang, Junlei Nature Photonics, Vol. 8, Issue 9 https://doi.org/10.1038/nphoton.2014.166	journal	August 2014
Er ³⁺ Sensitized 1530 nm to 1180 nm Second Near-Infrared Window Upconversion Nanocrystals for In Vivo Biosensing Liu, Lu; Wang, Shangfeng; Zhao, Baozhou Angewandte Chemie International Edition, Vol. 57, Issue 25 https://doi.org/10.1002/anie.201802889	journal	May 2018
Traumatic Brain Injury Imaging in the Second Near-Infrared Window with a Molecular Fluorophore Zhang, Xiao-Dong; Wang, Huasen; Antaris, Alexander L. Advanced Materials, Vol. 28, Issue 32 https://doi.org/10.1002/adma.201600706	journal	June 2016
Novel bright-emission small-molecule NIR-II fluorophores for in vivo tumor imaging and image-guided surgery Sun, Yao; Ding, Mingmin; Zeng, Xiaodong Chemical Science, Vol. 8, Issue 5 https://doi.org/10.1039/c7sc00251c	journal	January 2017
Near-Infrared II Dye-Protein Complex for Biomedical Imaging and Imaging-Guided Photothermal Therapy Zeng, Xiaodong; Xiao, Yuling; Lin, Jiacheng Advanced Healthcare Materials, Vol. 7, Issue 18 https://doi.org/10.1002/adhm.201800589	journal	July 2018
Ultrastable and Biocompatible NIR-II Quantum Dots for Functional Bioimaging Zebibula, Abudureheman; Alifu, Nuernisha; Xia, Liqun Advanced Functional Materials, Vol. 28, Issue 9 https://doi.org/10.1002/adfm.201703451	journal	December 2017
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
Novel dual-function near-infrared II fluorescence and PET probe for tumor delineation and image-guided surgery Sun, Yao; Zeng, Xiaodong; Xiao, Yuling Chemical Science, Vol. 9, Issue 8 https://doi.org/10.1039/c7sc04774f	journal	January 2018
Novel near-infrared II aggregation-induced emission dots for in vivo bioimaging Lin, Jiacheng; Zeng, Xiaodong; Xiao, Yuling Chemical Science, Vol. 10, Issue 4 https://doi.org/10.1039/C8SC04363A	journal	January 2019
Live imaging of follicle stimulating hormone receptors in gonads and bones using near infrared II fluorophore Feng, Yi; Zhu, Shoujun; Antaris, Alexander L. Chemical Science, Vol. 8, Issue 5 https://doi.org/10.1039/c6sc04897h	journal	January 2017
Molecular Cancer Imaging in the Second Near-Infrared Window Using a Renal-Excreted NIR-II Fluorophore-Peptide Probe Wang, Weizhi; Ma, Zhuoran; Zhu, Shoujun Advanced Materials, Vol. 30, Issue 22 https://doi.org/10.1002/adma.201800106	journal	April 2018
Fluorescence Imaging In Vivo at Wavelengths beyond 1500 nm Diao, Shuo; Blackburn, Jeffrey L.; Hong, Guosong Angewandte Chemie International Edition, Vol. 54, Issue 49 https://doi.org/10.1002/anie.201507473	journal	October 2015
Crucial breakthrough of second near-infrared biological window fluorophores: design and synthesis toward multimodal imaging and theranostics He, Shuqing; Song, Jun; Qu, Junle Chemical Society Reviews, Vol. 47, Issue 12 https://doi.org/10.1039/c8cs00234g	journal	January 2018
A bright organic NIR-II nanofluorophore for three-dimensional imaging into biological tissues Wan, Hao; Yue, Jingying; Zhu, Shoujun Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-03505-4	journal	March 2018
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
Novel benzo-bis(1,2,5-thiadiazole) fluorophores for in vivo NIR-II imaging of cancer Sun, Yao; Qu, Chunrong; Chen, Hao Chemical Science, Vol. 7, Issue 9 https://doi.org/10.1039/c6sc01561a	journal	January 2016
An Efficient 1064 nm NIR-II Excitation Fluorescent Molecular Dye for Deep-Tissue High-Resolution Dynamic Bioimaging Li, Benhao; Lu, Lingfei; Zhao, Mengyao Angewandte Chemie International Edition, Vol. 57, Issue 25 https://doi.org/10.1002/anie.201801226	journal	March 2018

Cited By (18)

Quaternary Ammonium Salt Based NIR‐II Probes for In Vivo Imaging Qu, Chunrong; Xiao, Yuling; Zhou, Hui Advanced Optical Materials, Vol. 7, Issue 15 https://doi.org/10.1002/adom.201900229	journal	May 2019
Deciphering of cerebrovasculatures via ICG-assisted NIR-II fluorescence microscopy Yu, Xiaoming; Feng, Zhe; Cai, Zhaochong Journal of Materials Chemistry B, Vol. 7, Issue 42 https://doi.org/10.1039/c9tb01381d	journal	January 2019
A novel near-infrared fluorescent light-up probe for tumor imaging and drug-induced liver injury detection Zeng, Xiaodong; Chen, Ziyang; Tang, Lin Chemical Communications, Vol. 55, Issue 17 https://doi.org/10.1039/c8cc10286d	journal	January 2019
A bright NIR-II fluorescent probe for breast carcinoma imaging and image-guided surgery Zeng, Xiaodong; Xie, Liru; Chen, Deliang Chemical Communications, Vol. 55, Issue 95 https://doi.org/10.1039/c9cc07694h	journal	January 2019
Stable, Wavelength‐Tunable Fluorescent Dyes in the NIR‐II Region for In Vivo High‐Contrast Bioimaging and Multiplexed Biosensing Lei, Zuhai; Sun, Caixia; Pei, Peng Angewandte Chemie, Vol. 131, Issue 24 https://doi.org/10.1002/ange.201904182	journal	May 2019
Mn-Loaded apolactoferrin dots for in vivo MRI and NIR-II cancer imaging Zhou, Hui; Yang, Han; Tang, Lin Journal of Materials Chemistry C, Vol. 7, Issue 31 https://doi.org/10.1039/c9tc01929d	journal	January 2019
An IR820 Dye–Protein Complex for Second Near‐Infrared Window and Photoacoustic Imaging Du, Bulin; Qu, Chunrong; Qian, Kun Advanced Optical Materials, Vol. 8, Issue 4 https://doi.org/10.1002/adom.201901471	journal	December 2019
Specific Small‐Molecule NIR‐II Fluorescence Imaging of Osteosarcoma and Lung Metastasis Zhou, Hui; Yi, Wanrong; Li, Anguo Advanced Healthcare Materials, Vol. 9, Issue 1 https://doi.org/10.1002/adhm.201901224	journal	October 2019
Advanced Nanotechnology Leading the Way to Multimodal Imaging‐Guided Precision Surgical Therapy Wang, Cong; Fan, Wenpei; Zhang, Zijian Advanced Materials, Vol. 31, Issue 49 https://doi.org/10.1002/adma.201904329	journal	September 2019
Produktive Modifikationen von Cyaninfarbstoff‐π‐Netzwerken Usama, Syed Muhammad; Thompson, Tye; Burgess, Kevin Angewandte Chemie, Vol. 131, Issue 27 https://doi.org/10.1002/ange.201902956	journal	May 2019
Improving Quantum Yield of a NIR‐II Dye by Phenylazo Group Zhang, Ling'e; Liu, Changren; Zhou, Sensen Advanced Healthcare Materials, Vol. 9, Issue 4 https://doi.org/10.1002/adhm.201901470	journal	January 2020
A Rationally Designed Semiconducting Polymer Brush for NIR‐II Imaging‐Guided Light‐Triggered Remote Control of CRISPR/Cas9 Genome Editing Li, Ling; Yang, Zhen; Zhu, Shoujun Advanced Materials, Vol. 31, Issue 21 https://doi.org/10.1002/adma.201901187	journal	April 2019
Monitoring the Real‐Time Circulatory System‐Related Physiological and Pathological Processes In Vivo Using a Multifunctional NIR‐II Probe Li, Daifeng; Qu, Chunrong; Liu, Qiang Advanced Functional Materials, Vol. 30, Issue 6 https://doi.org/10.1002/adfm.201906343	journal	November 2019
Productive Manipulation of Cyanine Dye π‐Networks Usama, Syed Muhammad; Thompson, Tye; Burgess, Kevin Angewandte Chemie International Edition, Vol. 58, Issue 27 https://doi.org/10.1002/anie.201902956	journal	May 2019
Molecular Engineering of an Organic NIR‐II Fluorophore with Aggregation‐Induced Emission Characteristics for In Vivo Imaging Wu, Wei; Yang, Yanqing; Yang, Yang Small, Vol. 15, Issue 20 https://doi.org/10.1002/smll.201805549	journal	March 2019
Molecular Imaging in the Second Near‐Infrared Window Wan, Hao; Du, Haotian; Wang, Feifei Advanced Functional Materials, Vol. 29, Issue 25 https://doi.org/10.1002/adfm.201900566	journal	April 2019
Stable, Wavelength‐Tunable Fluorescent Dyes in the NIR‐II Region for In Vivo High‐Contrast Bioimaging and Multiplexed Biosensing Lei, Zuhai; Sun, Caixia; Pei, Peng Angewandte Chemie International Edition, Vol. 58, Issue 24 https://doi.org/10.1002/anie.201904182	journal	June 2019
Extrahepatic cholangiography in near-infrared II window with the clinically approved fluorescence agent indocyanine green: a promising imaging technology for intraoperative diagnosis Wu, Di; Xue, Dingwei; Zhou, Jing Theranostics, Vol. 10, Issue 8 https://doi.org/10.7150/thno.41127	journal	January 2020

Similar Records

A high quantum yield molecule-protein complex fluorophore for near-infrared II imaging

Journal Article · Fri May 19 00:00:00 EDT 2017 · Nature Communications · OSTI ID:1485259

Antaris, Alexander L.; Chen, Hao; Diao, Shuo; +12 more

Flavylium Polymethine Fluorophores for Near‐ and Shortwave Infrared Imaging

Journal Article · Thu Sep 14 00:00:00 EDT 2017 · Angewandte Chemie · OSTI ID:1485259

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

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:1485259

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

Related Subjects

36 MATERIALS SCIENCE
59 BASIC BIOLOGICAL SCIENCES
Polymethine thiopyrylium salts
Second near-infrared window
U87MG glioma tumor
Molecular imaging

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

Citation Formats

References (38)

Cited By (18)

Similar Records

Related Subjects