Development of a series of near-infrared dark quenchers based on Si-rhodamines and their application to fluorescent probes

Journal of the American Chemical Society
Takuya MyochinYasuteru Urano

Abstract

Near-infrared (NIR) fluorescent probes based on the Förster resonance energy transfer (FRET) mechanism have various practical advantages, and their molecular design is generally based on the use of NIR dark quenchers, which are nonfluorescent dyes, as cleavable FRET acceptors. However, few NIR dark quenchers can quench fluorescence in the Cy7 region (over 780 nm). Here, we describe Si-rhodamine-based NIR dark quenchers (SiNQs), which show broad absorption covering this region. They are nonfluorescent independently of solvent polarity and pH, probably due to free rotation of the bond between the N atom and the xanthene moiety. SiNQs can easily be structurally modified to tune their water-solubility and absorption spectra, enabling flexible design of appropriate FRET pair for various NIR fluorescent dyes. To demonstrate the usefulness of SiNQs, we designed and synthesized a NIR fluorescent probe for matrix metalloproteinase (MMP) activity using SiNQ780. This probe 1 could detect MMP activity in vitro, in cultured cells and in a tumor-bearing mouse, in which the tumor was clearly visualized, by NIR fluorescence. We believe SiNQs will be useful for the development of a wide range of practical NIR fluorescent probes.

References

May 1, 1996·Bioconjugate Chemistry·S R MujumdarA S Waggoner
May 7, 2002·Nature Reviews. Cancer·Mikala Egeblad, Zena Werb
Aug 5, 2003·Chemistry : a European Journal·Mary Katherine Johansson, Ronald M Cook
Nov 19, 2003·Molecular and Cellular Biochemistry·Sajal ChakrabortiTapati Chakraborti
Mar 18, 2005·Journal of the American Chemical Society·Eita SasakiTetsuo Nagano
May 28, 2005·Journal of Cellular Physiology·Yoshifumi Itoh, Motoharu Seiki
Jan 13, 2006·Nature Chemical Biology·Galia BlumMatthew Bogyo
Sep 1, 2006·ChemMedChem·Jesus RazkinIsabelle Texier
Feb 20, 2008·Current Opinion in Chemical Biology·Schuyler B VanEngelenburg, Amy E Palmer
Apr 4, 2008·Nature·Ralph Weissleder, Mikael J Pittet
Mar 3, 2009·Analytical Biochemistry·Xinzhan PengD Michael Olive
Aug 27, 2009·The Journal of Physical Chemistry. B·Jonathan F LovellGang Zheng
Jan 26, 2010·Journal of Controlled Release : Official Journal of the Controlled Release Society·Tao ZhaoMasahiro Hiraoka
Jun 23, 2010·Proceedings of the National Academy of Sciences of the United States of America·Ying KongJeffrey D Cirillo
Oct 29, 2010·Journal of the American Chemical Society·Kazuki KiyoseTetsuo Nagano
Nov 20, 2010·The FEBS Journal·Chrisostomi GialeliNikos K Karamanos
Mar 2, 2011·Chemical Communications : Chem Comm·Takahiro EgawaTetsuo Nagano
Apr 5, 2011·Theranostics·Lei ZhuXiaoyuan Chen
Nov 1, 2011·Nature Methods·Daniel R StableyKhalid S Salaita
May 23, 2012·Bioorganic & Medicinal Chemistry Letters·Yu KushidaTetsuo Nagano
Jul 14, 2012·Journal of Hepato-biliary-pancreatic Sciences·Floris P R VerbeekAlexander L Vahrmeijer
Jul 24, 2012·Journal of the American Chemical Society·Lin YuanSasa Zhu
Nov 20, 2012·Journal of the American Chemical Society·Shodai TakahashiKenjiro Hanaoka
Jul 25, 2013·Nature Reviews. Clinical Oncology·Alexander L VahrmeijerJohn V Frangioni

❮ Previous
Next ❯

Citations

Jun 29, 2016·Journal of Controlled Release : Official Journal of the Controlled Release Society·Hong-Jun ChoYoon-Sik Lee
Aug 23, 2016·ACS Applied Materials & Interfaces·Jing LiuWei Guo
Dec 4, 2015·Organic & Biomolecular Chemistry·Ilkay BoraBo W Laursen
Jun 9, 2017·Chemistry, an Asian Journal·Arnaud ChevalierAnthony Romieu
Oct 25, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Wen-Jing ShiDennis K P Ng
Oct 7, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Tasuku HirayamaHideko Nagasawa
Dec 7, 2018·Chemical Society Reviews·Junji ZhangHe Tian
Apr 11, 2019·Organic & Biomolecular Chemistry·Shasha ZhengRajavel Srinivasan
Mar 28, 2019·Angewandte Chemie·Weijie ChiXiaogang Liu
Mar 8, 2019·Angewandte Chemie·Liulin WangWei Huang
Feb 28, 2020·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Jin GongXianshun Zeng
Jul 22, 2020·Organic & Biomolecular Chemistry·Joomyung V JunE James Petersson
Apr 30, 2017·Chemistry, an Asian Journal·Takayuki IkenoKenjiro Hanaoka
Dec 15, 2017·Chemical Communications : Chem Comm·Hiroaki OgasawaraShigehiro Yamaguchi
Feb 5, 2019·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Kenjiro Hanaoka
Jul 23, 2020·Chemical Society Reviews·Luling WuTony D James
Dec 12, 2018·Chemistry : a European Journal·Zhong WeiShuang-Quan Zang
Sep 6, 2017·Journal of the American Chemical Society·Wen PiaoYasuteru Urano
Jan 29, 2019·Journal of the American Chemical Society·Ling YinMingyuan Gao
Jul 3, 2019·Analytical Chemistry·Takayuki IkenoYasuteru Urano
Sep 4, 2019·The Journal of Organic Chemistry·Chathuranga S L RathnamalalaColleen N Scott
Aug 25, 2017·Journal of the American Chemical Society·Yuanhong MaZhaomin Hou
Oct 5, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Edward R H WalterNicholas J Long

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.