2591-17-5Relevant academic research and scientific papers
A simple bioluminescent method for measuring d-amino acid oxidase activity
Bailey, T. Spencer,Donor, Micah T.,Naughton, Sean P.,Pluth, Michael D.
, p. 5425 - 5428 (2015)
d-Amino acid oxidase (DAO) plays important roles in regulating d-amino acid neurotransmitters and was recently identified as a key enzyme integral to hydrogen sulfide production from d-Cys. We report here the development of a simple biocompatible, bioluminescent method for measuring DAO activity based on the highly selective condensation of d-Cys with 6-hydroxy-2-cyanobenzothiazole (CBT-OH) to form d-luciferin. This journal is
A bioluminescent probe for longitudinal monitoring of mitochondrial membrane potential
Bazhin, Arkadiy A.,Sinisi, Riccardo,De Marchi, Umberto,Hermant, Aurélie,Sambiagio, Nicolas,Maric, Tamara,Budin, Ghyslain,Goun, Elena A.
, p. 1385 - 1393 (2020)
Mitochondrial membrane potential (ΔΨm) is a universal selective indicator of mitochondrial function and is known to play a central role in many human pathologies, such as diabetes mellitus, cancer and Alzheimer’s and Parkinson’s diseases. Here, we report the design, synthesis and several applications of mitochondria-activatable luciferin (MAL), a bioluminescent probe sensitive to ΔΨm, and partially to plasma membrane potential (ΔΨp), for non-invasive, longitudinal monitoring of ΔΨm in vitro and in vivo. We applied this new technology to evaluate the aging-related change of ΔΨm in mice and showed that nicotinamide riboside (NR) reverts aging-related mitochondrial depolarization, revealing another important aspect of the mechanism of action of this potent biomolecule. In addition, we demonstrated application of the MAL probe for studies of brown adipose tissue (BAT) activation and non-invasive in vivo assessment of ΔΨm in animal cancer models, opening exciting opportunities for understanding the underlying mechanisms and for discovery of effective treatments for many human pathologies. [Figure not available: see fulltext.]
A Convenient Synthetic Method of 2-Cyano-6-methoxybenzothiazole, - A Key Intermediate for the Synthesis of Firefly Luciferin
Toya, Yoshiaki,Takagi, Masaharu,Nakata, Hisao,Suzuki, Nobutaka,Isobe, Minoru,Goto, Toshio
, p. 392 - 395 (1992)
The title compound was prepared in one step from commercially available 2-amino-6-methoxybenzothiazole by using the Sandmeyer cyanation reaction.The result enabled us to synthesize firefly luciferin effectively from this amino compound through three steps in 36percent overall yield.
Highly Sensitive Bioluminescent Probe for Thiol Detection in Living Cells
Hemmi, Mayu,Ikeda, Yuma,Shindo, Yutaka,Nakajima, Takahiro,Nishiyama, Shigeru,Oka, Kotaro,Sato, Moritoshi,Hiruta, Yuki,Citterio, Daniel,Suzuki, Koji
, p. 648 - 655 (2018)
The sensitive detection of thiols including glutathione and cysteine is desirable owing to their roles as indispensable biomolecules in maintaining intracellular biological redox homeostasis. Herein, we report the design and synthesis of SEluc-1 (sulfinate ester luciferin), a chemoselective probe exhibiting a ratiometric and turn-on response towards thiols selectively in fluorescence and bioluminescence, respectively. The probe, which was designed based on the “caged” luciferin strategy, displays excellent selectivity, high signal/noise ratio (>240 in the case of bioluminescence), and a biologically relevant limit of detection (LOD, 80 nm for cysteine), which are all desirable traits for a sensitive bioluminescent sensor. SEluc-1 was further applied to fluorescence imaging of thiol activity in living human cervical cancer HeLa cell cultures, and was successfully able to detect fluctuations in thiol concentrations induced by oxidative stress in a bioluminescent assay utilizing African green monkey fibroblast COS-7 cells and human breast adenocarcinoma MCF-7 cells.
Specific Imaging of Tyrosinase in Vivo with 3-Hydroxybenzyl Caged D -Luciferins
Li, Shuang,Hu, Rui,Wang, Shuangqing,Guo, Xudong,Zeng, Yi,Li, Yi,Yang, Guoqiang
, p. 9296 - 9300 (2018)
Tyrosinase (TYR), a key enzyme in biosynthesis of melanin, usually functions as a biomarker of severe skin diseases such as vitiligo and melanoma cancer. Accurate detection of TYR activity in vivo is urgent but still challenging. Inspired by the advantages of bioluminescence in vivo strategy in imaging and the specific hydroxylation of 3-hydroxybenzyloxy group by TYR, a bioluminogenic probe, TYR-LH2, was designed and synthesized through caging D-luciferin with 3-hydroxybenzyl. The probe exhibits high selectivity and sensitivity toward TYR with a detection limit of 0.11 U/mL in a small detection volume of 100 μL. Bioluminescence imaging results show that TYR-LH2 is fully competent for monitoring the dynamic changes of TYR in living cells and model animals and possesses the capability of discriminating melanocytes from other cell lines, thus offering a promising approach for investigation and diagnosis of melanoma cancer and other TYR-related diseases in vivo.
Real-Time Bioluminescence Imaging of Nitroreductase in Mouse Model
Feng, Ping,Zhang, Huateng,Deng, Quankun,Liu, Wei,Yang, Linghui,Li, Guobo,Chen, Guo,Du, Lupei,Ke, Bowen,Li, Minyong
, p. 5610 - 5614 (2016)
Nitroreductase (NTR) is an endogenous reductase overexpressed in hypoxic tumors; however, its precise detection in living cells and animals remains a considerable challenge. Herein, we developed three reaction-based probes and a related bioluminescence assay for the real-time NTR detection. The high sensitivity and selectivity of probe 3, combined with its remarkable potential of bioluminescence imaging, affords a valuable approach for in vivo imaging of NTR in a tumor model mouse.
A bioluminescent probe for imaging endogenous hydrogen polysulfides in live cells and a murine model of bacterial infection
Li, Jun-Bin,Wang, Qianqian,Liu, Hong-Wen,Yuan, Lin,Zhang, Xiao-Bing
, p. 4487 - 4490 (2019)
In this work, we report the first bioluminescent probe BP-PS for detecting H2Sn with high specificity and sensitivity. Owing to the bioluminescence imaging without requiring an excitation light source, tissue autofluorescence is eliminated and BP-PS shows a high signal-to-noise ratio. Moreover, BP-PS was successfully utilized to visualize endogenous H2Sn in live cells and a murine model of bacterial infection.
Real-Time Imaging and Quantification of Peptide Uptake in Vitro and in Vivo
Karatas, Hacer,Maric, Tamara,D'Alessandro, Pier Luca,Yevtodiyenko, Aleksey,Vorherr, Thomas,Hollingworth, Gregory J.,Goun, Elena A.
, p. 2197 - 2205 (2019)
Peptides constitute an important class of drugs for the treatment of multiple metabolic, oncological, and neurodegenerative diseases, and several hundred novel therapeutic peptides are currently in the preclinical and clinical stages of development. However, many leads fail to advance clinically because of poor cellular membrane and tissue permeability. Therefore, assessment of the ability of a peptide to cross cellular membranes is critical when developing novel peptide-based therapeutics. Current methods to assess peptide cellular permeability are limited by multiple factors, such as the need to introduce rather large modifications (e.g., fluorescent dyes) that require complex chemical reactions as well as an inability to provide kinetic information on the internalization of a compound or distinguish between internalized and membrane-bound compounds. In addition, many of these methods are based on end point assays and require multiple sample manipulation steps. Herein, we report a novel Split Luciferin Peptide (SLP) assay that enables the real-time noninvasive imaging and quantification of peptide uptake both in vitro and in vivo using a very sensitive bioluminescence readout. This method is based on a straightforward, stable chemical modification of the peptide of interest with a d-cysteine tag that preserves the overall peptidic character of the original molecule. This method can be easily adapted for screening peptide libraries and can thus become an important tool for preclinical peptide drug development.
Highly sensitive and selective bioluminescence based ozone probes and their applications to detect ambient ozone
Nam, Younseok,Kim, Beom Seok,Shin, Injae
, p. 1128 - 1130 (2016)
Highly selective and sensitive bioluminescence based probes, which respond to ozone but not to other ROS, have been developed. These probes were used to determine ozone concentrations in environmental samples.
Bioluminescent Turn-On Probe for Sensing Hypochlorite in Vitro and in Tumors
Chen, Peiyao,Zheng, Zhen,Zhu, Yunxia,Dong, Yu,Wang, Fuqiang,Liang, Gaolin
, p. 5693 - 5696 (2017)
Hypochlorite (ClO-) is one of the most important reactive oxygen species but using a BL probe for its selective detection (or imaging) still remains challenging. Herein, we report a latent BL probe benzoylhydrazine luciferin (1) for highly selective detection of ClO- in vitro and imaging ClO- in living cells and tumors. In vitro tests indicated that 1 could be applied for highly selective detection of ClO- within the range of 0-62.5 μM with a limit of detection of 0.705 μM. Using these unique features of 1, we successfully applied it to image ClO- in living cells and tumors. We envision that probe 1 might be applied to elucidate the biological roles of ClO- in wider physiological and pathological processes in the near future.
