2591-17-5Relevant articles and documents
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 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.
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.
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.
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.
Computation-Guided Rational Design of a Peptide Motif That Reacts with Cyanobenzothiazoles via Internal Cysteine-Lysine Relay
Keyser, Samantha G. L.,Utz, Ashley,Bertozzi, Carolyn R.
, p. 7467 - 7479 (2018)
Site-selective protein modification based on covalent reactions of peptide tags and small molecules is a key capability for basic research as well as for the development of new therapeutic bioconjugates. Here, we describe the computation-guided rational design of a cysteine- and lysine-containing 11-residue peptide sequence that reacts with 2-cyanobenzothiazole (CBT) derivatives. Our data show that the cysteine residue reversibly reacts with the nitrile group on the CBT moiety to form an intermediate thioimidate, which undergoes irreversible SN transfer to the lysine residue, yielding an amidine-linked product. The concepts outlined herein lay a foundation for future development of peptide tags in the context of site-selective modification of lysine residues within engineered microenvironments.
Using Bioluminescence Turn-On to Detect Cysteine in Vitro and in Vivo
Zhang, Miaomiao,Wang, Lin,Zhao, Yangyang,Wang, Fuqiang,Wu, Jindao,Liang, Gaolin
, p. 4951 - 4954 (2018)
Cysteine (Cys) is an essential amino acid and plays important roles in many biological processes. Bioluminescence (BL) is advantageous in sensitivity but BL probes that were intentionally developed for the selective detection of Cys were rarely reported. Herein, employing a fast conjugate addition between Cys and acrylic ester, we synthesized a caged BL probe acrylic ester luciferin (1) and used it to selectively detect Cys in vitro and image Cys in living cells and in tumor sites. We envision that, in the future, probe 1 might be used for evaluating the Cys roles in more biological processes.
Synthesis and evaluation of D-thioluciferin, a bioluminescent 6'-thio analog of Dluciferin
Rylands, Marwaan,Jardine, Anwar
, p. 176 - 189 (2021/03/17)
All known light-emitting firefly-bioluminescent luciferin analogs are either derived from the 6'-hydroxy- and/or 6'-aminoluciferin. We report the synthesis of D-thioluciferin, a 6'-thio analog or isostere of D-luciferin, starting from p-aminothiophenol, using a unique thioacrylate-S-protecting-group strategy. Upon treatment of Dthioluciferin with purified Photinus pyralis (Ppy) luciferase (Luc), a bioluminescence emission with a red-shift λmax relative to D-luciferin was observed. It was also shown that disulphide and sulphide analogs of Dthioluciferin did not produce similar bioluminescences relative to D-thioluciferin when treated with Ppy Luc under standard conditions, thus, providing a foundation for the development of D-thioluciferin based probes based on disulphide reduction and S-dealkylation.
DERIVATIVES OF LUCIFERIN AND METHODS FOR THEIR SYNTHESIS
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Page/Page column 28, (2019/02/13)
6-Thio derivatives of D-luciferin, also referred to as D-thioluciferins, having the general structure of Formula (I) are provided. Methods for synthesising D-luciferin, its derivatives, and their related 2-cyanobenzothiazole precursors are also provided. These compounds are commercially valuable due to their application in optical imaging, particularly in bioluminescence imaging.
