- A sequentially activated bioluminescent probe for observation of cellular H2O2production induced by cysteine
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We report herein a caged luciferin probeCy-Hyas a sequentially activated probe to selectively and sensitively sensel-Cys and H2O2. The probe displayed fluorescence and bioluminescence responses toward the two analytes. Utilizing the present probe, cellular excessl-Cys-induced H2O2up-regulation was observed for the first time in living MDA-MB-231 cells.
- Ma, Kaiqing,Yue, Yongkang,Zhao, Lingling,Chao, Jianbin,Yin, Caixia
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p. 10015 - 10018
(2021/10/06)
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- Synthesis and evaluation of D-thioluciferin, a bioluminescent 6'-thio analog of Dluciferin
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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.
- Rylands, Marwaan,Jardine, Anwar
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p. 176 - 189
(2021/03/17)
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- NOVEL CHEMILUMINESCENT SUBSTRATES FOR FACTOR XA
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The present invention relates to chemiluminescent substrates of formulas (I-3) and (I-4) for blood clotting enzyme Factor Xa. The substrates are particularly useful for assaying coagulation factors and for quantifying an anticoagulant in a sample.
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- Synthesis of N-Peptide-6-Amino-d-Luciferin Conjugates with Optimized Fragment Condensation Strategy
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Abstract: The synthesis of peptide-luciferin conjugates has a pivotal role in the development of bioluminescent detection systems that are based on the determination of protease enzyme activity. This work describes the optimized synthesis of an N-peptide-6-amino-d-luciferin conjugate (Fmoc-Gly-Pro-6-amino-d-luciferin) with a simple fragment condensation method in adequate yields. Fmoc-Gly-Pro-6-amino-d-luciferin was produced from a previously synthesized Fmoc-Gly-Pro-OH and also previously synthesized 6-amino-2-cyanobenzothiazole with an optimized method, to which conjugate cysteine was added in an also improved way. The resulting conjugate was successfully used in a bioluminescent system, in vitro, demonstrating the applicability of the method. Graphical Abstract: [Figure not available: see fulltext.].
- Kovács, Anita K.,Hegyes, Péter,Szebeni, Gábor J.,Bogár, Krisztián,Puskás, László G.,Tóth, Gábor K.
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p. 1209 - 1215
(2018/09/27)
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- Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole
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2-Cyanobenzothiazoles (CBTs) are useful building blocks for: 1) luciferin derivatives for bioluminescent imaging; and 2) handles for bioorthogonal ligations. A particularly versatile CBT is 6-amino-2-cyanobenzothiazole (ACBT), which has an amine handle for straight-forward derivatisation. Here we present an economical and scalable synthesis of ACBT based on a cyanation catalysed by 1,4-diazabicyclo[2.2.2]octane (DABCO), and discuss its advantages for scale-up over previously reported routes.
- Hauser, Jacob R.,Beard, Hester A.,Bayana, Mary E.,Jolley, Katherine E.,Warriner, Stuart L.,Bon, Robin S.
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p. 2019 - 2025
(2016/10/05)
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- Rapid and scalable assembly of firefly luciferase substrates
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Bioluminescence imaging with luciferase-luciferin pairs is a popular method for visualizing biological processes in vivo. Unfortunately, most luciferins are difficult to access and remain prohibitively expensive for some imaging applications. Here we report cost-effective and efficient syntheses of d-luciferin and 6′-aminoluciferin, two widely used bioluminescent substrates. Our approach employs inexpensive anilines and Appel's salt to generate the luciferin cores in a single pot. Additionally, the syntheses are scalable and can provide multi-gram quantities of both substrates. The streamlined production and improved accessibility of luciferin reagents will bolster in vivo imaging efforts. This journal is
- McCutcheon, David C.,Porterfield, William B.,Prescher, Jennifer A.
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p. 2117 - 2121
(2015/03/18)
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- A "caged" Luciferin for Imaging Cell-Cell Contacts
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Cell-cell interactions underlie fundamental biological processes but remain difficult to visualize over long times and large distances in tissues and live organisms. Bioluminescence imaging with luciferase-luciferin pairs is sufficiently sensitive to imag
- Porterfield, William B.,Jones, Krysten A.,McCutcheon, David C.,Prescher, Jennifer A.
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supporting information
p. 8656 - 8659
(2015/07/27)
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- Site-specific immobilization of biomolecules by a biocompatible reaction between terminal cysteine and 2-cyanobenzothiazole
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We report herein a new site-specific microarray immobilization method based on a biocompatible reaction between terminal cysteine and 2-cyanobenzothiazole (CBT). This immobilization strategy has been successfully applied to anchor small molecules, peptides and proteins onto microarrays.
- Wang, Ping,Zhang, Chong-Jing,Chen, Ganchao,Na, Zhenkun,Yao, Shao Q.,Sun, Hongyan
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p. 8644 - 8646
(2013/09/23)
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- Aminoluciferins as functional bioluminogenic substrates of firefly luciferase
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Firefly luciferase is widely used as a reporter gene in assays to study gene expression, gene delivery, and so on because of its extremely high signal-to-noise ratio. The availability of a range of bioluminogenic substrates would greatly extend the applicability of the luciferin-luciferase system. Herein, we describe a design concept for functional bioluminogenic substrates based on the aminoluciferin (AL) scaffold, together with a convenient, high-yield method for synthesizing N-alkylated ALs. We confirmed the usefulness of ALs as bioluminogenic substrates by synthesizing three probes. The first was a conjugate of AL with glutamate, Glu-AL. When Glu-AL, the first membrane-impermeable bioluminogenic substrate of luciferases, was applied to cells transfected with luciferase, luminescence was not observed; that is, by using Glu-AL, we can distinguish between intracellular and extracellular events. The second was Cy5-AL, which consisted of Cy5, a near-infrared (NIR) cyanine fluorescent dye, and AL, and emitted NIR light. When Cy5-AL reacted with luciferase, luminescence derived from Cy5 was observed as a result of bioluminescence resonance energy transfer (BRET) from AL to Cy5. The NIR emission wavelength would allow a signal to be observed from deeper tissues in bioluminescence in vivo imaging. The third was biotin-DEVD-AL (DEVD=the amino acid sequence Asp-Glu-Val-Asp), which employed a caspase-3 substrate peptide as a switch to control the accessibility of the substrate to luciferase, and could detect the activity of caspase-3 in a time-dependent manner. This generalized design strategy should be applicable to other proteases. Our results indicate that the AL scaffold is appropriate for a range of functional luminophores and represents a useful alternative substrate to luciferin.
- Takakura, Hideo,Kojima, Ryosuke,Urano, Yasuteru,Terai, Takuya,Hanaoka, Kenjiro,Nagano, Tetsuo
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p. 1800 - 1810
(2011/12/16)
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- METHODS AND SYSTEMS FOR SYNTHESIS OF A D-AMINOLUCIFERIN PRECURSOR AND RELATED COMPOUNDS
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Methods and systems to generate 6-amino-6-deoxy-D-luciferin precursor, 2-cyano-6-aminobenzothiazole and related compounds and derivatives
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- METHODS AND SYSTEMS FOR SYNTHESIS OF A D-AMINOLUCIFERIN PRECURSOR AND RELATED COMPOUNDS
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Methods and systems to generate 6-amino-6-deoxy-D-luciferin precursor, 2-cyano-6-aminobenzothiazole and related compounds and derivatives
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- Novel luciferin derivatives
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A compound represented by the following general formula (I) or a salt thereof: [wherein R1 and R2 represent hydrogen atom, a C1-6 alkyl group, or a group represented by the following formula (A): [wherein X1 and X2 represent hydrogen atom, or a group represented as —N(R3)(R4) (R3 and R4 represent hydrogen atom, a C1-6 alkyl group, a C1-6 alkylcarbonyl group, or a C1-6 alkyloxycarbonyl group); and n represents an integer of 1 to 6], provided that R1 and R2 do not simultaneously represent hydrogen atom), which is a novel luciferin derivative that serves as a luciferase substrate.
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Page/Page column 5
(2008/06/13)
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