939-69-5Relevant academic research and scientific papers
An allylated firefly luciferin analogue with luciferase specific response in living cells
Ikeda, Yuma,Saitoh, Tsuyoshi,Niwa, Kazuki,Nakajima, Takahiro,Kitada, Nobuo,Maki, Shojiro A.,Sato, Moritoshi,Citterio, Daniel,Nishiyama, Shigeru,Suzuki, Koji
, p. 1774 - 1777 (2018)
An allylated firefly luciferin was successfully synthesized and its bioluminescence properties were evaluated. When applied to cellular imaging in combination with Eluc, which is one of the commercially available luciferases, this analogue displayed a luciferase-specific bioluminescence signal with prolonged emission (>100 min).
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.
Reduction Triggered in Situ Polymerization in Living Mice
Chen, Zixin,Cui, Lina,Fréchet, Jean M. J.,Gambhir, Sanjiv S.,Kierstead, Paul H.,Kothapalli, Sri-Rajasekhar,Liu, Jun,Ma, Xiaowei,Rao, Jianghong,Smith, Bryan Ronain,Taylor, Madelynn,Vivona, Sandro
supporting information, p. 15575 - 15584 (2020/10/18)
"Smart"biomaterials that are responsive to physiological or biochemical stimuli have found many biomedical applications for tissue engineering, therapeutics, and molecular imaging. In this work, we describe in situ polymerization of activatable biorthogonal small molecules in response to a reducing environment change in vivo. We designed a carbohydrate linker- and cyanobenzothiazole-cysteine condensation reaction-based small molecule scaffold that can undergo rapid condensation reaction upon physiochemical changes (such as a reducing environment) to form polymers (pseudopolysaccharide). The fluorescent and photoacoustic properties of a fluorophore-tagged condensation scaffold before and after the transformation have been examined with a dual-modality optical imaging method. These results confirmed the in situ polymerization of this probe after both local and systemic administration in living mice.
Bioluminescent probe for detection of selenocysteine in organisms, preparation method and application thereof
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Paragraph 0107-0108, (2019/02/13)
Belonging to the field of organic synthesis and detection, the invention relates to a bioluminescent probe for detection of selenocysteine in organisms, a preparation method and application thereof. The bioluminescent probe BF-1 for recognition of Sec provided by the invention has the advantages of good selectivity, high sensitivity, low detection limit (8nM), good biocompatibility, etc. In a Tris-HCl buffer solution, the bioluminescent intensity and selenocysteine concentration show a good linear relationship, thus indicating that the probe is suitable for quantitative detection of selenocysteine. The probe BF-1 also realizes bioluminescence imaging of selenocysteine in MCF-7-luc cells. The probe BF-1 also achieves sensitive detection of endogenous Sec level in vivo (FVB-Luc transgenicmice), also is quick in response, and the bioluminescence signal is stable. The probe BF-1 prepared according to the invention is an effective tool for visual and quantitative detection of the selenocysteine content in cells, living bodies and tumor tissues.
DERIVATIVES OF LUCIFERIN AND METHODS FOR THEIR SYNTHESIS
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Page/Page column 27, (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.
Synthesis, spectroscopic characterization, and computational studies of 2-cyano-6-hydroxybenzothiazole: A key synthetic intermediate of firefly luciferin
Shahmoradi, Ghasem,Amani, Saeid
, p. 1499 - 1517 (2019/01/03)
Firefly luciferin is widely applied as a biotechnological tool for visualizing various biological processes in vitro and in vivo. Chemically, 2-cyano-6-hydroxybenzothiazole, as a key synthetic intermediate of firefly luciferin, is obtained from 2-cyano-6-methoxybenzothiazole by changing the methoxy with a hydroxy group. However, this approach is costly and not suited for large-scale synthesis. Here we report cost-effective and efficient syntheses of 2-cyano-6-hydroxybenzothiazole through the catalytic Sandmeyer-type cyanation reaction. Our approach employs diazonium tetrafluoroborate salt of 2-amino-6-hydroxybenzothiazole as a cyanation substrate. The cyanation reaction proceeds efficiently under mild conditions by using Cu(I)/Cu(II)/N,N,N',N'-tetramethylethylenediamine as a catalyst. In addition, computational studies of the 2-cyano-6-hydroxybenzothiazole structure were performed based on the density functional theory method. The theoretical parameters of the optimized geometry were derived from the B3LYP/6-311 ++ G(d, p) method. Time-dependent density functional theory was applied to assign the electronic absorption bands observed experimentally and the1 H NMR chemical shifts were computed using the GIAO method. There was a significant relationship between computational studies and experimental results.
The cyclized compound, and, cyclic compound solution containing a light-emitting method
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Paragraph 0048-0050, (2017/08/15)
PROBLEM TO BE SOLVED: To provide a method of producing a cyclized compound, and a method of causing a solution containing the cyclized compound to emit light.SOLUTION: A method of producing a cyclized compound represented by the chemical formula (II) comprises bringing an acid into contact with a compound represented by the general formula (I). (In the formula, R, Rand Rare each independently H or a substituent that becomes H upon the contact with the acid, and Ris OH or a substituent that becomes OH upon the contact with the acid.)
Synthesis of Firefly Luciferin Analogues and Evaluation of the Luminescent Properties
Ioka, Shuji,Saitoh, Tsuyoshi,Iwano, Satoshi,Suzuki, Koji,Maki, Shojiro A.,Miyawaki, Atsushi,Imoto, Masaya,Nishiyama, Shigeru
, p. 9330 - 9337 (2016/07/14)
Five new firefly luciferin (1) analogues were synthesized and their light emission properties were examined. Modifications of the thiazoline moiety in 1 were employed to produce analogues containing acyclic amino acid side chains (2–4) and heterocyclic rings derived from amino acids (5 and 6) linked to the benzothiazole moiety. Although methyl esters of all of the synthetic derivatives exhibited chemiluminescence activity, only carboluciferin (6), possessing a pyrroline-substituted benzothiazole structure, had bioluminescence (BL) activity (λmax=547 nm). Results of bioluminescence studies with AMP-carboluciferin (AMP=adenosine monophosphate) and AMP-firefly luciferin showed that the nature of the thiazoline mimicking moiety affected the adenylation step of the luciferin–luciferase reaction required for production of potent BL. In addition, BL of 6 in living mice differed from that of 1 in that its luminescence decay rate was slower.
Demethylating technology of 2-cyan-6-methoxy-benzothiazole, and D-fluorescein preparation method thereof
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Paragraph 0046; 0047, (2016/10/07)
The invention belongs to the field of chemical synthesis, and discloses a demethylating technology of 2-cyan-6-methoxy-benzothiazole. The technology comprises the following steps: 1, sequentially adding 2-cyan-6-methoxy-benzothiazole, metal iodide, mercaptan and acetonitrile to a reaction bottle, and stirring added materials for dissolving; 2, slowly adding an acetonitrile solution of trimethylchlorosilane to the above obtained system in a dropwise manner; 3, carrying out a heat insulation reaction after dropwise addition; and 4, adding an aqueous solution of an alkali in a dropwise manner after the reaction ends, adjusting the pH value to 7-12, adding an organic solvent, stirring the obtained solution, layering the stirred solution, backwashing the above obtained organic phase with water, drying the organic phase, and desolventizing the dried organic phase to obtain 2-cyan-6-hydroxy-benzothiazole. A reaction substrate and the above product can be well dissolved in the solvent selected in the invention, and the technology has the advantages of thorough reaction, high catalysis efficiency, reaction time shortening, mild reaction conditions, no high pressure, high temperature or other strict reaction conditions, high yield, and no generation of severely toxic substances. The final product is prepared from an intermediate through a one-kettle process without purification.
Rapid and scalable assembly of firefly luciferase substrates
McCutcheon, David C.,Porterfield, William B.,Prescher, Jennifer A.
, p. 2117 - 2121 (2015/03/18)
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
