174680-55-8Relevant academic research and scientific papers
Multicomponent synthesis of novel coelenterazine derivatives substituted at the C-3 position
Vece, Vito,Vuocolo, Giuseppina
, p. 8781 - 8785 (2015)
Three novel coelenterazine derivatives substituted at the C-3 position were synthesized through a multicomponent strategy based on Groebke-Blackburn-Bienaymé reaction without using protecting groups. An efficient one-pot tert-butyl group cleavage from an
Deuterated compound based on cavity enterostatin - h as well as preparation method and application thereof
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Paragraph 0029; 0086-0088, (2021/11/26)
The invention discloses a deuterated compound based on caescein - h, a preparation method and application thereof, and the chemical structural formula is as follows. In-flight R1 Phenyl or deuterated phenyl groups R2 Hydrogen or deuterium, R3 Hydrogen or deuterium, R4 Hydrogen or deuterium, R5 Hydrogen or deuterium, R6 Hydrogen or deuterium, R1 -R6 At least one group in the group is a deuterated group. The deuterated compound provided by the invention is used as a biological luminescent substrate, and can monitor the distribution of luciferase in vivo and outside. Compared with the cavity enterostatin - h, the method for preparing the deuterated compound of the cavity enterostatin - is simple, the reaction steps are classic, the operability is high, the cost - h is low, and the method has a good practical value.
C-6 site modified NanoLuc type analogues and preparation method and application thereof
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Paragraph 0057; 0087-0089, (2020/05/30)
The invention provides C-6 site modified NanoLuc type analogues and a preparation method and application thereof. The C-6 site modified NanoLuc type analogues have a structure as shown in a formula Iwhich is described in the specification. In the formula I, R1 is selected from a group consisting of a 4-fluorophenyl group, a 4-chlorphenyl group, a 4-bromophenyl group, a 3-fluoro-4-aminophenyl group, a thienyl group, a furyl group, a 5-methylfuryl group, a naphth-2-yl group, a benzofuryl group, a 4-methylphenyl group, a 3,5-dimethylphenyl group, a 4-hydroxymethylphenyl group, a 4-methoxyphenylgroup and a 4-mercaptophenyl group. The analogues can be used as a bioluminescent substrate for researching protein-protein and protein-ligand interactions, monitoring protein stability and bioluminescence resonance energy transfer and the like. The invention provides application of the analogues to in-vitro, cellular and in-vivo distribution imaging under the action of NanoLuc luciferase in virtue of bioluminescence and application of the analogues as a report signal to detect the pharmacological action and toxic action of a drug at an enzyme level, a cellular level and an animal level in thepresence of NanoLuc luciferase.
Novel NanoLuc-type substrates with various C-6 substitutions
Yan, Chongzheng,Du, Lupei,Li, Minyong
supporting information, (2020/03/19)
NanoLuc (NLuc)-furimazine bioluminescence system offers several advantages over established systems, including improved stability, smaller size, and >150-fold enhancement in bioluminescence. Herein, we designed and synthesized a series of bioluminescent substrates with varying at the C-6 position of furimazine for NLuc-furimazine bioluminescence system. Among all derivatives, compounds A6 and A11 provided excellent bioluminescence characteristics compared with furimazine in vitro and in vivo. We believe that these new NLuc substrates can broaden the application of NLuc bioluminescence techniques, especially in vivo bioluminescent imaging.
New bioluminescent coelenterazine derivatives with various C-6 substitutions
Jiang, Tianyu,Yang, Xingye,Zhou, Yubin,Yampolsky, Ilia,Du, Lupei,Li, Minyong
, p. 7008 - 7018 (2017/09/01)
A series of new coelenterazine analogs with varying substituents at the C-6 position of the imidazopyrazinone core have been designed and synthesized for the extension of bioluminescence substrates. Some of them display excellent bioluminescence properties compared to DeepBlueC or native coelenterazine with both in vitro and in vivo biological evaluations, thus placing these derivatives among the most ideal substrates for Renilla bioluminescence applications.
FLUOROCHROME-COUPLED COELENTERAZINE
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Paragraph 0057-0059, (2017/02/02)
PROBLEM TO BE SOLVED: To provide techniques of making the light emission wavelength of a Renilla luciferase (Rluc)-coelenterazine light-emitting system longer by modifying coelenterazine. SOLUTION: A fluorochrome-coupled coelenterazine is represented by t
Luminescence of coelenterazine derivatives with C-8 extended electronic conjugation
Yuan, Ming-Liang,Jiang, Tian-Yu,Du, Lu-Pei,Li, Min-Yong
supporting information, p. 550 - 554 (2016/04/26)
Replacement of the methylene group at the C-8 position with an extended electronic conjugation is a new promising method to develop red-shifted coelenterazine derivatives. In this paper, we have described an oxygen-containing coelenterazine derivative with a significant red-shifted (63 nm) bioluminescence signal maximum relative to coelenterazine 400a (DeepBlueC, 1). In cell imaging, the sulfur-containing coelenterazine derivative displayed a significantly (1.77 ± 0.09; P ≤ 0.01) higher luminescence signal compared to coelenterazine 400a and the oxygen-containing coelenterazine derivative exhibited a slightly (0.74 ± 0.08; P ≤ 0.05) lower luminescence signal. It is beneficial to understand further the underlying mechanisms of bioluminescence.
Novel bioluminescent coelenterazine derivatives with imidazopyrazinone C-6 extended substitution for: Renilla luciferase
Jiang, Tianyu,Yang, Xiaofeng,Yang, Xingye,Yuan, Mingliang,Zhang, Tianchao,Zhang, Huateng,Li, Minyong
, p. 5272 - 5281 (2016/07/06)
Two series of novel coelenterazine analogues (alkynes and triazoles) with imidazopyrazinone C-6 extended substitution have been designed and synthesized successfully for the extension of bioluminescent substrates. After extensive evaluation, some compounds display excellent bioluminescence properties compared with DeepBlueC in cellulo, thus becoming potential molecules for bioluminescence techniques.
Coelenterazine analog and preparing method and application thereof
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Paragraph 0144-0148, (2018/02/04)
The invention discloses a coelenterazine analog and a preparing method and application thereof. The coelenterazine analog has the general structure formula (I) shown in the description, wherein R1, R2 and R3 in the formula are different substituents. According to application of the compound as a bioluminescence substrate, the existence and quantity (including the enzyme level, the cell level and the animal level) of coelenterazine luciferase can be detected with bioluminescence, and the in vitro, cell and in vivo distribution imaging of luciferase can be detected; the compound can serve as a report signal to detect the pharmacologic action and the toxic effect of medicine on the enzyme level, the cell level and the animal level under the existence of luciferase.
Bioluminescent coelenterazine derivatives with imidazopyrazinone C-6 extended substitution
Nishihara, Ryo,Suzuki, Hideyuki,Hoshino, Emi,Suganuma, Sakura,Sato, Moritoshi,Saitoh, Tsuyoshi,Nishiyama, Shigeru,Iwasawa, Naoko,Citterio, Daniel,Suzuki, Koji
supporting information, p. 391 - 394 (2015/02/19)
Three novel coelenterazine (CTZ) derivatives with extension at the C-6 position of the imidazopyrazinone structure show significant bioluminescence emission with known renilla luciferase variants, indicating a promising method to develop CTZ derivatives w
