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1. CN109456264 - Fluorescent probe for detecting nitroreductase and preparation method and application thereof in enzymatic reaction

Office China
Application Number 201811454833.X
Application Date 30.11.2018
Publication Number 109456264
Publication Date 12.03.2019
Publication Kind A
IPC
C07D 215/14
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
215Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
02having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
12with substituted hydrocarbon radicals attached to ring carbon atoms
14Radicals substituted by oxygen atoms
C09K 11/06
CCHEMISTRY; METALLURGY
09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
KMATERIALS FOR APPLICATIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
11Luminescent, e.g. electroluminescent, chemiluminescent, materials
06containing organic luminescent materials
G01N 21/64
GPHYSICS
01MEASURING; TESTING
NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
21Investigating or analysing materials by the use of optical means, i.e. using infra-red, visible or ultra-violet light
62Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
63optically excited
64Fluorescence; Phosphorescence
CPC
C07D 215/14
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
215Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
02having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
12with substituted hydrocarbon radicals attached to ring carbon atoms
14Radicals substituted by oxygen atoms
C09K 11/06
CCHEMISTRY; METALLURGY
09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
11Luminescent, e.g. electroluminescent, chemiluminescent materials
06containing organic luminescent materials
C09K 2211/1007
CCHEMISTRY; METALLURGY
09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
2211Chemical nature of organic luminescent or tenebrescent compounds
10Non-macromolecular compounds
1003Carbocyclic compounds
1007Non-condensed systems
C09K 2211/1014
CCHEMISTRY; METALLURGY
09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
2211Chemical nature of organic luminescent or tenebrescent compounds
10Non-macromolecular compounds
1003Carbocyclic compounds
1014bridged by heteroatoms, e.g. N, P, Si or B
C09K 2211/1029
CCHEMISTRY; METALLURGY
09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
2211Chemical nature of organic luminescent or tenebrescent compounds
10Non-macromolecular compounds
1018Heterocyclic compounds
1025characterised by ligands
1029containing one nitrogen atom as the heteroatom
G01N 21/6428
GPHYSICS
01MEASURING; TESTING
NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
21Investigating or analysing materials by the use of optical means, i.e. using infra-red, visible or ultra-violet light
62Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
63optically excited
64Fluorescence; Phosphorescence
6428Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
Applicants SOUTH CHINA UNIVERSITY OF TECHNOLOGY
华南理工大学
Inventors WU SHUIZHU
吴水珠
XU LINGFENG
徐灵峰
NI LING
倪凌
ZENG FANG
曾钫
Agents 广州粤高专利商标代理有限公司 44102
广州粤高专利商标代理有限公司 44102
Title
(EN) Fluorescent probe for detecting nitroreductase and preparation method and application thereof in enzymatic reaction
(ZH) 一种检测硝基还原酶的荧光探针及其制备方法与酶促反应的应用
Abstract
(EN)
The invention discloses a fluorescent probe for detecting NTR (nitroreductase) and a preparation method and application thereof in enzymatic reaction, and belongs to the technical field of industrialanalysis detection. The fluorescent probe is a 3-(4-(2-(4'-(diphenylamino)-3-((4-nitrobenzyl)oxy)-[1,1'-biphenyl]-4-yl)vinyl)quinoline-1-bromo)propane-1-sulfonate. The fluorescent probe compound has the advantages that by leading hydrophilic group sulfonate and quinoline salt, the hydrophilia is enhanced; under the catalyzing function of NTR, the 1,6-rearrangement and elimination reaction is performed, the hydroxyl is produced, and the detection and analysis of NTR in the enzymatic reaction are realized by the fluorescence change caused by ICT (intramolecular charge transfer) effect. The preparation method has the advantages including that the preparation is simple and convenient, and the yield is high; the preparation method is suitable for detection of content of high-concentration enzyme in the enzymatic reaction, and the great application prospect is realized in the field of detection of enzyme in the enzymatic reaction system in the chemical engineering field.

(ZH)
本发明公开了一种检测硝基还原酶的荧光探针及其制备方法与酶促反应的应用,属于工业分析检测技术领域。所述荧光探针为3‑(4‑(2‑(4'‑(二苯胺基)‑3‑((4‑硝基苄基)氧基)‑[1,1'‑联苯基]‑4‑基)乙烯基)喹啉‑1‑溴)丙烷‑1‑磺酸盐。本发明的探针化合物通过引入亲水性基团磺酸根和喹啉盐类增强其亲水性,在硝基还原酶(NTR)的催化下发生1,6‑重排和消除反应,生成羟基,通过分子内电荷转移效应(ICT)引发的荧光变化来实现对酶促反应中NTR的检测分析。该方法具有制备简便、产率较高、且适用于检测酶促反应中高浓度酶含量等优点,在化工领域中的酶促反应体系酶检测领域显示了极大的应用前景。

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