Polymerisable fluorescent functional monomer and its prepn and use

A technology of functional monomers and synthesis methods, which is applied in the field of preparation of fluorescent functional monomers, can solve problems such as limitations, difficulty in additives, repeatability, and carcinogenesis-inducing effects, and achieve the effects of simple synthesis methods, easy-to-obtain raw materials, and reasonable synthesis routes

Inactive Publication Date: 2007-08-29
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] The research of biological macromolecules by fluorescence technology (such as protein conformation, DNA separation and sequencing, etc.), the in situ research of cell growth, apoptosis, and mutation have so far mainly focused on the introduction of small molecule fluorescent probes into the research system. Although this method is simple, fast and sensitive, some small molecular fluorescent probes are non-water-soluble and may cause some side effects (such as inducing carcinogenesis), and it is difficult to optimize the required additives (such as surfactants) and poor repeatability, which limits its application in life sciences, medicine and other fields

Method used

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  • Polymerisable fluorescent functional monomer and its prepn and use
  • Polymerisable fluorescent functional monomer and its prepn and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Pyrenidine hydrazide and acryloyl chloride in dimethylformamide (DMF) solvent (the molar ratio of pyrene hydrazide to acryloyl chloride is 1:1.2) was stirred at -3°C for 12 hours, and the reaction was carried out by DMF-EtOH-H 2 The functional monomer (I) was obtained by recrystallization from O mixed solvent with a yield of 58.3%. Product structure by MS, 1 H NMR identification: FAB-MS m / z (RI): 356 (38, M + ), 271(58, M-CH 2 CHCONHNH), 215 (43, M-CH 2 CHCONHNHCOCH 2 CH 2 ). 1 H NMR (DMSO-d 6 , δppm): 2.05(t, 2H, CH 2 CH 2 CO), 2.34 (m, 2H, CH 2 CH 2 CO), 2.91(t, 2H, PyCH 2 ), 5.70-6.29 (m, 3H, CH 2 =CH), 7.91-8.42 (m, 9H, PyH), 9.99, 10.12 (each s, 1H, NHNH).

Embodiment 2

[0015] Pyrenidine hydrazide and acryloyl chloride (the molar ratio of pyrene hydrazide to acryloyl chloride is 1:1.8) in dimethylformamide (DMF) solvent were stirred and reacted for 24 hours at 3°C. 2 O mixed solvent recrystallization obtains functional monomer (I), and the yield is 60.5%. Product structure by MS, 1 H NMR identification: FAB-MS m / z (RI): 356 (38, M + ), 271(58, M-CH 2 CHCONHNH), 215 (43, M-CH 2 CHCONHNHCOCH 2 CH 2 ). 1 H NMR (DMSO-d 6 , δppm): 2.05(t, 2H, CH 2 CH 2 CO), 2.34 (m, 2H, CH 2 CH 2 CO), 2.91(T, 2H, PyCH 2 ), 5.70-6.29 (m, 3H, CH 2 =CH), 7.91-8.42 (m, 9H, PyH), 9.99, 10.12 (each s, 1H, NHNH).

Embodiment 3

[0017] The synthetic method of functional monomer (II): pyrene hydrazine and methacryloyl chloride in a mixed solvent of toluene and dimethylformamide (DMF) At 0°C, the reaction was stirred for 15 hours, and the functional monomer (II) was obtained by column chromatography with a yield of 62.2%. Product structure by MS, 1 H NMR identification: FAB-MS m / z (RI): 371(48, M+1), 271(63, Py(CH 2 ) 3 CO + ), 215(52, PyCH 2 + ); 1 H NMR (CDCl 3 , δppm): 1.89 (s, 3H, CH 3 ), 2.19(t, 2H, CH 2 CH 2 CO), 2.34 (m, 2H, CH 2 CH 2 CO), 3.31(t, 2H, PyCH 2 ), 5.35, 5.76 (eachd, 1H, CH 2 =), 7.8-8.2 (m, 9H, PyH), 8.42, 8.51 (each b, 1H, NHNH).

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Abstract

The present invention relates to polymerisable fluorescent functional monomers in the structure as shown, and they have strong fluorescent reaction and part capable of reacting with biomacromolecular protein and non-covalent bond of DNA mutually. They may be polymerized with hydrophilic monomer to obtain fluorescent amphiphilic polymer with excellent biocompatibility, medicine carrying capacity and target administration capacity, and the polymer may find wide application foreground in high sensitivity fluorescent tracing detection technology, biomacromolecule separation and distinction, biosensor, medical diagnosis, medicine conveying, target material and other aspects. The present invention has reasonable synthesis path, simple synthesis process, easy-to-obtain material and high application value.

Description

technical field [0001] The invention relates to a preparation method of a polymerizable fluorescent functional monomer. Background technique [0002] The research of biological macromolecules by fluorescence technology (such as protein conformation, DNA separation and sequencing, etc.), the in situ research of cell growth, apoptosis, and mutation have so far mainly focused on the introduction of small molecule fluorescent probes into the research system. Although this method is simple, fast and sensitive, some small molecular fluorescent probes are non-water-soluble and may cause some side effects (such as inducing carcinogenesis), and it is difficult to optimize the required additives (such as surfactants) And poor repeatability, which limits its application in life sciences, medicine and other fields. Contents of the invention [0003] The object of the present invention is to provide a preparation method of a polymerizable fluorescent functional monomer, which has a re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C243/32C07C241/00C07C331/32
Inventor 孟令芝武照强何永炳
Owner WUHAN UNIV
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