Metal complex of double-cup[4]aromatic hydrocarbon derivative as well as synthetic method and application thereof

A technology of aromatic hydrocarbon derivatives and metal complexes, applied in the field of medical biological detection, can solve the problems of low sensitivity, unsuitable for labeling biomolecules, etc., and achieve the effects of improving yield, simple and easy synthesis process, and high yield

Active Publication Date: 2018-07-27
SUZHOU INST OF BIOMEDICAL ENG & TECH CHINESE ACADEMY OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Therefore, the technical problem to be solved by the present invention is that the calix[4]arene derivatives in the prior art combined with metal ions have the disadvantages of low sensit...

Method used

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  • Metal complex of double-cup[4]aromatic hydrocarbon derivative as well as synthetic method and application thereof
  • Metal complex of double-cup[4]aromatic hydrocarbon derivative as well as synthetic method and application thereof
  • Metal complex of double-cup[4]aromatic hydrocarbon derivative as well as synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] This embodiment provides a metal complex of a biscalix[4]arene derivative and a preparation method thereof. The biscalix[4]arene derivative has a molecular structure as shown in Formula I-1; the biscalix[4]arene derivative and rare earth metal ions Tb 3+ Coordinate to obtain complex, its molecular structure is as shown in formula II-1:

[0068]

[0069] Intermediate I'-1 was synthesized from intermediate E-1 and intermediate F-1, and intermediate I'-1 was oxidized to obtain biscalix[4]arene derivative I-1, biscalix[4]arene derivative I -1 complex rare earth metal ion Tb 3+ , to obtain biscalix [4] arene derivatives I-1 and Tb 3+ The complex II-1, the synthetic route is:

[0070]

[0071] (1) Preparation of Intermediate E-1

[0072] Step 1: Taking calix[4]arene as reaction raw material, get calix[4]arene (30.0g / 70.7mmol), anhydrous potassium carbonate (10.7g / 77.4mmol) and methyl p-toluenesulfonate (26.3g / 141.4mmol), dissolved in 500mL of CH 3 CN was refluxed...

Embodiment 2

[0102] This example provides a method for synthesizing the metal complex II-1 of biscalix[4]arene derivatives:

[0103] With Intermediate E-1, Intermediate E'-1 (equal to Intermediate E-1) and TsO-CH 2 -CH 2 -OsT synthesizes intermediate I'-1, intermediate I'-1 is oxidized to obtain biscalix[4]arene derivative I-1, biscalix[4]arene derivative I-1 is complexed with rare earth metal ion Tb 3+ , to obtain biscalix [4] arene derivatives I-1 and Tb 3+ The complex II-1, the synthetic route is:

[0104]

[0105] (1) Preparation of Intermediate E-1

[0106]Synthetic process is with the synthesis of the intermediate E-1 of embodiment 1, and intermediate E'-1 and intermediate E-1 are identical compound.

[0107] (2) Preparation of intermediate I'-1

[0108] Intermediate E-1 (0.8mmol), Intermediate E'-1 (1mmol) and K 2 CO 3 (7mmol) was dissolved in toluene, then added TsO-CH 2 -CH 2 -OsT (1.1mmol), under the protection of nitrogen, reflux at 105°C for 3h, then add a certain a...

Embodiment 3

[0114] This embodiment provides a metal complex of a biscalix[4]arene derivative and a preparation method thereof. The biscalix[4]arene derivative has a molecular structure as shown in Formula I-2; the biscalix[4]arene derivative and rare earth metal ions Eu 3+ Cooperate to obtain complex, its molecular structure is as shown in formula II-2:

[0115]

[0116] Synthesize intermediate I'-2 with intermediate E-2 and intermediate F-2 (the intermediate shown in formula F-2 is equivalent to the intermediate shown in formula F-1), after intermediate I'-2 is oxidized Two calix[4] arene derivatives I-2 are obtained, and two calix[4] arene derivatives I-2 are complexed with rare earth metal ions Eu 3+ , to obtain biscalix [4] arene derivatives I-2 and Eu 3+ The complex II-2, the synthetic route is:

[0117]

[0118] (1) Preparation of Intermediate E-2

[0119] Step 1: Taking calix[4]arene as the reaction raw material, take calix[4]arene (30.0g / 70.7mmol), anhydrous potassium ca...

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Abstract

The invention discloses a metal complex of a double-cup[4]aromatic hydrocarbon derivative. The metal complex has a chemical structure as shown in formula II. The complex is small in toxicity, high inbiological compatibility, suitable for being covalently combined with biological molecules such as nucleic acid, peptide or proteins to form a fluorescent probe molecule with high fluorescent quantumrate, long fluorescent service life and low detection limit, suitable for detecting the biological molecules in cells, tissues or living bodies and wide in application prospect in the field of biological medicine. The invention discloses a synthetic method of the complex, provides various selection ways for the synthesis of the complex, is simple and easy in synthesizing a route, high in yield ofprepared complex and suitable for the mass production of the complex.

Description

technical field [0001] The invention belongs to the technical field of medical biological detection, and specifically relates to a biscalix[4]arene derivative and a metal complex thereof, a synthesis method and an application thereof. Background technique [0002] Molecular recognition is the process in which the subject (receptor) selectively binds to the guest (substrate) and produces a specific function. The recognition process may cause changes in the magnetic, electrical, optical properties and conformation of the system, resulting in the storage, transmission and processing of chemical information. Therefore, molecular recognition plays an important role in information processing and transmission, and in the fabrication of molecular and supramolecular devices. [0003] Molecular recognition using the change of magnetic or fluorescent properties caused by the combination of host and guest molecules is the main research direction at present, and has a wide range of appl...

Claims

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Application Information

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IPC IPC(8): C07F5/00C09B57/00C09K11/06G01N21/64
CPCC07F5/003C09B57/00C09K11/06C09K2211/182G01N21/64G01N21/6428G01N21/6458G01N2021/6417G01N2021/6439
Inventor 刘元忠唐玉国刘涛董文飞
Owner SUZHOU INST OF BIOMEDICAL ENG & TECH CHINESE ACADEMY OF SCI
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