Polypeptide-manganese-carbonyl compound CO releasing molecule taking phenylazo pyridine as ligand as well as synthesis method and application of polypeptide-manganese-carbonyl compound CO releasing molecule

A technology of phenylazopyridine and complexes, which is applied in the field of synthesis and preparation of polypeptide-metal complexes, can solve the problems of low yield, achieve the effect of simplifying the number of synthesis steps and shortening the time required for synthesis

Pending Publication Date: 2021-11-12
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such coupling reactions usually require multi-step synthesis in a liquid-phase environment, thus requiring multi-step purification resulting in lower final yields...

Method used

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  • Polypeptide-manganese-carbonyl compound CO releasing molecule taking phenylazo pyridine as ligand as well as synthesis method and application of polypeptide-manganese-carbonyl compound CO releasing molecule
  • Polypeptide-manganese-carbonyl compound CO releasing molecule taking phenylazo pyridine as ligand as well as synthesis method and application of polypeptide-manganese-carbonyl compound CO releasing molecule
  • Polypeptide-manganese-carbonyl compound CO releasing molecule taking phenylazo pyridine as ligand as well as synthesis method and application of polypeptide-manganese-carbonyl compound CO releasing molecule

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Experimental program
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Effect test

Embodiment 1

[0085] Embodiment 1: The preparation method of the TAT-manganese carbonyl complex whose side chain coordinating group is phenylazopyridine (azpy):

[0086] (1) Preparation of Fmoc-Arg(Pbf)-MBHA resin: Take 500mg Rink Amide MBHA resin in a peptide synthesis tube with a loading capacity of 0.2-0.8mmol / g, add 15mL DMF to swell twice at room temperature, 15min each time, Drain, add 10mL 20% piperidine / DMF to the resin, shake at room temperature for 5min, wash twice with DMF, add 10mL 20%piperidine / DMF again, shake for 5min at room temperature, wash with DMF, DCM, DMF was washed twice each, and the solvent was drained to obtain the resin that the amino group removed Fmoc protection. Weighed Fmoc-Arg(Pbf)-OH(1mmol), TBTU(2mmol) and DIEA(0.98mmol), and Fmoc-Arg(Pbf )-OH and TBTU were dissolved with a small amount of DMF, added DIEA, and the carboxyl group was activated by shaking at room temperature for 2 minutes. After that, the activated amino acid was added to the resin, shaken an...

Embodiment 2

[0094] Example 2: TAT(Y11Aph(azpy)-Mn(CO) 3 ) light-controlled CO release experiment

[0095] Experimental material: TAT(Y11Aph(azpy)-Mn(CO) 3 ), PBS buffer, visible red light flashlight (~700nm, LED, 5W).

[0096] Experimental steps:

[0097] ① The PBS buffer was deoxygenated by bubbling nitrogen gas for 30 minutes.

[0098] ②Add TAT(Y11Aph(azpy)-Mn(CO) 3 ) polypeptide-manganese complex (final concentration is 0.16mg / mL).

[0099] ④Use the visible light and red light flashlight contrast cuvette for illumination, and use the ultraviolet-visible spectrum to record the spectrum of different cumulative illumination time. The result is as Figure 5 shown.

[0100] The following conclusions can be obtained from the changes of the characteristic peaks of the ultraviolet spectrum ① TAT-Mn(CO) without light 3 Will not release CO; ②After being illuminated by visible light and red light, TAT(Y11Aph(azpy)-Mn(CO) 3 ) in the metal-to-ligand electron transfer (MLCT) decreased, demo...

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Abstract

The invention provides a polypeptide-manganese-carbonyl compound CO releasing molecule taking phenylazo pyridine as a ligand as well as a synthesis method and application of the polypeptide-manganese-carbonyl compound CO releasing molecule. Polypeptide amino resin with a reaction site is obtained through a solid-phase polypeptide synthesis method based on an Fmoc protecting group and use of 4-amino phenylalanine with an orthogonal protecting group, and then a phenylazo pyridine coordination group is constructed at a polypeptide target site through a solid-phase Mills reaction; and finally, manganese-carbonyl-ligand coordination reaction is carried out by using pentacarbonyl manganese bromide, and extraction is performed by using diethyl ether to obtain a target product. According to the method, the phenylazo pyridine ligand is combined with the polypeptide-CO releasing molecule, the use of the ligand can obviously reduce the release light source energy of CO, and the wavelength of the light source moves to a near-infrared region, so that the practical application of the CO releasing molecule in physiological and biochemical research is facilitated, and the physiological and biochemical action on a specific part is facilitated by taking polypeptide as a carrier; and a good foundation is laid for CO in the aspect of treating related diseases.

Description

technical field [0001] The invention relates to the technical field of synthesis and preparation of polypeptide-metal complexes, in particular to a polypeptide-manganese-carbonyl complex CO release molecule with phenylazopyridine as a ligand, its synthesis method and application. Background technique [0002] Carbon monoxide (CO) has long been considered a toxic gas because of its strong binding to hemoglobin in the body. But at the same time, as an important gas molecule, CO plays a variety of physiological functions such as signal transduction and cell protection in mammals (R. Motterlini, Nat. Rev. Drug. Discov., 2010, 9, 728–743. ). In order to further explore the important role of CO in the life system and its application in clinical medicine, one of the key issues that needs to be solved first is how to realize the safe and controllable fixed-point transportation of CO. [0003] Carbon monoxide releasing molecule (CORM) is one of the technical means commonly used in ...

Claims

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Application Information

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IPC IPC(8): C07K1/20C07K1/107C07K1/06C07K1/04
CPCC07K1/20C07K1/107C07K1/06C07K1/04Y02P20/55
Inventor 何春茂周仪
Owner SOUTH CHINA UNIV OF TECH
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