A kind of synthetic method of water-soluble porphyrin and its photocatalytic application

A synthesis method and water-soluble technology, which is applied in the synthesis method of water-soluble porphyrin and its photocatalytic application field, can solve the problems of healthy cell toxicity and side effects, long residence time, poor solubility, etc. The effect of high purity and easy purification

Inactive Publication Date: 2016-11-23
NANKAI UNIV
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Problems solved by technology

First of all, the solubility of porphyrin compounds is poor, and it is inevitable to introduce some harmful solvents when acting on organisms; secondly, the residence time in the body is long, the selectivity is poor, and they are retained in the tissue, and have certain toxic side effects on healthy cells; in addition, Photobleaching of photodynamic therapeutic agents also occurs in porphyrins

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  • A kind of synthetic method of water-soluble porphyrin and its photocatalytic application
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Embodiment

[0026] A kind of synthetic method of water-soluble porphyrin, the compound name of described water-soluble porphyrin is tetraiodide 5,10,15,20-tetra{4-[2-(N,N-dimethyl-2-piper Pyridine) ethoxy] phenyl} porphyrin, the steps are as follows:

[0027] 1) Synthesis of 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin

[0028] Dissolve 6.1 g of benzaldehyde in 110 mL of propionic acid a, add 6 mL of dimethyl sulfoxide (DMSO) catalyst, stir mechanically, and then add 3.5 mL of freshly distilled pyrrole and 10 mL of propionic acid dropwise when heated to 128°C under reflux The mixed solution of b, 1 drop per second, heated up to 141°C, refluxed for 2 hours, suction filtered while it was hot, washed the filter cake twice with propionic acid, and obtained blue solid 5,10,15,20-tetrakis(4-hydroxybenzene Base) porphyrin crude product, drying stand-by;

[0029] Put 10 g of the dried crude product above into a 100 mL round-bottomed flask, add 20 mL of absolute ethanol and heat to reflux, stop...

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Abstract

The invention discloses a synthesis method for water-soluble porphyrin. The chemical compound is named as tetraiodide 5,10,15,20-tetra{4-[2-(N,N-dimethyl-2-piperidine) ethyoxyl]phenyl}porphyrin. The synthesis method comprises the following steps: 1) synthesizing 5,10,15,20-tetra(4-hydroxy phenyl) porphyrin; 2) synthesizing 5,10,15,20-tetra{4-[2-(N-methyl-2-piperidine) ethyoxyl] phenyl}porphyrin; 3) synthesizing the water-soluble porphyrin target object. The prepared water-soluble porphyrin is used for studying the influences of porphyrin in different concentrations on cutting pBR322 plasmid DNA under the acidity and neutrality conditions, as well as the lighting and dark conditions, through the photocatalytic DNA cutting experiments. The synthesis method has the advantages of being simple and easy in synthesis process and relatively high in product purity; chemicals used in the whole process are less in toxicity; the product is good in water solubility, and has good pH selectivity.

Description

technical field [0001] The patent of the present invention relates to the field of organic synthesis and chemical analysis, especially a synthesis method of water-soluble porphyrin and its photocatalytic application. Background technique [0002] Porphine is a kind of macromolecular heterocyclic compound formed by interconnecting α-carbon atoms of four pyrrole subunits through methine bridges (=CH-), and porphines with substituents are called porphyrins. The carbons (5, 10, 15, 20) between the four pyrrole rings are called the middle carbon, and the remaining 8 carbons that can be substituted are called the outer ring carbons. Different substituents can be connected to the middle carbon to form a series of porphyrins. Porphyrin compounds are aromatic and have two resonance isomers. There are 26 π electrons in the ring. It is a highly conjugated system and is generally a dark solid with a high melting point. [0003] Because of their unique structures and properties, porphy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22C12Q1/68B01J31/02
CPCB01J31/0271B01J2531/96C07D487/22C12N15/10
Inventor 孔德明赵婷张琦姜红新
Owner NANKAI UNIV
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