Amphiphilic peptide block copolymer containing porphyrin end group and its preparation method and application

A block copolymer and amphiphilic technology, which is applied in the field of amphiphilic temperature-sensitive polypeptide hybrid block copolymer and its preparation, which can solve the limitation of research on polypeptide hybrid block copolymer and product distribution index. Wide and small molecular weight, etc., to achieve the effect of large application potential, narrow distribution index and high selectivity

Active Publication Date: 2021-07-27
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the synthesis of polypeptide copolymers, hybrid block polypeptides are mostly, but there are few reports on hybrid block polypeptides containing porphyrin end groups, and the obtained products have a wide distribution index, small molecular weight, and few have Optical activities such as UV and fluorescence, which limit the research on peptide hybrid block copolymers

Method used

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  • Amphiphilic peptide block copolymer containing porphyrin end group and its preparation method and application
  • Amphiphilic peptide block copolymer containing porphyrin end group and its preparation method and application
  • Amphiphilic peptide block copolymer containing porphyrin end group and its preparation method and application

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preparation example Construction

[0058] i) The preparation process of the oil-soluble polypeptide is:

[0059]

[0060] Wherein, n=50-100; preferably, n=100.

[0061] Using L-glutamic acid-γ-benzyl ester-N-carboxy-cyclic acid anhydride as raw material, in organic solvent, 5-(4-aminophenyl)-10,15,20-triphenylporphyrin as Initiator, the reaction temperature is controlled at 20-40°C, and the reaction time is 72-96 hours; preferably, the reaction temperature is 25°C, and the reaction time is 72 hours. Then react with azidobutyric acid, the reaction temperature is controlled at 60-80°C, and the reaction time is 72-96 hours, preferably, the reaction temperature is 70°C, and the reaction time is 84 hours. The oil-soluble polypeptide represented by formula (a) is obtained.

[0062] Among them, the raw materials L-glutamic acid-γ-benzyl ester-N-carboxy-cyclic anhydride, 5-(4-aminophenyl)-10,15,20-triphenylporphyrin, azidobutyric acid The molar ratio is 50-100:1:1.5; preferably, it is 100:1:1.5.

[0063] Wherein...

Embodiment 1

[0078] Preparation of Amphiphilic Polypeptide Block Copolymers Containing Porphyrin Terminal Groups

[0079] Conversion of L-glutamic acid-γ-benzyl ester to monomeric L-glutamic acid-γ-benzyl ester-N-carboxy-cyclic anhydride via the triphosgene method to monomethyl ether polyethylene glycol methacrylate With L-glutamic acid-γ-benzyl ester-N-carboxyl-in-ring anhydride as a monomer, use atom transfer radical polymerization (ATRP), amino acid anhydride ring-opening polymerization (NCA-ROP), active Amidation reaction yielded a hydrophilic poly(monomethyl ether polyethylene glycol methacrylate) (PEGMA) temperature-sensitive homopolymer and a hydrophobic poly(L-glutamic acid-γ-benzyl ester) containing porphyrin end groups. ) (PBLG) homopolypeptide. Then click chemistry is used to link the two block chains to form an amphiphilic polypeptide block copolymer containing porphyrin end groups.

[0080] Under the protection of nitrogen, 6.02g (25.2mmol) of benzyl L-glutamate, 2.64g (8.4m...

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Abstract

The invention discloses an amphiphilic polypeptide block copolymer containing porphyrin terminal groups and its preparation method and application. The block copolymer is composed of an oil-soluble polypeptide block and a water-soluble temperature-sensitive block. Its preparation method is obtained by N-carboxyl-amino acid anhydride ring-opening polymerization (NCA-ROP) and active amidation reaction to obtain an oil-soluble homopolypeptide with a porphyrin end group at one end of the chain and an azide end group at the other end. ; Obtain a water-soluble temperature-sensitive homopolymer with a larger molecular weight end group as an alkynyl group by atom transfer radical polymerization; finally obtain the amphiphilic temperature-sensitive block containing a porphyrin end group through a click chemical process copolymer. The invention also discloses the self-assembled body obtained from the prepared block copolymer. The preparation method of the invention is simple and easy to operate and has a high success rate; the prepared block copolymer containing porphyrin end groups has great application prospects in the fields of drug release, photodynamic therapy, tissue functional materials and the like.

Description

technical field [0001] The invention belongs to the technical field of polymer peptide synthesis, and in particular relates to a novel amphiphilic temperature-sensitive polypeptide hybrid block copolymer containing porphyrin end groups and its preparation method and application. Background technique [0002] Amphiphilic block copolymer (block copolymer) refers to a single linear macromolecular polymer molecule with two different blocks arranged at both ends of the main chain with large differences in solubility in solvents. "Oil" type diblock copolymer, composed of a hydrophilic chain segment (Hydrophilic Chain) and a hydrophobic chain segment (Hydrophobic Chain). Such polymers tend to form an ordered assembly structure with the hydrophilic segment as the shell and the lipophilic segment as the core in poor solvents. Nanoreactors have a wide range of applications. [0003] Polypeptides are high molecular polymers obtained by the dehydration condensation of amino acid monom...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F293/00C08F2/50A61K47/42
Inventor 贺小华贺子花刘振舒文超施鑫杰
Owner EAST CHINA NORMAL UNIV
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