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First small molecule peptide with oxygen carrying potential, second small molecule peptide capable of generating active oxygen, and preparation method of first and second small molecule peptides

A small molecule peptide, reactive oxygen species technology, applied in the direction of peptide, fermentation, etc., can solve the problems of limiting the therapeutic effect of PDT, low energy, unsatisfactory efficiency of activating photosensitizers, etc., to avoid biological safety problems and simple reaction conditions.

Inactive Publication Date: 2019-11-26
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the energy of near-infrared light is low, and the efficiency of activating photosensitizers is not ideal
In addition, the hypoxic environment in the tumor area also limits the therapeutic effect of PDT

Method used

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  • First small molecule peptide with oxygen carrying potential, second small molecule peptide capable of generating active oxygen, and preparation method of first and second small molecule peptides
  • First small molecule peptide with oxygen carrying potential, second small molecule peptide capable of generating active oxygen, and preparation method of first and second small molecule peptides
  • First small molecule peptide with oxygen carrying potential, second small molecule peptide capable of generating active oxygen, and preparation method of first and second small molecule peptides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] This example provides a first small molecular peptide with oxygen-carrying potential, whose structural formula is C 17 h 31 -CONH-VRGDS-COOH, the specific synthesis steps are as follows:

[0041] 1) Weigh a certain amount of resin and place it in a peptide solid-phase synthesis column, wash it with DMF three times, empty the solvent, then swell with an appropriate amount of DMF for 1 hour and then empty the solvent.

[0042] 2) Add 3 times molar equivalents of FMOC-Ser(tBu)-OH and 6 times equivalents of DIEA in DMF to the synthesis column, and stir slowly for 2 hours.

[0043] 3) removing the FMOC protecting group in the first amino acid serine. Add 20% Piperiding / DMF (V / V) deprotection solution to the solid-phase synthesis column, stir for 30 min, wash with DMF three times, and empty the solvent.

[0044] 4) Add 2 times the molar equivalent of FMOC-Asp(OtBu)-OH, 2.4 times the molar equivalent of HBTU, HOBT and 6 times the equivalent of DIEA to the synthesis column, ...

Embodiment 2

[0059] This embodiment provides a method for generating a second small molecule peptide (OPA2) capable of generating active oxygen, the specific steps of which are as follows:

[0060] 1) Weigh an appropriate amount of OPA1 (C 17 h 31 -CONH-VRGDS-COOH) solid powder in a container, add an appropriate amount of PBS (0.1M, pH 9.0) buffer to dissolve, and inject air bubbles for 20 minutes under stirring;

[0061] 2) Weigh an appropriate amount of lipoxygenase into a container, add an appropriate amount of PBS (0.1M, pH 9.0) buffer to dissolve;

[0062] 3) Add the solution in 2) above to the solution in 1), keep the temperature at 5° C., react for 2 hours, and store the obtained solution in a sealed container at low temperature.

[0063] The second small molecular peptide (OPA2) that can generate active oxygen obtained in this embodiment is detected, Figure 5 The structural diagram of the second small molecule peptide provided in Example 2 of the present invention; Figure 6 T...

Embodiment 3

[0065] This embodiment provides a method for generating active oxygen by the second small molecular peptide that can generate active oxygen, which is based on the Fenton-like reaction, that is, in the Fe 2+ In the presence of , the hydroperoxide (-OOH) in the second small molecule peptide structure that can generate reactive oxygen species generates cytotoxic reactive oxygen species (ROS).

[0066] The active oxygen produced by the second small molecule peptide that can generate active oxygen obtained in this embodiment is detected, Figure 7 Fe 2+ (concentration used was 100 μM) oxidation to Fe 3+ The color change diagram; the results show that: in OPA2 (C 17 h 31 o 2 -CONH-VRGDS-COOH), Fe 2+ can be oxidized to Fe 3+ , FeCl 2 The solution changed from colorless and clear to yellow and clear.

[0067] In order to test the effect of OPA2 on generating reactive oxygen species, experiments were carried out with the materials in the following table to test the fluorescence...

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Abstract

The invention provides a first small molecule peptide with oxygen carrying potential, a second small molecule peptide capable of generating active oxygen, and a preparation method of the first and second small molecule peptides. The sequence of the first small molecule peptide with oxygen carrying potential of the present invention is C17H31-CONH-VRGDS-COOH. The unsaturated double bond functionalgroup in the structure can be oxidized by lipoxygenase to form a conjugated double bond and the side groups generate hydroperoxide. The method of constructing the second small molecule peptide by thefirst small molecule peptide is an enzymatic method, and the structure of the second small molecule peptide is C17H31O2-CONH-VRGDS-COOH. The method that the second small-molecule peptide generates active oxygen is a Fenton-like reaction. C17H31O2-CONH-VRGDS-COOH produces cytotoxic active oxygen under the catalysis of Fe<2+>.

Description

technical field [0001] The present invention relates to the technical field of biomaterials, more specifically, to a first small molecule peptide with oxygen-carrying potential, a second small molecule peptide capable of generating active oxygen and a preparation method thereof. Background technique [0002] Tumor is the number one disease threatening human health. In January 2019, the national cancer statistics released by the National Cancer Center of China showed that in 2015, there were about 3.929 million new cases of malignant tumors in the country, and about 2.338 million deaths, and an average of more than 10,000 people were diagnosed with cancer every day. Conventional means of cancer treatment mainly include surgical resection, radiotherapy and chemotherapy. In order to effectively adopt individualized treatment for different cancer patients and reduce the side effects of conventional treatment, a variety of new treatment methods have emerged in recent years, such...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P21/02C07K7/06
CPCC07K7/06C12P21/02
Inventor 秦四勇冯嘉茹张爱清
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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