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Photoactivated porphyrin prodrug ternary assembly as well as preparation method and application thereof

A technology of assembly and photoactivation, which is applied in the direction of pharmaceutical formulations, drug combinations, preparations for in vivo experiments, etc., can solve the problems of lack of targeting, damage to the human immune system, poor water solubility, etc., and achieve weakening of π-π accumulation Effect

Pending Publication Date: 2022-06-28
SHANDONG BINZHOU ZHIYUAN BIO TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the poor water solubility and lack of targeting of commonly used chemotherapeutic drugs, they will bring inevitable systemic toxicity to patients, and often kill a large number of normal cells while killing tumor cells, resulting in serious damage to the human immune system. Therefore, the cancer cannot be fundamentally cured

Method used

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  • Photoactivated porphyrin prodrug ternary assembly as well as preparation method and application thereof
  • Photoactivated porphyrin prodrug ternary assembly as well as preparation method and application thereof
  • Photoactivated porphyrin prodrug ternary assembly as well as preparation method and application thereof

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preparation example Construction

[0036] The application also provides a preparation method of the photoactivated porphyrin prodrug ternary assembly, including:

[0037] The aqueous solution of the porphyrin prodrug and the aqueous solution of the permethylated β-cyclodextrin-modified hyaluronic acid are mixed and sonicated to obtain a photoactivated porphyrin prodrug ternary assembly.

[0038]In the above process, the antitumor drug molecule modified by the carboxyphenyl porphyrin and the photooxidative active functional group is also called a porphyrin prodrug (TPP-CA4), and its preparation method is specifically:

[0039] The antitumor drug molecule modified by aminoacrylate bond is esterified with monocarboxyphenyl porphyrin under the action of a catalyst to obtain the antitumor drug molecule modified with carboxyphenyl porphyrin and photooxidative active functional group.

[0040] In the above process, the aminoacrylate bond-modified antitumor drug Combretastatin A-4 is synthesized according to the litera...

Embodiment 1

[0048] Embodiment 1 A preparation method of a light-activated permethylated-β-cyclodextrin-modified hyaluronic acid-porphyrin prodrug ternary supramolecular assembly based on in-situ drug release and photodynamic therapy, the steps are as follows :

[0049] 1) Synthesis of permethylated β-cyclodextrin-modified hyaluronic acid (HA-PMeCD)

[0050] 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (0.875 mmol, 167.7 mg), N-hydroxysuccinimide sulfonic acid sodium salt (NHSS) ( 0.875 mmol, 190 mg) was added to 100 mg of sodium hyaluronate (Mw=93,000) dissolved in 30 mL of phosphate buffer (PBS, 0.1 M, pH=7.2), and stirred at room temperature for 0.5 hours. Subsequently, 120 mg of mono-6-deoxy-6-amino-permethylated-β-cyclodextrin dissolved in 10 mL of PBS solution was added to the reaction solution, and stirring was continued at room temperature for 24 hours. After the reaction was completed, dialysis was performed with deionized water for 5 days, and the HA-PMeCD ...

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Abstract

The invention provides a photoactivated porphyrin prodrug ternary assembly, which is obtained by interaction of a subject and an object, the subject is fully methylated beta-cyclodextrin modified hyaluronic acid, the object is a porphyrin prodrug, and the subject is a photoactivated porphyrin prodrug. The porphyrin prodrug is obtained by covalent linkage of monocarboxyl phenyl porphyrin and anti-tumor drug molecules modified by photooxidation active functional groups. The invention further provides a preparation method and application of the photoactivated porphyrin prodrug ternary assembly. The porphyrin prodrug ternary assembly provided by the invention can be used for conveniently and effectively carrying out fluorescence imaging and tracing a tumor treatment process; the supramolecular assembly has a good treatment effect, can greatly reduce systemic toxicity caused by chemotherapeutic drugs, has remote operability and non-invasiveness, has efficient and sensitive imaging capability, and has potential application value in the fields of cancer and tumor treatment and imaging.

Description

technical field [0001] The invention relates to the technical field of cancer and tumor treatment, in particular to a light-activated porphyrin prodrug ternary assembly, a preparation method and application thereof. Background technique [0002] Chemotherapy is one of the main methods for the treatment of cancer and tumors at present, which can relieve the suffering of patients and prolong life to a certain extent. However, due to the poor water solubility and lack of targeting of commonly used chemotherapeutic drugs, it will bring inevitable systemic toxicity to patients, often killing a large number of normal cells while killing tumor cells, resulting in serious damage to the human immune system. Therefore, cancer cannot be fundamentally cured. To address these shortcomings of chemotherapeutic drugs, the design of tumor cell-targeted, stimuli-responsive prodrugs has become a popular strategy. [0003] A common strategy for prodrug design is to exploit relevant endogenous...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/69A61K41/00A61K31/09A61P35/00A61K49/00C08G81/00
CPCA61K47/6951A61K47/6949A61K41/0071A61K31/09A61P35/00A61K49/0036A61K49/0054C08G81/00A61K2300/00
Inventor 刘育唐冕张瀛溟陈湧梁宁宁王波申健
Owner SHANDONG BINZHOU ZHIYUAN BIO TECH CO LTD
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