Photodynamic therapy-chemotherapy combined prodrug capable of being activated by red light and preparation and application thereof

A technology of photodynamic therapy and red light, which is applied in the field of synthesis and anticancer drug design, can solve the problems of poor selectivity, tissue damage, toxic and side effects, etc., and achieve the effect of low cost, less side effects and easy purification

Active Publication Date: 2021-06-08
FUZHOU UNIV
View PDF8 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the chemotherapeutic drugs currently used clinically have poor selectivity. While treating tumor tissues, they will also cause great damage to normal tissues of the human body, which will lead to serious toxic and side effects.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Photodynamic therapy-chemotherapy combined prodrug capable of being activated by red light and preparation and application thereof
  • Photodynamic therapy-chemotherapy combined prodrug capable of being activated by red light and preparation and application thereof
  • Photodynamic therapy-chemotherapy combined prodrug capable of being activated by red light and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] (1) Compound (1.74 g, 20 mmol), triphosgene (2.08 g, 7 mmol), and p-dimethylaminopyridine (2.44 g, 20 mmol) were dissolved in dichloromethane (50 mL), and the solution was stirred in an ice-water bath for 0.5 hours. Continue to add to the reaction solution (3.93 g, 20 mmol), and the reaction was stirred overnight at room temperature. After the reaction is complete, extract with dichloromethane and water and collect the organic layer, dry the organic layer over anhydrous sodium sulfate and spin dry, then use petroleum ether-ethyl acetate (2 / 1, v / v) as eluent, silica gel Colorless liquid compound 1a was obtained by column chromatography (2.55 g, 41%). 1 H NMR (400 MHz, CDCl 3 ): δ 4.34-4.29 (m, 4 H, OCH 2 ), 3.79 (t, J = 5.6 Hz, 2 H, OCH 2 ), 3.54 (t, J = 4.8 Hz, 2H, CH 2 N 3 ), 2.94 (t, J = 6.8 Hz, 2 H, SCH 2 ), 2.86 (t, J = 5.6 Hz, 2 H, SCH 2 ), 1.63 (s, 6 H, CH 3 ); 13 C NMR (100.6 MHz, CDCl 3 ): δ 154.63, 67.03, 66.18, 61.47,56.28, 49.63, 33.50...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a photodynamic therapy-chemotherapy combined prodrug capable of being activated by red light and preparation and application thereof. The preparation method comprises the following steps: chemically modifying 20-site hydroxyl of a chemotherapeutic drug camptothecin, introducing a connecting arm containing a thioketal structure, and covalently adding the connecting arm to a boron dipyrromethene photosensitizer through a click reaction to obtain a red light activatable photodynamic therapy-chemotherapy combined prodrug, namely the camptothecin-boron dipyrromethene conjugate. Meanwhile, the camptothecin-BODIPY conjugate is used as a research object, human liver cancer cells HepG2, human esophageal cancer cells EC109 and human cervical cancer cells HeLa are respectively used as tested cell strains, in-vitro anticancer activity research of the camptothecin-BODIPY conjugate is developed, and a foundation is laid for application of the camptothecin-BODIPY conjugate to combined treatment of cancers. The synthesis method of the compound is simple, raw materials are easy to obtain, the cost is low, side reactions are few, the yield is high, purification is easy, and industrial production is facilitated.

Description

technical field [0001] The invention belongs to the field of anticancer drug design and synthesis, and in particular relates to a red light-activatable photodynamic therapy-chemotherapy combined prodrug and its preparation and application. Background technique [0002] Photodynamic therapy is a new, minimally invasive method for treating tumors. When a certain wavelength of light irradiates a photosensitizer, the molecules are excited to interact with molecular oxygen to generate highly cytotoxic active oxygen, which eventually induces apoptosis. Photodynamic therapy (PDT) is becoming a new tumor treatment method with great potential due to its advantages such as low toxicity, no drug resistance, and high selectivity. Due to the short half-life of active oxygen and extremely limited diffusion radius, photodynamic therapy can only be used for local treatment, and the effect is not good when facing large solid tumors and metastatic tumors, which limits the clinical application...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07F5/02A61P35/00C09K11/06A61K41/00
CPCC07F5/022A61P35/00C09K11/06A61K41/0057C09K2211/1048C09K2211/1055C09K2211/1059
Inventor刘见永许敢李小强张红霞
OwnerFUZHOU UNIV