A red light-activatable photodynamic therapy-chemotherapy combined prodrug and its preparation and application
A photodynamic therapy, red light technology, applied in photodynamic therapy, medical preparations containing active ingredients, chemical instruments and methods, etc., can solve the problems of tissue damage, poor selectivity, toxic and side effects, etc. The effect of less reaction and easy purification
Active Publication Date: 2022-06-21
FUZHOU UNIV
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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.
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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 (2.55g, 41%). 1 H NMR (400 MHz, CDCl 3 ): δ 4.34-4.29 (m, 4 H, OCH 2 ), 3.79 (t, J = 5.6Hz, 2 H, OCH 2 ), 3.54 (t, J = 4.8 Hz, 2 H, 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...
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Abstract
The invention discloses a red light-activatable photodynamic therapy-chemotherapy combined prodrug and its preparation and application. The present invention chemically modifies the 20-position hydroxyl group of the chemotherapeutic drug camptothecin, introduces a connecting arm containing a thioketal structure, and then covalently attaches it to the fluorobodipyrrole photosensitizer through a click reaction to obtain a red light-activatable Photodynamic therapy-chemotherapy combined prodrug: camptothecin-fluoroboron dipyrrole conjugate. At the same time, the present invention takes camptothecin-fluoroboron dipyrrole conjugate as the research object, and uses human liver cancer cell HepG2, human esophageal cancer cell EC109 and human cervical cancer cell HeLa as the test cell lines respectively to develop its anticancer activity in vitro The study laid the foundation for the application of camptothecin-fluoroborate dipyrrole conjugates in combination therapy for cancer. Moreover, the synthesis method of this type of compound is relatively simple, the raw materials are easily obtained, the cost is low, the side reactions are few, the yield is high, and the purification is easy, which is beneficial to industrial production.
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
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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