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Photosensitive prodrug-containing amphiphilic polymer in main chain, preparation method and nanomicelle thereof
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An amphiphilic polymer and photosensitive technology, applied in the field of nanomicelle, preparation, and main chain containing photosensitive prodrug amphiphilic polymer
Active Publication Date: 2017-12-26
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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However, the above works all start from tetravalent photosensitive platinum as an anticancer drug itself to realize the loading and photocontrollable release of platinum drugs, and tetravalent photosensitive platinum is used as a photostimuli-responsive group and introduced into the amphiphilic The work of designing and synthesizing photosensitive prodrug-containing amphiphilic polymer nanomicelles in the main chain of block polymers that are sensitive to different light wavelengths has hardly been reported so far.
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[0042] The present invention also provides a method for preparing amphiphilic polymers containing photosensitive prodrugs in the main chain, including the following steps:
[0043] Step 1: preparing a photoactive tetravalent platinum complex;
[0044] Step 2: reacting the photoactive tetravalent platinum complex obtained in step 1 with diisocyanate to obtain the first intermediate;
[0045] Step 3: React the first intermediate obtained in Step 2 with monomethyl ether polyethylene glycol to obtain an amphiphilic polymer containing a photosensitive prodrug in the main chain.
[0046] According to the present invention, the photoactive tetravalent platinum complex is first prepared, and the preparation method preferably includes:
[0047] ① put K 2 PtCl 4 React with the ligand to obtain the ligand compound;
[0048] ② The ligand compound obtained in ① and AgNO 3 , NaN 3 reaction, and then add H 2 o 2 reaction to obtain photoactive tetravalent platinum complexes.
[0049]...
Embodiment 1
[0063] Preparation K 2 PtCl 4 (400mg, 0.96mmol) in water, K 2 PtCl 4 The concentration is 10mg / mL, react with pyridine (303.74mg, 3.84mmol) at 75°C for 24h to generate pyridine compound; then add AgNO 3 (326.4mg, 1.92mmol), after reacting at 60°C for 4h, add 1.92mmol NaN 3 , at room temperature, stirring the reaction time 24h, then adding 4.8mmol H 2 o 2. , react at room temperature for 20 min, and purify the obtained product to obtain a photoactive tetravalent platinum complex.
[0064]
Embodiment 2
[0066] Preparation K 2 PtCl 4 (500mg, 1.2mmol) in water, K 2 PtCl 4 The concentration is 10mg / mL, react with pyridine (379.69mg, 4.8mg) at 75°C for 24h to generate pyridine compound; then add AgNO 3 (408mg, 2.4mmol), reacted at 60°C for 4h, then added 6mmol NaN 3 , at room temperature, stirring the reaction time 24h, then adding 6mmol H 2 o 2. , react at room temperature for 30 min, and purify the obtained product to obtain a photoactive tetravalent platinum complex.
[0067]
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Abstract
The invention provides an amphipathic polymer with a main chain containing a photosensitive prodrug, as well as a preparation method and a nano-micelle of the amphipathic polymer, and belongs to the technical field of chemical synthetic drugs. The structural formula of the amphipathic polymer is shown in the formula I. The invention further provides the preparation method of the mphipathic polymer. The method comprises the following steps: firstly, preparing a photoactive quadrivalent platinum complex; carrying out a reaction between the obtained photoactive quadrivalent platinum complex and diisocyanate, so as to obtain a first intermediate; finally, carrying out reactions between the first intermediate and methoxy polyethylene glycol of different molecular weights, so as to obtain the amphipathic polymer with the main chain containing the photosensitive prodrug. The invention further provides the nano-micelle of the amphipathic polymer. The amphipathic polymer is relatively low in cytotoxicity but relatively high in antitumor activity.
Description
technical field [0001] The invention belongs to the technical field of chemically synthesized drugs, and in particular relates to an amphiphilic macromolecule whose main chain contains a photosensitive prodrug, a preparation method and nano micelles thereof. Background technique [0002] With the continuous development of polymer nanotechnology, in recent years, more and more research efforts have focused on the development of multifunctional polymer nanomaterials for cancer-related research. Polymer nano-drug-loading materials have attracted particular attention, and their application prospects in the field of anticancer drug delivery and controlled release have been widely discussed. So far, polymer nano drug-loading material systems include polymer drug conjugates, polymer microspheres, nanogels, vesicles, and nanomicelles. Among them, self-assembled nanomicelles based on amphiphilic block copolymers have low critical micelle concentration, high colloidal stability, narr...
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