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Reductively degradable polyzwitterionic nano-micelle and preparation method thereof

A polyzwitterion and nanomicelle technology, which is applied in the directions of pharmaceutical formulations, inactive medical preparations, antitumor drugs, etc., can solve problems such as unsatisfactory use and difficulty in excretion, and achieve complete reaction, simple method and product. pure effect

Active Publication Date: 2015-07-22
NANTONG KANGERLE MEDICAL MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the polyzwitterions reported in the literature are usually obtained by polymerizing vinyl monomers containing positive and negative charge groups, which are non-degradable, difficult to excrete in the body, and do not meet the requirements for use in the human body. application bottlenecks

Method used

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  • Reductively degradable polyzwitterionic nano-micelle and preparation method thereof
  • Reductively degradable polyzwitterionic nano-micelle and preparation method thereof
  • Reductively degradable polyzwitterionic nano-micelle and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] 1) Synthesis of N,N-bis(acryloyl)cystamine:

[0042] Add 11.6 g of cystamine dihydrochloride into a 250 mL one-necked flask, then add 50 mL of distilled water to stir and dissolve cystamine dihydrochloride. Place the flask in a mixture of ice and water at 0°C; in addition, weigh 8g of solid sodium hydroxide and dissolve it in 20mL of distilled water, add the dissolved sodium hydroxide solution to the single-necked flask at one time, and add 19mL of pre-refined Acryloyl chloride was mixed with 3mL of dichloromethane to form a solution, which was added dropwise into a single-necked flask through a constant pressure dropping funnel. After the dropwise addition was completed within 40 minutes, the reaction was controlled at 25°C for 16h. The product was filtered, washed three times with deionized water, finally recrystallized with ethyl acetate, and dried in a vacuum oven for 24 hours to obtain the product.

[0043] 2) Synthesis of poly(taurine-co-N,N-bis(acryloyl)cystamin...

Embodiment 2

[0051] pH Sensitivity of Reductively Degradable Polyzwitterionic Nanomicelles:

[0052] The reductively degradable polyzwitterionic nanomicelles obtained in Example 1 were respectively placed in buffer solutions of pH=5.0, 6.5, 7.4, and 10.0, and the zeta potential changes were observed with a zeta potential measuring instrument. The results are shown in Figure 5 , wherein the molar ratio of N,N-bis(acryloyl)cystamine:taurine:dodecylamine=1:0.8:0.2; in Figure 5 Among them, when the pH value is 7.4, the solution is weakly alkaline, the amino groups in the micelles are difficult to take up protons, the positive charge is suppressed, and the negatively charged ions in the micelles are dominant, so the zeta potential value is negative. Under acidic conditions at pH 5.0 and 6.5, the amino groups in the micelles take up protons to form ammonium cations, and as time increases, the degree of protonation increases, so the Zeta potential turns into a positive value.

Embodiment 3

[0054] Reduction Sensitivity of Reductively Degradable Polyzwitterionic Nanomicelles:

[0055] The reductively degradable polyzwitterionic nanomicelles obtained in Example 1 were placed in a glutathione solution with a concentration of 10 mM, wherein N,N-bis(acryloyl) cystamine in the nanomicelles: taurine: ten The mol ratio of diamine=1:0.8:0.2, test the particle size change of nano-micelle with laser light scattering instrument at different times, observe reduction responsiveness; The result is as follows Figure 6 Shown, nanomicelle is in the PBS buffer solution that does not contain glutathione (GSH), experiences particle diameter not to change after 24 hours; But nanomicelle is in the glutathione (GSH) solution that contains 10mM, After 12 hours, the particle size became smaller, indicating that some disulfide bonds were broken, and the molecular weight of the copolymer decreased. At this time, the copolymer re-self-assembled to form nanomicelles with smaller particle siz...

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Abstract

The invention relates to the technical field of biomedical materials, in particular to a reductively degradable polyzwitterionic nano-micelle and a preparation method thereof. The preparation method comprises the following steps: producing a copolycondensation reaction of taurine, N,N-bis(acryloyl)cystamine and dodecylamine through a Michael addition mechanism, synthesizing to obtain poly(taurine-co-N,N-bis(acryloyl)cystamine-co-dodecylamine)terpolymer, and forming the nano-micelle through self-assembly in an aqueous solution. As a chain segment of the terpolymer contains structural units such as amino groups, disulfide bonds, zwitter-ions and the like, the nano-micelle has sensitive pH (potential of hydrogen) and reduction response properties, and the zwitter-ions endow the nano-micelle with excellent anti-protein non-specific adsorption performance; the nano-micelle does not have cell toxicity, is completely degradable in a human body and serves as an anti-cancer drug carrier, thereby having a relatively high application prospect.

Description

technical field [0001] The invention relates to the technical field of biomedical materials, in particular to a reductively degradable polyzwitterion nano-micelle and a preparation method thereof. Background technique [0002] Polymeric nanomicelles have shown bright prospects as chemotherapeutic drug carriers in the field of malignant tumor treatment. Injectable nanomicelles circulate with the blood and can pass through certain barriers of body tissues to reach the tumor site, allowing the drug to be released at the lesion, greatly improving the bioavailability of the drug and reducing side effects. An ideal nanomicelle as a drug carrier must meet the following basic conditions: suitable micelle particle size, generally within 200 nanometers; stable in the long-term circulation in the body, without non-specific protein adsorption; certain drug loading rate and targeting Controlled release properties; good biocompatibility and degradability. [0003] In order to ensure the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08J3/07C08L79/02C08G73/02A61K47/34A61K9/107A61P35/00
CPCA61K9/107A61K47/34C08G73/02C08J3/07C08L79/02
Inventor 倪才华吴鲁艳张丽萍石刚
Owner NANTONG KANGERLE MEDICAL MATERIALS CO LTD
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