CN108524942A - A kind of pH responsive type medicine-carried nano particles and preparation method thereof based on ganoderma lucidum polysaccharide-histidine conjugate - Google Patents
A kind of pH responsive type medicine-carried nano particles and preparation method thereof based on ganoderma lucidum polysaccharide-histidine conjugate Download PDFInfo
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Abstract
A kind of pH responsive type medicine-carried nano particles and preparation method thereof based on ganoderma lucidum polysaccharide histidine conjugate provided by the invention, it is characterized in that, the conjugate is hydrophobic section by hydrophilic section, histidine of ganoderma lucidum polysaccharide, it is keyed by chemistry, then the conjugate is self-assembly of the nano-particle with pH sensitivities in water.Imidazole radicals in the present invention in histidine molecule is in hydrophobicity under neutral and alkaline environment, it is in hydrophily under acidic environment, this conjugate is amphiphilic species i.e. under neutrallty condition, in the water of pH 7.2~7.4 can self assembly contain anticancer drug obtain medicine-carried nano particles, due to acidic environment after particle arrival inside tumor, histidine becomes hydrophily, and nano-particle decomposition makes drug be released；The ganoderma lucidum polysaccharide histidine conjugate molecular structure is novel, and medicine-carried nano particles have the characteristics that advance, safety, targeting, and are avoided that the toxic side effect that the incomplete release of drug brings patient.
Description
Technical field
The present invention relates to a kind of pH responsive types medicine-carried nano particles based on ganoderma lucidum polysaccharide-histidine conjugate and its preparations
Method belongs to biological medicine and technical field of polymer materials.
Background technology
Research both at home and abroad at present has carried out a large amount of reality in the extraction separation, purifying, Structural Identification etc. of ganoderma lucidum polysaccharide
It tests and works, the antitumor mechanism of ganoderma lucidum polysaccharide is furtherd investigate, it was found that ganoderma lucidum polysaccharide is being improved the immunity of the human body, controlled
There is bright foreground in terms for the treatment of tumour, but experimental result mostly concentrates on ImmunopharmacologicaResearch, immunological regulation research.By ganoderma lucidum polysaccharide
The nearly no report of research as drug carrier material.
Nano-medicament carrier can improve lacking for conventional medicament with its unique size, structure and the excellent performance played
Point is gathered around in terms of the targeted delivery of drug and is held out broad prospects.Other than it can increase the dissolubility of hydrophobic drug, nanometer
Pharmaceutical carrier can also extend its time in body circulation by the advantage on own dimensions, and utilize the high pass of solid tumor
Permeability and retention effect (EPR) effect realize passive targeting.Currently, the pharmaceutical carrier being often used is mostly by synthesis type macromolecule material
Prepared by material, often lack bioactivity, and some materials do not have biodegradability yet, and long-time service can be due to being enriched in vivo
Cause liver at a specified future date, renal toxicity.Therefore, research in recent years utilizes natural polymer to build pharmaceutical carrier more.
Polysaccharide is received significant attention as the high molecular material of a kind of good biocompatibility in terms of pharmaceutical carrier research.Cause
This, the present invention uses ganoderma lucidum polysaccharide for material preparation nano-medicament carrier.In addition, in recent years, it is thin according to normal cell and tumour
The surface of born of the same parents and the nature difference of internal environment, to design intelligent (pH sensitivities, photaesthesia, magnetic responsiveness or electroresponse etc.) control
As the research hotspot of this field, wherein pH sensitivities response type nano pharmaceutical carrier is most popular research for the research of system release
One of.Its principle is：The pH of normal cell and tissue is 7.4 or so, and the pH of inside tumor cells is 6.5 or so even more
It is low, if nano-medicament carrier is non-degradable in 7.0 or more pH, and degrades or dissolve in acid condition, so that it may to realize anticancer
The Targeting delivery of drug enhances its bioavilability to significantly reduce the toxic side effect of anticancer drug.
Therefore, the present invention is chemically modified ganoderma lucidum polysaccharide using histidine, prepares amphiphilic pH sensitivities response and receives
Rice pharmaceutical carrier is, it can be achieved that the targeted delivery of anticancer drug, significantly improve its bioavilability；In addition, ganoderma lucidum polysaccharide itself has
There is effect that is antitumor, improving immunity, has synergistic effect with anticancer drug, enhance the function and effect of anticancer drug.So far, also
Have no the report studied as the pH value sensitive type nano-medicament carrier of material using ganoderma lucidum polysaccharide.
Invention content
The purpose of the present invention is to provide a kind of pH responsive type drug-carrying nanometer particles based on ganoderma lucidum polysaccharide-histidine conjugate
Son and preparation method thereof, the pH responsive type drug-carrying nanometer particles based on ganoderma lucidum polysaccharide-histidine conjugate that the method for the present invention provides
Son has good biocompatibility and pH sensibility.Ganoderma lucidum polysaccharide heretofore described in the present invention-histidine combines
Object molecular structure is novel, and the medicine-carried nano particles for the pH responses that in neutral and alkaline aqueous solution prepared by self assembly have innovation
Property, and operating process is simple, any other surfactant is not used in formula, has the characteristics that safety, targeting, and energy
The toxic side effect for avoiding the incomplete release of drug from bringing patient.
A kind of pH responsive types medicine-carried nano particles and its system based on ganoderma lucidum polysaccharide-histidine conjugate provided by the invention
Preparation Method, which is characterized in that the ganoderma lucidum polysaccharide-histidine conjugate is hydrophobic section by hydrophilic section, histidine of ganoderma lucidum polysaccharide,
It is keyed by chemistry, then ganoderma lucidum polysaccharide-histidine the conjugate is self-assembly of the load with pH sensitivities in water
Medicine nano-particle；
Ganoderma lucidum polysaccharide of the present invention-histidine conjugate includes structure shown in formula I：
The preparation method of ganoderma lucidum polysaccharide of the present invention-histidine conjugate medicine-carried nano particles, includes the following steps：
(1) ganoderma lucidum polysaccharide is dissolved in deionized water, suitable n-hydroxysuccinimide (NHS) and carbon two is then added
Imines (EDC), is stirred to react 12h, and it (is respectively 5 with ganoderma lucidum polysaccharide molar ratio to add appropriate histidine：1,10：1,20：1),
After being stirred to react for 24 hours, reaction solution is packed into bag filter dialysis 48h, then the product after dialysis is freeze-dried, it is more to obtain ganoderma lucidum
Sugar-histidine conjugate；
(2) 5mg anticancer drugs are weighed to be dissolved in 1mL dimethyl sulfoxide (DMSO)s (DMSO), obtain anticancer drug solution A；
(3) it weighs 5mg ganoderma lucidum polysaccharide-histidine conjugate to be dissolved in the phosphate buffer of 5mL pH 7.2~7.4, obtain
Ganoderma lucidum polysaccharide-histidine conjugate aqueous solution B；
(4) step (2) the anticancer drug solution A step (3) ganoderma lucidum polysaccharide-histidine is slowly dropped into combine
In object aqueous solution B, 2h is stirred, obtains medicine-carried nano particles solution C；
(5) it by medicine-carried nano particles solution C obtained by step (4), is packed into the bag filter that molecular cut off is 3500Da and spends
Ionized water is dialysed for 24 hours, and medicine-carried nano particles are obtained, and freeze-drying obtains ganoderma lucidum polysaccharide-histidine conjugate medicine-carried nano particles.
Ganoderma lucidum polysaccharide of the present invention-histidine conjugate medicine-carried nano particles preparation method, which is characterized in that press matter
Measure ratio, histidine：Ganoderma lucidum polysaccharide=0.1：1~3：1, preferably 0.25：1；
Ganoderma lucidum polysaccharide of the present invention-histidine conjugate medicine-carried nano particles preparation method, which is characterized in that press matter
Measure ratio, NHS：Ganoderma lucidum polysaccharide=0.1：1~1：1, preferably 0.2：1；
Ganoderma lucidum polysaccharide of the present invention-histidine conjugate medicine-carried nano particles preparation method, which is characterized in that press matter
Measure ratio, EDC：Ganoderma lucidum polysaccharide=0.1：1~1：1, preferably 0.2：1；
Ganoderma lucidum polysaccharide of the present invention-histidine conjugate medicine-carried nano particles preparation method, which is characterized in that step
Anticancer drug described in 2 is any one in hydroxycamptothecin, taxol, dihydroartemisinine, betulic acid, adriamycin.
The present invention prepares a kind of ganoderma lucidum polysaccharide-histidine conjugate medicine-carried nano particles, based on improve immunity,
The natural polymer ganoderma lucidum polysaccharide of good biocompatibility is improving medicine stability, is reducing drug hypotoxicity as pharmaceutical carrier
While realize slow release effect.In addition, because it with pH responses can realize that targeting in tumor locus, reaches induction tumour
The purpose of apoptosis.
Description of the drawings
Fig. 1 is a kind of nuclear-magnetism figure of the medicine-carried nano particles of ganoderma lucidum polysaccharide-histidine conjugate
Fig. 2 is a kind of scanning electron microscope (SEM) photograph of the medicine-carried nano particles of ganoderma lucidum polysaccharide-histidine conjugate
Specific implementation mode
Embodiment 1：
1) it weighs 100mg ganoderma lucidum polysaccharide to be dissolved in 15ml deionized waters, 10mg NHS and 10mg EDC is added,
It is stirred to react 12h under 300rpm, 10mg histidines are then added, are stirred to react for 24 hours, then freezes the product after dialysis dry
It is dry, obtain ganoderma lucidum polysaccharide-histidine conjugate；
2) it weighs 5mg hydroxycamptothecin to be dissolved in 1mL dimethyl sulfoxide (DMSO)s (DMSO), obtains hydroxy-camptothecin aqueous slkali；
3) it weighs 5mg ganoderma lucidum polysaccharide-histidine conjugate to be dissolved in the phosphate buffer of 5mL pH 7.2~7.4, obtain
Ganoderma lucidum polysaccharide-histidine conjugate aqueous solution；
4) step 2) the hydroxy-camptothecin aqueous slkali is slowly dropped into the step 3) ganoderma lucidum polysaccharide-histidine conjugate
In aqueous solution, 2h is stirred, obtains medicine-carried nano particles solution；
5) by medicine-carried nano particles solution obtained by step 4), it is packed into the bag filter deionization that molecular cut off is 3500Da
Water is dialysed for 24 hours, and medicine-carried nano particles are obtained, and freeze-drying obtains the ganoderma lucidum polysaccharide-histidine conjugate for being loaded with hydroxycamptothecin
Medicine-carried nano particles.
Embodiment 2：
1) it weighs 120mg ganoderma lucidum polysaccharide to be dissolved in 15ml deionized waters, 100mg NHS and 100mg EDC is added,
It is stirred to react 12h under 350rpm, 300mg histidines are then added, are stirred to react for 24 hours, then freezes the product after dialysis dry
It is dry, obtain ganoderma lucidum polysaccharide-histidine conjugate；
2) 5mg taxols are weighed to be dissolved in 1mL dimethyl sulfoxide (DMSO)s (DMSO), obtain paclitaxel solution；
3) it weighs 5mg ganoderma lucidum polysaccharide-histidine conjugate to be dissolved in the phosphate buffer of 5mL pH 7.2~7.4, obtain
Ganoderma lucidum polysaccharide-histidine conjugate aqueous solution；
4) that the step 2) paclitaxel solution is slowly dropped into the step 3) ganoderma lucidum polysaccharide-histidine conjugate is water-soluble
In liquid, 2h is stirred, obtains medicine-carried nano particles solution；
5) by medicine-carried nano particles solution obtained by step 4), it is packed into the bag filter deionization that molecular cut off is 3500Da
Water is dialysed for 24 hours, and medicine-carried nano particles are obtained, and ganoderma lucidum polysaccharide-histidine conjugate that freeze-drying obtains being loaded with taxol carries medicine
Nano-particle.
Embodiment 3：
1) it weighs 120mg ganoderma lucidum polysaccharide to be dissolved in 15ml deionized waters, 20mg NHS and 20mg EDC is added,
It is stirred to react 12h under 350rpm, 50mg histidines are then added, are stirred to react for 24 hours, then freezes the product after dialysis dry
It is dry, obtain ganoderma lucidum polysaccharide-histidine conjugate；
2) 5mg dihydroartemisinines are weighed to be dissolved in 1mL dimethyl sulfoxide (DMSO)s (DMSO), obtain dihydroartemisinine solution；
3) it weighs 5mg ganoderma lucidum polysaccharide-histidine conjugate to be dissolved in the phosphate buffer of 5mL pH 7.2~7.4, obtain
Ganoderma lucidum polysaccharide-histidine conjugate aqueous solution；
4) step 2) the dihydroartemisinine solution is slowly dropped into the step 3) ganoderma lucidum polysaccharide-histidine conjugate
In aqueous solution, 2h is stirred, obtains medicine-carried nano particles solution；
5) by medicine-carried nano particles solution obtained by step 4), it is packed into the bag filter deionization that molecular cut off is 3500Da
Water is dialysed for 24 hours, and medicine-carried nano particles are obtained, and freeze-drying obtains the ganoderma lucidum polysaccharide-histidine conjugate for being loaded with dihydroartemisinine
Medicine-carried nano particles.
Embodiment 4：
1) it weighs 100mg ganoderma lucidum polysaccharide to be dissolved in 15ml deionized waters, 30mg NHS and 25mg EDC is added,
It is stirred to react 12h under 350rpm, 80mg histidines are then added, are stirred to react for 24 hours, then freezes the product after dialysis dry
It is dry, obtain ganoderma lucidum polysaccharide-histidine conjugate；
2) 5mg dihydroartemisinines are weighed to be dissolved in 1mL dimethyl sulfoxide (DMSO)s (DMSO), obtain dihydroartemisinine solution；
3) it weighs 5mg ganoderma lucidum polysaccharide-histidine conjugate to be dissolved in the phosphate buffer of 5mL pH 7.2~7.4, obtain
Ganoderma lucidum polysaccharide-histidine conjugate aqueous solution；
4) step 2) the dihydroartemisinine solution is slowly dropped into the step 3) ganoderma lucidum polysaccharide-histidine conjugate
In aqueous solution, 2h is stirred, obtains medicine-carried nano particles solution；
5) by medicine-carried nano particles solution obtained by step 4), it is packed into the bag filter deionization that molecular cut off is 3500Da
Water is dialysed for 24 hours, and medicine-carried nano particles are obtained, and freeze-drying obtains the ganoderma lucidum polysaccharide-histidine conjugate for being loaded with dihydroartemisinine
Medicine-carried nano particles.
Embodiment 5：
1) it weighs 110mg ganoderma lucidum polysaccharide to be dissolved in 15ml deionized waters, 60mg NHS and 55mg EDC is added,
It is stirred to react 12h under 350rpm, 60mg histidines are then added, are stirred to react for 24 hours, then freezes the product after dialysis dry
It is dry, obtain ganoderma lucidum polysaccharide-histidine conjugate；
2) 5mg dihydroartemisinines are weighed to be dissolved in 1mL dimethyl sulfoxide (DMSO)s (DMSO), obtain dihydroartemisinine solution；
3) it weighs 5mg ganoderma lucidum polysaccharide-histidine conjugate to be dissolved in the phosphate buffer of 5mL pH 7.2~7.4, obtain
Ganoderma lucidum polysaccharide-histidine conjugate aqueous solution；
4) step 2) the dihydroartemisinine solution is slowly dropped into the step 3) ganoderma lucidum polysaccharide-histidine conjugate
In aqueous solution, 2h is stirred, obtains medicine-carried nano particles solution；
5) by medicine-carried nano particles solution obtained by step 4), it is packed into the bag filter deionization that molecular cut off is 3500Da
Water is dialysed for 24 hours, and medicine-carried nano particles are obtained, and freeze-drying obtains the ganoderma lucidum polysaccharide-histidine conjugate for being loaded with dihydroartemisinine
Medicine-carried nano particles.
Embodiment 6：
1) it weighs 110mg ganoderma lucidum polysaccharide to be dissolved in 15ml deionized waters, 30mg NHS and 45mg EDC is added,
It is stirred to react 12h under 350rpm, 40mg histidines are then added, are stirred to react for 24 hours, then freezes the product after dialysis dry
It is dry, obtain ganoderma lucidum polysaccharide-histidine conjugate；
2) it weighs 5mg hydroxycamptothecin to be dissolved in 1mL dimethyl sulfoxide (DMSO)s (DMSO), obtains hydroxy-camptothecin aqueous slkali；
3) it weighs 5mg ganoderma lucidum polysaccharide-histidine conjugate to be dissolved in the phosphate buffer of 5mL pH 7.2~7.4, obtain
Ganoderma lucidum polysaccharide-histidine conjugate aqueous solution；
4) step 2) the hydroxy-camptothecin aqueous slkali is slowly dropped into the step 3) ganoderma lucidum polysaccharide-histidine conjugate
In aqueous solution, 2h is stirred, obtains medicine-carried nano particles solution；
5) by medicine-carried nano particles solution obtained by step 4), it is packed into the bag filter deionization that molecular cut off is 3500Da
Water is dialysed for 24 hours, and medicine-carried nano particles are obtained, and freeze-drying obtains the ganoderma lucidum polysaccharide-histidine conjugate for being loaded with hydroxycamptothecin
Medicine-carried nano particles.
Claims (7)
1. a kind of pH responsive type medicine-carried nano particles and preparation method thereof based on ganoderma lucidum polysaccharide-histidine conjugate, feature
It is, the ganoderma lucidum polysaccharide-histidine conjugate is hydrophobic section by hydrophilic section, histidine of ganoderma lucidum polysaccharide, is connected by chemical bond
It connects, then ganoderma lucidum polysaccharide-histidine the conjugate is self-assembly of the medicine-carried nano particles with pH sensitivities in water.
2. ganoderma lucidum polysaccharide according to claim 1-histidine conjugate includes structure shown in formula I：
3. the preparation method of ganoderma lucidum polysaccharide according to claim 1-histidine conjugate medicine-carried nano particles, including it is following
Step：
(1) ganoderma lucidum polysaccharide is dissolved in deionized water, suitable n-hydroxysuccinimide (NHS) and carbodiimide is then added
(EDC), it is stirred to react 12h, adds appropriate histidine, after being stirred to react for 24 hours, reaction solution is packed into bag filter dialysis 48h, so
The product after dialysis is freeze-dried afterwards, obtains ganoderma lucidum polysaccharide-histidine conjugate；
(2) 5mg anticancer drugs are weighed to be dissolved in 1mL dimethyl sulfoxide (DMSO)s (DMSO), obtain anticancer drug solution A；
(3) it weighs 5mg ganoderma lucidum polysaccharide-histidine conjugate to be dissolved in the phosphate buffer of 5mL pH 7.2~7.4, obtains ganoderma lucidum
Polysaccharide-histidine conjugate aqueous solution B；
(4) step (2) the anticancer drug solution A is slowly dropped into step (3) ganoderma lucidum polysaccharide-histidine conjugate water
In solution B, 2h is stirred, obtains medicine-carried nano particles solution C；
(5) by medicine-carried nano particles solution C obtained by step (4), it is packed into the bag filter deionization that molecular cut off is 3500Da
Water is dialysed for 24 hours, and medicine-carried nano particles are obtained, and freeze-drying obtains ganoderma lucidum polysaccharide-histidine conjugate medicine-carried nano particles.
4. ganoderma lucidum polysaccharide according to claim 3-histidine conjugate medicine-carried nano particles preparation method, feature exist
In, in mass ratio, histidine：Ganoderma lucidum polysaccharide=0.1：1~3：1.
5. ganoderma lucidum polysaccharide according to claim 3-histidine conjugate medicine-carried nano particles preparation method, feature exist
In, in mass ratio, NHS：Ganoderma lucidum polysaccharide=0.1：1~1：1.
6. ganoderma lucidum polysaccharide according to claim 3-histidine conjugate medicine-carried nano particles preparation method, feature exist
In, in mass ratio, EDC：Ganoderma lucidum polysaccharide=0.1：1~1：1.
7. ganoderma lucidum polysaccharide according to claim 3-histidine conjugate medicine-carried nano particles preparation method, feature exist
In the anticancer drug described in step 2 is arbitrary in hydroxycamptothecin, taxol, dihydroartemisinine, betulic acid, adriamycin
It is a kind of.
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