CN110384703A - Metal based on 6- thioguanine-drug coordination Nano medication and its preparation method and application - Google Patents
Metal based on 6- thioguanine-drug coordination Nano medication and its preparation method and application Download PDFInfo
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- CN110384703A CN110384703A CN201910656717.4A CN201910656717A CN110384703A CN 110384703 A CN110384703 A CN 110384703A CN 201910656717 A CN201910656717 A CN 201910656717A CN 110384703 A CN110384703 A CN 110384703A
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- thioguanine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/34—Copper; Compounds thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/52—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an inorganic compound, e.g. an inorganic ion that is complexed with the active ingredient
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
Abstract
The invention discloses a kind of metal based on 6- thioguanine-drug coordination Nano medications and its preparation method and application, belong to Nano medication field, the Nano medication is using small molecule chemotherapeutic drug 6- thioguanine as ligand, metal ion is connection anchor point, and the assembling of Nano medication is realized by coordination driving effect.The present invention realizes efficient drug delivery, greatly improves that poorly water-soluble existing for general chemotherapeutics, effective availability are low, are easily removed by body, the high problem of toxic side effect；Metal of the present invention based on 6- thioguanine-drug is coordinated Nano medication, shows good class Fenton's reaction catalytic effect under tumor microenvironment stimulation；The present invention prepares the metal based on 6- thioguanine-drug by simple ultrasonic method and is coordinated Nano medication, and preparation flow is short, easy to operate, at low cost.
Description
Technical field
The invention belongs to Nano medication fields, and in particular to a kind of metal based on 6- thioguanine-drug coordination nanometer
Drug and its preparation method and application.
Background technique
For the treatment of cancer, the current general generally existing following problems of chemotherapeutics: 1) it is in itself delivered to tumour portion
The medication amount of position is limited；2) chemotherapeutics 6- thioguanine poorly water-soluble, bioavilability are low；3) there is very high toxic side effect
Deng, be based on this, many seminars are prepared for the nano particle haveing excellent performance as carrier by some technologies, pass into cancer cell
Send anticancer drug.Such as metal organic coordination frame material (MOF), as the outstanding person in delivery vector, it is one kind by metal
The material that ion and organic molecules-ligands are constructed by Coordinate self-assembly has been used to some functional macromolecules and small molecule
Delivering, such as nucleic acid, protein, anticarcinogen etc. [C.He, K.Lu, D.Liu, W.Lin, J.Am.Chem.Soc.2014,136,
5181-5184.], present its great potential as nano-carrier.
But be at present usually the delivering that functional molecular is realized the effects of encapsulating or adsorb using the aperture of MOF, this is just
It is limited to the aperture of MOF and the interference of external environment, and the drug loading efficiencies of these transportation systems are low, usually less than
10%, the waste of expensive medication is not only caused, poor therapeutic effect is also resulted in.So for above-mentioned involved
Problem constructs a kind of efficient treatment of cancer nano platform and still has huge challenge.
It is well known that the microenvironment of tumor lesion area has autospecific, generally present such as slant acidity, high expression H2O2
With the features such as GSH, weary oxygen, played in terms of tumorigenesis and transfer and its important influence, it is wide by scientific research circle
General concern.Based on this, chemical kinetics treatment, a kind of emerging therapeutic strategy [C.Zhang, W.Bu, D.Ni, S.Zhang,
Q.Li, Z.Yao, J.Zhang, H.Yao, Z.Wang, J.Shi.Angew.Chem.Int.Edit.2016,55,2101-2106],
By utilizing Fenton or class Fenton's reaction, high toxicity ROS- hydroxyl radical free radical is generated in situ in tumor locus, kills cancer cell.It should
Therapeutic strategy has high selectivity, can greatly alleviate treatment bring side effect by tumor microenvironment differential stimulus.
Summary of the invention
The purpose of the present invention is to provide a kind of metal based on 6- thioguanine-drug coordination Nano medication and its preparations
Methods and applications, the Nano medication have drug loading efficiencies height, good water solubility, bioavilability height and small excellent of toxic side effect
Gesture.
In order to achieve the above object, the present invention the following technical schemes are provided:
The present invention provides a kind of metal based on 6- thioguanine-drug coordination Nano medication, and the Nano medication is with small point
Sub- chemotherapeutics 6- thioguanine is ligand, and metal ion is connection anchor point, realizes Nano medication by coordination driving effect
Assembling.
Preferably, the metal ion uses Cu2+、Mn2+、Zn2+In any one.
Preferably, the metal-drug coordination Nano medication partial size is 1~1000nm, drug loading 20%
~80%.
It is furthermore preferred that the metal-drug coordination Nano medication partial size is 50~150nm.
The present invention also provides a kind of metal based on 6- thioguanine-drug coordination Nano medication preparation method, packets
Include following steps:
(1) the DMF mother liquor of 6- thioguanine is prepared；
(2) the DMF mother liquor of preparing metal acetate；
(3) it is previously added a certain amount of DMF in the reaction vessel, equimolar ratio mixes 6- thioguanine and copper acetate
DMF mother liquor, ultrasonic treatment obtain deep blackish green color substance；
(4) centrifugal treating washs precipitating with DMF and deionized water, obtained precipitating is finally dispersed in water preservation.
Preferred scheme, in step (1), the concentration of the DMF mother liquor of the 6- thioguanine is 1~100 μm of ol/mL.
Preferred scheme, in step (2), the metal acetate is using any one in copper acetate, manganese acetate, zinc acetate
Kind, the concentration of the DMF mother liquor of metal acetate is 1~300 μm of ol/mL.
Preferred scheme in step (4), precipitating is dispersed in water, 4 DEG C of preservations are placed in.
The present invention also provides the metal based on 6- thioguanine-drug coordination Nano medications in chemotherapeutics and to swell
Application in tumor imaging.
The present invention has following advantageous effects:
The present invention is prepared for a kind of for efficient cancer combination therapy biological nano drug: the gold based on 6- thioguanine
Category-drug is coordinated Nano medication, the Nano medication using Common Chemotherapy drug 6- thioguanine itself as bridging ligand, respectively with
Metal ion (Cu2+、Mn2+、Zn2+) it is connection rivet, efficient drug delivery (~60%) is realized, is greatly improved general
Poorly water-soluble, effective availability existing for chemotherapeutics be low, is easily removed by body, the problem that toxic side effect is high.
Metal of the present invention based on 6- thioguanine-drug is coordinated Nano medication, stimulates following table in tumor microenvironment
Reveal good class Fenton's reaction catalytic effect, activates Cu using the GSH being overexpressed in tumor microenvironment+Release is catalyzed cancer
The highly expressed H of endogenous cellular2O2Hydroxyl radical free radical, while the GSH being effectively overexpressed in consumption cancer cell are generated, tumour is reduced
Oxidation resistance is realized and efficiently inhibits tumour growth.This double mode joint therapeutic modality realizes the efficient inhibition of tumour, and has
Effect reduces the physical toxicity of anticancer drug 6- thioguanine itself (mechanism is as shown in Figure 1).
The present invention prepares the metal based on 6- thioguanine-drug by simple ultrasonic method and is coordinated Nano medication, preparation stream
Journey is short, easy to operate, at low cost.
The present invention also provides the metal based on 6- thioguanine-drug coordination Nano medications in tumor chemotherapeutic drug
In application, can be realized the specific treatment of cancer, mitigate the toxic side effect to normal cell, solve small molecule chemotherapeutic medicine
Object itself is existing insufficient, such as poorly water-soluble, is easily removed by body, and combines the specificity of tumor locus, activated nano
Drug carries out cancer and efficiently treats, and has Clinical significance of MG to the diagnosis and treatment of cancer.
Detailed description of the invention
Fig. 1 is the mechanism schematic diagram that the metal based on 6- thioguanine-drug is coordinated Nano medication.
The TEM that Fig. 2 is 1 gained Cu-AdNP of embodiment schemes.
The TG that Fig. 3 is 1 gained Cu-AdNP of embodiment schemes.
Fig. 4 is that metal-drug of Examples 1 to 3 preparation is coordinated the DLS figure of Nano medication.
Fig. 5 is the proficiency testing result that Nano medication reduces GSH.
Fig. 6 is the class Fenton's reaction effect picture of Nano medication.
Fig. 7 is that Nano medication extends catalysis H at any time2O2It decomposes and generates O2Ability.
Fig. 8 is toxicity comparative analysis result of the various concentration Nano medication to normal cell and cancer cell.
Fig. 9 is that Cell apoptosis & necrosis analyzes result.
Figure 10 is tumor growth curve figure.
Figure 11 is that mouse survival rate analyzes result.
Specific embodiment
Present invention will be further explained below with reference to the attached drawings and specific examples.
Embodiment 1
Metal based on 6- thioguanine-drug coordination Nano medication (Cu-AdNP) preparation:
Cu-AdNP directlys adopt the synthesis of simple ultrasonic method, prepare respectively first 60 μm of ol/mL 6- thioguanine,
The DMF mother liquor of 180 μm of ol/mL copper acetates, takes 3.6mL DMF to set in a round bottom flask, and equimolar ratio mixes 6- thioguanine
With the DMF mother liquor of copper acetate, deep blackish green color substance, ultrasonic 2.5h are generated immediately；It is then centrifuged for (11000rpm, 10min), uses
DMF and deionized water washing precipitating, remove unreacted impurity；The precipitating finally obtained is dispersed in water, and is placed in 4 DEG C of preservations.
Embodiment 2
Using the DMF mother liquor of 180 μm of ol/mL manganese acetates, remaining condition is prepared fast based on 6- sulphur bird with embodiment 1
The metal of purine-drug coordination Nano medication (Mn-AdNP).
Embodiment 3
Using the DMF mother liquor of 180 μm of ol/mL zinc acetates, remaining condition is prepared fast based on 6- sulphur bird with embodiment 1
The metal of purine-drug coordination Nano medication (Zn-AdNP).
The TEM that Fig. 2 is 1 gained Cu-AdNP of embodiment schemes, and the Cu-AdNP partial size synthesized as can be seen from Figure 2 is 50nm.
Fig. 3 is the thermal gravimetric analysis results of 1 gained Cu-AdNP of embodiment, and drug loading is high as can be seen from Figure 3, about
40%.
Fig. 4 be Examples 1 to 3 preparation the metal based on 6- thioguanine-drug be coordinated Nano medication DLS as a result,
The hydration partial size of the three kinds of Nano medications synthesized as can be seen from Figure 4 be respectively Cu-AdNP (105nm), Mn-AdNP (250nm),
Zn-AdNP(500nm)。
It is detected by dynamic light scattering instrument (DLS), Cu-AdNP is positively charged, and Mn-AdNP, Zn-AdNP are negatively charged.
The proficiency testing of the reduction of embodiment 4 GSH
Using 1 gained Cu-AdNP of embodiment, different amounts of Nano medication is taken, 37 DEG C is placed in GSH and reacts 1h (GSH reaction
Final concentration of 1mM), centrifugation, take 100 μ L of supernatant and 100 μ L (2.5mg/mL) of DTNB, 37 DEG C of incubation 15min, by it is ultraviolet-can
(445nm) is tested in light-exposed spectrum absorption.
Fig. 5 is the proficiency testing that Nano medication reduces GSH, and Cu-AdNP has and well consumes as can be seen from Figure 5
The performance of GSH.
Analysis: Cu2+Redox reaction can occur with GSH, generate Cu+It is reduced with GSSG to reduce GSH content
Cancer cell cleans ROS ability, enhancing chemical kinetics treatment.
5 class Fenton's reaction effect of embodiment (MB degradation)
It using 1 gained Cu-AdNP of embodiment, is reacted with excessive GSH to solution journey glassy yellow, centrifugation is washed 2 times, and will
Precipitating (being named as Cu-GNP) is dispersed in water again, takes equivalent Cu-GNP (final concentration of 3 μ g/mL), MB (final concentration of 10 μ
G/mL), it is separately added into various concentration H2O2(final concentration is respectively 0,0.5,5mM) is centrifuged after 37 DEG C of incubation 1h, supernatant is taken to survey
Uv-visible absorption spectra (500~800nm).
Fig. 6 is the class Fenton's reaction effect picture of Nano medication, and Fig. 6 is proved in H2O2Under the conditions of existing, Cu-GNP can be produced
Raw enough hydroxyl radical free radicals, make MB degrade.
Analysis: GSH stimulates Cu+It generates, it can be with cancer cell endogenous H2O2Reaction generates high toxicity ROS-hydroxyl free
Base (hydroxyl radical free radical can make MB degrade), causes cancer cell DNA damage, Efficient killing effect cancer cell.
6 Nano medication decomposing H of embodiment2O2Generate O2
Using 1 gained Cu-AdNP of embodiment, it is placed in containing 500 μM of H2O2In solution, surveyed under stirring condition with dissolved oxygen meter
Examination, and record and change over time, the content of dissolved oxygen.
Fig. 7 is that Nano medication extends catalysis H at any time2O2It decomposes and generates O2Ability, Cu-AdNP can as can be seen from Figure 7
Effectively catalysis H2O2It decomposes and generates O2。
Analysis: biological nano drug can be catalyzed the endogenic H of cancer cell2O2It decomposes, generates O2, improve tumor hypoxia, suppression
DNA damage reparation processed and cancer development and transfer.
7 Nano medication of embodiment (Cu-AdNP) is to the toxicity of cell and apoptosis necrosis analysis (drug study)
A) oxicity analysis: normal cell (HEK293) and cancer cell (4T1) are incubated at 96 orifice plates respectively, cell is adherent
Afterwards, the material that various concentration is added is incubated for for 24 hours, then carries out toxotest with MTT method；
B) apoptosis necrosis detects: by 4T1 cell culture in 6 orifice plates, after cell is adherent, being separately added into various concentration material
(tri- groups of blank, Ad, Cu-AdNP, wherein 25 μ g/mL of drug containing Ad) after being incubated for 2h, is carried out according to apoptosis necrosis staining procedure
Operation, is tested after dyeing with flow cytometer.
Fig. 8 is for various concentration Nano medication to the toxicity comparative analysis of normal cell and cancer cell as a result, can from Fig. 8
Cu-AdNP Nano medication can distinguish normal cell and cancer cell out, have good lethal effect to cancer cell 4T1, mitigate it
To the toxic side effect of normal cell.
Fig. 9 is Cell apoptosis & necrosis analysis, and Cu-AdNP Nano medication can result in cancer cell-apoptosis as can be seen from Figure 9.
Therefore, which can realize chemotherapy-chemomotive force of tumor microenvironment response by the efficient endocytosis of cancer cell
Treatment is learned, and there is insignificant toxicity to normal cell；Meanwhile the Nano medication has suppression well to cancer cell (4T1)
Effect processed, and the physical toxicity of small molecule chemotherapeutic drug 6- thioguanine can be effectively reduced.
8 Nano medication of embodiment calculates the inhibition of tumour growth and mouse survival rate
Zoopery is divided into three groups (blank, Ad, Cu-AdNP), using intratumor injection (drug containing 9.2mg/mL), exists respectively
50 μ L are injected within 0,3,6 day respectively, and every 1 day record tumor size since the 0th day.
Figure 10 is tumor growth curve, and Cu-AdNP Nano medication can significantly inhibit the life of tumour as can be seen from Figure 10
It is long.
Figure 11 is that mouse survival rate is analyzed as a result, as can be seen from Figure 11 compared to small molecule chemotherapeutic medicine group, nanometer medicine
Object can significantly reduce chemotherapeutics to the toxic side effect of body, increase mouse survival rate.
The foregoing is merely presently preferred embodiments of the present invention, all equivalent changes done according to scope of the present invention patent with
Modification, is all covered by the present invention.
Claims (9)
1. a kind of metal based on 6- thioguanine-drug is coordinated Nano medication, which is characterized in that the Nano medication is with small molecule
Chemotherapeutics 6- thioguanine is ligand, and metal ion is connection anchor point, and the group of Nano medication is realized by coordination driving effect
Dress.
2. the metal according to claim 1 based on 6- thioguanine-drug is coordinated Nano medication, which is characterized in that institute
Metal ion is stated using Cu2+、Mn2+、Zn2+In any one.
3. the metal according to claim 1 based on 6- thioguanine-drug is coordinated Nano medication, which is characterized in that institute
Stating metal-drug coordination Nano medication partial size is 1~1000nm, and drug loading is 20%~80%.
4. the metal according to claim 3 based on 6- thioguanine-drug is coordinated Nano medication, which is characterized in that institute
Stating metal-drug coordination Nano medication partial size is 50~150nm.
5. the metal according to any one of claims 1 to 4 based on 6- thioguanine-drug coordination Nano medication system
Preparation Method, which comprises the following steps:
(1) the DMF mother liquor of 6- thioguanine is prepared；
(2) the DMF mother liquor of preparing metal acetate；
(3) it is previously added a certain amount of DMF in the reaction vessel, equimolar ratio mixes the DMF of 6- thioguanine and copper acetate
Mother liquor, ultrasonic treatment obtain deep blackish green color substance；
(4) centrifugal treating washs precipitating with DMF and deionized water, obtained precipitating is finally dispersed in water preservation.
6. the metal according to claim 5 based on 6- thioguanine-drug coordination Nano medication preparation method, special
Sign is, in step (1), the concentration of the DMF mother liquor of the 6- thioguanine is 1~100 μm of ol/mL.
7. the metal according to claim 5 based on 6- thioguanine-drug coordination Nano medication preparation method, special
Sign is, in step (2), the metal acetate is using any one in copper acetate, manganese acetate, zinc acetate, metal acetic acid
The concentration of the DMF mother liquor of salt is 1~300 μm of ol/mL.
8. the metal according to claim 5 based on 6- thioguanine-drug coordination Nano medication preparation method, special
Sign is, in step (4), precipitating is dispersed in water, and is placed in 4 DEG C of preservations.
9. the metal according to any one of claims 1 to 4 based on 6- thioguanine-drug coordination Nano medication is being changed
Treat the application in drug and tumor imaging.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112552519A (en) * | 2020-11-30 | 2021-03-26 | 魏爽 | Preparation method and application of soft metal Au and Cu coordinated sulfur guanosine copolymer |
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