CN104288174A - Controlled-release hydrogen sulfide donor as well as preparation method and application thereof - Google Patents
Controlled-release hydrogen sulfide donor as well as preparation method and application thereof Download PDFInfo
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- CN104288174A CN104288174A CN201410551362.XA CN201410551362A CN104288174A CN 104288174 A CN104288174 A CN 104288174A CN 201410551362 A CN201410551362 A CN 201410551362A CN 104288174 A CN104288174 A CN 104288174A
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- hydrogen sulfide
- donor
- sulfide donor
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/06—Tripeptides
- A61K38/063—Glutathione
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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
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
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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
- A61K33/04—Sulfur, selenium or tellurium; 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
- A61K47/69—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6921—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere
- A61K47/6923—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere the form being an inorganic particle, e.g. ceramic particles, silica particles, ferrite or synsorb
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B17/00—Sulfur; Compounds thereof
- C01B17/16—Hydrogen sulfides
Abstract
The invention relates to a controlled-release hydrogen sulfide donor. The donor is obtained by reacting diallyl trisulfide with an ordered mesoporous silicon dioxide nanoparticle materials. The invention also provides a preparation method and application of the hydrogen sulfide donor. The controlled-release hydrogen sulfide donor is capable of slowly releasing medium-concentration hydrogen sulfide, can be regulated by use of glutathione and has no obvious cytotoxicity; as a result, the controlled-release hydrogen sulfide donor is an ideal hydrogen sulfide donor for in-vivo and in-vitro experiments and clinical application.
Description
Technical field
The present invention relates to technical field of molecular biology, specifically, is a kind of slow release hydrogen sulfide donor and preparation method thereof, application.
Background technology
Along with hydrogen sulfide is as a kind of announcement of endogenous metabolites, over nearly 10 years, Chinese scholars has carried out large quantifier elimination to the physiological significance of hydrogen sulfide and the important function in various diseases thereof.Large quantifier elimination display: the reduction of hydrogen sulfide levels take part in the pathophysiological process of myocardial ischemia reperfusion injury.It also can cause coronary artery diastole at nitric oxide synergism, thus increases coronary blood flow, improves multiple microcirculation of filling with rear arteria coronaria, reduces myocardial ischemia/reperfusion injury further, promote the recovery of cardiac function, reduce the apoptosis of myocardial cell.But current hydrogen sulfide research still lacks desirable sulfur donor.The most frequently used hydrogen sulfide donor is hydrogen sulfide saturated solution or NaHS (NaHS) solution.Though both effectively can provide hydrogen sulfide, extremely unstable, and toxicity is comparatively large, and the smell is awful.In existing document, applying NaHS often occur inconsistent or be difficult to the experimental phenomena of repetition, may be caused by the characteristic due to its instability.Another kind of hydrogen sulfide donor GYY4137 can in vivo with external slow release hydrogen sulfide, but concentration of hydrogen sulfide is lower, and can not Co ntrolled release speed, therefore limits its application.All more or less there is above-mentioned shortcoming in other hydrogen sulfide donor, makes the searching of the new donor of hydrogen sulfide more urgent.
Garlicin (DATS) is a kind of garlicin extract, and it effectively can discharge hydrogen sulfide under the existence of glutathion (reduced glutathione, GSH), but its rate of release is fast, and concentration is higher, can not be conditioned.And DATS is water insoluble, these all limit its application as hydrogen sulfide donor.The invention provides a kind of hydrogen sulfide donor that yet there are no report.
Summary of the invention
The object of the invention is, for deficiency of the prior art, to provide a kind of hydrogen sulfide donor.
Of the present invention again one object be that a kind of preparation method of hydrogen sulfide donor is provided.
Another object of the present invention provides a kind of application of hydrogen sulfide donor.
For achieving the above object, the technical scheme that the present invention takes is: a kind of hydrogen sulfide donor, and described donor reacts gained by garlicin and ordered mesoporous silica dioxide nanometer particle material.
Described donor obtains by the following method: garlicin is scattered in water, adds ordered mesoporous silica dioxide nanometer particle material, and stir, then by product separation, abandoning supernatant, namely obtains hydrogen sulfide donor.
For realizing above-mentioned second object, the technical scheme that the present invention takes is: a kind of preparation method of hydrogen sulfide donor, described method comprises the following steps: in 500 mL there-necked flasks, add 300 mL deionized waters, the sodium hydroxide solution of the 2mol/L of 2.1mL, 0.6g template cetyl trimethyl ammonium bromide, 80 DEG C of waters bath with thermostatic control, 200 revs/min of mechanical agitation; After 1 hour, add 3mL ethyl orthosilicate, react two hours, close heating and stir, product by centrifugalize, and with deionized water and absolute ethanol washing twice; And then product is scattered in 100mL ethanol, add 1g ammonium nitrate, at 80 DEG C, stir 2 hours removing template cetyl trimethyl ammonium bromide; Ethanol washes twice, then washes; Get 10 mg ordered mesoporous silica dioxide nanometer particle materials, ultrasonic disperse is in 2mL water, and add 5 μ L garlicins, magnetic agitation, after 12 hours, by product centrifugalize, abandoning supernatant, namely obtains hydrogen sulfide donor.
For realizing above-mentioned 3rd object, the technical scheme that the present invention takes is: the application of a kind of hydrogen sulfide donor slow release or controlled release hydrogen sulfide.
The application of a kind of hydrogen sulfide donor in the medicine preparing external or sustained release profile in vivo test or controlled release hydrogen sulfide.
Glutathion is as activating molecules.
The invention has the advantages that:
1, hydrogen sulfide donor of the present invention can the hydrogen sulfide of slow releasing intermediate concentration, and can pass through GSH adjustment release speed.
2, hydrogen sulfide donor of the present invention is desirable hydrogen sulfide donor in body, external, without obvious cytotoxicity.
Accompanying drawing explanation
Accompanying drawing 1 is hydrogen sulfide release mechanism.
Accompanying drawing 2 is size and the structure of DATS-MSN.
Accompanying drawing 3 is particle size distribution of DATS-MSN.
Accompanying drawing 4 is specific surface areas of DATS-MSN.
Accompanying drawing 5 is the release of GSH concentration regulation and control hydrogen sulfide.
Accompanying drawing 6 is impacts that pH value discharges hydrogen sulfide.
Accompanying drawing 7 is impacts that temperature discharges hydrogen sulfide.
Accompanying drawing 8 is the interior release of body of DATS-MSN and NaHS.
Accompanying drawing 9 is cytotoxicities of DATS-MSN.
Detailed description of the invention
Below in conjunction with accompanying drawing, detailed description of the invention provided by the invention is elaborated.
Ordered mesoporous silica dioxide nanometer particle material (MSN) is drug-loading system the most frequently used at present.Have can regulate continuously within the scope of 2-50 nm homogeneous mesoporous pore size, rule duct, stable framing structure, be easy to modify surfaces externally and internally and without features such as physiological-toxicity, its huge specific surface area (>900 m in addition
2/ g) and pore volume (>0.9 cm
3/ g), make MSNs be suitable as very much the carrier of drug molecule, improve the persistency of drug effect.Therefore we consider to use MSN to change the characteristic of existing medicine as carrier.DATS effectively can discharge hydrogen sulfide when there being GSH to exist, and GSH does not participate in the generation of hydrogen sulfide as activating molecules, become oxidation state after reaction.But its rate of release is very fast, concentration is higher, can not be conditioned, and water insoluble, and these all limit its application as hydrogen sulfide donor.When DATS enters after in MSN nano aperture, it can utilize the slow releasing function of MSN on the one hand, slowly releases particle, reacts generate hydrogen sulfide with GSH.GSH molecule can enter silicon dioxide granule on the other hand, reacts with DATS, generates hydrogen sulfide, the reaction of these DATS molecules that all slowed down and dispose procedure (as shown in Figure 1).Simultaneously dispose procedure can control by GSH concentration, thus reach the process of slow release and controlled release.
the preparation of embodiment 1 ordered mesoporous silica dioxide nanometer particle material (MSN)
300 mL deionized waters are added, the sodium hydroxide solution of the 2mol/L of 2.1mL, 0.6 gram of template cetyl trimethyl ammonium bromide (CTAB), 80 DEG C of waters bath with thermostatic control, 200 revs/min of mechanical agitation in 500 mL there-necked flasks.After 1 hour, add 3mL ethyl orthosilicate (TEOS).React two hours, close heating and stir, product by centrifugalize, and with deionized water and absolute ethanol washing twice.And then product is scattered in 100mL ethanol, add 1g ammonium nitrate, at 80 DEG C, stir 2 hours removing template CTAB.Ethanol washes twice, washed several times with water.
the synthesis of embodiment 2 DATS-MSN
Get 10 mg MSN, ultrasonic disperse, in 2mL water, adds 5 μ L DATS, magnetic agitation, and after 12 hours, by product centrifugalize, abandoning supernatant, obtains the particle of medicine carrying, i.e. DATS-MSN.
embodiment 3 DATS-MSN material characterizes
The size of DATS-MSN and surface texture can be determined (HRTEM, JEM-2100F) by high-resolution-ration transmission electric-lens.Dispersion index (PDI) is carried out particle size distribution analysis by Autosizer 4700 (Malvern) instrument and is drawn (25 DEG C, 5 μ g/mL).BET(Multipoint Brunauer, Emmett, and Teller) analytic process calculates the surface area mass ratio of MSN.
the hydrogen sulfide release assessment of embodiment 4 DATS-MSN
release in vitro
Hydrogen sulfide release conditions is measured by high performance liquid chromatography (high-performance liquid chromatography, HPLC) method.By DATS-MSN(100 μ g/mL) add in the phosphate solution (PBS) of 4 mL 100mM, add the GSH of (2mM or 200 μMs of or 20 μMs) afterwards respectively.Carry out hydrogen sulfide measurement subsequently.During measurement, get Tris-HCl (100mM, pH 9.5, the 0.1 Mm DPTA) mixing that 30 μ L obtain sample and 70 μ L, then mix with 50 μ L of monobromobimane solution.React after 30 minutes and add 50 μ L glacial acetic acid (200mM) cessation reactions.After get chromatographic column (the XDB-C18 column that 100 μ L supernatant add HPLC instrument (1260 infinity), 150 * 4.6 mm, 5 μm), fluorescent method detects concentration of hydrogen sulfide (λ ex:390 nm and λ em:475 nm), and does ratio with standard curve.Detection time is 0 to 12 hour, detects (8.0,7.4 and 6.0) respectively under different temperatures (37 DEG C, 20 DEG C and 4 DEG C) and different PH situation.
release in body
SD rat (200-220 gram) gives DATS-MSN (10mg/kg) and NaHS (100 μm of ol/kg) end of line intravenous injection after being anesthetized respectively, after injection, timing in 0 to 9 hour is put in pipe from carotid artery and is got blood 0.2mL, anticoagulant (heparin sodium 50U/mL) and centrifugal (3000 revs/min, 15 points) after obtain blood plasma, its Methods For Determining Hydrogen Sulfide is the same, but under 4 degree, centrifugal 10 minutes (12000 revs/min) need enter Instrumental Analysis again after adding glacial acetic acid.
the safety testing of embodiment 5 DATS-MSN
Conventional method obtains primary neonatal rat myocardial cell.Myocardial cell (10
5/ mL) conventional use DMEM/F12 and 10% calf serum be incubated at CO2 gas incubator (37 DEG C, 5%CO
2) cultivate 12 hours.By DATS-MSN(0-100 μ g/mL) add 96 orifice plates of transplantation of cardiomyocytes, changed by cardiomyocyte culture liquid for for CCK-8 solution reaction is after 24 hours, microplate reader measures cytoactive (450 nm).
DATS-MSN successfully synthesizes, and possesses the unique texture (as shown in Figure 2) of homogeneous size and porous.Possess narrower particle size distribution (PDI=0.08, as shown in Figure 3) and large specific surface area (813 m
2/ g, as shown in Figure 4).As hydrogen sulfide donor, DATS-MSN effectively, slowly can discharge hydrogen sulfide in solution in vitro, and its dispose procedure by GSH concentration adjustment, thus can reach controlled-release effect (as shown in Figure 5).Hydrogen sulfide is released in sour environment and is suppressed (as shown in Figure 6), but temperature is for hydrogen sulfide release impact little (as shown in Figure 7).In body, release aspect, compares with NaHS, and DATS-MSN more effectively and slowly discharges hydrogen sulfide, more meets physiological conditions (as shown in Figure 8) to the raising of concentration of hydrogen sulfide in blood plasma.Under application concentration the DATS-MSN of (0-100 μ g/mL) for neonatal rat myocardial cell without overt toxicity (as shown in Figure 9).
The above is only the preferred embodiment of the present invention; it should be pointed out that for those skilled in the art, under the prerequisite not departing from the inventive method; can also make some improvement and supplement, these improve and supplement and also should be considered as protection scope of the present invention.
Claims (6)
1. a hydrogen sulfide donor, is characterized in that, described donor reacts gained by garlicin and ordered mesoporous silica dioxide nanometer particle material.
2. hydrogen sulfide donor according to claim 1, is characterized in that, described donor obtains by the following method: garlicin is scattered in water, add ordered mesoporous silica dioxide nanometer particle material, stir, then by product separation, abandoning supernatant, namely obtains hydrogen sulfide donor.
3. the preparation method of hydrogen sulfide donor according to claim 1, it is characterized in that, described method comprises the following steps: in 500 mL there-necked flasks, add 300 mL deionized waters, the sodium hydroxide solution of the 2mol/L of 2.1mL, 0.6g template cetyl trimethyl ammonium bromide, 80 DEG C of waters bath with thermostatic control, 200 revs/min of mechanical agitation; After 1 hour, add 3mL ethyl orthosilicate, react two hours, close heating and stir, product by centrifugalize, and with deionized water and absolute ethanol washing twice; And then product is scattered in 100mL ethanol, add 1g ammonium nitrate, at 80 DEG C, stir 2 hours removing template cetyl trimethyl ammonium bromide; Ethanol washes twice, then washes; Get 10 mg ordered mesoporous silica dioxide nanometer particle materials, ultrasonic disperse is in 2mL water, and add 5 μ L garlicins, magnetic agitation, after 12 hours, by product centrifugalize, abandoning supernatant, namely obtains hydrogen sulfide donor.
4. the application of hydrogen sulfide donor slow release according to claim 1 or controlled release hydrogen sulfide.
5. the application of hydrogen sulfide donor according to claim 1 in the medicine preparing external or sustained release profile in vivo test or controlled release hydrogen sulfide.
6., according to the arbitrary described application of claim 4,5, it is characterized in that, glutathion is as activating molecules.
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Cited By (4)
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| CN106539818A (en) * | 2015-09-20 | 2017-03-29 | 复旦大学 | Hydrogen sulfide and its donor sodium hydrosulfide are preparing the purposes promoted in hemopoietic medicine |
| CN111000979A (en) * | 2019-12-04 | 2020-04-14 | 南京师范大学 | Keratin-based hydrogen sulfide donor, and synthesis method and application thereof |
| CN113041221A (en) * | 2021-03-23 | 2021-06-29 | 潍坊中医药产业技术研究院 | ROS (reactive oxygen species) sensitivity and H2Preparation method and application of S donor response type nano micelle |
| CN113350520A (en) * | 2020-05-27 | 2021-09-07 | 复旦大学附属华山医院 | Hydrogen sulfide controlled-release brain targeting nano system for protecting nervous system after cardiac arrest and preparation method thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106539818A (en) * | 2015-09-20 | 2017-03-29 | 复旦大学 | Hydrogen sulfide and its donor sodium hydrosulfide are preparing the purposes promoted in hemopoietic medicine |
| CN111000979A (en) * | 2019-12-04 | 2020-04-14 | 南京师范大学 | Keratin-based hydrogen sulfide donor, and synthesis method and application thereof |
| CN111000979B (en) * | 2019-12-04 | 2022-11-25 | 南京师范大学 | Hydrogen sulfide donor based on keratin and synthesis method and application thereof |
| CN113350520A (en) * | 2020-05-27 | 2021-09-07 | 复旦大学附属华山医院 | Hydrogen sulfide controlled-release brain targeting nano system for protecting nervous system after cardiac arrest and preparation method thereof |
| CN113041221A (en) * | 2021-03-23 | 2021-06-29 | 潍坊中医药产业技术研究院 | ROS (reactive oxygen species) sensitivity and H2Preparation method and application of S donor response type nano micelle |
| CN113041221B (en) * | 2021-03-23 | 2022-11-01 | 潍坊中医药产业技术研究院 | ROS (reactive oxygen species) sensitivity and H2Preparation method and application of S donor response type nano micelle |
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