CN103785366B - A kind of iodine/hydrophobic cyclodextrin clathrate and its preparation method and application - Google Patents
A kind of iodine/hydrophobic cyclodextrin clathrate and its preparation method and application Download PDFInfo
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- CN103785366B CN103785366B CN201210425473.7A CN201210425473A CN103785366B CN 103785366 B CN103785366 B CN 103785366B CN 201210425473 A CN201210425473 A CN 201210425473A CN 103785366 B CN103785366 B CN 103785366B
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Abstract
The invention belongs to the field of pharmaceutical preparations of pharmaceutical engineering, being specifically related to a kind of iodine/hydrophobic cyclodextrin clathrate and preparation method thereof, described iodine/hydrophobic cyclodextrin, it is made up of in molar ratio following raw material, iodine: hydrophobic cyclodextrin==1: 0.5～2, use sealing temperature controlled technology to prepare.Prepared iodine/hydrophobic cyclodextrin clathrate, can effectively suppress the volatilization of iodine, enhanced stability；Further, iodine/hydrophobic cyclodextrin clathrate can also overcome the iodine zest to skin mucosa；Reduce the corrosivity of iodine；Iodine/hydrophobic cyclodextrin clathrate toxicity is little；Drug effect is high；Not easy coloring；Have and slowly discharge iodine molecule, action time lasting feature, additionally, iodine/hydrophobic cyclodextrin clathrate also has extremely strong absorption property, can active adsorption abnormal flavour and toxic gas.
Description
Technical field
The invention belongs to the field of pharmaceutical preparations of pharmaceutical engineering, be specifically related to a kind of iodine/hydrophobic cyclodextrin clathrate and preparation method thereof, its range of application relates to the fields such as clinic, health, daily life, agriculture and animal husbandry aquaculture and environmental conservation.
Background technology
Iodine is a kind of important element, and the permeability that free-iodine tool is good can readily penetrate through cell wall, and iodine can hydroxyl on gal4 amino acid chain, amino, alkyl, sulfydryl be combined and cause protein denaturation precipitation, and generation halogenation, so that it loses biological activity.Can kill the almost all of pathogenic microorganism including including antibacterial, virus, Mycoplasma, coccidiosis, soft capsule, spore etc. accordingly, as disinfection sanitizer iodine, its sterilization scope relates to the fields such as clinic, health, daily life, agriculture and animal husbandry aquaculture and environmental conservation.At present, conventional iodine disinfectant has iodine tincture, iodine tincture and povidone iodine etc., although Disinfection Effect is definite, but still suffers from some problems in use, and such as, iodine tincture is by iodine, potassium iodide, ethanol, purified water preparation, during use to skin, irritation on mucous membrane greatly, color depth；The macromolecular compound that povidone iodine is iodide ion and surfactant is bound up, existence and stability is poor, problem [the Dong Juhong etc. such as release is slow, iodine disinfectant application present situation [J]. HEILONGJIANG ANIMAL SCIENCE AND VETERINARY MEDICINE, 2010,6,111-112.], additionally, due to iodine is volatile, iodide ion is oxidizable.In order to make up the problem that existing iodine disinfectant exists, improve the stability of iodine, prepare the stable multi-functional Operands such as long-acting slow-release sterilizing, deodorization that have and be applied to have great importance.
Iodine is water insoluble, and has sublimability, thus reduces its effect used.It is thus desirable to select a kind of preferably formulation method to make it overcome its sublimability, enhanced stability, thus improve its using effect.
Cyclodextrin (Cyclodextrin, it is called for short CD) it is the general name of one group of oligosaccharide by D-glucopyranose units annular arrangement, as cyclic oligomer, the hydrophobic annular cavity all kinds of object of energy inclusion of cyclodextrin, such as organic molecule, inorganic molecule, coordination compound even noble gas etc., form host-gust inclusion complexes by intermolecular Physical interaction.The physicochemical property of object can be effectively improved, as improved dissolubility, enhanced stability etc. after forming clathrate.
Currently, the method preparing cyclodextrin clathrate mainly has polishing, coprecipitation, saturated water solution method etc..Wherein polishing majority needs to add harmful organic solvent；Coprecipitation needs higher temperature and the cyclodextrin of excess, is not suitable for heat-labile medicine；Saturated water solution method needs cyclodextrin to have preferable water solublity, additionally needs to add the inclusion material of excess.
With conventional inclusion method, as saturated solution method, polishing, freeze-drying, spray drying method are compared, sealing temperature controlled inclusion technique prepares the feature of clathrate: 1. be not required in preparation process add organic solvent, do not have organic solvent to remain, convenient post-treatment in clathrate；2. inclusion temperature-controllable, inclusion speed is fast；3. inclusion rate is high；4. preparation technology is easy.At present, use sealing temperature controlled inclusion technique to prepare iodine/hydrophobic cyclodextrin clathrate and there is not yet relevant report.
Summary of the invention
It is an object of the invention to provide a kind of iodine/hydrophobic cyclodextrin clathrate, it can effectively suppress the volatilization of iodine, enhanced stability；Further, iodine/hydrophobic cyclodextrin clathrate can also overcome the iodine zest to skin mucosa；Reduce the corrosivity of iodine；Iodine/hydrophobic cyclodextrin clathrate toxicity is little；Drug effect is high；Not easy coloring；Have and slowly discharge iodine molecule, action time lasting feature, additionally, iodine/hydrophobic cyclodextrin clathrate also has extremely strong absorption property, can active adsorption abnormal flavour and toxic gas.
The present invention uses the sealing temperature controlled inclusion technique of advanced person to prepare clathrate, the method can effectively overcome the various drawbacks in above-mentioned preparation method, select hydrophobicity beta-cyclodextrin derivative to make iodine/hydrophobic cyclodextrin clathrate simultaneously, can effectively suppress the volatilization of iodine, enhanced stability, and have and slowly discharge iodine molecule, action time lasting feature.
When this technology prepares clathrate, it is not required to use organic solvent solubilizing hydrophobic cyclodextrin, and, make medicine distil and cyclodextrin inclusion compound by controlling temperature, therefore remain without solvent, environmentally safe, and technical process simple operations is convenient.This technology is used to prepare the problem that iodine/hydrophobic cyclodextrin clathrate can avoid above-mentioned preparation method to exist.At present, yet there are no the pertinent literature report using sealing temperature controlled inclusion technique to prepare iodine/hydrophobic cyclodextrin.This invention can be widely applied to the fields such as clinic, health, daily life, agriculture and animal husbandry aquaculture and environmental conservation.
The present invention is achieved through the following technical solutions, described iodine/hydrophobic cyclodextrin, and it is made up of in molar ratio following raw material, iodine: hydrophobic cyclodextrin==1: 0.5～2, preferably 1:0.5～1, uses sealing temperature controlled technology to prepare.
Above-mentioned hydrophobic cyclodextrin refers to: (1) is acylated beta-cyclodextrin derivative, including 2, and 3,6 triacetyl beta-schardinger dextrin-s, 2,3,6 three propiono beta-schardinger dextrin-s, 2,3,6 three bytyry beta-schardinger dextrin-s, 2,3,6 three acyl group beta-schardinger dextrin-s；(2) Ethylated β-Cyclodextrins derivant, including 2,6 diethyl beta-schardinger dextrin-s, 2,3,6 triethyl group beta-schardinger dextrin-s.
The technology of preparing of iodine/hydrophobic cyclodextrin clathrate of the present invention comprises the following steps:
A, hydrophobic cyclodextrin is put into vacuum drying oven, 70 DEG C of vacuum drying 1h；
B, weighing hydrophobic cyclodextrin and appropriate iodine by above-mentioned mol ratio, vortex mixed 5～10min makes iodine/hydrophobic cyclodextrin mixture；
C, weigh iodine/hydrophobic cyclodextrin mixture 1g and inject 5ml glass ampoule, be filled with N2Gas, sealing；
D, powder charge ampulla is placed in temp controlling heater, design temperature 45～60 DEG C of heating 60～90min；
E, by sample from ampulla take out, cross 200 mesh sieves, obtain solid iodine/hydrophobic cyclodextrin clathrate.
Thermogravimetric analysis test result
With iodine/2, as a example by 3,6 triacetyl beta-schardinger dextrin-s (iodine/TA-β-CD) clathrate; weigh the iodine/TA-β-CD mixture and iodine/each 10mg of TA-beta-CD inclusion prepared by the present invention respectively; putting in thermogravimetric analyzer, the weightless change of test sample, result is shown in Fig. 1.Iodine/TA-β-CD mixture, from the beginning of 50 DEG C, begins with weight change with iodine distillation, arrives near the fusing point of iodine therewith, and weightless change becomes apparent from；And change without obvious weight less than 180 DEG C of region iodine/TA-beta-CD inclusions in temperature.Thus result is inferred, in mixture with clathrate, the existence of iodine molecule is different, iodine simply exists with original state in the mixture, in clathrate, iodine is then to enter in cyclodextrin hole with molecularity, host and guest is intermolecular forms firm intermolecular force by hydrophobic binding, it is suppressed that the distillation of iodine.
Differential scanning test result
In order to analyze the existence of iodine in clathrate further, as a example by iodine/TA-beta-CD inclusion, respectively iodine, TA-β-CD, iodine/TA-β-CD mixture and iodine/TA-beta-CD inclusion are carried out differential scanning test, result is shown in Fig. 2, contrast pure iodine and TA-β-CD, find out that its iodine/TA-β-CD mixture occurs the endothermic peak of iodine at 113.5 DEG C, the endothermic peak of cyclodextrin occurs at 185 DEG C；And iodine and the cyclodextrin endothermic peak at original place all disappear in iodine/TA-beta-CD inclusion, at 217.6 DEG C, new endothermic peak occurs.This result again shows that, the not simple physical mixed of iodine and cyclodextrin in clathrate, but iodine is embedded in the hole of cyclodextrin with molecularity, defines the molecular clathrate of novel crystal forms structure, thus occurs in that new differential scanning endothermic peak.
Sterilizing experimental result
List of references (Bears letter swallow etc., the preparation of cross linked starch iodine and to research [J] .1999 of killing bacteria effect in water, 16,1-6.) as a example by iodine/TA-beta-CD inclusion, determine the fungistatic effect of iodine/TA-beta-CD inclusion, result is as shown in table 1.Be respectively the laboratory sample of mol ratio 1:2,1:1,1:0.5 by the ratio selecting iodine and cyclodextrin, result draws, when the mol ratio of iodine Yu cyclodextrin is that 1:1 i.e. can reach effective fungistatic effect.
The fungistatic effect of table 1 iodine/TA-beta-CD inclusion
Note: the assay method of content of iodine with reference to (Yang Xiqin etc., the preparation of soluble starch crosslinked microsphere and character investigate [J].
China's journal of Practical Pharmacy, 2009,7 (3): 161-170).The bacteriostasis time is 20min.
Adsorption experimental results
Under room temperature, in air detection bag, enclose 3L air, bag is put into 5g test sample, compare test TA-β-CD, iodine/TA-beta-CD inclusion adsorption effect to harmful gas respectively with blank.The concentration changes with time of residual harmful gas formaldehyde and toluene is as shown in Figure 3,4.TA-β-CD, iodine/TA-beta-CD inclusion have adsorption effect compared with blank, but, iodine/TA-beta-CD inclusion is significantly better than TA-β-CD, its reason is, though TA-β-CD itself can adsorb harmful gas by physisorption, but in iodine/TA-beta-CD inclusion in addition to TA-β-CD, inclusion iodine molecule also has Oxidation, the collaborative adsorption enhancing TA-β-CD, adsorption effect effect is obvious.Additionally, Fig. 5 can be seen that ratio is 1:0.5, the iodine of 1:1,1:2/TA-beta-CD inclusion and blank sample relatively all have preferable adsorption effect to harmful gas.Equally, the most other kinds of hydrophobic cyclodextrin such as 2,6 diethyl beta-schardinger dextrin-s, also have and have and 2, the adsorption effect that 3,6 triacetyl beta-schardinger dextrin-s are identical.
Drawn by above experimental result and the method have the benefit that:
1, iodine/hydrophobic cyclodextrin clathrate that the present invention provides belongs to natural component antibiosis and sterilization agent, has broad spectrum antibacterial, can kill rapidly the microorganisms such as antibacterial, virus, yeast, mycete, and will not produce drug resistance；
2, iodine/hydrophobic cyclodextrin clathrate is antibiosis and sterilization agent free from extraneous odour, can adsorb harmful gas, has the effect eliminating abnormal flavour；
3, iodine/hydrophobic cyclodextrin clathrate can be used as powder body or liquid disinfectant uses, and safety is good, long action time；
4, iodine/hydrophobic cyclodextrin clathrate non-corrosiveness, will not cause damage to container when therefore using；
5, the invention provides a kind of temperature control inclusion technique and prepare iodine/hydrophobic cyclodextrin clathrate；
6, the present invention does not use organic solvent solubilizing hydrophobic cyclodextrin in the preparation process of iodine/hydrophobic cyclodextrin clathrate, and, make iodine distil and cyclodextrin inclusion compound by Autonomous Control temperature, therefore remain without solvent, environmentally safe.And technical process simple operations is convenient；
7, inclusion technique of the present invention especially suitable hydrophobicity inclusion carrier and have distillation character object.
Accompanying drawing explanation
Fig. 1 thermal gravimetric analysis curve.
Wherein (a) iodine/TA-beta-CD inclusion；(b) iodine/TA-β-CD mixture.
Fig. 2 differential scanning figure.
Wherein (a) iodine；(b)TA-β-CD；(c) iodine/TA-β-CD mixture；(d) iodine/TA-beta-CD inclusion.
The adsorption effect of formaldehyde in air is tested by Fig. 3.
Wherein ◆ for blank；■ is TA-β-CD；▲ for iodine/TA-beta-CD inclusion.
Fig. 4 is to the adsorption effect experiment of toluene in air.
Wherein ◆ for blank；■ is TA-β-CD；▲ for iodine/TA-beta-CD inclusion.
The absorption of Fig. 5 different proportion iodine/TA-beta-CD inclusion is harmful to gas effectiveness comparative experiments.
Wherein: (◆) is blank；(, △, zero) is iodine: TA-β-CD is 1:0.5,1:1,1:2 respectively
Fig. 6 variety classes iodine/hydrophobicity beta-CD inclusion adsorption experiment to harmful gas.
Wherein: (◆) is blank；(、、) it is 2,6 diethyl β-CD, 2,3,6 triacetyl β-CD, 2,3,6 3 acyl group β-CD respectively.
Detailed description of the invention
Embodiment 1
Iodine/hydrophobic cyclodextrin clathrate of the present invention, is made up of in molar ratio following raw material, iodine: 2,3,6 triacetyl beta-schardinger dextrin-s (TA-β-CD)=1:2, and TA-β-CD is put into vacuum drying oven, 70 DEG C of vacuum drying 1h；Weighing iodine by above-mentioned mol ratio appropriate with cyclodextrin, vortex mixed 5～10min makes mixture；Weigh mixture 1g and inject 5ml glass ampoule, be filled with N2Gas, sealing；Medicine carrying ampulla is placed in temp controlling heater, design temperature 45～60 DEG C of heating 60～90min；Sample is taken out from ampulla, crosses 200 mesh sieves, obtain solid-state iodine/TA-beta-CD inclusion.
Embodiment 2
Iodine of the present invention/TA-beta-CD inclusion, is made up of in molar ratio following raw material, iodine: TA-β-CD=1:1；
In addition to above-mentioned mol ratio takes various material, other are with embodiment 1.
Embodiment 3
Iodine of the present invention/TA-beta-CD inclusion, is made up of in molar ratio following raw material, iodine: TA-β-CD=1:0.5；
In addition to above-mentioned mol ratio takes various material, other are with embodiment 1.
Embodiment 4
With hydrophobicity 2,6 diethyl beta-cyclodextrin inclusion compound iodine, it is made up of in molar ratio following raw material, iodine: 2,6 diethyl beta-schardinger dextrin-s=1:2；In addition to above-mentioned mol ratio takes various material, other are with embodiment 1.
Embodiment 5
With hydrophobicity 2,3,6 three acyl group β-cdinclusion iodine, it is made up of in molar ratio following raw material, iodine: 2,3,6 three acyl group β-CD=1:2；In addition to above-mentioned mol ratio takes various material, other are with embodiment 1.
Embodiment 6
Iodine of the present invention/TA-beta-CD inclusion, is made up of in molar ratio following raw material, iodine: TA-β-CD=1:2；In addition to above-mentioned mol ratio takes various material, other are with embodiment 1.
Embodiment 7 embodiment and comparative example result of the comparison
Weighing by the iodine in the present invention/TA-β-CD mixture and iodine/each 10mg of TA-beta-CD inclusion respectively, use TG DTA2000 thermogravimetric analyzer, intensification region 25～350 DEG C, programming rate is 5 DEG C/min, the weightless change of test sample.
Embodiment 8
Weigh iodine, TA-β-CD, iodine/TA-β-CD mixture and iodine/TA-beta-CD inclusion respectively each in right amount, use DSC-60 differential scanning instrument, temperature range 25 DEG C ~ 300 DEG C, 10 DEG C of min of ramp-1, N2Environment.
Embodiment 9
3L air is enclosed in air detection bag, iodine/TA-the beta-CD inclusion (ratio is 1:2) of the about 5g present invention it is respectively put in Dai, being passed through a certain amount of tested gas formaldehyde and toluene, the gaseous sample of certain volume is taken out in timing, uses KD-128 detector to detect tested gas concentration.Compare with blank and TA-β-CD with same operation, detect adsorption effect.Result of the test is shown in Fig. 3 and Fig. 4.
Embodiment 10
Enclosing 3L air in air detection bag, (ratio is respectively 1:0.5,1:1 to put into the iodine/TA-beta-CD inclusion of the about 5g present invention in bag, 1:2), being passed through a certain amount of tested gas formaldehyde, the gaseous sample of certain volume is taken out in timing, uses KD-128 detector to detect tested gas concentration.Compare with blank and TA-β-CD with same operation, detect adsorption effect.Result of the test is shown in Fig. 5.
Embodiment 11
3L air is enclosed in air detection bag; (both mol ratios are 1:2 to put into the iodine/hydrophobic cyclodextrin clathrate of the about 5g present invention in Dai; hydrophobic cyclodextrin is respectively 2; 3,6 triacetyl β-CD, 2,6 diethyl β-CD, 2; 3; 6 three acyl group β-CD are passed through a certain amount of tested gas formaldehyde, and the gaseous sample of certain volume is taken out in timing, use KD-128 detector to detect tested gas concentration.Compare with blank and TA-β-CD with same operation, detect adsorption effect.Result is shown in Fig. 6.
Claims (7)
1. iodine/hydrophobic cyclodextrin clathrate application in absorption abnormal flavour and toxic gas, it is characterised in that in described iodine/hydrophobic cyclodextrin clathrate, iodine is 1:0.5～1 with the mol ratio of cyclodextrin, uses sealing temperature controlled technology to prepare.
Apply the most as claimed in claim 1, it is characterised in that described cyclodextrin is for being acylated β-cdderivatives or ethylization β-cdderivatives.
Apply the most as claimed in claim 2, it is characterised in that described acylation β-cdderivatives is selected from 2,3,6 triacetyl β-CD, 2,3,6 three propiono β-CD, 2,3,6 three bytyry β-CD or 2,3,6 three acyl group β-CD；Described ethylization β-cdderivatives is selected from 2,6 diethyl β-CD or 2,3,6 triethyl group β-CD.
Apply the most as claimed in claim 1, it is characterised in that described iodine/hydrophobic cyclodextrin clathrate is prepared via a method which: 1. hydrophobic cyclodextrin is put into vacuum drying oven, vacuum drying；2. weigh appropriate cyclodextrin and iodine, be mixed and made into mixture；3. weigh mixture appropriate implantation glass ampulla, be filled with N2Gas, sealing；4. powder charge ampulla is placed in temp controlling heater, heating；5. sample is taken out from ampulla, sieve, obtain solid iodine/hydrophobic cyclodextrin clathrate.
Apply the most as claimed in claim 4, it is characterised in that step 1. middle vacuum drying temperature is 70 DEG C, and the time is 1h.
Apply the most as claimed in claim 4, it is characterised in that step is 2. middle uses vortex mixed 5～10min.
Apply the most as claimed in claim 4, it is characterised in that step 4. design temperature 45～60 DEG C, the time is 60～90min.
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| CN112759667A (en) * | 2021-01-05 | 2021-05-07 | 淄博千汇生物科技有限公司 | Preparation method of triacetyl-beta-cyclodextrin |
| CN114917267B (en) * | 2022-04-25 | 2023-04-11 | 杭州西子卫生消毒药械有限公司 | Iodine-containing disinfectant for skin and preparation method thereof |
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| JP2006169152A (en) * | 2004-12-15 | 2006-06-29 | Toyo Ink Mfg Co Ltd | Antimicrobial composition, and filter using the same |
| CN102349541A (en) * | 2011-08-10 | 2012-02-15 | 寇志民 | New application of iodine cyclodextrin inclusion compound |
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