CN105288724A - Method for treatment of titanium dioxide nanotubes with curcumin derivative - Google Patents
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Abstract
The invention discloses a method for treatment of titanium dioxide nanotubes with a curcumin derivative. The method includes the steps of: 1) preparing a curcumin derivative; 2) dissolving 0.1-0.6 part by weight of cyclodextrin in 3.5-20 parts by weight of water, stirring the materials evenly, adding 0.5-1.5 parts by weight of titanium dioxide nanotubes, and performing soaking for 20-60min; 3) adding 0.2-1.2 parts by weight of the curcumin derivative, then using 15-30kHz ultrasonic wave to perform treatment for 30-60min; and 4) taking out the titanium dioxide nanotubes and conducting drying. Through the effect of cyclodextrin and the curcumin derivative on titanium dioxide nanotubes, the titanium dioxide nanotubes have good antibacterial and anticancer properties, and the surfaces of the titanium dioxide nanotubes can be beneficial to the growth of bone cells, the complication incidence of titanium dioxide nanotubes in osseointegration operations can be reduced, and safer and more reliable materials can be provided to osseointegration operations.
Description
Technical field
The present invention relates to the technical field of titania nanotube in Integrated implant operation, a kind of method utilizing curcumin derivate process titania nanotube more specifically.
Background technology
To be a class to be joined end to end the macrocyclic compound formed by α-Isosorbide-5-Nitrae glycosidic bond by 6 D-glucopyranose units alpha-cyclodextrin.Its intramolecule is a hydrophobic cavities in " V " font, shows unique molecule distinguishability.Titania nanotube has the effect that can promote that osteoblast generates, and is presenting huge potentiality and advantage as implant application aspect.But the serious problems faced are relevant bacteriological infection problems, result in the failure of a large amount of transplant operation.Recently, researcher is devoted to the antibacterial ability and other abilities that improve titania nanotube.How to obtain the more excellent titania nanotube material of performance and become the research direction that has very big science meaning and application value.We find under study for action, and some curcumin derivates have good antibacterial ability, if can be used for TiO 2 nanotubes modified by the curcumin derivate with special physiological performance, are expected to obtain the more excellent titania nanotube material of performance.But the water solublity of curcumin derivate is poor, if curcumin derivate is directly introduced titania nanotube surface, need to use more organic solvent, environment is produced and pollutes, and dissolvent residual may be had on titania nanotube, danger is produced to patient.Cyclodextrin has outer hydrophilic, interior hydrophobic feature, curcumin derivate and cyclodextrin is combined, improves its water solublity, can solve this pollution problem.
Summary of the invention
An object of the present invention is to solve at least the problems referred to above and/or defect, and the advantage will illustrated at least is below provided.
A further object of the invention is just to provide a kind of alpha-cyclodextrin that utilizes and the curcumin derivate of poorly water-soluble is introduced the method that antibacterial action is improved on titania nanotube surface, titania nanotube is made not only to have good antibacterial and anti-cancer properties, and make the surface of titania nanotube be beneficial to the growth of osteocyte, reduce the sickness rate of titania nanotube at Integrated implant Intra operative complica-tions, the material of safety and reliability is provided to Integrated implant operation.
In order to realize, according to these objects of the present invention and other advantages, providing a kind of method utilizing curcumin derivate process titania nanotube, comprise the following steps:
1) hydroxy benzaldehyde 2-5 weight portion is dissolved in the ethyl acetate of 5-10 weight portion, add 4-nitrobenzyl chlorine 1-3 weight portion, control 60-80 DEG C, stir 2-3h, obtain the compound with formula (1), be (4-nitro benzyloxy) benzaldehyde;
2) will be dissolved in the ethyl acetate of 2-8 weight portion to (4-nitro benzyloxy) benzaldehyde 1-4 weight portion and butyl borate 1-4 weight portion, the solution that acetylacetone,2,4-pentanedione 0.2-1 weight portion mixes with boron oxide 0.1-0.8 weight portion is added after stirring 3-7min under room temperature, n-butylamine 0.2-1 weight portion is added after continuing stirring at normal temperature 20-30min, continue to stir 3-5h, then stop stirring rear standing 12-18h, then add the hydrochloric acid 5-10 weight portion that concentration is 0.4mol/L, control 50-65 DEG C is stirred 0.5-1.5h; Then stratification, isolate organic facies, aqueous layer with ethyl acetate is extracted 2-4 time, ethyl acetate layer and organic facies are merged, pressure reducing and steaming solvent, then recrystallization obtains the curcumin derivate with formula (2), be 1, two (to (4-nitro benzyloxy) phenyl)-1,6-heptadiene-3, the 5-diketone of 7-;
3) cyclodextrin 0.1-0.6 weight portion is dissolved in the water of 3.5-20 weight portion, stirs, then add titania nanotube 0.5-1.5 weight portion, soak 20-60min;
4) add curcumin derivate 0.2-1.2 weight portion, then use 15-30kHz ultrasound wave 30-60min;
5) titania nanotube is taken out dry.
Preferably, in described step 4) add curcumin derivate after carry out the centrifugal 5-10min of 5000rpm, then ultrasonic Treatment.
Preferably, step 5) described in drying be infrared drying.
Preferably, step 3) in, described cyclodextrin is alpha-cyclodextrin, and the temperature of described water is 50 DEG C.
Preferably, the caliber of described titania nanotube is 5-10nm, and pipe range is 50-80nm.
Preferably, described baking temperature is 100-120 DEG C, dry 22-24h.
The present invention at least comprises following beneficial effect:
1. alpha-cyclodextrin raw material of the present invention is easy to get, and intramolecule is a hydrophobic cavities in " V " font, and cavity heights is 0.79nm, and diameter is 0.47nm, is applicable to holding curcumin derivate micromolecule and enters.
2. the preparation method of curcumin derivate is simple, and the curcumin derivate obtained shows good antibacterial ability and anti-cancer ability.
3. method of the present invention can make alpha-cyclodextrin enter and be incorporated in titania nanotube; Make water-fast curcumin derivate dispersed by ultrasonic and enter the alpha-cyclodextrin hydrophobic cavities in titania nanotube.The antibacterial effect persistent period of curcumin derivate of the present invention in this individual system is 2.3 times of independent curcumin derivate system, and antibacterial effect is more lasting.This processing method is not only simple, and the solvent used is water, green, environmental protection.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in further detail, can implement according to this with reference to description word to make those skilled in the art.
Embodiment 1
This programme utilizes the method for curcumin derivate process titania nanotube, comprises the following steps:
1) hydroxy benzaldehyde 3 weight portion is dissolved in the ethyl acetate of 7 weight portions, adds 4-nitrobenzyl chlorine 1 weight portion, control 70 DEG C, stir 2h, obtain the compound with formula (1), be (4-nitro benzyloxy) benzaldehyde;
2) will be dissolved in the ethyl acetate of 3 weight portions to (4-nitro benzyloxy) benzaldehyde 2 weight portion and butyl borate 2 weight portion, the solution that acetylacetone,2,4-pentanedione 0.5 weight portion mixes with boron oxide 0.5 weight portion is added after stirring 5min under room temperature, n-butylamine 0.5 weight portion is added after continuing stirring at normal temperature 25min, continue to stir 4h, then stop stirring rear standing 12h, then add hydrochloric acid 6 weight portion that concentration is 0.4mol/L, control 55 DEG C and stir 1h; Then stratification, isolate organic facies, aqueous layer with ethyl acetate is extracted 3 times, ethyl acetate layer and organic facies are merged, pressure reducing and steaming solvent, then recrystallization obtains the curcumin derivate with formula (2), be 1, two (to (4-nitro benzyloxy) phenyl)-1,6-heptadiene-3, the 5-diketone of 7-;
3) cyclodextrin 0.5 weight portion is dissolved in the water of 10 weight portions, stirs, then add titania nanotube 1 weight portion, soak 30min;
4) add curcumin derivate 1 weight portion, then use 20kHz ultrasound wave 40min;
5) titania nanotube is taken out, dry.
Embodiment 2
This programme utilizes the method for curcumin derivate process titania nanotube, comprises the following steps:
1) hydroxy benzaldehyde 2 weight portion is dissolved in the ethyl acetate of 5 weight portions, adds 4-nitrobenzyl chlorine 1 weight portion, control 60 DEG C, stir 2h, obtain the compound with formula (1), be (4-nitro benzyloxy) benzaldehyde;
2) will be dissolved in the ethyl acetate of 2 weight portions to (4-nitro benzyloxy) benzaldehyde 1 weight portion and butyl borate 1 weight portion, the solution that acetylacetone,2,4-pentanedione 0.2 weight portion mixes with boron oxide 0.1 weight portion is added after stirring 3min under room temperature, n-butylamine 0.2 weight portion is added after continuing stirring at normal temperature 20min, continue to stir 3h, then stop stirring rear standing 12h, then add hydrochloric acid 5 weight portion that concentration is 0.4mol/L, control 50 DEG C and stir 0.5h; Then stratification, isolate organic facies, aqueous layer with ethyl acetate is extracted 2 times, ethyl acetate layer and organic facies are merged, pressure reducing and steaming solvent, then recrystallization obtains the curcumin derivate with formula (2), be 1, two (to (4-nitro benzyloxy) phenyl)-1,6-heptadiene-3, the 5-diketone of 7-;
3) be dissolved in for alpha-cyclodextrin 0.1 weight portion in 50 DEG C of water of 3.5 weight portions, stir, then adding caliber is 5nm, and pipe range is titania nanotube 0.5 weight portion of 50nm, soaks 20min;
4) add curcumin derivate 0.2 weight portion, then carry out the centrifugal 5min of 5000rpm, then use 15kHz ultrasound wave 30min;
5) take out titania nanotube, infrared drying titania nanotube, temperature controls 100 DEG C, dry 22h.
Embodiment 3
This programme utilizes the method for curcumin derivate process titania nanotube, comprises the following steps:
1) hydroxy benzaldehyde 5 weight portion is dissolved in the ethyl acetate of 10 weight portions, adds 4-nitrobenzyl chlorine 3 weight portion, control 80 DEG C, stir 3h, obtain the compound with formula (1), be (4-nitro benzyloxy) benzaldehyde;
2) will be dissolved in the ethyl acetate of 8 weight portions to (4-nitro benzyloxy) benzaldehyde 4 weight portion and butyl borate 4 weight portion, the solution that acetylacetone,2,4-pentanedione 1 weight portion mixes with boron oxide 0.8 weight portion is added after stirring 7min under room temperature, n-butylamine 1 weight portion is added after continuing stirring at normal temperature 30min, continue to stir 5h, then stop stirring rear standing 18h, then add hydrochloric acid 10 weight portion that concentration is 0.4mol/L, control 65 DEG C and stir 1.5h; Then stratification, isolate organic facies, aqueous layer with ethyl acetate is extracted 4 times, ethyl acetate layer and organic facies are merged, pressure reducing and steaming solvent, then recrystallization obtains the curcumin derivate with formula (2), be 1, two (to (4-nitro benzyloxy) phenyl)-1,6-heptadiene-3, the 5-diketone of 7-;
3) be dissolved in for alpha-cyclodextrin 0.6 weight portion in 50 DEG C of water of 20 weight portions, stir, then adding caliber is 10nm, and pipe range is titania nanotube 1.5 weight portion of 80nm, soaks 60min;
4) add curcumin derivate 1.2 weight portion, then carry out the centrifugal 10min of 5000rpm, then use 30kHz ultrasound wave 60min;
5) take out titania nanotube, infrared drying titania nanotube, temperature controls 120 DEG C, dry 24h.
Embodiment 4
This programme utilizes the method for curcumin derivate process titania nanotube, comprises the following steps:
1) hydroxy benzaldehyde 4 weight portion is dissolved in the ethyl acetate of 8 weight portions, adds 4-nitrobenzyl chlorine 2 weight portion, control 75 DEG C, stir 3h, obtain the compound with formula (1), be (4-nitro benzyloxy) benzaldehyde;
2) will be dissolved in the ethyl acetate of 5 weight portions to (4-nitro benzyloxy) benzaldehyde 2 weight portion and butyl borate 3 weight portion, the solution that acetylacetone,2,4-pentanedione 0.8 weight portion mixes with boron oxide 0.4 weight portion is added after stirring 6min under room temperature, n-butylamine 0.6 weight portion is added after continuing stirring at normal temperature 25min, continue to stir 4h, then stop stirring rear standing 15h, then add hydrochloric acid 8 weight portion that concentration is 0.4mol/L, control 60 DEG C and stir 1h; Then stratification, isolate organic facies, aqueous layer with ethyl acetate is extracted 3 times, ethyl acetate layer and organic facies are merged, pressure reducing and steaming solvent, then recrystallization obtains the curcumin derivate with formula (2), be 1, two (to (4-nitro benzyloxy) phenyl)-1,6-heptadiene-3, the 5-diketone of 7-;
3) be dissolved in for alpha-cyclodextrin 0.3 weight portion in 50 DEG C of water of 15 weight portions, stir, then adding caliber is 6nm, and pipe range is titania nanotube 1 weight portion of 60nm, soaks 40min;
4) add curcumin derivate 1 weight portion, then carry out the centrifugal 6min of 5000rpm, then use 25kHz ultrasound wave 40min;
5) take out titania nanotube, infrared drying titania nanotube, temperature controls 110 DEG C, dry 23h.
Wherein, the chemical name of the curcumin derivate of embodiment 1-4 is two (to (4-nitro benzyloxy) phenyl)-1,6-heptadiene-3, the 5-diketone of 1,7-;
Its physicochemical property is: orange crystal, is soluble in organic solvent, and its hydrogen nuclear magnetic resonance modal data is 1HNMR (CDCl
3) δ: 2.52 (s, 2H, CH2), 4.11 ~ 4.31 (m, 4H, OCH2Ph), 6.73 (d, 4H, J=7.8Hz ,=CH), 7.12 ~ 7.69 (m, 16H, Ar-H).
Pharmaceutically active and the application thereof of the titania nanotube that this method obtains is further illustrated below by pharmacodynamic experiment.
Experiment one: antibacterial ability is tested:
In 6 sterilizing test tubes, add 1mL concentration is 10
6the bacterium liquid of cfu/ml, then adds product, ordinary titanium dioxide nanotube, conventional curcumin derivate that 1mg embodiment 1-4 obtains respectively, cultivates 24h for 37 DEG C.Cultivate after time point, culture medium collects with doubling dilution, and extension rate is 10 times and spread plate method detection viable count.Result of the test shows: the product obtained by the present invention is to staphylococcus aureus (ATCC6538), colon bacillus (ATCC25922), candida albicans (ATCC10231), Bacillus subtilis endophyticus (ATCC9372) all has very strong bactericidal properties, wherein, the sterilizing rate adding embodiment 1 reaches more than 99.92%, the sterilizing rate adding embodiment 2 reaches more than 99.95%, the sterilizing rate adding embodiment 3 reaches more than 99.991%, the sterilizing rate adding embodiment 4 reaches more than 99.99%, and the sterilizing rate adding ordinary titanium dioxide nanotube only has about 15%, the sterilizing rate adding conventional curcumin derivate is about 60%.
Experiment two: anti tumor activity in vitro is tested
Adopt MTT method, carry out vitro cytotoxicity mensuration.The product obtained by embodiment 1-4, ordinary titanium dioxide nanotube, conventional curcumin derivate and osteocarcinoma U2-OS cell strain and nasopharyngeal carcinoma CNE-1 cell strain carry out the IC of comparative determination respectively 72 hours action time
50(umol/mL) value, comparing result is as shown in table 1.IC
50refer to the medium effective concentration to tumor cell line.
Table 1:
From experiment one and the result of testing two, the titania nanotube obtained through method of the present invention has good antibacterial and anti-cancer properties; And the titania nanotube antibacterial effect of routine is poor, and the IC50 value > 100 of its effect, show that it does not have active anticancer; The antibacterial anti-cancer ability of conventional curcumin derivate is not good, and be difficult to directly play a role for a long time in the whole operation of bone, and the antibacterial effect persistent period of product of the present invention is more than 2.3 times of independent curcumin derivate system, and antibacterial anticancer effect is also better.Therefore, the present invention is that the new orthopaedics with premium properties of research and development and dental implant thing material provide new thinking.
Although embodiment of the present invention are open as above, but it is not restricted to listed in description and embodiment utilization, it can be applied to various applicable the field of the invention completely, for those skilled in the art, can easily realize other amendment, therefore do not deviating under the general concept that claim and equivalency range limit, the present invention is not limited to specific details and illustrates here and the embodiment described.
Claims (6)
1. utilize a method for curcumin derivate process titania nanotube, it is characterized in that, comprise step as follows:
1) hydroxy benzaldehyde 2-5 weight portion is dissolved in the ethyl acetate of 5-10 weight portion, add 4-nitrobenzyl chlorine 1-3 weight portion, control 60-80 DEG C, stir 2-3h, obtain the compound with formula (1), be (4-nitro benzyloxy) benzaldehyde;
2) will be dissolved in the ethyl acetate of 2-8 weight portion to (4-nitro benzyloxy) benzaldehyde 1-4 weight portion and butyl borate 1-4 weight portion, the solution that acetylacetone,2,4-pentanedione 0.2-1 weight portion mixes with boron oxide 0.1-0.8 weight portion is added after stirring 3-7min under room temperature, n-butylamine 0.2-1 weight portion is added after continuing stirring at normal temperature 20-30min, continue to stir 3-5h, then stop stirring rear standing 12-18h, then add the hydrochloric acid 5-10 weight portion that concentration is 0.4mol/L, control 50-65 DEG C is stirred 0.5-1.5h; Then stratification, isolate organic facies, aqueous layer with ethyl acetate is extracted 2-4 time, ethyl acetate layer and organic facies are merged, pressure reducing and steaming solvent, then recrystallization obtains the curcumin derivate with formula (2), be 1, two (to (4-nitro benzyloxy) phenyl)-1,6-heptadiene-3, the 5-diketone of 7-;
3) cyclodextrin 0.1-0.6 weight portion is dissolved in the water of 3.5-20 weight portion, stirs, then add titania nanotube 0.5-1.5 weight portion, soak 20-60min;
4) add curcumin derivate 0.2-1.2 weight portion, then use 15-30kHz ultrasound wave 30-60min;
5) titania nanotube is taken out dry.
2. the method utilizing curcumin derivate process titania nanotube according to claim 1, is characterized in that, in described step 4) add curcumin derivate after carry out the centrifugal 5-10min of 5000rpm, then ultrasonic Treatment.
3. the method utilizing curcumin derivate process titania nanotube according to claim 1, is characterized in that, step 5) described in drying be infrared drying.
4. the method utilizing curcumin derivate process titania nanotube according to any one of claim 1-3, is characterized in that, step 3) in, described cyclodextrin is alpha-cyclodextrin, and the temperature of described water is 50 DEG C.
5. the method utilizing curcumin derivate process titania nanotube according to claim 4, is characterized in that, the caliber of described titania nanotube is 5-10nm, and pipe range is 50-80nm.
6. the method utilizing curcumin derivate process titania nanotube according to claim 5, is characterized in that, described baking temperature is 100-120 DEG C, dry 22-24h.
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Cited By (3)
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| CN106115680A (en) * | 2016-07-05 | 2016-11-16 | 安徽中医药大学 | A kind of curcumin derivate modifies method and the product thereof of graphene oxide |
| CN106139241A (en) * | 2016-07-27 | 2016-11-23 | 中国人民解放军第四军医大学 | Curcumin is the application in medical titanium alloy implants under diabetic conditions |
| CN114031635A (en) * | 2021-12-14 | 2022-02-11 | 洛阳师范学院 | Difluoroborocurcumin derivative and preparation method and application thereof |
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| CN102911022A (en) * | 2012-10-25 | 2013-02-06 | 山东鲁诺动物药业有限公司 | Method for artificially synthesizing natural curcumin compound |
| CN104826159A (en) * | 2015-04-24 | 2015-08-12 | 湖北大学 | Medical titanium metal implant material and preparation method thereof |
| CN104873983A (en) * | 2015-05-25 | 2015-09-02 | 福建省力菲克药业有限公司 | Curcumin cyclodextrin clathrate compound and preparation method thereof |
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| EP1604697A1 (en) * | 2004-06-09 | 2005-12-14 | J.A.C.C. GmbH | Implantable device |
| CN102719824A (en) * | 2012-06-12 | 2012-10-10 | 天津大学 | Dopamine-nanosilver composite coating and preparation method thereof |
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| CN106139241B (en) * | 2016-07-27 | 2019-05-28 | 中国人民解放军第四军医大学 | Application of the curcumin under diabetic conditions in medical titanium alloy implants |
| CN114031635A (en) * | 2021-12-14 | 2022-02-11 | 洛阳师范学院 | Difluoroborocurcumin derivative and preparation method and application thereof |
| CN114031635B (en) * | 2021-12-14 | 2024-02-13 | 洛阳师范学院 | Difluoroborocurcumin derivative and preparation method and application thereof |
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