CN114272152A - Photosensitizer for inhibiting tooth biomembrane and whitening teeth by combining photodynamic method - Google Patents
Photosensitizer for inhibiting tooth biomembrane and whitening teeth by combining photodynamic method Download PDFInfo
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- CN114272152A CN114272152A CN202111504547.1A CN202111504547A CN114272152A CN 114272152 A CN114272152 A CN 114272152A CN 202111504547 A CN202111504547 A CN 202111504547A CN 114272152 A CN114272152 A CN 114272152A
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- 239000003504 photosensitizing agent Substances 0.000 title abstract description 29
- 230000002087 whitening effect Effects 0.000 title abstract description 21
- 238000000034 method Methods 0.000 title abstract description 11
- 230000002401 inhibitory effect Effects 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
- 238000005286 illumination Methods 0.000 description 21
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
- 241000194019 Streptococcus mutans Species 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 241000894006 Bacteria Species 0.000 description 9
- 238000011534 incubation Methods 0.000 description 8
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 5
- 229960003260 chlorhexidine Drugs 0.000 description 5
- 239000008363 phosphate buffer Substances 0.000 description 5
- 239000003642 reactive oxygen metabolite Substances 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 208000002925 dental caries Diseases 0.000 description 4
- 210000003298 dental enamel Anatomy 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 210000004379 membrane Anatomy 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 208000002064 Dental Plaque Diseases 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 230000032770 biofilm formation Effects 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000036344 tooth staining Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 230000035899 viability Effects 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 206010016818 Fluorosis Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 208000004509 Tooth Discoloration Diseases 0.000 description 1
- 206010044032 Tooth discolouration Diseases 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 229940078916 carbamide peroxide Drugs 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 208000004042 dental fluorosis Diseases 0.000 description 1
- 201000002170 dentin sensitivity Diseases 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000010794 food waste Substances 0.000 description 1
- 208000007565 gingivitis Diseases 0.000 description 1
- -1 hexafluorophosphate Chemical compound 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 239000013588 oral product Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000001706 oxygenating effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000036367 tooth discoloration Effects 0.000 description 1
- 230000036347 tooth sensitivity Effects 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Abstract
Description
Technical Field
The invention belongs to the technical field of tooth care, and particularly relates to a photosensitizer for inhibiting a tooth biofilm and whitening teeth by combining a photodynamic method, which is used for inhibiting the tooth biofilm and whitening teeth.
Background
Microorganisms such as streptococcus mutans and the like can form a biofilm on teeth, the tightly packed biofilm is dental plaque, and the winkle bacteria in the dental plaque are decomposed by food residues to generate acidic substances which can act on the teeth to demineralize enamel and collapse organic matters, so that the dental caries can be developed finally. Furthermore, bacteria of the biofilm can also cause gingivitis. Inhibiting the formation of biofilm on teeth, and preventing dental caries. The oral care product contains fluorine and chlorhexidine to inhibit the growth of streptococcus mutans.
In addition, more and more people have improved their own image by tooth whitening. In products for whitening teeth (such as tooth whitening patches), hydrogen peroxide and carbamide peroxide are generally used to oxidize colored substances on teeth so as to achieve the whitening effect.
Fluorine and chlorhexidine in oral care products, but both compounds have been reported in the literature to be unable to alter the composition and toxicity of biofilm (1, 2), even with the frequent use of fluorine-containing oral products, caries can still develop when sugar is consumed more than six times per day (3); furthermore, high concentrations of fluorine can cause fluorosis, skeletal embrittlement, and developmental neurotoxicity (4). The toxicity and resulting immune response of chlorhexidine to humans has also been reported (5). In addition, both compounds can cause tooth discoloration (6). Therefore, the development of a novel biofilm elimination method is still strongly urgent.
Tooth whitening products typically contain more than 10% hydrogen peroxide. Such high concentrations of hydrogen peroxide, which are similar to the oxidizing power of household disinfectants, can cause burning gums and damage mucosal tissue (7) and produce tooth sensitivity (8). In addition, prolonged exposure to such high concentrations of hydrogen peroxide can result in changes in enamel morphology, decrease enamel hardness (9), and increase tooth surface porosity. These cavities in the teeth can make the teeth more susceptible to discoloration and to adsorption of some carcinogenic microorganisms (10).
There are also currently some methods (11) for tooth whitening and biofilm removal using photodynamic methods, but these methods have been reported to require high concentrations of photosensitizing agents (above 50 micromolar) and long periods of violet light irradiation (6 hours) to achieve good results, and are not suitable for practical applications.
Reference documents:
1.Thurnheer T,Belibasakis GN.Effect of sodium fluoride on oral biofilm microbiota and enamel 556demineralization.Arch Oral Biol.2018;89:77-83.
2Niu Y,WangK,Zheng S,Wang Y,Ren Q,Li H,etal.Antibacterial Effect of Caffeic Acid Phenethyl Ester on Cariogenic Bacteria and Streptococcus mutans Biofilms.Antimicrob Agents Chemother.2020;64(9).
3.Philip N,Suneja B,Walsh LJ.Ecological Approaches to Dental Caries Prevention:Paradigm Shift or ShibbolethCaries Res.2018;52(1-2):153-65.
4.Duangthip D,Fung MHT,WongMCM,Chu CH,Lo ECM.Adverse Effects of Silver Diamine Fluoride TreatmentamongPreschool Children.J Dent Res.2018;97(4):395-401.
5.Pemberton MN,Gibson J.Chlorhexidine and hypersensitivity reactions in dentistry.Br Dent J.2012;213(11):547-50.
6van Maanen-Schakel NW,Slot DE,Bakker EW,Van der Weijden GA.The effect of an oxygenating agenton chlorhexidine-induced extrinsic tooth staining:a systematic review.IntJ Dent Hyg.2012;10(3):198-208.
7.Pretty IA,Ellwood RP,Brunton PA,Aminian A.Vital tooth bleaching in dental practice:1.Professional bleaching.Dent Update.2006;33(5):288-90,93-6,99-300passim.
8.Gokay O,Tuncbilek M,Ertan R.Penetration of the pulp chamber by carbamide peroxide bleaching agents on teeth restored with a composite resin.J Oral Rehabil.2000;27(5):428-31.
9.Hegedus C,Bistey T,Flora-Nagy E,Keszthelyi G,Jenei A.An atomic force microscopy study on the effect of bleaching agents on enamel surface.J Dent.1999;27(7):509-15.
10.Wongpraparatana I,Matangkasombut O,Thanyasrisung P,Panich M.Effect of Vital Tooth Bleaching on Surface Roughness and Streptococcal Biofilm Formation on Direct Tooth-Colored Restorative Materials.Oper Dent.2018;43(1):51-9.
11.Zhang H,Zhu Y,Li Y,Qi X,Yang J,Qi H,et al.A Bifunctional Zwitterion-Modified Porphyrin for 582Photodynamic Nondestructive Tooth Whitening and Biofilm Eradication.Advanced Functional 583Materials.2021:2104799.
disclosure of Invention
In view of the problems of the prior art, the present invention aims to develop a method capable of eliminating biofilm on teeth, avoiding dental caries, and whitening teeth simultaneously. The photosensitizer adopted by the invention can achieve the effects of clearing a biological film and whitening teeth in a short time irradiation at a lower concentration.
The invention is realized by the following technical scheme, comprising the following steps: use of a compound having a chromophore of formula for the preparation of a composition for photodynamic tooth biofilm removal and tooth whitening.
Wherein A is1,A2,A3,A4,B1,B2,B3,B4,B5,B6The organic chromophore groups can be the same or different and are independently selected from hydrogen, alkyl chains (the length of the alkyl chain can be from 1 to 20, and one or more unsaturated double bonds can be arranged on the alkyl chain), polyethylene glycol (preferably with the molecular weight of 200-10000), and the groups can be directly connected or indirectly connected to the chromophore compound, and can also be connected to the chromophore through any common mode such as amido bonds, ester bonds, ether bonds, thioether bonds, triazole rings and the like.
As a preferred technical scheme of the invention, the corresponding anion on the chromophore can be any anion (such as fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate and the like), and the modified anion does not influence the protection content of the invention.
In a preferred embodiment of the present invention, these compounds are capable of sensitizing the production of reactive oxygen species (reactive oxygen species) in the presence of light and/or oxygen.
These compounds are capable of binding to bacterial surfaces (including gram-negative and gram-positive bacteria) by electrostatic interaction, hydrophobic interaction, or by specific recognition of one or more of these interactions.
These compounds are mixed with bacteria or fungi, with or without washing away excess photosensitizers, and under light conditions they are able to generate reactive oxygen species to kill germs in solution.
The compounds can inhibit the growth of bacteria and the formation of a biofilm by incubating with the bacteria and illuminating.
These compounds inhibit the growth of bacteria by incubating with the bacteria and illuminating them, enabling the biofilm to be formed.
These compounds are capable of generating reactive oxygen species in the presence of light to provide stain removal from teeth.
The compounds and tooth whitening patches and other means for whitening teeth by adopting hydrogen peroxide do not generate holes on enamel, and the whitening effect is better.
As a preferred embodiment of the invention, the compound is present in the composition at a concentration ranging from 0.01 micromolar to 10 millimolar. Preferably from 0.1 micromoles to 1 millimole. More preferably from 1 micromole to 500 micromoles.
In principle, although there is no limitation on the wavelength and intensity of the light, a preferred embodiment of the present invention requires a shorter time for the light to be irradiated as the intensity of the light is higher.
As a preferred technical scheme of the invention, the compound is a compound with the following formula:
the photosensitizer adopted by the invention has an amphiphilic structure and positive charges, and researches show that molecules with the structure can interact with bacteria. These photosensitizers are capable of activating the production of reactive oxygen species with high efficiency, which can disrupt the molecular structure of bacteria leading to bacterial death and failure to continue to produce biofilms. For the formed biological membrane, on one hand, the molecule can be combined with the biological membrane, and active oxygen substances are generated under illumination, and the active oxygen substances can destroy extracellular links between the biological membranes, so that the structure of the biological membrane is destroyed and disintegrated. On the other hand, the generated active oxygen substances can also effectively oxidize the pigment substances adsorbed on the teeth. So as to achieve the effect of whitening teeth. Compared with a method for whitening teeth by using hydrogen peroxide, the amphiphilic photosensitizing agent adopted in the invention can interact with tooth staining substances, locally generate high-activity active oxygen substances, and play a role of a surfactant to a certain extent, so that the shedding of the staining substances is promoted, and the teeth are whitened.
Compared with the traditional photosensitizer with a large rigid bottle, the photosensitizer adopted in the invention has the advantages that the generation of active oxygen substances can be efficiently activated in an aggregation state, high concentration and adsorption to a target. In addition, the photosensitizer has relatively long absorption wavelength and can promote the generation of active oxygen substances by white light illumination.
Drawings
FIG. 1 viability of Streptococcus mutans in solution incubated with a photosensitizer under both light and non-light conditions with white light illumination of 36mW/cm2And the illumination time is 10 minutes.
FIG. 2-biofilm formation after light and non-light irradiation of Streptococcus mutans incubated with a photosensitizer with white light illumination of 36mW/cm2And the illumination time is 10 minutes.
FIG. 3 survival of Streptococcus mutans after incubation with a photosensitizer in the absence of light. The concentration of the photosensitizer is 20 micromoles, and the white light illumination is 36mW/cm2And the illumination time is 10 minutes.
FIG. 4. clinical teeth incubated with photosensitizing agent at 20 picomolar with white light illumination of 36mW/cm2Tooth color changes with time of illumination.
FIG. 5 clinical teeth incubated with photosensitizing agent at 20 micromolar with white light illumination of 36mW/cm2And the tooth surface morphology is irradiated by light for 60 minutes and the tooth surface morphology treated by hydrogen peroxide.
Detailed Description
The technical solutions of the present invention are further described below by referring to specific embodiments and drawings, but the present invention is not limited thereto.
Example 1
Compounds of the formula are obtained by literature methods (Wu MY, et al. A Membrane-Targeting Photosenizer with Aggregation-Induced emulsions Characteristics for high alcohol impact Photodynamics Combat of Human Coronavir. Small.2021 Jul; 17(30): e2101770.doi:10.1002/smll.202101770.Epub 2021 Jun 30.PMID: 34190409; PMC ID: PMC 8420407.):
example 2
The photosensitizing agents of example 1 were added at different concentrations (0, 2, 5, 10 μm) to the solution incubated with Streptococcus mutans (10)5CFU mL-1Phosphate buffer, incubation at 37 ℃ for 2 hours), testing the survival rate of the streptococcus mutans under the conditions of illumination and no illumination, and illuminating with white light for 36mW/cm2And the illumination time is 10 minutes.
As shown in FIG. 1, photosensitizers of 2, 5 and 10 μm were found to be effective in inhibiting the survival of Streptococcus mutans in light.
Example 3
The photosensitizing agents of example 1 were added at different concentrations (0, 5, 10 μm) to the solution in which Streptococcus mutans was incubated (OD)600Streptococcus mutans with a value of 1, phosphate buffer, incubation for 15min at 37 ℃), testing for biofilm formation with and without light, white light illumination36mW/cm2And the illumination time is 10 minutes.
As shown in FIG. 2, the photosensitizing agents of 5 μm and 10 μm were found to be effective in inhibiting biofilm formation by Streptococcus mutans under light conditions.
Example 4
The photosensitizing agents of example 1 at various concentrations (0, 20 μm) were added to the incubation solution of Streptococcus mutans that had formed a biofilm (phosphate buffer, incubation at 37 ℃ for 15 minutes), and the viability was tested with and without light, with white light illumination of 36mW/cm2And the illumination time is 10 minutes.
As shown in FIG. 3, 20 μm of the photosensitizer was found to be effective in inhibiting the survival rate of biofilm-forming Streptococcus mutans under light conditions.
Example 5
20 μm of the photosensitizer of example 1 was added to the incubation solution of clinical teeth (phosphate buffer, incubation at 37 ℃ for 15 minutes), and the color of the teeth was measured as a function of the time of illumination, with white light illumination of 36mW/cm2And the illumination time is 60 minutes.
As shown in FIG. 4, the 20 μm photosensitizer can achieve tooth color whitening under light conditions.
Example 6
Clinical teeth were incubated with the photosensitizing agent of example 1 at 20 micromolar (phosphate buffer, incubation for 15 minutes at 37 ℃) with white light illumination of 36mW/cm2And the tooth surface morphology is irradiated by light for 60 minutes and the tooth surface morphology treated by hydrogen peroxide.
As shown in FIG. 5, 20 μm photosensitizers were used to reduce the surface porosity of teeth under light.
The above-mentioned embodiments are intended to illustrate the objects, technical solutions and advantages of the present invention in further detail, and it should be understood that the above-mentioned embodiments are only exemplary embodiments of the present invention and are not intended to limit the present invention, and any modifications, equivalents, improvements and the like made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (9)
1. Use of a compound having a chromophore of the formula:
Wherein A is1,A2,A3,A4,B1,B2,B3,B4,B5,B6The groups can be the same or different and are independently selected from hydrogen, alkyl chains and polyethylene glycol, and the groups can be directly connected or indirectly connected to the chromophore compound.
2. Use according to claim 1, characterized in that: the alkyl chain may be from 1 to 20 in length and may have one or more unsaturated double bonds in the alkyl chain.
3. Use according to claim 1, characterized in that: the polyethylene glycol molecular weight is selected from 200-10000.
4. Use according to claim 1, characterized in that: the indirect linkage refers to linkage to the chromophore via amide linkage, ester linkage, ether linkage, thioether linkage, triazole ring, and the like.
5. Use according to claim 1, characterized in that: the corresponding anion on the chromophore can be any other anion.
7. use according to claim 1, wherein the concentration of the compound in the composition is in the range of 0.01 micromolar to 10 millimolar. Preferably from 0.1 micromoles to 1 millimole. More preferably from 1 micromole to 500 micromoles.
8. Use according to claim 1, characterized in that it is carried out in the presence of oxygen.
9. Use according to claim 1, characterized in that it is carried out under light conditions.
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