CN114272152B - Photosensitizers for tooth biofilm inhibition and tooth whitening by combining photodynamic method - Google Patents
Photosensitizers for tooth biofilm inhibition and tooth whitening by combining photodynamic method Download PDFInfo
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- 230000002087 whitening effect Effects 0.000 title claims abstract description 19
- 239000003504 photosensitizing agent Substances 0.000 title abstract description 30
- 238000000034 method Methods 0.000 title abstract description 10
- 230000005764 inhibitory process Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 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
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- 238000005286 illumination Methods 0.000 description 26
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
- 241000194019 Streptococcus mutans Species 0.000 description 14
- 238000011534 incubation Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 10
- 241000894006 Bacteria Species 0.000 description 7
- 239000003642 reactive oxygen metabolite Substances 0.000 description 6
- 230000004083 survival effect Effects 0.000 description 6
- 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
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 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
- 239000000047 product Substances 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 208000002064 Dental Plaque Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000001179 sorption measurement 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
- 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
- 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
- 239000002202 Polyethylene glycol Substances 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
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940078916 carbamide peroxide Drugs 0.000 description 1
- 230000008859 change Effects 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
- 150000002148 esters Chemical class 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
- 230000003993 interaction 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
- 231100000590 oncogenic Toxicity 0.000 description 1
- 230000002246 oncogenic effect Effects 0.000 description 1
- 239000013588 oral product Substances 0.000 description 1
- 230000001706 oxygenating effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000007430 reference method Methods 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
- 241000894007 species Species 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
- 238000012360 testing method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 230000036367 tooth discoloration Effects 0.000 description 1
- 230000036347 tooth sensitivity Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention belongs to the technical field of tooth care, and particularly relates to a photosensitizing agent for inhibiting tooth biomembrane and whitening teeth by combining a photodynamic method.
Description
Technical Field
The invention belongs to the technical field of tooth care, and particularly relates to a photosensitizing agent for inhibiting tooth biomembrane and whitening teeth by combining a photodynamic method.
Background
Microorganisms such as streptococcus mutans can form biological films on teeth, the closely packed biological films are dental plaques, xu Jun in the dental plaques are decomposed by food residues to generate acidic substances, the acidic substances can act on the teeth to demineralize dental enamel, organic matters collapse, and finally dental caries can be developed. In addition, bacteria of the biofilm can also cause gingivitis. Inhibiting the formation of biofilm by microorganisms on teeth is of great importance in preventing dental caries. The oral care product contains fluorine and chlorhexidine to inhibit the growth of streptococcus mutans.
In addition, more and more people improve their own image through 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 to achieve the whitening effect.
Fluorine and chlorhexidine in oral care products, but both compounds have been reported to not alter the composition and toxicity of biological films (1, 2), even with frequent use of fluorine-containing oral products, caries can still develop when eating sugar six or more times per day (3); in addition, high concentrations of fluorine can cause fluorosis, skeletal embrittlement, and developmental neurotoxicity (4). There are also many reports of chlorhexidine toxicity to humans and immune responses elicited (5). Furthermore, both compounds are capable of causing tooth discoloration (6). Thus, development of a novel biofilm removal method is still highly urgent.
Tooth whitening products typically contain greater than 10% hydrogen peroxide. Such high concentrations of hydrogen peroxide have similar oxidizing power to household disinfectant water, can cause burning gums and damage mucosal tissue (7), and create tooth sensitivity (8). In addition, prolonged exposure to such high concentrations of hydrogen peroxide can result in changes in enamel morphology, reduce enamel hardness (9), and increase cavities in the tooth surface. The cavities on these teeth can make the teeth more prone to discoloration and to adsorption of some oncogenic microorganisms (10).
There are also some photodynamic methods for tooth whitening and biofilm removal (11), but these methods have been reported to require high concentrations of photosensitizers (above 50 micromolar) and long exposure times to violet light (6 hours) to be effective and unsuitable for practical application scenarios.
Reference is made to:
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 has been made in an effort to develop a method capable of removing a biofilm on teeth, avoiding dental caries, and simultaneously whitening teeth by colleagues. The photosensitizing agent adopted by the invention can achieve the effects of clearing biological films and whitening teeth in a low concentration and short-time irradiation.
The invention is realized by the following technical scheme that: use of a chromophore compound having the structure of formula in the preparation of a composition for photodynamic tooth biofilm removal and tooth whitening.
Wherein R1, R2 are independently selected from
Wherein A is 1 ,A 2 ,A 3 ,A 4 ,B 1 ,B 2 ,B 3 ,B 4 ,B 5 ,B 6 The groups may be the same or different and independently selected from hydrogen, alkyl chains (the length of the alkyl chain may be from 1 to 20, and there may be one or more unsaturated double bonds in the alkyl chain), polyethylene glycol (preferably having a molecular weight of 200-10000), which may be directly or indirectly attached to the chromophore compound, or may be attached to the chromophore by any of the usual means such as amide, ester, ether, thioether, triazole rings, etc.
As a preferred embodiment of the present invention, the corresponding anion on the chromophore may be any anion (e.g., fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, etc.), the modification of which does not affect the protection of the present invention.
As a preferred embodiment of the invention, these compounds are capable of sensitizing the production of reactive oxygen species upon illumination and/or in the presence of oxygen (reactive oxygen species).
These compounds are capable of binding to bacterial surfaces (including gram-negative and gram-positive bacteria) by electrostatic interactions, hydrophobic interactions, or a combination of specific recognition of one or more species.
These compounds are mixed with bacteria or fungi, with or without washing off excess photosensitizing agent, and are capable of generating reactive oxygen species under light conditions to kill pathogens in solution.
These compounds can inhibit the growth of bacteria and inhibit the formation of biofilms by Streptococcus mutans and the like by incubation with the bacteria and irradiation with light.
These compounds can inhibit the growth of bacteria by incubation with the bacteria and illumination, enabling biofilms to have formed.
These compounds are capable of generating reactive oxygen species upon illumination to clean stains from teeth.
The compounds and the teeth whitening patches adopt the means of whitening by hydrogen peroxide, and the method can not generate holes on tooth enamel and has better whitening effect.
As a preferred embodiment of the invention, the concentration of said compound in the composition ranges from 0.01 micromolar to 10 millimoles. Preferably 0.1 micromoles to 1 millimole. More preferably 1 to 500. Mu. Mol.
As a preferred embodiment of the invention, the wavelength and intensity of the light are in principle not limited, but in general the higher the intensity the shorter the time required for the light irradiation.
As a preferred technical scheme of the invention, the compound is a compound with the following formula:
the photosensitizers adopted by the invention have amphiphilic structures and have positive charges, and the molecules with the structures are found to be capable of interacting with bacteria through research. These photosensitizers can efficiently activate the production of reactive oxygen species that can destroy bacterial molecular structure leading to bacterial death and failure to continue to produce biofilm. For the already formed biofilm, on the one hand this molecule is able to bind to the biofilm, generating reactive oxygen species under light, which are able to disrupt the extracellular links between the biofilms, causing structural disruption of the biofilm, and disintegration. On the other hand, the generated active oxygen substances can efficiently oxidize the pigment substances adsorbed on the teeth. Achieving the effect of whitening teeth. Compared with the method of oxidizing teeth with hydrogen peroxide, the amphiphilic photosensitizing agent adopted in the invention can interact with tooth staining substances to locally generate high-activity active oxygen substances, plays a role of a surfactant to a certain extent, promotes the shedding of the staining substances and whitens the teeth.
Compared with the traditional photosensitizer with a large rigid bottle, the photosensitizer adopted in the invention has the advantages of capability of generating active oxygen substances in an aggregation state, high concentration and high adsorption on a target, and high efficiency. In addition, the photosensitizer in the invention has a relatively long absorption wavelength, and can promote the generation of active oxygen substances by white light illumination.
Drawings
FIG. 1 survival of Streptococcus mutans in solution incubated with photosensitizers under light and no light conditions, white light illumination at 36mW/cm 2 The illumination time was 10 minutes.
FIG. 2A biological film formed after exposure to light and absence of light of Streptococcus mutans incubated with photosensitizers, 36mW/cm white light 2 The illumination time was 10 minutes.
FIG. 3 survival of biofilm formed by Streptococcus mutans after incubation with photosensitizers under light and no light conditions. Photosensitizers at 20. Mu. Mol, white light illumination at 36mW/cm 2 The illumination time was 10 minutes.
FIG. 4 clinical teeth were incubated with photosensitizers at 20 picomoles with white light illumination at 36mW/cm 2 Changes in tooth color with time of illumination.
FIG. 5 clinical teeth were incubated with photosensitizers at 20. Mu. Mol, with white light illumination at 36mW/cm 2 And illuminating the tooth surface morphology with light for 60 minutes and treating the tooth surface morphology with hydrogen peroxide.
Detailed Description
The technical scheme of the invention is further described below by means of specific embodiments in conjunction with the accompanying drawings, but the invention is not limited thereto.
Example 1
Compounds of the formula are obtained by reference methods (Wu MY, et al A Membrane-Targeting Photosensitizer with Aggregation-Induced Emission Characteristics for Highly Efficient Photodynamic Combat of Human Coronavirues.Small.2021 Jul;17 (30): e2101770.Doi: 10.1002/small.202101770. Epub 2021 Jun 30.PMID:34190409;PMCID:PMC8420407.):
example 2
The photosensitizers of example 1 were added to the Streptococcus mutans incubation solution at various concentrations (0, 2, 5, 10 μm) (10 5 CFU mL -1 Phosphate buffer, incubation at 37 ℃ for 2 hours), testing the survival rate of streptococcus mutans under the conditions of illumination and no illumination, and white light illumination of 36mW/cm 2 The illumination time was 10 minutes.
As shown in FIG. 1, photosensitizers of 2, 5 and 10 μm can effectively inhibit the survival of Streptococcus mutans under the illumination condition.
Example 3
The photosensitizers of example 1 were added at various concentrations (0, 5, 10 μm) to the Streptococcus mutans incubation solution (OD 600 Streptococcus mutans with a value of 1, phosphate buffer, incubation at 37deg.C for 15 min), and formation of biofilm under both light and no light conditions, with white light illumination of 36mW/cm 2 The illumination time was 10 minutes.
As shown in FIG. 2, photosensitizers of 5 and 10 μm can effectively inhibit formation of biological film by Streptococcus mutans under illumination.
Example 4
The photosensitizers of example 1 were added at various concentrations (0, 20 μm) to incubation solutions of Streptococcus mutans (phosphate buffer, incubation at 37 ℃ C. For 15 min) in which biofilm had been formed, and survival was tested under light and no light conditions, with a white light illumination of 36mW/cm 2 The illumination time was 10 minutes.
As shown in FIG. 3, the photosensitizing agent of 20 μm was effective in inhibiting survival of biofilm-forming Streptococcus mutans under light conditions.
Example 5
The photosensitizing agent of example 1, 20 μm, was added to an incubation solution of clinical teeth (phosphate buffer, incubation at 37 ℃ C. For 15 minutes) and the change in tooth color with time was tested for illumination, 36mW/cm white light illumination 2 The illumination time was 60 minutes.
Specific results as shown in fig. 4, tooth color whitening can be achieved by exposing the photosensitizers of 20 μm to light.
Example 6
Clinical teeth were incubated with the photosensitizing agent of example 1 (phosphate buffer, incubation at 37 ℃ C. For 15 minutes) at 20. Mu. Moles, with a white light illumination of 36mW/cm 2 And illuminating the tooth surface morphology with light for 60 minutes and treating the tooth surface morphology with hydrogen peroxide.
Specific results As shown in FIG. 5, exposure of 20 μm photosensitizers to light reduced tooth surface cavities.
The foregoing description of the embodiments has been provided for the purpose of illustrating the general principles of the invention, and is not meant to limit the invention thereto, but to limit the invention thereto, and any modifications, equivalents, improvements and equivalents thereof may be made without departing from the spirit and principles of the invention.
Claims (7)
1. Use of a chromophore compound having the structure of the formula for preparing a composition for photodynamic tooth biofilm removal and tooth whitening, characterized by:
wherein R1, R2 are independently selected from
Wherein A is 1 ,A 2 ,A 3 ,A 4 Independently selected from hydrogen, alkyl chains, which are directly attached to the chromophore compound, the alkyl chains having a length ranging from 1 to 20, the compound being present in the composition at a concentration ranging from 0.01 micromolar to 10 millimoles.
2. Use according to claim 1, characterized in that: the alkyl chain has one or more unsaturated double bonds.
3. The use according to claim 1, wherein the compound is of the formula:
4. the use according to claim 1, characterized in that the concentration of the compound in the composition ranges from 0.1 micromolar to 1 millimole.
5. The use according to claim 1, wherein the concentration of the compound in the composition ranges from 1 micromolar to 500 micromolar.
6. Use according to claim 1, characterized in that the use is carried out in the presence of oxygen.
7. Use according to claim 1, characterized in that the use is performed under lighting conditions.
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