CN106699751A - Novel compound XQH-3-7, and application of novel compound in streptococcus mutans resistance and streptococcus mutans biological membrane formation inhibition - Google Patents
Novel compound XQH-3-7, and application of novel compound in streptococcus mutans resistance and streptococcus mutans biological membrane formation inhibition Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
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Abstract
The invention discloses a novel thiazole compound. The number of the compound is XQH-3-7; a molecular formula of the compound is C16H17N5O4S2; the molecular weight of the compound is 391.47; and the name of the compound is N-(5-nitryl thiazolyl-2)-1-(phenyl methyl sulfamide) piperidine-4-formamide. Experiments confirm that the compound shows good antibacterial activity and bactericidal activity to streptococcus mutans type strains and clinical strains. At the same time, an inhibition rate for a streptococcus mutans biological membrane reaches above 96% when a final concentration of the compound XQH-3-7 in a culture medium reaches 4mg/L. The compound is small in molecular weight and relatively simple in structure; the antibacterial experiments confirm that the compound has strong inhibition, good killing effect and the like; and the compound can significantly inhibit formation of streptococcus mutans floating cells and the biological membrane and is expected to serve as a novel candidate target drug for decayed teeth.
Description
Technical field
The present invention relates to a kind of thiazole compound, more particularly to a kind of novel thiazole class compounds X QH-3-7 and its
Streptococcus mutans and the application for suppressing in its biofilm formation.The compound can suppress the growth of oral cavity periodontal bacterium,
Can be used to prevent and treat carious tooth, belong to oral disease prevention and control field of medicine preparing technology.
Background technology
Compared to the growth pattern of (planktonic) of swimming, most of bacterium is more likely to adopt in natural environment
The mode for taking biomembrane (biofilm) is grown.So-called biomembrane (being also referred to as biofilm) refers to that bacterium utilizes
Itself secretion macromolecular extracellular matrix by own cells wrap up and be attached to life or lifeless object surface one
The highly organized cell colony of class.Exist in biomembrane macromolecular substances including protein, polysaccharide, DNA, RNA, peptide glycan,
The material such as fat and phosphatide.Substantial amounts of microorganism is there is also in human oral cavity, they are using the carbohydrate remained in oral cavity
The surface of human teeth is resided in the form of biomembrane with saliva.Under normal circumstances, the microorganism in oral cavity is in dental surface
In a kind of metastable physiological equilibrium state, once this balance be broken will trigger carious tooth (Selwitz et al.,
2007)。
Carious tooth is commonly called as decayed tooth, decayed tooth, is caused enamel, the chronic disease of dentine demineralization decomposition that a kind of bacterium induces
Disease.Sick incidence of disease is high for this, dabble scope wide, especially relatively common in teenager and children.Eurodonticus is to cold and hot sour-sweet
Become quite sensitive and along with pain (Fejerskov and Kidd, 2009) Deng stimulation.Severe patient can trigger dental pulp disease, root
A series of complication such as sharp disease, or even lose whole tooth and then influence healthy and quality of life.Carious tooth has turned into tight
Endanger again one of main oral disease of human body health (Pitts, 2004).In the forming process of carious tooth, deform hammer
Bacterium (Streptococcus mutans) plays vital effect.
Streptococcus mutans is the gram-positive bacteria of a class amphimicrobian, be main cariogenic hedgehog fungus in human oral cavity it
One.Streptococcus mutans not only can produce substantial amounts of acidic materials to corrode enamel by being metabolized, and can be by producing Portugal
The sucrose remained in oral cavity is changed into glucan by glycan transferase.Glucan is difficult to be eliminated after adhering to tooth, and energy
Other bacteriums in enough optionally absorption oral cavities, form bacterial plaque.Bacterial metabolism in bacterial plaque produce acid product long term in
Tooth can make tooth demineralization produce tooth hole, and carious tooth (Lemos et al., 2013) will be formed in the course of time.
Therefore, searching can suppress streptococcus mutans planktonic cells and the new compound of biofilm formation will be helpful to people
Develop the remedy measures and related drugs of new anticaries.
The content of the invention
For the demand of prior art, it is an object of the invention to provide a kind of novel thiazole class compounds X QH-3-7 and its
Application in Streptococcus mutans and in suppressing its biofilm formation.
Thiazole compound XQH-3-7 of the present invention, it is characterised in that：The compound chemical molecular formula is
C16H17N5O4S2, Chinese is N- (5- nitrothiazole -2- bases) -1- (phenyl first sulphamide) piperidines -4- formamide, English name
Referred to as N- (3-bromophenyl) -4- (2- ((5-nitrothiazol-2-yl) amino) -2-oxoethyl)
Piperazine-1-carboxamide, molecular weight is 391.47, shown in its chemical constitution such as formula (1)：
Above-claimed cpd is soluble in dimethyl sulfoxide (DMSO) (DMSO), is insoluble in water.
The synthetic route of above-claimed cpd XQH-3-7 is shown in following reaction equation：
Wherein：(a) HOBT, EDCI, triethylamine, room temperature；(b) ethyl acetate hydrogen chloride saturated solution, room temperature；(d) three light
Gas, anhydrous ethyl acetate, 0 DEG C to backflow；(e) triethylamine, anhydrous tetrahydro furan, 0 DEG C is arrived room temperature.Dried according to conventional standard
Method dries used various solvents.
Thiazole compound XQH-3-7 of the present invention is preparing suppression and is killing streptococcus mutans (Streptococcus
Mutans) the application in the planktonic cells medicine of type strain and clinical strains.
Thiazole compound XQH-3-7 of the present invention is preparing suppression streptococcus mutans (Streptococcus
Mutans) the application formed in medicine of type strain and clinical strains biomembrane.
Thiazole compound XQH-3-7 of the present invention is preparing oral cavity streptococcus mutans (Streptococcus
Mutans) the application in bioflm inhibiting agents.
Applications of the thiazole compound XQH-3-7 of the present invention in the targeted drug for preventing and treating carious tooth is prepared.
Thiazole compound XQH-3-7 of the present invention is preparing toothpaste, mouthwash or sterilization as antibacterial adding ingredient
Application in liquid.
Compounds X QH-3-7 is dissolved with DMSO during test, the mother liquor storage of final concentration of 1024mg/L is made into.
The present invention determines compounds X QH-3-7 to streptococcus mutans type strain and the inhibition of clinical strains.
Result shows that compounds X QH-3-7 has good bacteriostatic activity to the streptococcus mutans under floating state and kills
Bacterium activity, its minimal inhibitory concentration to streptococcus mutans UA159 bacterial strains is 4mg/L, and MBC is 32mg/L, half
Maximum suppression concentration (IC50) it is 0.918mg/L.When compounds X QH-3-7 final concentrations reach 4mg/L in culture medium to deformation chain
The inhibiting rate of coccus UA159 bacterial strain biomembranes is 96.62%.Compounds X QH-3-7 to streptococcus mutans 6715-13 bacterial strains most
Small Mlc is 4mg/L, and MBC is 32mg/L, half maximum suppression concentration (IC50) it is 0.546mg/L.Work as training
Compounds X QH-3-7 final concentrations are to the inhibiting rate of streptococcus mutans 6715-13 bacterial strain biomembranes when reaching 4mg/L in supporting base
96.18%.
Wherein, the streptococcus mutans UA159 bacterial strains for being used are type strain, in ncbi database (http://
Www.ncbi.nlm.nih.gov/ the reference gene group # in) is NC_004350.Streptococcus mutans used in the present invention
6715-13 bacterial strains are clinical strains, are isolated from the middle of the oral cavity with carious tooth patient.Its preferred brain heart infusion of most suitable culture medium
(Brain Heart Infusion) culture medium (Brain infusion solids 12.5g/L, Beef heart
Infusion solids 5.0g/L, Proteose peptone 10.0g/L, Glucose 2.0g/L, Sodium
Chloride 5.0g/L, Di-sodium phosphate 2.5g/L, pH 7.4 ± 0.2), most suitable condition of culture is preferably detested
Oxygen, 37 DEG C of quiescent cultures.
Thiazole compound XQH-3-7 molecular weight disclosed by the invention is small, structure is relatively easy, and bacteriostatic experiment confirms have
The features such as strong inhibition capability, fragmentation effect are good, can significantly inhibit the formation of streptococcus mutans planktonic cells and biomembrane, with pre-
The potentiality of anti-dental caries, are expected to as the novel targeted drug candidate of pre- anti-caries.
Specific embodiment
A kind of novel thiazole class compounds X QH-3-7 provided with reference to the present invention further describes it and is killing, pressing down
Application during streptococcus mutans planktonic cells processed and its biofilm formation.The content be explanation of the invention rather than
Limit.
Embodiment 1：The preparation of compounds X QH-3-7
The synthetic route of compounds X QH-3-7 is shown in following reaction equation：
Wherein：(a) HOBT, EDCI, triethylamine, room temperature；(b) ethyl acetate hydrogen chloride saturated solution, room temperature；(d) three light
Gas, anhydrous ethyl acetate, 0 DEG C to backflow；(e) triethylamine, anhydrous tetrahydro furan, 0 DEG C is arrived room temperature.Dried according to conventional standard
Method dries used various solvents.
Specific course of reaction is described as follows：
(1) the intermediate 4- tert-butyl groups-(preparation of (5- nitrothiazole -2- bases) carbamyl -1- carboxylic acids (1).
1-Boc-4- piperidine carboxylic acids (1eq) are dissolved in DMF, then be separately added into HOBt (1.2eq) and
EDCI (1.2eq), is added dropwise triethylamine (1.2eq).Completion of dropping, adds 5- nitros thiazolamine (1.2eq), at normal temperatures
Overnight, to the distilled water for adding 200ml in reaction solution, water is mutually extracted with ethyl acetate three times (3 × 200ml), merges organic for reaction
Washed (2 × 100ml) twice with saturation NaCl, anhydrous magnesium sulfate is dried, and is then concentrated by evaporation to obtain crude product with Rotary Evaporators.Slightly
Product are through silica gel chromatographic column post purifies and separates (dichloromethane:Methyl alcohol=v:V, 200:1) yellow solid, yield 75% are obtained.
(2) preparation of intermediate 2- (4- amino -1- bases)-N- (5- nitrothiazole -2- bases) piperidines -4- formamides (2)
Chloroacetic chloride is slowly instilled (v in absolute ethyl alcohol:v,4:5) HCl and ethyl acetate, are generated, then by the middle of previous step
Body is dissolved in wherein, stirs 15 minutes at normal temperatures, detects that reaction is complete with TLC, and solvent evaporated obtains yellow solid, and crude product is produced
Rate 100%, it is unprocessed directly to carry out next step.
(3) preparation of N- (5- nitrothiazole -2- bases -) -1- (phenyl formyl sulfydryl) piperidines -4- acyls (XQH-3-7)
Intermediate 3 (1eq) and triethylamine (1.2eq) are dissolved in anhydrous tetrahydro furan at 0 DEG C, add dropwise phenyl
Isothiocyanates (1.2eq), stirs 3h, is detected with TLC and reacted, and steams tetrahydrofuran, to the distilled water for adding 50ml in reaction solution,
Water is mutually extracted with ethyl acetate three times (3 × 50ml), merges organic phase saturated nacl aqueous solution and washes (2 × 50ml), nothing twice
Water magnesium sulfate is dried 30 minutes, then obtains crude product through vacuum evaporation.Crude product is through silica gel chromatographic column (200-300 mesh) purifying point
From (dichloromethane:Methyl alcohol=v:v,50:1) as eluant, eluent, off-white powder, yield 61% are obtained.
1H NMR(400MHz,DMSO-d6)：δ 13.19 (s, 1H), 9.31 (s, 1H), 8.64 (s, 1H), 7.29 (d, J=
6.0Hz, 4H), 7.10 (d, J=2.6Hz, 1H), 4.72 (d, J=13.3Hz, 2H), 3.20 (t, J=11.7Hz, 2H), 2.92
(t, J=12.9Hz, 1H), 1.94 (d, J=11.2Hz, 2H), 1.74-1.60 (m, 2H) .ppm；ESI-MS:390.1[M-H].
Embodiment 2：The preparation of streptococcus mutans
(1) culture medium of culture streptococcus mutans is brain heart infusion (Brain Heart Infusion) culture medium (brand
OXOID, article No. CM1135), culture medium main component is Brain infusion solids 12.5g/L, Beef heart
Infusion solids 5.0g/L, Proteose peptone 10.0g/L, Glucose 2.0g/L, Sodium
Chloride 5.0g/L, Di-sodium phosphate 2.5g/L, pH 7.4 ± 0.2.Need to such as solid be configured to, it is necessary to add
Plus agar powder 15g/L.115 DEG C of 30min that sterilize, it is stand-by after cooling.
(2) culture medium of culture streptococcus mutans biomembrane is brain heart infusion-SM, i.e., in brain heart infusion culture
Final concentration of 1% sucrose is added in base.Sucrose need in advance be made into 20% storage liquid and be crossed with 0.22 μm of sterile filters and filter
Bacterium.
(3) with aseptic inoculation ring by streptococcus mutans type strain UA159 and the deformation that is isolated from carious tooth patient's mouth
Strains of streptococcus 6715-13 is rule on the flat board containing brain heart infusion agar solid medium, is inverted in 37 DEG C and is detested
Culture in oxygen incubator is until there is obvious single bacterium colony.
(4) scraping streptococcus mutans UA159 and 6715-13 bacterial strain is shoveled with aseptic inoculation, is transferred to respectively equipped with the brain heart
In the test tube of immersion liquid fluid nutrient medium, stood in 37 DEG C of anaerobic culture box, culture is muddy to liquid.
(5) absorbance (OD of the streptococcus mutans under 600nm is detected with ultraviolet-uisible spectrophotometer600nm)。
(6) assay balance accurate weighing compounds X QH-3-7 is used, adds DMSO to be dissolved, be then 0.22 μ with aperture
The sterile filters filtration sterilization of m, is made into the storage liquid of final concentration of 1024mg/L, deposit in -20 DEG C it is stand-by.
Embodiment 3：Activity determinations of the compounds X QH-3-7 to streptococcus mutans planktonic cells
(1) prepare streptococcus mutans bacterium solution and compounds X QH-3-7 according to the method described in embodiment 2, culture is made
The streptococcus mutans UA159 and 6715-13 bacterium solution (OD of logarithmic phase600nm=0.8~1.0) it is diluted to end with brain-heart infusion medium
Concentration is 5 × 105Cfu/ml is stand-by.
(2) streptococcus mutans UA159 and 6715-13 are swum using micro broth dilution method detection compound XQH-3-7
The minimal inhibitory concentration of cell.Aseptic 96 will be added separately to by the compounds X QH-3-7 solution of various concentrations after doubling dilution
In orifice plate, the 1st to the 11st hole be plus liquid experimental group, the 12nd hole be not dosing as growth control group, in each hole deform
Streptococcus bacterium solution final concentration of 5 × 105Cfu/ml, now, the 1st hole to the 12nd hole drug concentration is respectively 256,128,64,32,
16、8、4、2、1、0.5、0.25、0μg/ml.It is minimum antibacterial dense with the least concentration positioning that bacterial growth is completely inhibited in aperture
Degree (MIC).
(3) by after on the bacterium solution even spread in aperture to brain heart infusion agar solid medium, in 37 DEG C of Anaerobic culturels
Culture 24 hours is inverted in case, MBC (MBC) is positioned with the least concentration produced without bacterium.
(4) absorbance in each aperture under 600nm is detected with ELIASA, calculates thin under the conditions of each drug concentration
The inhibiting rate of born of the same parents, computing formula is inhibiting rate=(1- experimental groups/growth control group) × 100%, and the data obtained is united using SPSS
Meter software calculates half maximum suppression concentration (IC50), experimental result is as shown in table 1.
Activity determinations of the compounds X QH-3-7 of table 1. to streptococcus mutans UA159 and 6715-13 planktonic cells
MIC：Minimal inhibitory concentration；MBC：MBC；IC50：Half maximum suppression concentration
From table 1 it will be seen that compounds X QH-3-7 has to streptococcus mutans UA159 and 6715-13 planktonic cells
Good bacteriostatic activity and killing activity.Compounds X QH-3-7 is substantially good to the activity of streptococcus mutans UA159 planktonic cells
In streptococcus mutans 6715-13.
Embodiment 4：Inhibitory activity of the compounds X QH-3-7 to streptococcus mutans biomembrane
(1) prepare streptococcus mutans bacterium solution and compounds X QH-3-7 according to the method described in embodiment 2 and 3, use the brain heart
Streptococcus mutans in logarithmic phase is diluted to final concentration of 5 × 10 by immersion liquid-SM5Cfu/ml is stand-by.
(2) to the μ l of bacterium solution 150 added in 96 aseptic orifice plates in (1), and to add the hole of compounds X QH-3-7 (whole
Concentration 4mg/L) as experimental group, be not added with compounds X QH-3-7 hole as a control group.It is put in quiet in 37 DEG C of anaerobic culture boxes
Put culture 40 hours.
(3) planktonic cells in each hole are removed, and unadsorbed cell is rinsed with substantial amounts of water.
(4) to the μ l of crystal violet solution 200 that 0.1% is added in each hole, standing 5min is contaminated under conditions of room temperature
Color, then removes crystal violet solution, and rinse out the unadsorbed crystal violet of removing with a large amount of water.
(5) to the crystal violet of the μ l of the acetic acid solution 200 dissolving absorption that 33% is added in each hole, then examined using ELIASA
The absorbance surveyed under 590nm, calculates the inhibiting rate of biomembrane, and computing formula is with embodiment 1.
Result shows, when compounds X QH-3-7 final concentrations reach 4mg/L in culture medium to streptococcus mutans UA159 bacterium
The inhibiting rate of strain biomembrane is 96.62%, and the inhibiting rate to streptococcus mutans 6715-13 bacterial strain biomembranes is 96.18%.
Claims (6)
1. a kind of thiazole compound XQH-3-7, it is characterised in that：The compound chemical molecular formula is C16H17N5O4S2, Chinese name
Referred to as N- (5- nitrothiazole -2- bases) -1- (phenyl first sulphamide) piperidines -4- formamides, English name is N- (3-
bromophenyl)-4-(2-((5-nitrothiazol-2-yl)amino)-2-oxoethyl)piperazine-1-
Carboxamide, molecular weight is 391.47, shown in its chemical constitution such as formula (1)：
2. thiazole compound XQH-3-7 described in claim 1 is preparing suppression and is killing streptococcus mutans
Application in the planktonic cells medicine of (Streptococcus mutans) type strain and clinical strains.
3. thiazole compound XQH-3-7 described in claim 1 is preparing suppression streptococcus mutans (Streptococcus
Mutans) the application formed in medicine of type strain and clinical strains biomembrane.
4. thiazole compound XQH-3-7 described in claim 1 is preparing oral cavity streptococcus mutans (Streptococcus
Mutans) the application in bioflm inhibiting agents.
5. applications of the thiazole compound XQH-3-7 described in claim 1 in the targeted drug for preventing and treating carious tooth is prepared.
6. thiazole compound XQH-3-7 described in claim 1 is preparing toothpaste, mouthwash or sterilization as antibacterial adding ingredient
Application in liquid.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108078822A (en) * | 2018-01-17 | 2018-05-29 | 山东大学 | A kind of morning-night special type toothpaste |
| CN108210385A (en) * | 2018-01-17 | 2018-06-29 | 山东大学 | A kind of g., jelly-like mouthwash with preventing decayed tooth antibacterial and strong root permanent tooth |
| CN112174943A (en) * | 2019-07-03 | 2021-01-05 | 四川大学 | Application of indole-2-ketone compound in preparation of oral bacteria prevention and treatment product |
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| WO1998005332A1 (en) * | 1996-08-01 | 1998-02-12 | Isis Pharmaceuticals, Inc. | Novel heterocycle compositions |
| WO2014179144A1 (en) * | 2013-04-29 | 2014-11-06 | E. I. Du Pont De Nemours And Company | Fungicidal heterocyclic compounds |
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2016
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Patent Citations (2)
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| WO1998005332A1 (en) * | 1996-08-01 | 1998-02-12 | Isis Pharmaceuticals, Inc. | Novel heterocycle compositions |
| WO2014179144A1 (en) * | 2013-04-29 | 2014-11-06 | E. I. Du Pont De Nemours And Company | Fungicidal heterocyclic compounds |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108078822A (en) * | 2018-01-17 | 2018-05-29 | 山东大学 | A kind of morning-night special type toothpaste |
| CN108210385A (en) * | 2018-01-17 | 2018-06-29 | 山东大学 | A kind of g., jelly-like mouthwash with preventing decayed tooth antibacterial and strong root permanent tooth |
| CN108210385B (en) * | 2018-01-17 | 2020-08-18 | 山东大学 | A jelly-like collutory with effects of preventing dental caries, resisting bacteria, strengthening root and consolidating teeth |
| CN112174943A (en) * | 2019-07-03 | 2021-01-05 | 四川大学 | Application of indole-2-ketone compound in preparation of oral bacteria prevention and treatment product |
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