WO2014109550A1 - Composition antibactérienne de remplissage osseux contenant un ester phénéthylique d'acide caféique, et son procédé de préparation - Google Patents

Composition antibactérienne de remplissage osseux contenant un ester phénéthylique d'acide caféique, et son procédé de préparation Download PDF

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WO2014109550A1
WO2014109550A1 PCT/KR2014/000209 KR2014000209W WO2014109550A1 WO 2014109550 A1 WO2014109550 A1 WO 2014109550A1 KR 2014000209 W KR2014000209 W KR 2014000209W WO 2014109550 A1 WO2014109550 A1 WO 2014109550A1
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caffeic acid
acid ester
filling composition
bone filling
antibacterial
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PCT/KR2014/000209
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English (en)
Korean (ko)
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장정호
이혜선
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한국세라믹기술원
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Publication of WO2014109550A1 publication Critical patent/WO2014109550A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/54—Biologically active materials, e.g. therapeutic substances
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F15—FLUID-PRESSURE ACTUATORS; HYDRAULICS OR PNEUMATICS IN GENERAL
    • F15B—SYSTEMS ACTING BY MEANS OF FLUIDS IN GENERAL; FLUID-PRESSURE ACTUATORS, e.g. SERVOMOTORS; DETAILS OF FLUID-PRESSURE SYSTEMS, NOT OTHERWISE PROVIDED FOR
    • F15B13/00—Details of servomotor systems ; Valves for servomotor systems
    • F15B13/02—Fluid distribution or supply devices characterised by their adaptation to the control of servomotors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/40—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
    • A61L27/44—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having a macromolecular matrix
    • A61L27/446—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having a macromolecular matrix with other specific inorganic fillers other than those covered by A61L27/443 or A61L27/46
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2430/00—Materials or treatment for tissue regeneration
    • A61L2430/02—Materials or treatment for tissue regeneration for reconstruction of bones; weight-bearing implants
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F15—FLUID-PRESSURE ACTUATORS; HYDRAULICS OR PNEUMATICS IN GENERAL
    • F15B—SYSTEMS ACTING BY MEANS OF FLUIDS IN GENERAL; FLUID-PRESSURE ACTUATORS, e.g. SERVOMOTORS; DETAILS OF FLUID-PRESSURE SYSTEMS, NOT OTHERWISE PROVIDED FOR
    • F15B2211/00—Circuits for servomotor systems
    • F15B2211/20—Fluid pressure source, e.g. accumulator or variable axial piston pump
    • F15B2211/205—Systems with pumps
    • F15B2211/20507—Type of prime mover
    • F15B2211/20515—Electric motor
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F15—FLUID-PRESSURE ACTUATORS; HYDRAULICS OR PNEUMATICS IN GENERAL
    • F15B—SYSTEMS ACTING BY MEANS OF FLUIDS IN GENERAL; FLUID-PRESSURE ACTUATORS, e.g. SERVOMOTORS; DETAILS OF FLUID-PRESSURE SYSTEMS, NOT OTHERWISE PROVIDED FOR
    • F15B2211/00—Circuits for servomotor systems
    • F15B2211/20—Fluid pressure source, e.g. accumulator or variable axial piston pump
    • F15B2211/205—Systems with pumps
    • F15B2211/20576—Systems with pumps with multiple pumps
    • F15B2211/20584—Combinations of pumps with high and low capacity
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F15—FLUID-PRESSURE ACTUATORS; HYDRAULICS OR PNEUMATICS IN GENERAL
    • F15B—SYSTEMS ACTING BY MEANS OF FLUIDS IN GENERAL; FLUID-PRESSURE ACTUATORS, e.g. SERVOMOTORS; DETAILS OF FLUID-PRESSURE SYSTEMS, NOT OTHERWISE PROVIDED FOR
    • F15B2211/00—Circuits for servomotor systems
    • F15B2211/20—Fluid pressure source, e.g. accumulator or variable axial piston pump
    • F15B2211/205—Systems with pumps
    • F15B2211/20576—Systems with pumps with multiple pumps
    • F15B2211/20592—Combinations of pumps for supplying high and low pressure
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F15—FLUID-PRESSURE ACTUATORS; HYDRAULICS OR PNEUMATICS IN GENERAL
    • F15B—SYSTEMS ACTING BY MEANS OF FLUIDS IN GENERAL; FLUID-PRESSURE ACTUATORS, e.g. SERVOMOTORS; DETAILS OF FLUID-PRESSURE SYSTEMS, NOT OTHERWISE PROVIDED FOR
    • F15B2211/00—Circuits for servomotor systems
    • F15B2211/20—Fluid pressure source, e.g. accumulator or variable axial piston pump
    • F15B2211/275—Control of the prime mover, e.g. hydraulic control

Definitions

  • the present invention relates to an antimicrobial bone filling composition and a method for preparing the same, and more particularly, it contains caffeic acid ester (caffeic acid phenethyl ester) known to have antimicrobial activity as an active ingredient of propolis. It relates to a caffeic acid ester-containing antibacterial bone filling composition and a method for producing the same.
  • caffeic acid ester caffeic acid phenethyl ester
  • bone filling compositions that is, bone cement compositions
  • bone cement compositions have been widely used all over the world as adhesives for fixing a bone defect or a metal artificial joint such as artificial hip joint with surrounding bone. Due to the damage of the spine and bones, the method of inserting and inserting artifacts into the body is used, and the total knee replacement and hip replacement and reoperation are widely performed due to the damage of various joints, spine and bones. Bone cement has been used to fix the location of artifacts in the body for the purpose of filling bone defects.
  • Such a bone filling composition is usually divided into a powder part and a liquid part, and kneading immediately before application during surgery or the like to initiate the polymerization reaction of the monomers, and leaving the kneaded material to a certain degree of high viscosity. It is used as being applied to the application target site by a handling operation at the time when it became a state.
  • PMMA polymethyl methacrylate
  • copolymers such as methacrylate and styrene
  • benzoyl peroxide is added as a polymerization initiator in a liquid phase, and a barium sulfate or zirconium oxide, which is a radiographic contrast agent, is mainly used as a filler to enhance opacity to X-rays.
  • the main component of liquid phase is methyl methacrylate, which is a monomer, and N, N-dimethyl-P-toluidine (or dimethylaminophenyl ethanol) is added as an activator, and N, N-dimethyl-P-toluidine ( Or dimethylaminophenyl ethanol) acts as a free-radical activator to activate the production of free radicals.
  • hydroquinone is added as a stabilizer to inhibit the polymerization reaction during storage of bone cement.
  • gentamicin or the like is added to the powder part as an antibiotic for preventing bacterial infection during surgery.
  • these antibiotics had a problem in that resistance was increased when used excessively.
  • the present invention to solve the above problems
  • caffeic acid ester-containing antimicrobial bone filling composition comprising a liquid portion containing an acrylate-based monomer, a polymerization accelerator, a polymerization inhibitor and caffeic acid ester.
  • the liquid portion contains 80 to 99 parts by weight of the acrylate monomer, 0.5 to 3 parts by weight of the polymerization initiator, and 50 to 200 ppm of the polymerization inhibitor. Characterized in that.
  • the caffeic acid ester is characterized in that it is added at a concentration of 10 mM to 20 mM relative to the liquid portion.
  • the powder part comprises 70 to 90 parts by weight of an acrylate polymer, 0.5 to 5 parts by weight of the polymerization initiator, and 5 to 20 parts by weight of the filler. It is done.
  • the filler is characterized in that the barium sulfate, zirconium oxide or titanium dioxide.
  • the caffeic acid ester is one of the active ingredients of propolis, is a kind of flavonoid-based components known as vitamin P having an antimicrobial effect, and is known to mainly act as antibacterial and anti-inflammatory in propolis.
  • the molecular formula of the caffeic acid ester is C 17 H 16 O 4
  • the chemical structure is shown in the formula (1) below.
  • the caffeic acid ester has an antibacterial, antifungal and antiviral effect in the human body.
  • the caffeic acid esters inhibit inflammation by blocking the secretion of enzymes that act to cause inflammation.
  • it because it is water-soluble, its range of use is diverse, and even if ingested excessively characterized by nontoxic.
  • Caffeic acid ester an active component of propolis, exhibits anti-inflammatory activity because it simultaneously inhibits lipoxygenase and cyclooxygenase, two enzymes that produce leucotriene (LT) and prostaglandin (PG). It is more potent than regular painkillers.
  • the caffeic acid ester is contained in the liquid portion, and it is preferable that the concentration is added at a concentration of 10 mM to 20 mM with respect to the liquid portion.
  • the ratio of the caffeic acid ester is 20 mM or more, as shown in Experimental Example 2 below, the polymerization time is increased so that it is difficult to use as a bone filling composition, and when the ratio of the caffeic acid ester is 10 mM or less, the caffeic acid ester is added. Even if there is a problem that does not exhibit antimicrobial efficacy.
  • the antimicrobial bone filling composition according to the present invention comprises a powdered portion containing an acrylate polymer, a polymerization initiator and a filler, and an caffeic acid ester which is an active ingredient of a propolis having an acrylate monomer, a polymerization accelerator, a polymerization inhibitor, and antibacterial properties. Consists of a liquid portion containing, and used to mix the liquid portion and the powder portion during the procedure to the patient.
  • the polymerization initiator and the acrylate monomer of the liquid part react with each other to perform a polymer polymerization reaction of the acrylate monomer.
  • the promoter acts to promote the reaction so that polymerization can occur better at room temperature.
  • the liquid portion comprises 80 to 99 parts by weight of the acrylate monomer, 0.5 to 3 parts by weight of the polymerization initiator, and 50 to 200 ppm of the polymerization inhibitor,
  • the addition of the caffeate ester at a concentration of 10 mM to 20 mM for the liquid portion may increase the release rate of the caffeate ester after applying the bone filling composition to bone filling.
  • the powder part comprises 70 to 90 parts by weight of the acrylate polymer, 0.5 to 5 parts by weight of the polymerization initiator, and 5 to 20 parts by weight of the filler. It is preferred that the strength of the bone filling portion produced from the bone filling composition according to the present invention be the highest.
  • the acrylate polymer which is an essential component of the antimicrobial bone filling composition of the present invention is preferably selected from the group consisting of PMMA polymer (polymethyl methacrylate), polymethyl acrylate, polystyrene, and copolymers thereof. Since the acrylate polymer is pre-dissolved in the liquid portion, the acrylate polymer is preferably in the form of beads of 10 to 100 ⁇ m.
  • benzoyl peroxide As a polymerization initiator which is an essential component of the antimicrobial bone filling composition of this invention, benzoyl peroxide, tert- butyl peroxide, lauroyl peroxide, azobisisobutyronitrile etc. can be used, for example.
  • benzoyl peroxide since the polymerization reaction of the acrylate-type monomer contained in the said liquid part starts quickly, and it is easy to continue the reaction, it is preferable to use benzoyl peroxide.
  • the said powder part contains 0.5-5 weight part of said polymerization initiators.
  • the content rate of a polymerization initiator is too small, there exists a possibility that the polymerization reaction of an acrylate-type monomer may become difficult to advance.
  • the content ratio of the polymerization initiator is excessive, there is a problem that the polymerization initiator remains in the polymer formed by polymerization of the acrylate monomer.
  • the filler consists of inorganic materials such as titanium dioxide, calcium phosphate (hydroxyapatite, tricalcium phosphate), barium sulfate, silicon oxide (silica), aluminum oxide (alumina), zirconium oxide (zirconia), and these inorganic materials alone or It is possible to use what consists of a combination of 2 or more types suitably, and among these, it is preferable to use zirconium oxide and barium sulfate which have an X-ray contrast effect.
  • inorganic materials such as titanium dioxide, calcium phosphate (hydroxyapatite, tricalcium phosphate), barium sulfate, silicon oxide (silica), aluminum oxide (alumina), zirconium oxide (zirconia), and these inorganic materials alone or It is possible to use what consists of a combination of 2 or more types suitably, and among these, it is preferable to use zirconium oxide and barium sulfate which have an X-ray contrast effect.
  • the acrylate monomer which is an essential component as a powder component of the bone cement composition constitutes a component for forming a base material of bone cement, and the bone cement composition is cured by polymerizing an acrylate monomer which is the polymerizable monomer. As a result, a cured product is obtained.
  • At least one selected from the group consisting of acrylate, N-isopropyl (meth) acrylamide, hydroxyethyl methacrylate and acrylonitrile is preferred.
  • the bone cement composition of this invention contains a polymerization promoter with a polymerization initiator for the purpose of advancing the polymerization reaction of an acrylate-type monomer more quickly.
  • N, N-dimethyl-p-toluidine, 2,4,6-tris (dimethylaminomethyl) phenol and the like can be used.
  • N, N- dimethyl- p-toluidine 2,4,6-tris (dimethylaminomethyl) phenol and the like.
  • the antimicrobial bone filling composition according to the present invention contains a separate antibiotic by containing caffeic acid ester which is an active ingredient of natural propolis which has antibacterial and anti-inflammatory effect, which has confirmed stability problems such as reverse mutation and micronucleus test that may occur when administered in the human body. It is possible to prevent the development of fungus, which is a cause of secondary infection during surgery, without the use of.
  • Figure 1 shows the manufacturing process of the antimicrobial bone filling composition to which the caffeic acid ester of the active ingredient propolis with antibacterial properties of the present invention.
  • Figure 2 (a) and Figure 2 (b) is a UV-Vis of caffeic acid ester which is the active ingredient of propolis according to an embodiment of the present invention. Analytical spectra and a calibration curve graph for the solution of caffeic acid ester, the active ingredient of propolis.
  • Figure 3 is a graph measuring the amount of the release caffeate ester according to the amount of caffeic acid ester addition of the antimicrobial bone filling composition according to an embodiment of the present invention with concentration and time.
  • Figure 4 is a graph confirming the change in polymerization time according to the amount of caffeic acid ester addition of the antimicrobial bone filling composition according to an embodiment of the present invention.
  • 5 is a graph confirming the difference of the antimicrobial activity according to the amount of caffeic acid ester addition of the antimicrobial bone filling composition according to an embodiment of the present invention.
  • FIG. 1 shows a manufacturing process and a mixing process of the antimicrobial bone filler according to the present invention.
  • the powder portion used PMMA, BPO, and BaSO 4 The component structure constituting the powder portion of the antimicrobial bone filler composition according to the present embodiment was described by the following formula.
  • PMMA, BPO, and BaSO 4 constituting the powder portion were stirred for 3 hours in a tube mixer so as to be weighed and mixed to the weight parts of each component.
  • PMMA, BaSO 4 , and BPO which are powders used in the present invention, were manufactured by Sigma Aldrich, a chemical company. After that, the powder is divided into 20g and packed. The packaged powder was sterilized by gamma-ray.
  • the structure of each component constituting the liquid portion of the antimicrobial bone filler composition according to the present embodiment was described by the following formula.
  • the liquid part is weighed by M%, DMPT, HQ, caffeine ester, an active ingredient of propolis with antibacterial properties, in each%, packaged 8.5g after antibacterial filtering (0.2 ⁇ m) so as not to contain impurities,
  • the packaged liquid portion was sterilized with ethylene oxide (EO) gas.
  • DMPT also used Sigma Aldrich's product, MMA used Junsei's product and HQ used Riedel-Dehaen's product.
  • Samples having concentrations of caffeic acid ester added to the liquid portion were 2 mM, 4 mM, 6 mM, 8 mM, 10 mM, 20 mM, 40 mM, 60 mM, 80 mM and 100 mM.
  • the powder part and the liquid part of the antimicrobial bone filler thus prepared were mixed at room temperature (23 ⁇ 2 ° C.) atmosphere. 20g of powder and caffeic acid ester are added to the liquid mixture evenly at 8.5 °C for about 6 ( ⁇ 2) minutes to take the form of an atherosclerosis. This state is injected into a syringe to prepare a sample.
  • Heat is generated during the polymerization process and the temperature of heat is 70 ( ⁇ 10) °C.
  • the completion time of the polymerization is about 12 minutes 30 seconds ( ⁇ 1 minute 30 seconds) within 15 minutes of ISO 5833 standard.
  • PBS Phosphate Buffer Calculator, Monobasic monohydrate: 1.1832g, Dibasic ACS reagent: 8.1572g 0.01M as a solvent for the release test was prepared, pH was adjusted to 7.4.
  • the calibration curve for caffeic acid ester was obtained by measuring absorbance using a JASCO V-550 UV-Vis Spectrometer (Wavelength Range: 200900nm; Bandwidth Selectable: 0.5nm; Scanning Speed: 400nm / min; Data Pitch: 1nm). Is shown in FIG. 2.
  • the calibration curve shown in FIG. 2 was as follows.
  • the release behavior of the caffeic acid ester contained in the antimicrobial bone filler according to the present invention was confirmed in a certain time in vivo.
  • the polymerization time for a typical bone filler should be in accordance with ISO 5833, as set by the International Organization for Standardization, within 15 minutes.
  • Example 1 The sample prepared in Example 1 was placed at room temperature (23 ⁇ 2 ° C.), and then confirmed to polymerize within minutes or hours, and the results are shown in FIG. 4.
  • caffeic acid ester is not included in FIG. 4 and when caffeic acid ester is contained in 2mM, 4mM, 6mM, 8mM, and 10mM, the polymerization is carried out within 15 minutes in accordance with international standards, but polymerization is performed when caffeic acid ester is contained in 20mM or more. You can see that it takes more than a day.
  • the antimicrobial activity of the antimicrobial bone filling composition prepared in Example was measured by cell growth in a shaker method using a shake flask method, and by measuring the growth of the strain by UV-Vis.
  • Antimicrobial activity was measured by using a staphylococcus aureus (ATCC 6538) as a test strain, JASCO V-550 UV-Vis Spectrometer (Wavelength Range: 200900nm; Bandwidth Selectable: 0.5nm; Scanning Speed: UV-Vis. 400 nm / min; Data Pitch: 1 nm). was measured to measure the change of the strain, and the results are shown in FIG. 5.
  • the concentration of caffeate ester decreased by 13.76% at 10 mM, 35.79% at 20 mM, 36.44% at 40 mM, 38.06% at 60 mM, 38.10% at 80 mM, and finally at 41.13% at 100 mM. You can see the decrease.
  • the strain was used Staphylococcus aureus (ATCC 6538) of Experimental Example 3, and the staining agent used in the strain was LIVE / DEADBacLightBacterial Viability Kit for microscopy and quantitative assays of Invitrogen.
  • Petri dishes were divided by the concentration of caffeic acid esters, and inoculated with the cultured strains, and then cultured in an incubator (37 ° C.) for 24 hours. After 24 hours, each sample was washed with 1 mL of 3rd order, and 2 ⁇ L mix dye was mixed with 1 mL 0.3% DMSO in two dyes, LIVE / DEADBacLight TM, Green and Red. Wrap in foil for 15 minutes, react in the dark, and observe with a fluorescence microscope.
  • Fluorescence microscopy is Olympus IX71 (Exfo 120 xenon-Hg excitation light coupled by optic fiber, fast remote controlled excitation filter wheel, mono-, trippel- and quarto- emission filters, polarization filter, phase contrast, objectives with magnification ranging from 4X to 60X , high sensitivity monochrome CCD camera XM10, color CCD camera XC30) were used, and the measured results are shown in FIG. 6.
  • the antimicrobial bone filling composition according to the present invention contains a separate antibiotic by containing caffeic acid ester which is an active ingredient of natural propolis which has antibacterial and anti-inflammatory effect, which has confirmed stability problems such as reverse mutation and micronucleus test that may occur when administered in the human body. It is possible to prevent the development of fungus, which is a cause of secondary infection during surgery, without the use of.

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Abstract

La présente invention concerne une composition antibactérienne de remplissage osseux et son procédé de préparation, et plus particulièrement une composition antibactérienne de remplissage osseux contenant un ester phénéthylique d'acide caféique, qui est un principe actif de propolis, et son procédé de préparation. La composition antibactérienne de remplissage osseux de la présente invention contient un ester phénéthylique d'acide caféique, qui est un principe actif de propolis naturelle, dont les problèmes de stabilité tels que ceux liés à la mutation inverse, à un test du micronoyau et autres pouvant se produire lors de l'administration au corps humain sont identifiés, et présente des effets antibactériens et anti-inflammatoires, et permet ainsi de prévenir l'apparition de champignons, qui est la cause de surinfection se produisant au cours d'une opération chirurgicale, sans utiliser d'antibiotiques supplémentaires.
PCT/KR2014/000209 2013-01-12 2014-01-08 Composition antibactérienne de remplissage osseux contenant un ester phénéthylique d'acide caféique, et son procédé de préparation WO2014109550A1 (fr)

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KR10-2013-0003707 2013-01-12
KR1020130003707A KR101458060B1 (ko) 2013-01-12 2013-01-12 카페인산에스테르 함유 항균 골충진 조성물 및 이의 제조방법

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Cited By (1)

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KR101945972B1 (ko) * 2018-05-18 2019-02-08 하방 토르말린이 함유된 도트가 형성된 기능성 원단 및 이를 이용한 제품

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KR102005757B1 (ko) 2017-06-02 2019-07-31 한국세라믹기술원 생체활성 유리 섬유를 이용한 구조체용 생체 세라믹 및 그 제조방법
KR102106312B1 (ko) * 2017-12-12 2020-05-29 주식회사 오쎄인 페이스트 형태의 골 대체용 합성골 및 이의 제조방법
KR102021734B1 (ko) * 2018-05-24 2019-09-16 김선희 내향성 발톱교정 및 이에 사용되는 발톱보호코팅제

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WO2006105196A2 (fr) * 2005-03-28 2006-10-05 Bioresponse, L.L.C. Compositions a base de diindolylmethane et leurs procedes d'utilisation pour favoriser la sante de la muqueuse buccale et la sante des os
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KR20040021604A (ko) * 2001-05-21 2004-03-10 코니스 프랑스, 에스.에이. 화장용 제제
WO2006105196A2 (fr) * 2005-03-28 2006-10-05 Bioresponse, L.L.C. Compositions a base de diindolylmethane et leurs procedes d'utilisation pour favoriser la sante de la muqueuse buccale et la sante des os
WO2008097855A2 (fr) * 2007-02-05 2008-08-14 Dfine, Inc. Systèmes et procédés de traitement des os

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PARLAKPINAR, H. ET AL.: "Protective role of caffeic acid phenethyl ester (cape) on gentamicin-induced acute renal toxicity in rats", TOXICOLOGY, vol. 207, no. 2, 2005, pages 169 - 177, XP004681063, DOI: doi:10.1016/j.tox.2004.08.024 *
PASSUTI, N. ET AL.: "Antibiotic-loaded bone cement in orthopedic surgery", JOINT BONE SPINE, vol. 70, no. 3, 2003, pages 169 - 174 *

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101945972B1 (ko) * 2018-05-18 2019-02-08 하방 토르말린이 함유된 도트가 형성된 기능성 원단 및 이를 이용한 제품

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