WO2015130096A1 - Film de traitement de plaie à libération d'oxyde d'azote et son procédé de préparation - Google Patents

Film de traitement de plaie à libération d'oxyde d'azote et son procédé de préparation Download PDF

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Publication number
WO2015130096A1
WO2015130096A1 PCT/KR2015/001864 KR2015001864W WO2015130096A1 WO 2015130096 A1 WO2015130096 A1 WO 2015130096A1 KR 2015001864 W KR2015001864 W KR 2015001864W WO 2015130096 A1 WO2015130096 A1 WO 2015130096A1
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Prior art keywords
film
nitric oxide
polymer
wound
wound treatment
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PCT/KR2015/001864
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English (en)
Korean (ko)
Inventor
유진욱
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부산대학교 산학협력단
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Priority claimed from KR1020150026410A external-priority patent/KR101555523B1/ko
Application filed by 부산대학교 산학협력단 filed Critical 부산대학교 산학협력단
Priority to US15/122,182 priority Critical patent/US9861591B2/en
Priority to EP15755452.8A priority patent/EP3120840B1/fr
Priority to CN201580022323.3A priority patent/CN106456563A/zh
Publication of WO2015130096A1 publication Critical patent/WO2015130096A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7007—Drug-containing films, membranes or sheets
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/04—Nitro compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/15—Oximes (>C=N—O—); Hydrazines (>N—N<); Hydrazones (>N—N=) ; Imines (C—N=C)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • 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
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/44—Medicaments
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
    • A61L2300/114—Nitric oxide, i.e. NO

Definitions

  • the present invention relates to a nitric oxide-releasing wound treatment film and a method for producing the same, which can inhibit pathogens which are the main cause of wound infection and can cure wounds promptly.
  • a wound is a state in which the anatomical continuity of a human tissue has lost its original continuity by external action.
  • our skin is composed of epidermis, dermis, and subcutaneous fat, and the loss of continuity such as epidermis, dermis, and subcutaneous fat by trauma such as cut or falling is called wound.
  • wound dressing In general, dressing is used to effectively treat wounds of the skin such as wounds and traumas.
  • Wound dressings require the ability to maintain adequate moisture at the contact surface with wounds, the ability to control wound secretions, ease of attachment and removal of dressings to wounds, and air and vapor penetration between external wounds. Sex, insulation of the wound area against the outside, resistance to the invasion of bacteria, non-toxic to the human body, excellent mechanical properties are required.
  • the present invention provides a nitric oxide releasing wound treatment film, characterized in that the nitric oxide donor is encapsulated in a polymer.
  • the nitric oxide donor may be selected from the group consisting of s-nitrosoglutathione, diaeniumdiolate, organic nitrate and iron-nitrosyl complexes. .
  • the polymer may be a biocompatible polymer selected from the group consisting of chitosan, silicone, polyurethane and calcium alginate.
  • the film may contain 2.5 to 30% by weight of a nitrogen oxide donor in 100% by weight of the film.
  • the nitric oxide donor may be selected from the group consisting of s-nitrosoglutathione, diaeniumdiolate, organic nitrate and iron-nitrosyl complexes. .
  • the polymer may be selected from the group consisting of chitosan, silicone, polyurethane and calcium alginate.
  • the plasticizer may be selected from the group consisting of polyethylene glycol, sorbitol, and glycerol.
  • the step of preparing a polymer solution may be adjusted to pH 4.0 to pH 6.0 using 0.1 M acetate buffer solution.
  • the nitrogen oxide donor may be added in an amount of 2.5 to 30 parts by weight based on 100 parts by weight of the polymer solution.
  • drying may be dried for 1 to 2 days at 25 to 37 °C.
  • the nitric oxide releasing film containing s-nitroglutathione (GSNO), a nitric oxide donor spontaneously formed in the human body not only has mechanical properties applicable to the human body, but also gradually releases nitric oxide.
  • the film can be usefully used for wound healing because it can inhibit pathogens which are the main cause of wound infection and can heal wounds quickly.
  • Figure 2 shows the thermal properties of the GSNO film 10, chitosan film (B), chitosan (C), GSNO (G) and a mixture (GC) of a mixture of GSNO and chitosan,
  • Figure 4 shows the antimicrobial and anti-biofilm effect of the NO release film for Gram-positive bacteria and Gram-negative bacteria
  • Figure 5 shows the macroscopic changes in the wound over time according to the application of NO release film
  • Figure 6 shows the wound size reduction effect of the application of NO release film
  • Figure 7 shows the epithelialization rate according to the application of NO release film
  • FIG. 8 shows histopathological findings of wounds following application of NO release film (A-C: gauze control, D-F: NO 0 mg; G-I: NO 10 mg).
  • NO release film was prepared using a solvent evaporation method. That is, chitosan was dissolved in acetone buffer (100 mM) and the pH of the solution was adjusted to 4.4 using acetic acid. Glycerol was added to the chitosan solution to a final concentration of 1% (w / w). 10 mg GSNO was added to the solution and stirred for 20 minutes. The resulting solution was cast in Petri dishes and dried in a dark room at 37 ° C. for 2 days in a dryer equipped with a dehumidifier. The film thus prepared (hereinafter 'CS / NO film') was stored at 7 ° C. under vacuum and stored in the dark until use. At this time, a blank film containing no GSNO was prepared as a control.
  • acetone buffer 100 mM
  • Glycerol was added to the chitosan solution to a final concentration of 1% (w / w). 10 mg GSNO was added to the solution and stirred for 20 minutes.
  • the film was dried under dark and dehumidification conditions to promote evaporation.
  • a reddish, transparent and homogeneous film having a loading efficiency of 47% nitric oxide donor can be obtained.
  • the loading efficiency was less than 20%.
  • polyvinyl alcohol polyvinyl alcohol
  • PVA polyvinyl alcohol
  • MO polyvinyl alcohol
  • a film was prepared by the same process as the CS / NO film (hereinafter 'PVA / NO film').
  • GSNO s-nitroglutathione
  • the present invention provides a nitric oxide releasing wound treatment film, characterized in that the nitric oxide donor is encapsulated in a polymer.
  • the nitric oxide donor may be selected from the group consisting of s-nitrosoglutathione, diaeniumdiolate, organic nitrate and iron-nitrosyl complexes, In particular, it is more preferable to use s-nitrosoglutathione which is spontaneously formed in the human body and has high stability in the film manufacturing process and storage process.
  • the polymer may be a biocompatible polymer selected from the group consisting of chitosan, silicone, polyurethane, and calcium alginate, but more preferably chitosan, which absorbs wound secretions and maintains the surface of the wound while maintaining its own wound healing effect. .
  • Nitric oxide donors are substances that release nitric oxide ('NO') after being mixed with a polymer solution and dried, and when the nitric oxide donor is added at less than 2.5% by weight, the amount of NO released is low and the wound healing effect is continuously decreased. When it is not possible to release NO, and in excess of 30% by weight, the overall efficiency of the manufacture of the wound care film is reduced and the mechanical properties and stability may be reduced.
  • the present invention also provides a method for producing a nitric oxide releasing wound treatment film by a solvent evaporation method. More specifically, the manufacturing method comprises the steps of dissolving the polymer in a solvent, adjusting the pH, and then preparing a polymer solution by adding a plasticizer; Adding a nitric oxide donor to the polymer solution and stirring to prepare a reactant; And casting the reactants in a film form and drying in a dark room dehumidified state.
  • the manufacturing method comprises the steps of dissolving a polymer such as chitosan in a solvent, adjusting the pH with an acidifying agent, and preparing a polymer solution by adding glycerol; Preparing a reactant by adding and stirring a nitric oxide donor such as s-nitrosoglutathione (hereinafter 'GSNO') to the polymer solution; Casting the reactant in the form of a film, and drying in a dark room dehumidified state.
  • a polymer such as chitosan in a solvent
  • adjusting the pH with an acidifying agent adjusting the pH with an acidifying agent
  • preparing a polymer solution by adding glycerol Preparing a reactant by adding and stirring a nitric oxide donor such as s-nitrosoglutathione (hereinafter 'GSNO') to the polymer solution
  • a nitric oxide donor such as s-nitrosoglutathione
  • acetic acid buffer solution may be adjusted to pH 4.0 to pH 6.0 using acetic acid buffer solution of 0.1 M.
  • GSNO When the nitric oxide donor is mixed by maintaining the polymer solution with a weak acid, GSNO may be homogeneously mixed in the polymer solution, and does not affect the stability of the GSNO.
  • the plasticizer may be selected from the group consisting of polyethylene glycol, sorbitol, and glycerol, and the glycerol may increase mechanical properties by increasing solubility of the wound healing film.
  • the nitrogen oxide donor may be added in an amount of 2.5 to 30 parts by weight based on 100 parts by weight of the polymer solution, and then stirred for 10 minutes to 60 minutes, preferably 20 minutes. If the nitrogen oxide donor is added in excess of the content range, phase separation may occur, which may cause problems such as appearance problems and deterioration of mechanical properties.
  • the drying may be dried for 1 to 2 days at 25 to 37 °C. If dried outside the temperature range, problems may occur in film transparency and stability of GSNO.
  • the loading efficiency of the nitric oxide donor is 47%.
  • the loading efficiency of the nitric oxide donor is 20% or less. May be caused.
  • GSNO was synthesized according to a known method (Tetrahedron Lett, 1985; 26: 2013 ?? 6). That is, 1.005 g of reducing L-glutathione (Sigma Adlrich, MO, USA) was dissolved in 2M HCl (Daejung) at 4 ° C to prepare a solution having a final concentration of 0.625 mM. To the solution was added 220.6 mg of sodium nitrate (Sigma Adlrich, Mo., USA) and stirred on an ice bath for 30 minutes. After 40 minutes the solution so obtained was precipitated with cold 80% acetone and stirred for 20 minutes. The stirred solution was centrifuged at 4 ° C., 20,000 g for 30 minutes.
  • the obtained precipitate was centrifuged by adding 20 mL of cold 100% acetone under the same conditions.
  • the obtained precipitate was centrifuged by adding 20 mL of 100% dimethyl ether under the same conditions.
  • the pink powder GSNO thus obtained was lyophilized for 24 hours, stored at ⁇ 20 ° C., and used for later experiments.
  • NO release film was prepared using a solvent evaporation method. That is, chitosan was dissolved in acetone buffer (100 mM) and the pH of the solution was adjusted to 4.4 using acetic acid. Glycerol was added to the chitosan solution to a final concentration of 1% (w / w). 10 mg GSNO was added to the solution and stirred for 20 minutes. The resulting solution was cast in Petri dishes and dried in a dark room at 37 ° C. for 2 days in a dryer equipped with a dehumidifier. The film thus prepared (hereinafter 'CS / NO film') was stored at 7 ° C. under vacuum and stored in the dark until use. At this time, a blank film containing no GSNO was prepared as a control.
  • acetone buffer 100 mM
  • Glycerol was added to the chitosan solution to a final concentration of 1% (w / w). 10 mg GSNO was added to the solution and stirred for 20 minutes.
  • the film was dried under dark and dehumidification conditions to promote evaporation.
  • a reddish, transparent and homogeneous film having a loading efficiency of 47% nitric oxide donor can be obtained.
  • the loading efficiency was less than 20%.
  • polyvinyl alcohol polyvinyl alcohol
  • PVA polyvinyl alcohol
  • MO polyvinyl alcohol
  • a film was prepared by the same process as the CS / NO film (hereinafter 'PVA / NO film').
  • the thickness of the film prepared in Example 2 was measured at five different locations (center and four corners) using a digital outer micrometer (Bluebird Multinational Co.). The average value of five positions was used as the thickness of the film.
  • the average thickness of each of the center and four corners of the blank film and the NO emitting film was 61.2 ⁇ 4.5 ⁇ m and 64.6 ⁇ 8.6 ⁇ m, confirming that the thickness of the film did not change with the addition of GSNO.
  • the surface shape of the CS / NO film prepared in Example 2 was investigated using SEM (FE-SEM, S4800, Hitachi, Japan). A 1.5 x 1.5 cm 2 sample was placed on a double sided carbon tape and coated with platinum for 2 minutes under vacuum. The samples thus prepared were observed under FE-SEM at an acceleration voltage of 1-5 kV.
  • the blank film exhibited a homogeneous and smooth surface shape, and there was no change in the surface shape of the film by the insertion of GSNO.
  • GSNO showed a strong endothermic peak at 195 ° C.
  • chitosan showed a weak endothermic peak compared to GSNO.
  • the endothermic peak of GSNO was not observed in the CS / NO film, and it was confirmed that GSNO completely dissolved in the film and disappeared molecularly. Broad endothermic peaks of both films were observed below 140 ° C., which was due to moisture evaporation.
  • the tensile strength (TS) and elongation at break were evaluated using a tensile tester (Instron 3345, Instron, Norwood, MA).
  • TS tensile strength
  • elongation at break were evaluated using a tensile tester (Instron 3345, Instron, Norwood, MA).
  • the prepared film was cut into specific dogbone shapes (80 mm long, 30 mm wide). All tests were performed at an elongation of 10 mm / min, and the film thickness was measured using a caliper just before the test. Elongation at break (E%) was calculated from the difference between the initial length of the sample (30 mm) and the elongation at break.
  • the elongation at break was not affected by the addition of NO.
  • the blank film was drawn to 134.4 ⁇ 11.5% relative to the original length, but the NO release film was only recorded at 129.9 ⁇ 18.1%.
  • the addition of GSNO reduced the tensile strength and Young's modulus.
  • NO was shown as a first-order exponential graph from the NO emitting film.
  • NO showed a slow release pattern until the first hour and then released according to the first order equation.
  • the initial slow release is due to the time required for the film to hydrate. Since the CS / NO film had to swell for NO to be released, a delay was expected before the NO was released for the first time, and the CS / NO film had to release enough NO during the wound healing period.
  • CS / NO films included CS / NO films containing 20% by weight of GSNO were found to consistently release the highest amount of NO for 48 hours.
  • Figure 4 shows the antimicrobial and anti-biofilm effect of the NO release film for Gram-positive bacteria and Gram-negative bacteria.
  • P. aeruginosa PAO1 wild type prototroph, Peerson et al. , 1997), Staphylococcus aureus strain RN4220 (Kreiswirth et al. , 1983), or Methicillin-resistant Staphylococcus aureus (Methicillin-resistant) Staphylococcus) was used.
  • Staphylococcus aureus was grown overnight with vigorous shaking in 3 mL of LB broth. These cells were seeded on a cover glass of a 12 well plate and incubated in 2 mL LB broth medium containing 2 ⁇ l antibiotic at 37 ° C.
  • the blank film and the CS / NO film were cut to a size of 1.3 cm x 1.3 cm and added to each well.
  • the cover glass was lightly washed with sterile water at predetermined time intervals to remove unstained Staphylococcus aureus, and then observed under a fluorescence microscope.
  • For Pseudomonas aeruginosa 2 mL of a medium containing 25 ⁇ l antibiotic and plasmid inducer were dispensed onto a 12 well plate containing cover glass. 40 ⁇ l Pseudomonas aeruginosa was inoculated onto the cover glass of each well, and then a film was added to each well.
  • the cover glass was lightly washed with sterile water at predetermined time intervals to remove unattached Pseudomonas aeruginosa, and observed with a fluorescence microscope.
  • the medipom ® a PVA / NO film or CS / NO film prepared in Example 2 (Mundie Pharma, control group), each wound were applied. Each material was applied and then fixed using an elastic adhesive tape (Micropore, 3M Consumer Health Care, St Paul, MN, USA). All dressings treated on wound lesions were replaced with new ones at appropriate times.
  • Epithelialization rate (%) E t / (W t + W 0 ) x 100
  • Figure 5 shows the macroscopic observation results according to the temporary change after surgery, very severe inflammation was observed in the film except the CS / NO film on the fourth day of surgery, while the CS / NO film was confirmed that the wound is closed very quickly .
  • Figure 6 shows the wound size reduction effect according to the application of the NO release film, CS / NO film showed a significantly faster wound healing effect compared to Medifoam confirmed that the wound almost healed after 10 days.
  • Another NO-releasing film, PVA / NO film showed a faster healing effect than Mediform, but showed a slower healing effect than CS / NO film.
  • Figure 7 shows the rate of epithelialization
  • CS / NO film applied wounds showed epithelialization at a faster rate than the Mediform control on the fourth day of surgery, in particular, wounds with CS / NO releasing film applied epithelialization at the fastest rate.
  • the wounds with CS / NO releasing film after 7 to 10 days post surgery showed epithelialization at a higher rate compared to wounds with Mediform control.
  • the NO release film showed better wound healing ability
  • the CS / NO film using chitosan as a substrate showed a better healing effect than the PVA / NO film using PVA as a substrate.
  • the results show that chitosan has excellent ability to encapsulate NO and release it stably, and the antibacterial action and wound healing action of chitosan itself have led to synergy.
  • the epithelial skin was peeled off using a computer equipped with an automated digital image analyzer (i Solution FL ver 9.1, IMT i- solution Inc., Quebec, Canada) on each of the cross-cut skin samples.
  • Eight wounds from each experimental group were analyzed by a histopathologist to perform a blind test.
  • the re-epithelialization rate was calculated by changing a previously known method (Biol Pharm Bull 2007 Dec; 30 (12): 2406-2411).
  • Re-epithelialization rate (%) [total length of wound (10mm)-bare epithelial area (mm)] / wound total length X 100
  • the histopathological findings are shown in FIGS. 8 and 2, and histopathological and histological measurements were significantly reduced in epithelial tissues peeled from the film-applied experimental group, and the re-epithelialization rate was significantly increased in the film-applied experimental group.
  • the NO release film application group showed significantly faster wound healing effects than the blank film or gauze application, and showed rapid reconstruction of granulation tissue, lower inflammatory cell infiltration and lower angiogenesis.
  • NO release film in the experimental group significantly accelerated collagen fiber regeneration.

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Abstract

L'invention concerne un film de traitement de plaie à libération d'oxyde d'azote et son procédé de préparation. Le film à libération d'oxyde d'azote contenant de la S-nitroglutathione, qui est un agent donneur d'oxyde d'azote formé spontanément dans le corps humain, présente des caractéristiques mécaniques pouvant être appliquées au corps humain, libère lentement l'oxyde d'azote et inhibe un agent pathogène qui est la cause principale de l'infection d'une plaie, et peut rapidement cicatriser une plaie, ce qui permet d'utiliser le film pour traiter une plaie.
PCT/KR2015/001864 2014-02-28 2015-02-26 Film de traitement de plaie à libération d'oxyde d'azote et son procédé de préparation WO2015130096A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US15/122,182 US9861591B2 (en) 2014-02-28 2015-02-26 Nitric oxide-releasing wound treatment film and preparation method therefor
EP15755452.8A EP3120840B1 (fr) 2014-02-28 2015-02-26 Film de traitement de plaie à libération d'oxyde d'azote et son procédé de préparation
CN201580022323.3A CN106456563A (zh) 2014-02-28 2015-02-26 释放一氧化氮的伤口处理膜及其制备方法

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20140024051 2014-02-28
KR10-2014-0024051 2014-02-28
KR1020150026410A KR101555523B1 (ko) 2014-02-28 2015-02-25 산화질소 방출성 상처치료 필름 및 이의 제조방법
KR10-2015-0026410 2015-02-25

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007149520A2 (fr) * 2006-06-21 2007-12-27 Albert Einstein College Of Medicine Of Yeshiva University Compositions de libération prolongée d'oxyde nitrique, leurs méthodes d'élaboration et leurs applications
KR20080037677A (ko) * 2005-08-23 2008-04-30 노랩스 에이비 중합체로부터 산화 질소의 방출을 위한 마이크로캡슐화된양성자 공여체를 포함하는 디바이스, 시스템 및 방법
US20130084336A1 (en) * 2011-06-27 2013-04-04 Albert Einstein College Of Medicine Of Yeshiva University Enhanced nitric oxide delivery and uses thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080037677A (ko) * 2005-08-23 2008-04-30 노랩스 에이비 중합체로부터 산화 질소의 방출을 위한 마이크로캡슐화된양성자 공여체를 포함하는 디바이스, 시스템 및 방법
WO2007149520A2 (fr) * 2006-06-21 2007-12-27 Albert Einstein College Of Medicine Of Yeshiva University Compositions de libération prolongée d'oxyde nitrique, leurs méthodes d'élaboration et leurs applications
US20130084336A1 (en) * 2011-06-27 2013-04-04 Albert Einstein College Of Medicine Of Yeshiva University Enhanced nitric oxide delivery and uses thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
SEABRA, A. B. ET AL.: "Poly (vinyl alcohol) and poly (vinyl pyrrolidone) blended films for local nitric oxide release", BIOMATERIALS, vol. 25, no. 17, 2004, pages 3773 - 3782, XP004496106, ISSN: 0142-9612 *
SEABRA, A. B. ET AL.: "Solid films of blended poly (vinyl alcohol)/poly (vinyl pyrrolidone) for topical S-nitrosoglutathione and nitric oxide release", JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 94, no. 5, 2005, pages 994 - 1003, XP008079458, ISSN: 0022-3549 *

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