WO2024085848A1 - A biocomposite wound dressing with antifungal, anti-inflammatory and antibacterial properties and the production method thereof - Google Patents

A biocomposite wound dressing with antifungal, anti-inflammatory and antibacterial properties and the production method thereof Download PDF

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Publication number
WO2024085848A1
WO2024085848A1 PCT/TR2023/051177 TR2023051177W WO2024085848A1 WO 2024085848 A1 WO2024085848 A1 WO 2024085848A1 TR 2023051177 W TR2023051177 W TR 2023051177W WO 2024085848 A1 WO2024085848 A1 WO 2024085848A1
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Prior art keywords
solution
pla
wound dressing
cbd
wound
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PCT/TR2023/051177
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French (fr)
Inventor
Sevim ALISIR
Ayyuce BAS
Abdurrahman AKSOY
Original Assignee
Ondokuz Mayis Universitesi
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Priority claimed from TR2022/016019 external-priority patent/TR2022016019A1/en
Application filed by Ondokuz Mayis Universitesi filed Critical Ondokuz Mayis Universitesi
Publication of WO2024085848A1 publication Critical patent/WO2024085848A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F13/00—Bandages or dressings; Absorbent pads
    • A61F13/00051—Accessories for dressings
    • A61F13/00063—Accessories for dressings comprising medicaments or additives, e.g. odor control, PH control, debriding, antimicrobic
    • 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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
    • A61L26/0052—Mixtures of macromolecular compounds
    • 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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0057—Ingredients of undetermined constitution or reaction products thereof
    • 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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0061—Use of materials characterised by their function or physical properties
    • A61L26/0066—Medicaments; Biocides
    • 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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0061—Use of materials characterised by their function or physical properties
    • A61L26/0085—Porous materials, e.g. foams or sponges
    • 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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0061—Use of materials characterised by their function or physical properties
    • A61L26/009—Materials resorbable by the body
    • 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
    • A61L2300/102—Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
    • A61L2300/104—Silver, e.g. silver sulfadiazine
    • 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
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/216—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups
    • 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
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/30—Compounds of undetermined constitution extracted from natural sources, e.g. Aloe Vera
    • 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
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
    • 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
    • A61L2400/00—Materials characterised by their function or physical properties
    • A61L2400/12—Nanosized materials, e.g. nanofibres, nanoparticles, nanowires, nanotubes; Nanostructured surfaces

Definitions

  • the invention relates to the biodegradable, antifungal, anti-inflammatory and antibacterial biocomposite wound dressing based on polylactic acid (PLA) comprising cold-pressed hemp seed oil and cannabidiol (CBD) and the production method of this wound dressing by electrospinning method.
  • PLA polylactic acid
  • CBD cannabidiol
  • Wound is the disruption of skin integrity due to various reasons and the inability of living tissue to maintain its structure and function. With the increase in chronic diseases such as diabetes and peripheral vascular diseases in society, the incidence of acute or chronic wounds that disrupt skin integrity has also increased. This situation has enhanced new wound treatment methods and options [1].
  • Wound healing is affected by systemic and local factors. Therefore, for effective wound treatment, the patient should be evaluated in all aspects and treatment planning should be made individually. For the ideal treatment method, applications that allow cell regeneration, do not cause pain to the patient, and ensure recovery in the shortest time should be chosen. Modern wound dressings, which have emerged in parallel with the developing medicine and technology in recent years, have changed the course of treatment positively. Wound dressings that do not stick, retain moisture, prevent odour and are non-toxic are ideal for wound treatment. Applications such as negative pressure wound therapy, hyperbaric oxygen therapy, stem cell therapy, growth factors, topical agents, electrical stimulation, ultrasound, laser, maggot therapy, ozone therapy, and honey are alternative approaches to wound treatment. Positive results have been achieved in chronic wound treatment with these practices that require expertise.
  • wound dressings used vary depending on wound types. Modern wound dressings have an important place in recent years in terms of correct diagnosis and healing of the wound. Today, various wound dressings are used for wounds. The most commonly used wound dressings are alginate dressings, polyurethane films, hydrogel dressings, hydrocolloid dressings and foams [2],
  • Alginate dressings a type of wound dressing, are frequently used, absorbent and have unique ion exchange properties.
  • the ions in the fibre in the alginate dressing replace the sodium ions in the body and some of these fibres turn into alginate, and the fibres that turn into alginate can absorb discharge from the wound 20- 30 times more than their own weight.
  • the fibres in calcium alginate dressings used on the wound swell and a gel forms on the wound surface. This formed hydrophilic alginate gel provides a moist wound environment for wound healing.
  • these calcium alginate dressings can cause moisture damage to healthy tissues if they are not removed immediately when saturated with liquid.
  • Calcium alginate dressings have low antimicrobial effects, and bacteria can be passively trapped in the gel and removed by changing the dressing. Additionally, zinc can be added to alginate dressings to increase their haemostatic properties. In alginate dressings, as connective tissue develops in the wound, the amount of fluid absorbed decreases. When the gel reaches saturation, leakage (bleeding) occurs [3].
  • Polyurethane films are semi-permeable. One side of these films is acrylic, and the other side is polyurethane. In this way, polyurethane films prevent airborne microbes from reaching the wound, while allowing the wound to receive oxygen from the air. Polyurethane films are mostly used on dry wounds and a moist wound environment can be created in dry wounds. Since polyurethane films are transparent, they provide the opportunity to observe the wound area. By means of these films, moisture vapour of 3000 g/m 2 or higher can be provided to the wound in 24 hours. They are light and flexible, have good compatibility with the wound surface, prevent skin damage due to friction, and do not adversely affect the patient's comfort. However, polyurethane films can cause excessive moisture of the skin; and these films have disadvantages such as having to be changed frequently and the need for intact skin around the wound to be applied [4],
  • Hydrogel dressings another type of wound dressing, consist of polymers containing 90- 95% water, absorb wound discharge to a high degree, do not stick to the wound surface, and create a cooling effect by reducing the fever of the wound. Since hydrogel dressings are water and vapour permeable, these dressings can be easily separated from the wound because the moist interface between the dressing and the wound prevents the dressing from adhering to the wound. However, since hydrogel dressings have poor resistance to microbes, these covers require a second dressing for protection. Although hydrogel dressings used today have many of the properties of ideal wound dressings, they can weaken sensitive skin [5].
  • Hydrocolloid dressings another type of wound dressing, consist of dissolved hydrophilic polymer particles. When these dressings come into contact with wound discharge, the hydrophilic particles absorb excess liquid and turn into a gel. They can remain on the wound for 7 days and tend to adhere to both wet and dry tissues. They also increase the rate of epithelisation of the wound and the production of connective tissue. Since they adhere directly to the wound, they do not require a second dressing. It also has properties such as reducing pain and keeping germs out of the wound. While they are used in partial and complete wounds and wounds with mild and moderate discharge, they are not preferred if there is infection. Since they are sticky, they can damage sensitive skin during removal [6].
  • Foams another type of wound dressing, are polymeric and silicone-based wound dressings that are both flexible and have high absorption capacity. These are used combined like sponges. They fill the gaps in deep wounds and expand over time to fully adapt to the wound. They reduce oedema by applying gentle pressure to the wound, increasing wound closure and oxygenation. When placed on a wet wound surface, wound fluid is absorbed into the foam and sent to the other side of the dressing. When placed on a relatively dry wound surface, it reduces moisture vapour loss and prevents the wound surface from drying out. While these covers allow air passage, they are impermeable. They can be easily removed from the wound, but their antimicrobial power is limited. They are used on wounds with dead tissue and moderately leaky wounds. They are not suitable for use on dry and crusty wounds. Extra product is required to reinforce the dressing [7],
  • the patent application EP0630629A1 in the state of the art relates to wound dressings and, more specifically, to a flexible wound dressing product comprising a hydrogel material and preferably a porous layer.
  • the wound dressing product of the invention that is the subject of patent application EP0630629A1 comprises an optional release liner, an optional removable strip and wound dressing.
  • the dressing preferably comprises a thin film layer of polyurethane, an adhesive layer, an optional porous backing layer, an optional support layer, and a hydrogel material.
  • the thin film sheet which may have any suitable shape but is typically rectangular, may have a centre portion and a periphery surrounding the centre portion, in addition to a first side and an opposing second side.
  • the thin film layer may also be transparent.
  • the first side of the thin film forms the outer surface of the dressing product.
  • the thin film layer may be constructed from materials other than polyurethane, such as polyethylene, vinyl, or other suitable materials, and may be perforated throughout to improve the moisture and vapour permeability of the dressing.
  • the wound dressing that is the subject of the patent application no EP0630629A1 comprises hydrogel material, its ability to resist microbes is weak, and therefore this dressing requires a second dressing for protection.
  • the invention describes a biocomposite wound dressing based on polylactic acid (PLA) comprising hemp seed oil and cannabidiol (CBD) with antifungal, anti-inflammatory and antibacterial properties, and the production of this wound dressing by electrospinning method.
  • PHA polylactic acid
  • CBD cannabidiol
  • the dressing that is the subject of the invention comprises polylactic acid, cold- pressed hemp seed oil, cannabidiol (CBD), silver nitrate (AgNOs) and chitosan.
  • the most important aim of the invention is to provide biocompatible and biodegradable wound dressing to be used in the treatment of open wounds that occur on the body for any reason.
  • the wound dressing that is the subject of the invention comprises polylactic acid (PLA).
  • PLA is a biodegradable polymer and by means of this property, it provides biodegradable properties to the wound dressing that is the subject of the invention.
  • PLA turns into lactate through the body's natural metabolism and is thus eliminated without leaving any residue in the tissue.
  • the wound dressing that is the subject of the invention comprises chitosan, which has high biocompatibility and biodegradable properties, as well as PLA. Biocompatible and biodegradable wound dressing is provided by using chitosan with PLA.
  • the wound dressing that is the subject of the invention comprises cold- pressed hemp seed oil.
  • Cold-pressed hemp seed oil is produced by squeezing the seeds of the hemp plant using the cold press method without being exposed to high temperatures.
  • Hemp seeds comprises 80% unsaturated fatty acids.
  • Hemp seed oil is rich in omega-3 (linolenic acid) and omega-6 (linoleic acid). Hemp seed oil increases the healing speed of irritated epidermal tissue or wounds, by means of its high content of unsaturated linoleic acid.
  • the wound dressing that is the subject of the invention is produced by the electrospinning method.
  • a wound dressing comprising a unique and versatile nanofibrous surface is produced.
  • nanofibrous surfaces allow oxygen to pass through the wound and prevent bacterial passage.
  • Nanofibres also exhibit haemostatic properties by means of their high surface areas.
  • the wound dressing of the invention accelerates the healing process of irritated epidermal tissue or wound with its nanofibrous structure.
  • Another aim of the invention is to provide a wound dressing with anti-inflammatory, antiviral and antifungal properties to be used in the treatment of open wounds that occur on the body for any reason.
  • the wound dressing that is the subject of the invention contains cannabidiol (CBD) and silver nitrate (AgNOs).
  • Cannabidiol (CBD) has antiinflammatory properties
  • silver nitrate (AgNOs) has antibacterial and antifungal properties.
  • a wound dressing with anti-inflammatory, antiviral and antifungal properties is provided by using cannabidiol (CBD) and silver nitrate (AgNOs) together.
  • the wound dressing that is the subject of the invention comprises cold-pressed hemp seed oil as well as cannabidiol (CBD) and silver nitrate (AgNOs).
  • Hemp seed oil also provides anti-inflammatory, antiviral and antifungal properties to the wound dressing, by means of the terpene components it contains.
  • a biocompatible and biodegradable wound dressing with antiinflammatory, antiviral and antifungal properties which accelerates the healing process of irritated epidermal tissue or wounds, is provided for use in the treatment of open wounds that occur on the body for any reason.
  • the invention relates to a biocomposite wound dressing based on polylactic acid (PLA) comprising hemp seed oil and cannabidiol (CBD) with antifungal, anti-inflammatory and antibacterial properties, and the production of this wound dressing by electrospinning method.
  • the wound dressing that is the subject of the invention comprises polylactic acid (PLA), cold-pressed hemp seed oil, cannabidiol (CBD), silver nitrate (AgNOs) and chitosan.
  • the wound dressing comprises polylactic acid (PLA) and for 1 unit of PLA by weight;
  • CBD cannabidiol
  • AgNOs silver nitrate
  • the amounts of cold-pressed hemp seed oil, cannabidiol (CBD), silver nitrate (AgNOs) and chitosan in the wound dressing that is the subject of the invention are calculated in proportion to PLA. For this reason, the amounts of cold-pressed hemp seed oil, cannabidiol (CBD), silver nitrate (AgNOs) and chitosan are stated in proportion to 1 unit of PLA by weight.
  • said dressing comprises polylactic acid (PLA) and for 1 unit of PLA by weight, 0.3 units by weight of cold-pressed hemp seed oil, 0.01 units by weight of cannabidiol (CBD), 0.05 units by weight of silver nitrate (AgNO3) and 0.03 units by weight of chitosan, suitable fluidity and viscosity are provided for weaving to obtain fibrous wound dressing.
  • PLA polylactic acid
  • CBD cannabidiol
  • AgNO3 silver nitrate
  • suitable fluidity and viscosity are provided for weaving to obtain fibrous wound dressing.
  • hemp seed oil contains 80% unsaturated fatty acids. Hemp seed oil is also rich in omega-3 (linolenic acid) and omega-6 (linoleic acid). Hemp seed oil increases the healing rate of irritated epidermal tissue due to its high content of unsaturated linoleic acid.
  • hemp seed oil provides anti-inflammatory, antiviral and antifungal properties to the wound dressing of the invention by means of the terpene components it comprises, and provides an effective treatment during the wound healing process.
  • polylactic acid PLA
  • PLA polylactic acid
  • CBD cannabidiol
  • AgNOs silver nitrate
  • Chitosan is used at the rate of 0.03 units for 1 unit of PLA, in addition to PLA, in order to increase the biocompatible and biodegradable properties of the wound dressing.
  • the wound dressing is made more active in the wound healing process, that is, in the repair of damaged skin tissue.
  • the wound dressing that is subject of the invention is produced by the electrospinning method.
  • the most effective method in the production of polymer-based nanofibres is the electrospinning method.
  • Unique and versatile nanofibres are produced using this method.
  • the wound dressing that is the subject of the invention is produced by the electrospinning method, providing a wound dressing comprising unique and versatile nanofibres.
  • the wound dressing allows oxygen to pass through the wound and prevents bacterial passage.
  • the wound dressing also exhibits haemostatic properties.
  • Production method of the wound dressing comprises the process steps of; i. preparing a solution with the chloroform/dimethyl formamide (CHCI3/DMF) binary solvent system and dissolving polylactic acid (PLA) in this solution, ii. mixing the resulting PLA solution, ill. dissolving cannabidiol (CBD) in chloroform (CHCI3) in a separate place, iv. adding the obtained CBD solution to the PLA solution and mixing the CBD-PLA solution, v. preparing chitosan solution by dissolving chitosan in acetic acid:pure water binary solvent system in a separate place, vi.
  • CHCI3/DMF chloroform/dimethyl formamide
  • PDA polylactic acid
  • CBD cannabidiol
  • the chloroform/dimethyl formamide (CHCI3/DMF), chloroform (CHCI3) and acetic acid:pure water solvents used in said method are evaporated in a vacuum oven.
  • the production method of the wound dressing comprises process steps of; i. preparing a solution with a binary solvent system of chloroform :dimethyl formamide (CHCl3:DMF) at a ratio of 1 :2 by volume and dissolving 1 weight unit of polylactic acid (PLA) in this solution, ii. mixing the obtained PLA solution at 25°C for 24 hours, ill. dissolving 0.01 unit of cannabidiol (CBD) in chloroform (CHCI3) in a separate place, iv. adding the obtained CBD solution to the PLA solution and mixing the CBD-PLA solution for 12 hours, v.
  • CBD cannabidiol
  • chitosan solution by dissolving 0.03 units of chitosan by weight compared to PLA in acetic acid:pure water binary solvent system at a ratio of 1 :49 by volume in a separate place, vi. obtaining the final solution by adding the chitosan solution comprising 0.3 unit by weight of cold-pressed hemp seed oil, 0.05 unit by weight of silver nitrate (AgNOs) and 0.03 unit by weight of chitosan, compared to 1 unit of PLA into the CBD-PLA solution obtained in step (iv), vii. obtaining the wound dressing by making nanofibrous weaving into the final solution by electrospinning method, and viii. drying the resulting wound dressing in a vacuum oven.
  • AgNOs silver nitrate
  • chloroform/dimethyl formamide (CHCI3/DMF), chloroform (CHCI3) and acetic acid:pure water solvents used in said method are evaporated in a vacuum oven.
  • the wound dressing that is the subject of the invention has a biofilm structure.
  • the invention provides a biodegradable, antifungal, anti-inflammatory, and antibacterial biocomposite wound dressing based on polylactic acid (PLA) comprising cold-pressed hemp seed oil and cannabidiol (CBD) to be used in the treatment of open wounds that occur on the body for any reason.
  • PLA polylactic acid
  • CBD cannabidiol
  • the wound dressing that is the subject of the invention is a biocompatible wound dressing that protects the wound against bacteria and inflammation and at the same time contributes to the healing process of patients and increases the healing rate of irritated epidermal tissue.

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  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

The invention relates to the biodegradable, antifungal, anti-inflammatory and antibacterial biocomposite wound dressing based on polylactic acid (FLA) comprising cold-pressed hemp seed oil and cannabidiol (CBD) and the production method of this wound dressing by electrospinning method. The dressing that is the subject of the invention comprises polylactic acid, cold-pressed hemp seed oil, cannabidiol (CBD), silver nitrate (AgNOs) and chitosan.

Description

A BIOCOMPOSITE WOUND DRESSING WITH ANTIFUNGAL, ANTIINFLAMMATORY AND ANTIBACTERIAL PROPERTIES AND THE PRODUCTION METHOD THEREOF
Technical Field of the Invention
The invention relates to the biodegradable, antifungal, anti-inflammatory and antibacterial biocomposite wound dressing based on polylactic acid (PLA) comprising cold-pressed hemp seed oil and cannabidiol (CBD) and the production method of this wound dressing by electrospinning method.
State of the Art
Wound is the disruption of skin integrity due to various reasons and the inability of living tissue to maintain its structure and function. With the increase in chronic diseases such as diabetes and peripheral vascular diseases in society, the incidence of acute or chronic wounds that disrupt skin integrity has also increased. This situation has enhanced new wound treatment methods and options [1].
Wound healing is affected by systemic and local factors. Therefore, for effective wound treatment, the patient should be evaluated in all aspects and treatment planning should be made individually. For the ideal treatment method, applications that allow cell regeneration, do not cause pain to the patient, and ensure recovery in the shortest time should be chosen. Modern wound dressings, which have emerged in parallel with the developing medicine and technology in recent years, have changed the course of treatment positively. Wound dressings that do not stick, retain moisture, prevent odour and are non-toxic are ideal for wound treatment. Applications such as negative pressure wound therapy, hyperbaric oxygen therapy, stem cell therapy, growth factors, topical agents, electrical stimulation, ultrasound, laser, maggot therapy, ozone therapy, and honey are alternative approaches to wound treatment. Positive results have been achieved in chronic wound treatment with these practices that require expertise. Wound dressings used vary depending on wound types. Modern wound dressings have an important place in recent years in terms of correct diagnosis and healing of the wound. Today, various wound dressings are used for wounds. The most commonly used wound dressings are alginate dressings, polyurethane films, hydrogel dressings, hydrocolloid dressings and foams [2],
Alginate dressings, a type of wound dressing, are frequently used, absorbent and have unique ion exchange properties. When applied to the wound, the ions in the fibre in the alginate dressing replace the sodium ions in the body and some of these fibres turn into alginate, and the fibres that turn into alginate can absorb discharge from the wound 20- 30 times more than their own weight. The fibres in calcium alginate dressings used on the wound swell and a gel forms on the wound surface. This formed hydrophilic alginate gel provides a moist wound environment for wound healing. However, these calcium alginate dressings can cause moisture damage to healthy tissues if they are not removed immediately when saturated with liquid. Calcium alginate dressings have low antimicrobial effects, and bacteria can be passively trapped in the gel and removed by changing the dressing. Additionally, zinc can be added to alginate dressings to increase their haemostatic properties. In alginate dressings, as connective tissue develops in the wound, the amount of fluid absorbed decreases. When the gel reaches saturation, leakage (bleeding) occurs [3].
Polyurethane films, another type of wound dressing, are semi-permeable. One side of these films is acrylic, and the other side is polyurethane. In this way, polyurethane films prevent airborne microbes from reaching the wound, while allowing the wound to receive oxygen from the air. Polyurethane films are mostly used on dry wounds and a moist wound environment can be created in dry wounds. Since polyurethane films are transparent, they provide the opportunity to observe the wound area. By means of these films, moisture vapour of 3000 g/m2 or higher can be provided to the wound in 24 hours. They are light and flexible, have good compatibility with the wound surface, prevent skin damage due to friction, and do not adversely affect the patient's comfort. However, polyurethane films can cause excessive moisture of the skin; and these films have disadvantages such as having to be changed frequently and the need for intact skin around the wound to be applied [4],
Hydrogel dressings, another type of wound dressing, consist of polymers containing 90- 95% water, absorb wound discharge to a high degree, do not stick to the wound surface, and create a cooling effect by reducing the fever of the wound. Since hydrogel dressings are water and vapour permeable, these dressings can be easily separated from the wound because the moist interface between the dressing and the wound prevents the dressing from adhering to the wound. However, since hydrogel dressings have poor resistance to microbes, these covers require a second dressing for protection. Although hydrogel dressings used today have many of the properties of ideal wound dressings, they can weaken sensitive skin [5].
Hydrocolloid dressings, another type of wound dressing, consist of dissolved hydrophilic polymer particles. When these dressings come into contact with wound discharge, the hydrophilic particles absorb excess liquid and turn into a gel. They can remain on the wound for 7 days and tend to adhere to both wet and dry tissues. They also increase the rate of epithelisation of the wound and the production of connective tissue. Since they adhere directly to the wound, they do not require a second dressing. It also has properties such as reducing pain and keeping germs out of the wound. While they are used in partial and complete wounds and wounds with mild and moderate discharge, they are not preferred if there is infection. Since they are sticky, they can damage sensitive skin during removal [6].
Foams, another type of wound dressing, are polymeric and silicone-based wound dressings that are both flexible and have high absorption capacity. These are used combined like sponges. They fill the gaps in deep wounds and expand over time to fully adapt to the wound. They reduce oedema by applying gentle pressure to the wound, increasing wound closure and oxygenation. When placed on a wet wound surface, wound fluid is absorbed into the foam and sent to the other side of the dressing. When placed on a relatively dry wound surface, it reduces moisture vapour loss and prevents the wound surface from drying out. While these covers allow air passage, they are impermeable. They can be easily removed from the wound, but their antimicrobial power is limited. They are used on wounds with dead tissue and moderately leaky wounds. They are not suitable for use on dry and crusty wounds. Extra product is required to reinforce the dressing [7],
The patent application EP0630629A1 in the state of the art relates to wound dressings and, more specifically, to a flexible wound dressing product comprising a hydrogel material and preferably a porous layer. The wound dressing product of the invention that is the subject of patent application EP0630629A1 comprises an optional release liner, an optional removable strip and wound dressing. The dressing preferably comprises a thin film layer of polyurethane, an adhesive layer, an optional porous backing layer, an optional support layer, and a hydrogel material. The thin film sheet, which may have any suitable shape but is typically rectangular, may have a centre portion and a periphery surrounding the centre portion, in addition to a first side and an opposing second side. The thin film layer may also be transparent. When the dressing is applied to the wound, the first side of the thin film forms the outer surface of the dressing product. Alternatively, the thin film layer may be constructed from materials other than polyurethane, such as polyethylene, vinyl, or other suitable materials, and may be perforated throughout to improve the moisture and vapour permeability of the dressing. However, since the wound dressing that is the subject of the patent application no EP0630629A1 comprises hydrogel material, its ability to resist microbes is weak, and therefore this dressing requires a second dressing for protection.
Due to disadvantages such as the facts that if the wound dressings in the state of the art are not removed immediately when they become saturated with fluid, they cause excessive moisture in the skin and thus moisture damage in healthy tissues, requirie a second dressing due to their weak resistance to microbes, they have low antimicrobial effects, cause leakage (bleeding), weaken the skin, and cause both product waste and economic waste due to the necessity of frequent replacement, it has become necessary to develop a biodegradable, antifungal, anti-inflammatory and antibacterial biocomposite wound dressing in the relevant field. Brief Description and Aims of the Invention
The invention describes a biocomposite wound dressing based on polylactic acid (PLA) comprising hemp seed oil and cannabidiol (CBD) with antifungal, anti-inflammatory and antibacterial properties, and the production of this wound dressing by electrospinning method. The dressing that is the subject of the invention comprises polylactic acid, cold- pressed hemp seed oil, cannabidiol (CBD), silver nitrate (AgNOs) and chitosan.
The most important aim of the invention is to provide biocompatible and biodegradable wound dressing to be used in the treatment of open wounds that occur on the body for any reason. The wound dressing that is the subject of the invention comprises polylactic acid (PLA). PLA is a biodegradable polymer and by means of this property, it provides biodegradable properties to the wound dressing that is the subject of the invention. PLA turns into lactate through the body's natural metabolism and is thus eliminated without leaving any residue in the tissue. The wound dressing that is the subject of the invention comprises chitosan, which has high biocompatibility and biodegradable properties, as well as PLA. Biocompatible and biodegradable wound dressing is provided by using chitosan with PLA.
Another aim of the invention is to accelerate the healing process of irritated epidermal tissue or wound. The wound dressing that is the subject of the invention comprises cold- pressed hemp seed oil. Cold-pressed hemp seed oil is produced by squeezing the seeds of the hemp plant using the cold press method without being exposed to high temperatures. Hemp seeds comprises 80% unsaturated fatty acids. Hemp seed oil is rich in omega-3 (linolenic acid) and omega-6 (linoleic acid). Hemp seed oil increases the healing speed of irritated epidermal tissue or wounds, by means of its high content of unsaturated linoleic acid. In addition, the wound dressing that is the subject of the invention is produced by the electrospinning method. Using this method, a wound dressing comprising a unique and versatile nanofibrous surface is produced. With their large surface areas and porous structures, nanofibrous surfaces allow oxygen to pass through the wound and prevent bacterial passage. Nanofibres also exhibit haemostatic properties by means of their high surface areas. The wound dressing of the invention accelerates the healing process of irritated epidermal tissue or wound with its nanofibrous structure.
Another aim of the invention is to provide a wound dressing with anti-inflammatory, antiviral and antifungal properties to be used in the treatment of open wounds that occur on the body for any reason. The wound dressing that is the subject of the invention contains cannabidiol (CBD) and silver nitrate (AgNOs). Cannabidiol (CBD) has antiinflammatory properties, and silver nitrate (AgNOs) has antibacterial and antifungal properties. In the invention, a wound dressing with anti-inflammatory, antiviral and antifungal properties is provided by using cannabidiol (CBD) and silver nitrate (AgNOs) together. In addition, the wound dressing that is the subject of the invention comprises cold-pressed hemp seed oil as well as cannabidiol (CBD) and silver nitrate (AgNOs). Hemp seed oil also provides anti-inflammatory, antiviral and antifungal properties to the wound dressing, by means of the terpene components it contains.
With the invention, a biocompatible and biodegradable wound dressing with antiinflammatory, antiviral and antifungal properties, which accelerates the healing process of irritated epidermal tissue or wounds, is provided for use in the treatment of open wounds that occur on the body for any reason.
Detailed Description of the Invention
The invention relates to a biocomposite wound dressing based on polylactic acid (PLA) comprising hemp seed oil and cannabidiol (CBD) with antifungal, anti-inflammatory and antibacterial properties, and the production of this wound dressing by electrospinning method. The wound dressing that is the subject of the invention comprises polylactic acid (PLA), cold-pressed hemp seed oil, cannabidiol (CBD), silver nitrate (AgNOs) and chitosan.
In a preferred embodiment of the invention the wound dressing comprises polylactic acid (PLA) and for 1 unit of PLA by weight;
• 0.3 units by weight of cold-pressed hemp seed oil, • 0.01 units by weight of cannabidiol (CBD),
• 0.05 units by weight of silver nitrate (AgNOs) and
• 0.03 units by weight of chitosan.
The amounts of cold-pressed hemp seed oil, cannabidiol (CBD), silver nitrate (AgNOs) and chitosan in the wound dressing that is the subject of the invention are calculated in proportion to PLA. For this reason, the amounts of cold-pressed hemp seed oil, cannabidiol (CBD), silver nitrate (AgNOs) and chitosan are stated in proportion to 1 unit of PLA by weight.
By means of the fact that said dressing comprises polylactic acid (PLA) and for 1 unit of PLA by weight, 0.3 units by weight of cold-pressed hemp seed oil, 0.01 units by weight of cannabidiol (CBD), 0.05 units by weight of silver nitrate (AgNO3) and 0.03 units by weight of chitosan, suitable fluidity and viscosity are provided for weaving to obtain fibrous wound dressing.
In the wound dressing that is the subject of the invention, 0.3 units of cold-pressed hemp seed oil is used for 1 unit of PLA. Hemp seed oil contains 80% unsaturated fatty acids. Hemp seed oil is also rich in omega-3 (linolenic acid) and omega-6 (linoleic acid). Hemp seed oil increases the healing rate of irritated epidermal tissue due to its high content of unsaturated linoleic acid. In addition, hemp seed oil, provides anti-inflammatory, antiviral and antifungal properties to the wound dressing of the invention by means of the terpene components it comprises, and provides an effective treatment during the wound healing process.
By means of the use of polylactic acid (PLA) in the invention, biocompatible and biodegradable wound dressing is provided. Polylactic acid (PLA) is a versatile, biodegradable, aliphatic polyester derived from 100% renewable resources such as corn and sugar beets. PLA turns into lactate through the body's natural metabolism and is thus eliminated without leaving any residue in the tissue.
In order to increase the wound healing and anti-inflammatory properties of the wound dressing that is the subject of the invention, cannabidiol (CBD) is used as a pure isolate at the rate of 0.01 units for 1 unit of PLA. Silver nitrate (AgNOs) is used at 0.05 units per unit PLA to provide antibacterial and antifungal properties to the wound dressing.
Chitosan, on the other hand, is used at the rate of 0.03 units for 1 unit of PLA, in addition to PLA, in order to increase the biocompatible and biodegradable properties of the wound dressing. In addition, by means of the combined use of chitosan and cannabidiol (CBD), the wound dressing is made more active in the wound healing process, that is, in the repair of damaged skin tissue.
The wound dressing that is subject of the invention is produced by the electrospinning method. The most effective method in the production of polymer-based nanofibres is the electrospinning method. Unique and versatile nanofibres are produced using this method. The wound dressing that is the subject of the invention is produced by the electrospinning method, providing a wound dressing comprising unique and versatile nanofibres. By means of its nanofibrous structure, the wound dressing allows oxygen to pass through the wound and prevents bacterial passage. In addition, by means of its nanofibrous structure and high surface area, the wound dressing also exhibits haemostatic properties.
Production method of the wound dressing that is the subject of the invention comprises the process steps of; i. preparing a solution with the chloroform/dimethyl formamide (CHCI3/DMF) binary solvent system and dissolving polylactic acid (PLA) in this solution, ii. mixing the resulting PLA solution, ill. dissolving cannabidiol (CBD) in chloroform (CHCI3) in a separate place, iv. adding the obtained CBD solution to the PLA solution and mixing the CBD-PLA solution, v. preparing chitosan solution by dissolving chitosan in acetic acid:pure water binary solvent system in a separate place, vi. obtaining the final solution by adding cold-pressed hemp seed oil, silver nitrate (AgNOs) and chitosan solution into the CBD-PLA solution obtained in step (iv), vii. obtaining the wound dressing by making nanofibrous weaving into the final solution by electrospinning method, and viii. drying the resulting wound dressing in a vacuum oven. The chloroform/dimethyl formamide (CHCI3/DMF), chloroform (CHCI3) and acetic acid:pure water solvents used in said method are evaporated in a vacuum oven.
In the preferred embodiment of the invention, the production method of the wound dressing that is the subject of the invention comprises process steps of; i. preparing a solution with a binary solvent system of chloroform :dimethyl formamide (CHCl3:DMF) at a ratio of 1 :2 by volume and dissolving 1 weight unit of polylactic acid (PLA) in this solution, ii. mixing the obtained PLA solution at 25°C for 24 hours, ill. dissolving 0.01 unit of cannabidiol (CBD) in chloroform (CHCI3) in a separate place, iv. adding the obtained CBD solution to the PLA solution and mixing the CBD-PLA solution for 12 hours, v. preparing chitosan solution by dissolving 0.03 units of chitosan by weight compared to PLA in acetic acid:pure water binary solvent system at a ratio of 1 :49 by volume in a separate place, vi. obtaining the final solution by adding the chitosan solution comprising 0.3 unit by weight of cold-pressed hemp seed oil, 0.05 unit by weight of silver nitrate (AgNOs) and 0.03 unit by weight of chitosan, compared to 1 unit of PLA into the CBD-PLA solution obtained in step (iv), vii. obtaining the wound dressing by making nanofibrous weaving into the final solution by electrospinning method, and viii. drying the resulting wound dressing in a vacuum oven.
The chloroform/dimethyl formamide (CHCI3/DMF), chloroform (CHCI3) and acetic acid:pure water solvents used in said method are evaporated in a vacuum oven.
The wound dressing that is the subject of the invention has a biofilm structure. The invention provides a biodegradable, antifungal, anti-inflammatory, and antibacterial biocomposite wound dressing based on polylactic acid (PLA) comprising cold-pressed hemp seed oil and cannabidiol (CBD) to be used in the treatment of open wounds that occur on the body for any reason. The wound dressing that is the subject of the invention is a biocompatible wound dressing that protects the wound against bacteria and inflammation and at the same time contributes to the healing process of patients and increases the healing rate of irritated epidermal tissue.
a Urnki.voergrs. titre/tsr/ip Suabg/gliukm Builsimsalegrbi i Dl/eisrsguisei/5 , 086 (548)/ ,5448013-34694 . Retrieved from https ://derg ip
REFERENCES
[1] Yara A/ec//r? (n.d.). Sagligim, “Tek Tikla Bilgi Elinde.” Retrieved October 12, 2022, from https://sagligim.gov.tr/yaralanmalarda-ilk-yardim/yara-nedir.html
[2] Kurtoglu, A. H. & Karata§, A. (2009). CURRENT APPROACHES TO WOUND
THERAPY: MODERN WOUND DRESSINGS . Journal of Faculty of Pharmacy of Ankara University , 38 (3) , 211 -232 . DOI: 10.1501 /Eczfak_0000000562
[3] Mutlu, S. & Yilmaz, E. (2019). Yara Yonetiminde Yenilik i Yakla§imlar . Gumu§hane
[4] Kdytepe, S., Ate§, B., Karaca Agan, I., & Ozcan, I. (n.d.). Poliuretan Temelli Yara Ortu
Malzemeleri. ResaerchGate. Retrieved October 12, 2022, from https://www.researchgate.net/publication/351736697_Poliuretan_Temelli_Yara_O rtu_Malzemeleri
[5] Hidrojel Temelli Yara Ortulerinde Kullamlan Dogal Biyopolimerler. (n.d.). Retrieved
October 12, 2022, from http://www.plastik-ambalaj.com/tr/plastik-ambalaj- makale/3135-hidrojel-temelli-yara-oertuelerinde-kullan-lan-dogal-biyopolimerler
[6] Medikal Portali. (2019, February 16). Suprasorb ® H Hidrokolloid Yara Ortusu.
Retrieved October 12, 2022, from https://www.medikalportali.net/yatan-hasta-yara- bakim-urunleri-ortuleri-hidrokolloid-suprasorb-h-nedir-ne-ise-yarar-neden-nasil- kullanilir-fiyatlari-nereden-nasil-satin-alinir/
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Claims

CLAIMS Production method of a biocomposite wound dressing with antifungal, antiinflammatory and antibacterial properties comprising polylactic acid (PLA), cold- pressed hemp seed oil, cannabidiol (CBD), silver nitrate (AgNOs) and chitosan, comprising the process steps of: i. preparing a solution with the chloroform/dimethyl formamide (CHCI3/DMF) binary solvent system and dissolving polylactic acid (PLA) in this solution, ii. mixing the resulting PLA solution, ill. dissolving cannabidiol (CBD) in chloroform (CHCI3) in a separate place, iv. adding the obtained CBD solution to the PLA solution and mixing the CBD- PLA solution, v. preparing chitosan solution by dissolving chitosan in acetic acid:pure water binary solvent system in a separate place, vi. obtaining the final solution by adding cold-pressed hemp seed oil, silver nitrate (AgNOs) and chitosan solution into the CBD-PLA solution obtained in step (iv), vii. obtaining the wound dressing by making nanofibrous weaving into the final solution by electrospinning method, and viii. drying the resulting wound dressing in a vacuum oven. A production method according to claim 1 , comprising the process steps of: i. preparing a solution with a binary solvent system of chloroforrmdimethyl formamide (CHCl3:DMF) at a ratio of 1 :2 by volume and dissolving 1 weight unit of polylactic acid (PLA) in this solution, ii. mixing the obtained PLA solution at 25°C for 24 hours, ill. dissolving 0.01 unit of cannabidiol (CBD) in chloroform (CHCI3) in a separate place, iv. adding the obtained CBD solution to the PLA solution and mixing the CBD- PLA solution for 12 hours, v. preparing chitosan solution by dissolving 0.03 units of chitosan by weight compared to PLA in acetic acid:pure water binary solvent system at a ratio of 1 :49 by volume in a separate place, vi. obtaining the final solution by adding the chitosan solution comprising 0.3 unit by weight of cold-pressed hemp seed oil, 0.05 unit by weight of silver nitrate (AgNOs) and 0.03 unit by weight of chitosan, compared to 1 unit of PLA into the CBD-PLA solution obtained in step (iv), vii. obtaining the wound dressing by making nanofibrous weaving into the final solution by electrospinning method, and viii. drying the resulting wound dressing in a vacuum oven. Biocomposite wound dressing with antifungal, anti-inflammatory and antibacterial properties produced from nanofibres by a method according to claim 1 or 2. A wound dressing according to claim 3, wherein it has a porous biofilm structure. A wound dressing according to claims 3 or 4 for use in the treatment of open wounds.
PCT/TR2023/051177 2022-10-21 2023-10-20 A biocomposite wound dressing with antifungal, anti-inflammatory and antibacterial properties and the production method thereof WO2024085848A1 (en)

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