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WO2025099040A1 - Tubes ou enveloppes électro-filés à couche interne fonctionnalisée à des fins de croissance nerveuse - Google Patents

Tubes ou enveloppes électro-filés à couche interne fonctionnalisée à des fins de croissance nerveuse Download PDF

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Publication number
WO2025099040A1
WO2025099040A1 PCT/EP2024/081291 EP2024081291W WO2025099040A1 WO 2025099040 A1 WO2025099040 A1 WO 2025099040A1 EP 2024081291 W EP2024081291 W EP 2024081291W WO 2025099040 A1 WO2025099040 A1 WO 2025099040A1
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WO
WIPO (PCT)
Prior art keywords
electro
spun
pcl
nhs
wrap
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/EP2024/081291
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English (en)
Inventor
Mahrokh Dadsetan
John TIPTON
Gianluigi LUPPI
Ryan Lawson
Ethan MCCARTHY
Jian-feng ZHANG
Marshall Scott Jones
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Evonik Operations GmbH
Original Assignee
Evonik Operations GmbH
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Filing date
Publication date
Application filed by Evonik Operations GmbH filed Critical Evonik Operations GmbH
Publication of WO2025099040A1 publication Critical patent/WO2025099040A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • 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
    • A61L27/28—Materials for coating prostheses
    • A61L27/34—Macromolecular materials
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
    • A61N1/00—Electrotherapy; Circuits therefor
    • A61N1/18—Applying electric currents by contact electrodes
    • A61N1/20—Applying electric currents by contact electrodes continuous direct currents
    • A61N1/205—Applying electric currents by contact electrodes continuous direct currents for promoting a biological process
    • 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
    • A61L2420/00—Materials or methods for coatings medical devices
    • A61L2420/08—Coatings comprising two or more layers
    • 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
    • A61L2430/32—Materials or treatment for tissue regeneration for nerve reconstruction

Definitions

  • Electro-spun tubes or wraps with functionalized inner layer for nerve growth are Electro-spun tubes or wraps with functionalized inner layer for nerve growth
  • the present invention refers to an electro-spun multilayer tube or wrap to protect or bridge damaged nerve comprising an electro-spun isolating outer layer comprising at least one polymer selected from poly(caprolactone), polylactide, polyglycolide, poly(trimethylene carbonate), poly(dioxanone), polyethylene glycol, polyurethane, their copolymers or mixtures thereof and at least one electro-spun inner layer comprising a reagent which is able to undergo covalent bonds with proteins and peptides, which comprises at least one group selected from N-hydroxy succinimide, maleimide, sulfur-NHS and biotin-NHS, isocyanate, or aldehydes.
  • the present invention refers to methods of manufacturing such tubes or wraps as well as their use in protecting or bridging nerves or to stimulate nerve growth and cell proliferation.
  • This invention refers to an electro-spun nerve conduit made from a specific polymer, e.g., polycaprolactone (PCL) with an inner layer comprising a specific reagent, which can for example be functionalized using N-hydroxy succinimide (NHS).
  • PCL-PEG-NHS is a biocompatible amphiphilic polymer, where hydrophobic PCL is chemically bonded to hydrophilic PEG, which is bounded to NHS.
  • the polymer forms micelles with NHS ester migrating to the surface to react with amine nucleophiles from proteins or hydrolyze into hydroxy acid.
  • Succinimides like ethosuximide, are primarily used to treat absence seizures by reducing nerve transmission in the brain, stabilizing neuronal activity.
  • Some succinimides have shown potential in protecting neurons from damage, which could be beneficial in preventing neurodegenerative diseases, possibly due to their ability to modulate ion channels and neurotransmitter systems, for example disclosed in Zefeng Zhao , Jiangxin Yue , Xiaotong Ji , Meng Nian, Kaiwen Kang, Haifa Qiao, Xiaohui Zheng, Bioorganic Chemistry 2021 , 108 104557.
  • N-hydroxysuccinimide (NHS) moieties stimulates axonal growth by migrating to the surface, in contrast to the findings of Kamil Rahme and Nazih Dagher, Pharmaceutics 2019, 11 , 327.
  • NHS N-hydroxysuccinimide
  • DRG dorsal root ganglion
  • the present invention refers to an electro-spun multilayer tube or wrap, to preferably protect or bridge damaged nerve, comprising or consisting of i) an electro-spun isolating outer layer comprising at least one polymer selected from poly(caprolactone), polylactide, polyglycolide, poly(trimethylene carbonate), poly(dioxanone), polyethylene glycol, polyurethane, their copolymers or mixtures thereof; and ii) at least one electro-spun inner layer comprising a reagent which is able to undergo covalent bonds with proteins and peptides and preferably stimulate neurite outgrowth, which comprises at least one group selected from N-hydroxy succinimide, maleimide, sulfur-NHS and biotin-NHS, carboxylic acids or aldehydes.
  • an electro-spun isolating outer layer comprising at least one polymer selected from poly(caprolactone), polylactide, polyglycolide, poly(trimethylene carbonate), poly(dioxan
  • the present invention refers to a method of manufacturing a multilayer tube or wrap according to the present invention comprising or consisting of the following steps: i) preparing a physical blend of at least one polymer selected from poly(caprolactone), polylactide, polyglycolide, poly(trimethylene carbonate), poly(dioxanone), polyethylene glycol, and polyurethane with N-hydroxy succinimide ester or its copolymers thereof, preferably polycaprolactone and N-hydroxy succinimide ester more preferably poly(ethylene glycol)-b-poly(e- caprolactone) (PCL-PEG-NHS) at a weight ratio ranging 65:35 to 35:65; ii) PCL-PEG-NHS consists of PCL blocks of 2000 to 8000 g/mol Mn number average molecular weight, preferably 5,000 g/mol Mn number average molecular weight and PEG block of 200 to 10000 g/mol, preferably 5,000 g/
  • the present invention refers to the use of the electro-spun multilayer tube or wrap according to the present invention for protecting or bridging nerves or to stimulate nerve growth and cell proliferation.
  • Fig 1 Shows a scanning electron micrograph of a PCL and PCL-PEG-NHS scaffolds spun from hexafluoro isopropanol (HFIP).
  • HFIP hexafluoro isopropanol
  • DRG Dorsal root ganglion
  • the conjunctive term “or” includes any and all combinations of one or more listed elements associated by the conjunctive term.
  • the phrase “an apparatus comprising A or B” may refer to an apparatus including A where B is not present, an apparatus including B where A is not present, or an apparatus where both A and B are present.
  • the phrases “at least one of A, B, . . . and N” or “at least one of A, B, . . . N, or combinations thereof’ are defined in the broadest sense to mean one or more elements selected from the group comprising A, B, . . . and N, that is to say, any combination of one or more of the elements A, B, . . . or N including any one element alone or in combination with one or more of the other elements which may also include, in combination, additional elements not listed.
  • the modifier “about” used in connection with a quantity is inclusive of the stated value and has the meaning dictated by the context (for example, it includes at least the degree of error associated with the measurement of the particular quantity).
  • the modifier “about” should also be considered as disclosing the range defined by the absolute values of the two endpoints.
  • the expression “from about 2 to about 4” also discloses the range “from 2 to 4”.
  • the term “about” may refer to plus or minus 10% of the indicated number.
  • “about 10%” may indicate a range of 9% to 11%
  • “about 1” may mean from 0.9-1 .1 .
  • Other meanings of “about” may be apparent from the context, such as rounding off, so, for example “about 1 ” may also mean from 0.5 to 1 .4.
  • wt% means weight percent
  • w/w means weight per weight.
  • the term “degradation” refers to polymers that dissolve or degrade in vitro or in vivo within a period of time that is acceptable in a particular therapeutic situation. Such dissolved or degraded product may include a smaller chemical species. Degradation can result, for example, by enzymatic, chemical and/or physical processes. Biodegradation takes typically less than five years and usually less than one year after exposure to a physiological pH and temperature, such as a pH ranging from 6 to 9 and a temperature ranging from 22 °C to 40 °C. Sample characterization was performed using standard test machines. SEM was performed on a desktop machine (commercially available from the company Hitachi). Mechanical data were performed on a standard Instron Mechanical Tester and a dynamic mechanical analyzer commercially available from TA Instruments.
  • Polymeric tube/sheets were electro-spun on an electrospinner commercially available from the company Tongli.
  • An electro-spun multilayer tube or wrap to preferably protect or bridge damaged nerve, comprising or consisting of i) an electro-spun isolating outer layer comprising at least one polymer selected from poly(caprolactone), polylactide, polyglycolide, poly(trimethylene carbonate), poly(dioxanone), polyethylene glycol, polyurethane, their copolymers or mixtures thereof, preferably poly(caprolactone); and ii) at least one electro-spun inner layer comprising a reagent which is able to undergo covalent bonds with proteins and peptides and preferably stimulate neurite outgrowth, including but not limited to N-hydroxy succinimide, maleimide, sulfur-NHS and biotin-NHS, carboxylic acid, or aldehydes.
  • an electro-spun isolating outer layer comprising at least one polymer selected from poly(caprolactone), polylactide, polyglycolide, poly(trimethylene carbonate), poly(dioxan
  • the ratio of inner layer to outer layer thickness is in a range of 1 :1 to 1 :20, preferably in a range of 1 :1 to 1 :10, and more preferably in a range of 1 :1 to 1 :5.
  • the electro-spun layers have a fibrous structure with fibres diameters ranging 0.1 to 2 pm.
  • the tube or wrap has a tensile strength of from 0.2 to 20 MPa, preferably 0.5 to 5 MPa; and/or has an elastic modulus ranging of from 0.2 to 100 MPa, preferably 0.2 to 20 MPa, and/or has a thickness of from 0.1 to 1 mm preferably 0.5 mm.
  • the tube has a nanofibrous structure and has an average diameter of 2 to 6 mm; and/or a length of 3 to 25 cm, preferably 3 to 10 cm; and/or a thickness ranging of from 0.1 to 1 mm preferably 0.5 mm.
  • the reagent of the at least one electro-spun inner layer comprises PCL-PEG-NHS, which preferably consists of PCL blocks of 2000 to 8000 g/mol Mn number average molecular weight, preferably 5,000 g/mol Mn number average molecular weight and PEG block of 200 to 10000 g/mol, preferably 5,000 g/mol Mn number average molecular weight.
  • the tube or wrap is semi-permeable.
  • the present invention refers to a method of manufacturing a multilayer tube or wrap according to the present invention comprising or consisting of the following steps: i) preparing a physical blend of at least one polymer selected from poly(caprolactone), polylactide, polyglycolide, poly(trimethylene carbonate), poly(dioxanone), polyethylene glycol, polyurethane, with N-hydroxy succinimide ester or its copolymers thereof, preferably polycaprolactone and N- hydroxy succinimide ester preferably poly(ethylene glycol)-b-poly(e-caprolactone) (PCL-PEG- NHS) at a weight ratio ranging 65:35 to 35:65; ii) PCL-PEG-NHS consists of PCL blocks of 2000 to 8000 g/mol Mn number average molecular weight, preferably 5,000 g/mol Mn number average molecular weight and PEG block of 200 to 10000 g
  • the present invention refers to the use of the electro-spun multilayer tube or wrap according to the present invention for protecting or bridging nerves or to stimulate nerve growth and cell proliferation.
  • HFIP hexafluroisopropanol
  • the internal layer was made using the PCI/PCI-PEG-NHS solution using a positive voltage of 6.6 kV, at a 20 ga stainless steel needle tip and a negative voltage of -1.2 kV on a rotating collector.
  • the second syringe channel was activated with the PCL solution and set to a flow rate of 0.4 mL/hr.
  • the flow rate of the PCI/PCI-PEG-NHS solution was reduced to 0.4 mL/hr and the voltage was increased to 22.2 kV.
  • the flow of the PCI/PCI-PEG-NHS solution was stopped and the flow rate of the PCL solution was increased to 0.75 mL/hr. Spinning continued for an additional 2.5 mL.
  • the SEM images of PCL and PCL/PCL-PEG-NHS are shown in Figure 1 .
  • the images reveal slight morphological differences, which could be attributed to variations in electrical properties or jet stability during spinning.
  • the surface of the electrospun sheet was characterized using X-ray photoelectron spectroscopy (XPS), as shown in Figure 2.
  • XPS X-ray photoelectron spectroscopy
  • the oxygen content in the PCL/PCL-PEG-NHS samples was higher than in the unmodified PCL samples, due to the presence of additional oxygen bonds from the polyethylene glycol (PEG) linker polymer. This suggests surface migration of the PEG and NHS moieties, influencing surface properties and nerve cell behavior.
  • the resulting sheet was used for cell culture studies to assess nerve outgrowth.
  • DRG Dorsal root ganglion
  • Mouse tissue was resuspended and triturated in culture media consisting of Neurobasal medium supplemented with 2% v/v B27 supplement, 1 % v/v N2 supplement, 1 % v/v GlutaMAX, nerve growth factor 2.5S native mouse protein (20 ng/ml), recombinant human/murine/rat brain-derived neurotrophic factor (10 ng/ml; PeproTech, Cranbury, NJ, USA), recombinant human glial cell-derived neurotrophic factor (10 ng/ml; PeproTech), and 1 % v/v antibiotic/antimycotic solution (all from Thermo Fisher Scientific, Waltham, MA, unless otherwise noted).
  • Neurobasal medium supplemented with 2% v/v B27 supplement, 1 % v/v N2 supplement, 1 % v/v GlutaMAX
  • nerve growth factor 2.5S native mouse protein (20 ng/ml
  • recombinant human/murine/rat brain-derived neurotrophic factor (10 ng
  • This solution was aspirated and a Matrigel solution was added at a 1 :100 dilution in Neurobasal (ESC-qualified; Corning). This was allowed to incubate at 37°C in a humidified incubator for a minimum of 3h. Once all substrates were prepared, they were placed in minimal cell culture media (described Above) and a single DRG spheroid was placed in the middle. These were allowed to adhere for 2h prior to the addition of more media.
  • Neurite-J uses a modified Sholl analysis approach that generates concentric circles around a central organoid/organotypic culture. Samples were analyzed with a distance interval of 25pm and were thresholded using the same values for p3-tubulin stained neurites. Values obtained from Neurite-J included an intersection profile (number of intersections at each distance interval), Nmax (maximum number of intersections), and Critical Value (RC, the distance where the maximum number of intersections occurred) were recorded for each condition.
  • Figure 3 illustrates p3 Tubulin-stained neurites on various specimens.
  • p3-Tubulin serves as a neuronal marker, confirming and visualizing neurite outgrowth and highlighting network extensions on modified surfaces.
  • Figure 4 quantifies neurite outgrowth using Imaged analysis.
  • the data shows a significant enhancement in neurite intersections on PCL/PCL-PEG-NHS surfaces compared to unmodified PCL.
  • the modified PCL exhibited a 16% increase in maximum intersections, with 141 intersections versus 122 for the unmodified one.
  • the critical value (RC) indicating the length where the maximum number of neurites was detected, revealed a 75% increase compared to unmodified PCL. This substantial improvement highlights the positive impact of NHS modification on neural connectivity, likely due to enhanced surface properties that facilitate cellular adhesion and growth.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Dermatology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Epidemiology (AREA)
  • Radiology & Medical Imaging (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Materials For Medical Uses (AREA)

Abstract

La présente invention concerne un tube ou une enveloppe multicouche électro-filé pour protéger ou ponter un nerf endommagé comprenant une couche externe isolante électro-filée comprenant au moins un polymère sélectionné parmi la poly(caprolactone), le polylactide, le polyglycolide, le poly(carbonate de triméthylène), la poly(dioxanone), le polyéthylène glycol, le polyuréthane, leurs copolymères ou leurs mélanges et au moins une couche interne électro-filée comprenant un réactif qui peut subir des liaisons covalentes avec des protéines et des peptides, qui comprend au moins un groupe sélectionné parmi le N-hydroxysuccinimide, le maléimide, le soufre-NHS et la biotine-NHS, l'acide carboxylique ou les aldéhydes. En outre, la présente invention concerne des procédés de fabrication de tels tubes ou enveloppes, ainsi que leur utilisation dans la protection ou le pontage de nerfs ou pour stimuler la croissance nerveuse et la prolifération cellulaire.
PCT/EP2024/081291 2023-11-06 2024-11-06 Tubes ou enveloppes électro-filés à couche interne fonctionnalisée à des fins de croissance nerveuse Pending WO2025099040A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP23207910.3 2023-11-06
EP23207910 2023-11-06

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PCT/EP2024/081291 Pending WO2025099040A1 (fr) 2023-11-06 2024-11-06 Tubes ou enveloppes électro-filés à couche interne fonctionnalisée à des fins de croissance nerveuse
PCT/EP2024/081336 Pending WO2025099063A1 (fr) 2023-11-06 2024-11-06 Tube de guidage multicouche pour régénération nerveuse

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Citations (4)

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Publication number Priority date Publication date Assignee Title
CN101500508A (zh) * 2006-06-09 2009-08-05 加利福尼亚大学董事会 生物分子连接的仿生支架
CN104307039A (zh) * 2014-04-18 2015-01-28 长春工业大学 一种同时固定rgd和ha纤维膜的制备方法
US20150297791A1 (en) * 2008-10-07 2015-10-22 Nanonerve, Inc. Multilayer Fibrous Polymer Scaffolds, Methods of Production and Methods of Use
US9707000B2 (en) * 2008-01-25 2017-07-18 The Johns Hopkins University Biodegradable nerve guides

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WO2006044904A2 (fr) 2004-10-15 2006-04-27 Vanderbilt University Elaboration a nano-echelle et a micro-echelle d'echafaudages polymeres pour l'elaboration de tissus vasculaires
KR101649457B1 (ko) 2006-04-25 2016-08-19 칠드런'즈 메디컬 센터 코포레이션 개방창 및 폐쇄창 척수 손상의 치료를 위한 방법 및 조성물
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US9707000B2 (en) * 2008-01-25 2017-07-18 The Johns Hopkins University Biodegradable nerve guides
US20150297791A1 (en) * 2008-10-07 2015-10-22 Nanonerve, Inc. Multilayer Fibrous Polymer Scaffolds, Methods of Production and Methods of Use
CN104307039A (zh) * 2014-04-18 2015-01-28 长春工业大学 一种同时固定rgd和ha纤维膜的制备方法

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