WO2017194786A1 - Post-fonctionnalisation de matériaux supramoléculaires - Google Patents

Post-fonctionnalisation de matériaux supramoléculaires Download PDF

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WO2017194786A1
WO2017194786A1 PCT/EP2017/061593 EP2017061593W WO2017194786A1 WO 2017194786 A1 WO2017194786 A1 WO 2017194786A1 EP 2017061593 W EP2017061593 W EP 2017061593W WO 2017194786 A1 WO2017194786 A1 WO 2017194786A1
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supramolecular
supramolecular material
material according
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compound
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Olga Joseph Gertrudis Maria GOOR
Patricia Yvonne Wilhelmina Dankers
Henk Martin KEIZER
Henricus Marie Janssen
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Eindhoven Technical University
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    • 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
    • A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/59—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
    • A61K47/593—Polyesters, e.g. PLGA or polylactide-co-glycolide
    • 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
    • A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/59—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
    • A61K47/60—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
    • 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
    • A61L27/14—Macromolecular materials
    • A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/52—Hydrogels or hydrocolloids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/008—Supramolecular polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/46—Diels-Alder reactions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/70—Post-treatment
    • C08G2261/75—Reaction of polymer building blocks for the formation of block-copolymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/70—Post-treatment
    • C08G2261/80—Functional group cleavage, e.g. removal of side-chains or protective groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule

Definitions

  • Figure 3d Surface analyses of the supramolecular films after post-modification with TCO-I.
  • Figure 6 Surface analysis of click chemistry with a TCO-iodine at the surface of drop- cast PCLdiUPy films analyzed by MALDI-ToF MS and corresponding chemical structures.
  • linker L(b) comprises a polymer P(b)
  • linker L(b) comprises the formula -D(b)- P(b)-E(b)-, wherein D(b) and E(b) are independently a direct bond or a connecting group. If D(b) is a direct bond to the supramolecular subunit S(b) and E(b) is a direct bond to the first orthogonal reaction partner 01 , the formula of compound (b) is simply S(b)-P(b)-01 .
  • Linker L(b) may comprise a further subunit between the hydrogen bonding group B(b) and the supramolecular subunit S(b).
  • linker L(b) comprises the formula - A(b)-B(b)-C(b)-D(b)-P(b)-E(b)-F(b)-G(b)-, wherein A(b) is an aliphatic subunit.
  • compound (b) comprises a formula selected from the group consisting of:
  • polymer P(a) also affects the nature of the supramolecular material based on a compound (a).
  • polymer P(a) therefor has an Mn from about 100 to 100,000 Dalton, such as from about 100 to 60,000, from about 800 to about 40,000 or from about 2,000 to about 35,000 Dalton. Mn is defined in the art as "total weight of all the polymer molecules in a sample, divided by the total number of polymer molecules in a sample".
  • the polymer P(a) is a polycaprolactone of about 2,000 Da.
  • one of 01 or 02 is a irans-cyclooctene and the other of 01 or 02 is a tetrazine.
  • the first and second orthogonal reaction partners 01 and 02 are bio- orthogonal reaction partners.
  • step 2 Subjecting the polymer solution obtained in step 1 ) to any of the following steps: a) Evaporating at least 70% (v/v) of the solvent off from from the polymer solution obtained in step 1 ) to obtain supramolecular material, or b) Decreasing the pH in the polymer solution obtained in step 1 ) to obtain a hydrogel supramolecular material.
  • Compound (a) is preferably dispersed or dissolved in the one or more solvents used in step 1 ) in an amount of from about 5 to about 100 mg/ml, such as from about 10 to about 80 mg/ml, from about 15 to about 65 mg/ml, from about 20 to about 50 mg/ml.
  • 01 and 02 are selected such that the reaction in step 3 is an inverse electron demand Diels-Alder (iEDDA) cycloaddition reaction.
  • iEDDA inverse electron demand Diels-Alder
  • the supramolecular material according to the present invention can suitably be used as a biomaterial.
  • biomaterial means a material engineered to interact with biological systems for a medical purpose, e.g. to treat, augment, repair or replace a tissue or a tissue function of the body.
  • the present invention also relates to a biomaterial comprising the supramolecular material according to the present invention.
  • the supramolecular material according to the invention and the biomaterial according to the invention are preferably suitable for applications related to biomedical applications, such as in regenerative medicine including tissue-engineering, or as materials for the manufacture of a prosthesis or an implant.
  • the supramolecular material according to the present invention and the biomaterial according to the invention can also be applied as a coating on prostheses, implants, stents, catheters, or other medical devices that come in contact with living tissue.
  • UPy-Ce-U-Ce-Ut-OEGe-COOH (48) 20 (169 mg, 0.22 mmol) was dissolved in DMF (3 mL) and HATU (87 mg, 2.23 mmol) and pyridine (0.1 1 mL, 2.18 mmol) were added. The solution was stirred for 30 minutes under argon. Thereafter, tetrazine (19) (170 mg, 0.39 mmol) dissolved in 3 mL DMF was added. The reaction mixture was stirred overnight and subsequently poured into 2% FA water solution and centrifuged (2x).
  • FT-IR (ATR): u (cm "1 ) 3299, 2930, 2857, 1701 , 1667, 1616, 1580, 1526, 1462, 1440 1405, 1382, 1331 , 1257, 1 1 19, 1081 , 1014, 941 , 923, 878, 854, 768, 741 , 621 , 602, 583, 526, 481.
  • u (cm "1 ) 3299, 2930, 2857, 1701 , 1667, 1616, 1580, 1526, 1462, 1440 1405, 1382, 1331 , 1257, 1 1 19, 1081 , 1014, 941 , 923, 878, 854, 768, 741 , 621 , 602, 583, 526, 481.
  • Example 4 Preparation of polymer solutions
  • Step IV Synthesis of 4-lodobenzamide-Lvs(OEG 4 -TCO)-NH ? (3)
  • XPS measurements show an increase of an additional iodine peak in line with the increase in fluorine peak intensity upon the addition of higher amounts of UPy- Tz (Fig. 3a-c).
  • the spectrum of the reference surface i.e. pristine PCLdiUPy, shows a minor iodine signal (0.12 atom%) suggesting slight nonspecific adsorption of the TCO- iodine, which is attributed to the hydrophobic nature of the surface (Fig. 3b).
  • Upon the incorporation of 5 and 10 mol% UPy-Tz an increase in iodine intensity to 0.34 atom% is observed in both cases, indicative for a successful reaction at the surface.
  • the frequency and dissipation of the sensors were measured in air for 1 minute. After mounting the sensors with the spincoated material, sensors were again measured in air for 1 minute. The frequency and dissipation changes of the sensor before spincoating and after spincoating were stitched and Sauerbrey was applied to the stitched data to determine the layer thickness. After mounting the PEG-BCN to the sensor surfaces, PBS was passed over the surface at 0.1 mL/min until the signal equilibrated. Subsequently, the protein solution was passed over the surface at 0.1 mL/min. Frequency and dissipation changes were recorded for 30 minutes, and the sensors were rinsed with PBS.

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  • Health & Medical Sciences (AREA)
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  • Medicinal Chemistry (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • Oral & Maxillofacial Surgery (AREA)
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  • Polymers & Plastics (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Dispersion Chemistry (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

La présente invention concerne un matériau supramoléculaire qui peut être fonctionnalisé, en particulier fonctionnalisé en surface, par une réaction orthogonale avec un composé comprenant un groupe de fonctionnalisation. Le matériau supramoléculaire de la présente invention comprend un composé (a) et un composé (b), le composé (a) comprenant au moins deux sous-unités supramoléculaires S(a) liées par un lieur L(a) comprenant un polymère P(a), et le composé (b) comprend une sous-unité supramoléculaire S(b) et un premier partenaire de réaction orthogonale O1 capable de former une liaison covalente avec un second partenaire de réaction orthogonale O2. Lors de la fonctionnalisation du matériau supramoléculaire de l'invention, l'O1 du composé (b) est lié de manière covalente à un O2 d'un composé (c), le composé (c) comprenant un O2 et un groupe de fonctionnalisation F. L'invention concerne également un procédé de préparation du matériau supramoléculaire et l'utilisation du matériau supramoléculaire comme biomatériau.
PCT/EP2017/061593 2016-05-13 2017-05-15 Post-fonctionnalisation de matériaux supramoléculaires Ceased WO2017194786A1 (fr)

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Cited By (7)

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CN111286075A (zh) * 2019-12-02 2020-06-16 哈尔滨工程大学 一种可回收的超分子聚合物泡沫材料及制备方法
CN112933240A (zh) * 2019-12-11 2021-06-11 香港城市大学 超分子聚合物组合物及其制备方法
CN113274548A (zh) * 2021-06-23 2021-08-20 右江民族医学院附属医院 脊髓损伤修复用材料和骨脊髓组织工程支架的制备方法
CN113527708A (zh) * 2021-08-11 2021-10-22 常州大学 基于桥连四苯乙烯基的超分子聚合物光捕获体系、制备及应用
CN113817433A (zh) * 2021-09-17 2021-12-21 中国科学院宁波材料技术与工程研究所 一种热塑性聚氨酯热熔胶、制备方法及应用
JP2023520783A (ja) * 2020-04-03 2023-05-19 コベストロ （ネザーランズ） ビー．ヴィー． 自己修復オリゴマーとその使用
CN120118609A (zh) * 2025-04-21 2025-06-10 扬州市祥华新材料科技有限公司 一种自修复型uv固化电化铝色层涂料及其制备方法

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