WO2011069474A2 - Dérivé oxydé d'acide hyaluronique, procédé d'élaboration et procédé de modification - Google Patents
Dérivé oxydé d'acide hyaluronique, procédé d'élaboration et procédé de modification Download PDFInfo
- Publication number
- WO2011069474A2 WO2011069474A2 PCT/CZ2010/000128 CZ2010000128W WO2011069474A2 WO 2011069474 A2 WO2011069474 A2 WO 2011069474A2 CZ 2010000128 W CZ2010000128 W CZ 2010000128W WO 2011069474 A2 WO2011069474 A2 WO 2011069474A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hyaluronic acid
- oxidized
- hyaluronan
- acid derivative
- water
- Prior art date
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
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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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
Definitions
- the oxidation can be performed by use of DMP (Dess-Martin Periodinane) agent in polar aprotic solvents,
- solvent includes for example dimethylsulfoxide.
- Hyaluronic acid is an important polysaccharide, composed of two repeating units of ⁇ - -(l,3)-D-glucuronic acid and P-(l,4)-N-acetyl-D-glucosamine.
- the molecular weight depending on the method its isolation and on the source material, is within the range from 5.10 4 to 5.10 6 g-mol "1 .
- Hyaluronic acid or its sodium salt hyaluronan is an essential component of connective tissues, synovial fluid of joints, and plays an important role in biological processes such as hydratation, organization of proteoglycans, cells differentiation, proliferation and angiogenesis.
- Hyaluronic acid is a considerably hydrophilic polysaccharide that is water-soluble in the form of its salt within the whole range of pH.
- Oxidation of polysaccharides is a process in which the oxidation degree of the polysaccharide functional groups is changing. Most frequently, the carboxylic acids or aldehydes are formed, which can dramatically change the properties of the polysaccharide. In most cases, the reaction is performed by use of agents containing atoms in higher oxidation degrees.
- the oxidation of cyclodextrin to monoaldehyde was described by Cornwell, Tetrahedron Letters 1995, 36 (46), 8371 - 8374.
- the oxidation was performed by adding Dess-Martin periodinane (DMP) in DMSO or in DMF at the temperature of 20°C as an oxidizing agent.
- DMP Dess-Martin periodinane
- Oxidation of hyaluronan by use of TEMPO/NaCIO system was described in the patent application WO 02/18448 A2. The authors also dealt with interactions of percarboxylated polysaccharides, while forming biological complexes.
- the physico-chemical properties of the resulting hydrogels have been elucidated by instrumental analyses FT-IR, SEM (scanning electron microscopy) and rheometry. Increasing the oxidation degree of the hyaluronan lead to a corresponding increase of hydrogels compatibility and decrease of water absorption capacity. Dermal fibroblasts were used to study the cell-hydrogel interactions. Both the hydrogels and their degradation products are biocompatible, as proved by the long-term cell viability assay. When cultured with cells, the hydrogel underwent a degradation within 4 weeks, with an obvious loss of cohesiveness. The good biocompatibility and biodegradability was further demonstrated in mice subdermal implantations. Lastly, in vitro and in vivo depositions of extracellular matrix in hydrogels were demonstrated by SEM analysis.
- the present invention relates to a method of selective oxidation of the primary hydroxyl group of hyaluronic acid in position 6 of the glucosamine part of the polysaccharide to aldehyde.
- the reaction is performed in an aprotic environment by use of Dess-Martin periodinane DMP as an oxidizing agent.
- the presented procedure is original in that it introduces an aldehydic group to the position 6 of the hyaluronan glucosamine part (scheme 6, structure 3).
- the method according to the invention is more advantageous in that the respective oxidation product (structure 3, scheme 6) maintains the structure of conjugated saccharide rings. Ring opening in the product oxidized to dialdehyde (structure 2, scheme 6) gives rise to the chain linearity subreakage" and, therefore, a significant change of the polysaccharide 3- dimensional structure compared to the non-modified hyaluronan. Although in the product oxidized to a carboxylic acid (structure 1, scheme 6) the chain linearity impartbreakage" does not occur, the carboxyl group does not enable such various modification (binding) possibilities like the aldehydic group.
- the oxidation to the structure 1 brings only an increase of the polysaccharide polarity, not a development of new quality utilizable for binding new substitutes.
- the prepared oxidized hyaluronan can be used for binding of compounds containing for example amino group.
- the binding can be realized either in an imine form or after the
- the modification of the hyaluronic acid derivative can be performed by a reaction of the oxidized derivative with an amine of the general formula H 2 N-R or with a hyaluronan substituted by an -R-N3 ⁇ 4 group, wherein R is an alkyl, linear or branched chain CI- C30, optionally containing aromatic or heteroaromatic groups.
- This amine can be an alkylamine, e.g. butylamine or hexanediamine, amino acid, peptide or polysaccharide containing a free amino group.
- cross-linked hyaluronan derivatives can be prepared.
- the cross-linked derivatives can be prepared also by the reaction of an aldehyde with a hyaluronan substituted by an aminoalkyl group HA-alkyl-NH 2 .
- equivalent (eq) refers to a hyaluronic acid dimer, unless otherwise indicated.
- the percentages as used herein mean a percentage by weight, unless otherwise indicated..
- the molecular weight of the starting hyaluronan was determined by the SEC-MALLS assay.
- logD (3.05 ppm, polymer-CH 2 -NH-CH2-) ⁇ -10.3 m 2 /s logD (2.03 ppm, CH 3 -CO-NH-polymer) ⁇ -10.3 m 2 /s
- Example 3 was mixed with hexanediamine (0.4 eq). The mixture was stirred for 24 hours at the temperature of 20°C. The solution was then mixed with NaBH 3 CN (3 eq) in 0.5 ml of water. The mixture was stirred for 24 hours at the temperature of 20°C. The solution was then diluted to 0.1% and dialyzed against the mixture (0.1% NaCl, 0.1% NaHC0 3 ) 3 x 5 liters (once per day) and against distilled water 7 x 5 liters (twice per day). The resulting solution was evaporated and analyzed.
- logD (1.7 ppm, -NH-CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -) ⁇ -10.5 m 2 /s logD (3.02 ppm, -CH 2 -NH 2 ) ⁇ -10.5 m 2 /s
- Example 4 was mixed with lysine (20 eq). The mixture was stirred for 24 hours at the temperature of 20°C. The solution was then mixed with NaBH 3 CN (10 eq) in 0.5 ml of water. The mixture was stirred for 24 hours at the temperature of 20°C. The solution was diluted to 0.1% and dialyzed against the mixture (0.1% NaCl, 0.1% NaHC0 3 ) 3 x 5 liters (once per day) and against distilled water 7 x 5 liters (twice per day). The resulting solution was then evaporated and analyzed.
- a solution of the oxidized hyaluronic acid (1%) (0.1 g, oxidation degree DS 10 %, Example 1) in a water/isopropanol system 2/1 was mixed with a 1% solution of substituted pentapeptide PAL-KTTKS (0.05 eq) in isopropyl alcohol. The mixture was stirred for 24 hours at the temperature of 20°C. The solution was then mixed with NaBH 3 CN (3 eq) in 0.5 ml of water. The mixture was stirred for 24 hours at the temperature of 20°C.
- the solution was diluted to 0.1% and dialyzed against the mixture (0.1% NaCl, 0.1% NaHC0 3 ) 3 x 5 liters (once per day) and against distilled water 7 x 5 liters (twice per day). The resulting solution was evaporated and analyzed.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR112012013954A BR112012013954B8 (pt) | 2009-12-11 | 2010-12-10 | derivado de ácido hialurônico, método de preparação do derivado de ácido hialurônico |
RU2012122313/13A RU2550602C2 (ru) | 2009-12-11 | 2010-12-10 | Производное гиалуроновой кислоты, способ его получения и способ его модификации |
KR1020127017920A KR101710432B1 (ko) | 2009-12-11 | 2010-12-10 | 히알루론산의 산화된 유도체, 이의 제조 방법 및 이의 변형 방법 |
JP2012542355A JP5945504B2 (ja) | 2009-12-11 | 2010-12-10 | ヒアルロン酸の酸化誘導体,その調製方法及びその修飾方法 |
EP10812976.8A EP2510017B1 (fr) | 2009-12-11 | 2010-12-10 | Dérivé oxydé d'acide hyaluronique, procédé d'élaboration et procédé de modification |
ES10812976T ES2531292T3 (es) | 2009-12-11 | 2010-12-10 | Derivado oxidado del ácido hialurónico, un método para su preparación y un método para su modificación |
PL10812976T PL2510017T3 (pl) | 2009-12-11 | 2010-12-10 | Utleniona pochodna kwasu hialuronowego, sposób jej wytwarzania i sposób jej modyfikacji |
US13/514,759 US9403918B2 (en) | 2009-12-11 | 2010-12-10 | Oxidized derivative of hyaluronic acid, a method of preparation thereof and a method of modification thereof |
DK10812976.8T DK2510017T3 (en) | 2009-12-11 | 2010-12-10 | Oxidized derivative of hyaluronic acid, a process for its preparation and a process for its modification |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CZPV2009-836 | 2009-12-11 | ||
CZ20090836A CZ302504B6 (cs) | 2009-12-11 | 2009-12-11 | Derivát kyseliny hyaluronové oxidovaný v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd, zpusob jeho prípravy a zpusob jeho modifikace |
Publications (2)
Publication Number | Publication Date |
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WO2011069474A2 true WO2011069474A2 (fr) | 2011-06-16 |
WO2011069474A3 WO2011069474A3 (fr) | 2013-03-14 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/CZ2010/000128 WO2011069474A2 (fr) | 2009-12-11 | 2010-12-10 | Dérivé oxydé d'acide hyaluronique, procédé d'élaboration et procédé de modification |
Country Status (11)
Country | Link |
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US (1) | US9403918B2 (fr) |
EP (1) | EP2510017B1 (fr) |
JP (1) | JP5945504B2 (fr) |
KR (1) | KR101710432B1 (fr) |
BR (1) | BR112012013954B8 (fr) |
CZ (1) | CZ302504B6 (fr) |
DK (1) | DK2510017T3 (fr) |
ES (1) | ES2531292T3 (fr) |
PL (1) | PL2510017T3 (fr) |
RU (1) | RU2550602C2 (fr) |
WO (1) | WO2011069474A2 (fr) |
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WO2013159757A1 (fr) * | 2012-04-25 | 2013-10-31 | Contipro Biotech S.R.O. | Dérivé d'hyaluronane réticulé, son procédé de préparation, hydrogel et microfibres à base du dérivé |
WO2014023272A1 (fr) | 2012-08-08 | 2014-02-13 | Contipro Biotech S.R.O. | Dérivé d'acide hyaluronique, procédé de préparation de celui-ci, procédé de modification de celui-ci et d'utilisation de celui-ci |
WO2014082610A1 (fr) | 2012-11-27 | 2014-06-05 | Contipro Biotech S.R.O. | Fibres sans fin à base d'hyaluronane sélectivement oxydé en position 6 du groupe n-acétyl-d-glucosamine, leur préparation et utilisation, filés, fibres courtes, fils et tissus constitués de celles-ci et procédé pour la modification de celles-ci |
KR20140136922A (ko) * | 2012-02-07 | 2014-12-01 | (주)화이바이오메드 | 경피 전달용 히알루론산-단백질 컨쥬게이트의 제조 방법 및 이에 따라 제조된 경피 전달용 히알루론산-단백질 컨쥬게이트 |
US9403918B2 (en) | 2009-12-11 | 2016-08-02 | Contipro Pharma A.S. | Oxidized derivative of hyaluronic acid, a method of preparation thereof and a method of modification thereof |
US9434791B2 (en) | 2009-12-11 | 2016-09-06 | Contipro Pharma A.S. | Method of preparation of an oxidized derivative of hyaluronic acid and a method of modification thereof |
US9492586B2 (en) | 2012-02-28 | 2016-11-15 | Contipro Biotech S.R.O. | Derivatives of hyaluronic acid capable of forming hydrogels |
WO2016202314A1 (fr) | 2015-06-15 | 2016-12-22 | Contipro A.S. | Procédé de réticulation de polysaccharides à l'aide de groupes protecteurs photoamovibles |
WO2016206661A1 (fr) | 2015-06-26 | 2016-12-29 | Contipro A.S. | Dérivés de polysaccharides sulfatés, procédé de préparation, modification et utilisation correspondants |
US9999678B2 (en) | 2012-11-27 | 2018-06-19 | Contipro A.S. | C6-C18-acylated derivative of hyaluronic acid and method of preparation thereof |
US10023658B2 (en) | 2014-03-11 | 2018-07-17 | Contipro A.S. | Conjugates of oligomer of hyaluronic acid or of a salt thereof, method of preparation thereof and use thereof |
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KR101664444B1 (ko) * | 2013-12-13 | 2016-10-12 | 재단법인 유타 인하 디디에스 및 신의료기술개발 공동연구소 | 생분해성 의료용 접착제 또는 실란트 조성물 |
US20210008249A1 (en) | 2018-03-12 | 2021-01-14 | Merz Pharma Gmbh & Co. Kgaa | Porous biomaterials for tissue regeneration |
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Also Published As
Publication number | Publication date |
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EP2510017A2 (fr) | 2012-10-17 |
CZ2009836A3 (cs) | 2011-06-22 |
CZ302504B6 (cs) | 2011-06-22 |
BR112012013954A2 (pt) | 2016-06-07 |
WO2011069474A3 (fr) | 2013-03-14 |
US20120245323A1 (en) | 2012-09-27 |
KR101710432B1 (ko) | 2017-02-27 |
JP2013513671A (ja) | 2013-04-22 |
US9403918B2 (en) | 2016-08-02 |
RU2012122313A (ru) | 2014-01-20 |
BR112012013954B8 (pt) | 2021-05-25 |
DK2510017T3 (en) | 2015-03-23 |
PL2510017T3 (pl) | 2015-06-30 |
EP2510017B1 (fr) | 2015-01-21 |
JP5945504B2 (ja) | 2016-07-05 |
KR20120091449A (ko) | 2012-08-17 |
RU2550602C2 (ru) | 2015-05-10 |
ES2531292T3 (es) | 2015-03-12 |
BR112012013954B1 (pt) | 2020-12-22 |
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