WO2011069474A2 - Oxidized derivative of hyaluronic acid, a method of preparation thereof and a method of modification thereof - Google Patents

Oxidized derivative of hyaluronic acid, a method of preparation thereof and a method of modification thereof Download PDF

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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
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WO
WIPO (PCT)
Prior art keywords
hyaluronic acid
oxidized
hyaluronan
acid derivative
water
Prior art date
Application number
PCT/CZ2010/000128
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English (en)
French (fr)
Other versions
WO2011069474A3 (en
Inventor
Radovan Buffa
Sofiane Kettou
Lucie POSPIŠILOVÁ
Miroslava BERKOVÁ
Vladimir VELEBNÝ
Original Assignee
Contipro C A.S.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Contipro C A.S. filed Critical Contipro C A.S.
Priority to DK10812976.8T priority Critical patent/DK2510017T3/en
Priority to EP10812976.8A priority patent/EP2510017B1/en
Priority to RU2012122313/13A priority patent/RU2550602C2/ru
Priority to KR1020127017920A priority patent/KR101710432B1/ko
Priority to US13/514,759 priority patent/US9403918B2/en
Priority to JP2012542355A priority patent/JP5945504B2/ja
Priority to ES10812976T priority patent/ES2531292T3/es
Priority to PL10812976T priority patent/PL2510017T3/pl
Priority to BR112012013954A priority patent/BR112012013954B8/pt
Publication of WO2011069474A2 publication Critical patent/WO2011069474A2/en
Publication of WO2011069474A3 publication Critical patent/WO2011069474A3/en

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Classifications

    • 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
    • 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
    • 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)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
PCT/CZ2010/000128 2009-12-11 2010-12-10 Oxidized derivative of hyaluronic acid, a method of preparation thereof and a method of modification thereof WO2011069474A2 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
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
EP10812976.8A EP2510017B1 (en) 2009-12-11 2010-12-10 Oxidized derivative of hyaluronic acid, a method of preparation thereof and a method of modification thereof
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
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
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
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
BR112012013954A BR112012013954B8 (pt) 2009-12-11 2010-12-10 derivado de ácido hialurônico, método de preparação do derivado de ácido hialurônico

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
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
CZPV2009-836 2009-12-11

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WO2011069474A2 true WO2011069474A2 (en) 2011-06-16
WO2011069474A3 WO2011069474A3 (en) 2013-03-14

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US (1) US9403918B2 (pt)
EP (1) EP2510017B1 (pt)
JP (1) JP5945504B2 (pt)
KR (1) KR101710432B1 (pt)
BR (1) BR112012013954B8 (pt)
CZ (1) CZ302504B6 (pt)
DK (1) DK2510017T3 (pt)
ES (1) ES2531292T3 (pt)
PL (1) PL2510017T3 (pt)
RU (1) RU2550602C2 (pt)
WO (1) WO2011069474A2 (pt)

Cited By (14)

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WO2013159757A1 (en) * 2012-04-25 2013-10-31 Contipro Biotech S.R.O. Crosslinked hyaluronan derivative, method of preparation thereof, hydrogel and microfibers based thereon
WO2014023272A1 (en) 2012-08-08 2014-02-13 Contipro Biotech S.R.O. Hyaluronic acid derivative, method of preparation thereof, method of modification thereof and use thereof
WO2014082610A1 (en) 2012-11-27 2014-06-05 Contipro Biotech S.R.O. Endless fibres on the basis of hyaluronan selectively oxidized in the position 6 of the n-acetyl-d-glucosamine group, preparation and use thereof, threads, staples, yarns, fabrics made thereof and method for modifying the same
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 (en) 2015-06-15 2016-12-22 Contipro A.S. Method of crosslinking of polysaccharides using photoremovable protecting groups
WO2016206661A1 (en) 2015-06-26 2016-12-29 Contipro A.S. Derivatives of sulfated polysaccharides, method of preparation, modification and use thereof
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
CZ308106B6 (cs) * 2016-06-27 2020-01-08 Contipro A.S. Nenasycené deriváty polysacharidů, způsob jejich přípravy a jejich použití
US10617711B2 (en) 2014-06-30 2020-04-14 Contipro A.S. Antitumor composition based on hyaluronic acid and inorganic nanoparticles, method of preparation thereof and use thereof
US10689464B2 (en) 2015-03-09 2020-06-23 Contipro A.S. Self-supporting, biodegradable film based on hydrophobized hyaluronic acid, method of preparation and use thereof

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CZ304072B6 (cs) * 2011-04-26 2013-09-25 Contipro Biotech S.R.O. Amfoterní materiál na bázi sítované kyseliny hyaluronové, zpusob jeho prípravy, materiály obsahující aktivní cinidla uzavrené v síti hyaluronanu, zpusob jejich prípravy a jejich pouzití
CZ201224A3 (cs) * 2012-01-16 2013-04-03 Contipro Biotech S.R.O. Kyselina hyaluronová znacená tritiem, zpusob znacení kyseliny hyaluronové tritiem a její pouzití
KR101664444B1 (ko) * 2013-12-13 2016-10-12 재단법인 유타 인하 디디에스 및 신의료기술개발 공동연구소 생분해성 의료용 접착제 또는 실란트 조성물
EP3765103A1 (en) 2018-03-12 2021-01-20 Merz Pharma GmbH & Co. KGaA Porous biomaterials for tissue regeneration
WO2023056433A1 (en) * 2021-10-01 2023-04-06 Northwestern University Supramolecular-covalent composite slurry for cartilage repair
CN116789869A (zh) * 2023-06-25 2023-09-22 吉林省奇健生物技术有限公司 一种透明质酸-蛋白偶联体的制备方法及其应用

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