CA2369758A1 - Functionalized poly(propylene fumarate) and poly(propylene fumarate-co-ethylene glycol) - Google Patents

Functionalized poly(propylene fumarate) and poly(propylene fumarate-co-ethylene glycol) Download PDF

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Publication number
CA2369758A1
CA2369758A1 CA002369758A CA2369758A CA2369758A1 CA 2369758 A1 CA2369758 A1 CA 2369758A1 CA 002369758 A CA002369758 A CA 002369758A CA 2369758 A CA2369758 A CA 2369758A CA 2369758 A1 CA2369758 A1 CA 2369758A1
Authority
CA
Canada
Prior art keywords
peg
ppf
poly
propylene fumarate
tethered
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.)
Granted
Application number
CA002369758A
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French (fr)
Other versions
CA2369758C (en
Inventor
Antonios G. Mikos
Seongbong Jo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
William Marsh Rice University
Original Assignee
Wm. Marsh Rice University
Antonios G. Mikos
Seongbong Jo
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 Wm. Marsh Rice University, Antonios G. Mikos, Seongbong Jo filed Critical Wm. Marsh Rice University
Publication of CA2369758A1 publication Critical patent/CA2369758A1/en
Application granted granted Critical
Publication of CA2369758C publication Critical patent/CA2369758C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/06Unsaturated polyesters
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14Macromolecular materials
    • A61L27/18Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/58Materials at least partially resorbable by the body
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66Polyesters containing oxygen in the form of ether groups
    • C08G63/668Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/676Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/91Polymers modified by chemical after-treatment
    • C08G63/914Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/918Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G81/00Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • C08G81/02Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C08G81/024Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
    • C08G81/025Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G containing polyether sequences
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/06Unsaturated polyesters
    • C08L67/07Unsaturated polyesters having terminal carbon-to-carbon unsaturated bonds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02Polyalkylene oxides
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S530/00Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
    • Y10S530/81Carrier - bound or immobilized peptides or proteins and the preparation thereof, e.g. biological cell or cell fragment as carrier
    • Y10S530/812Peptides or proteins is immobilized on, or in, an organic carrier
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S530/00Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
    • Y10S530/81Carrier - bound or immobilized peptides or proteins and the preparation thereof, e.g. biological cell or cell fragment as carrier
    • Y10S530/812Peptides or proteins is immobilized on, or in, an organic carrier
    • Y10S530/815Carrier is a synthetic polymer

Abstract

Polyethylene glycol) (PEG), a highly biocompatible hydrophilic polyether, is tethered to poly(propylene fumarate) (PPF), a biodegradable polyester. To avoid change in molecular weight distribution of PPF, end hydroxyl groups of PPF are reacted with bis-carboxymethyl PEG after being treated with thionyl chloride. New end carboxyl groups of the PEG-tethered PPF are further reacted with N-hydroxysuccinimide (NHS) in the presence of dicyclohexylcarbodiimide (DCC) to couple bioactive molecules. Glutamine and glycine-arginine-glycine-aspartic acid (GRGD) are attached to the PEG-tethered PPF in 50 mM phosphate buffer of pH of 7.4. The method is valuable for the preparation of a triblock copolymer with PEG end blocks and the coupling of biologically active molecules.
CA002369758A 1999-04-16 2000-04-14 Functionalized poly(propylene fumarate) and poly(propylene fumarate-co-ethylene glycol) Expired - Fee Related CA2369758C (en)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
US12957799P 1999-04-16 1999-04-16
US60/129,577 1999-04-16
US14699199P 1999-08-03 1999-08-03
US60/146,991 1999-08-03
US16732899P 1999-11-24 1999-11-24
US16738899P 1999-11-24 1999-11-24
US60/167,388 1999-11-24
US60/167,328 1999-11-24
PCT/US2000/010139 WO2000062630A1 (en) 1999-04-16 2000-04-14 Functionalized poly(propylene fumarate) and poly(propylene fumarate-co-ethylene glycol)

Publications (2)

Publication Number Publication Date
CA2369758A1 true CA2369758A1 (en) 2000-10-26
CA2369758C CA2369758C (en) 2007-04-03

Family

ID=27494811

Family Applications (3)

Application Number Title Priority Date Filing Date
CA002370330A Expired - Fee Related CA2370330C (en) 1999-04-16 2000-04-14 Biodegradable poly(propylene fumarate) networks cross linked with poly(propylene fumarate)-diacrylate macromers
CA002370357A Expired - Fee Related CA2370357C (en) 1999-04-16 2000-04-14 Poly(propylene fumarate) cross linked with poly(ethylene glycol)
CA002369758A Expired - Fee Related CA2369758C (en) 1999-04-16 2000-04-14 Functionalized poly(propylene fumarate) and poly(propylene fumarate-co-ethylene glycol)

Family Applications Before (2)

Application Number Title Priority Date Filing Date
CA002370330A Expired - Fee Related CA2370330C (en) 1999-04-16 2000-04-14 Biodegradable poly(propylene fumarate) networks cross linked with poly(propylene fumarate)-diacrylate macromers
CA002370357A Expired - Fee Related CA2370357C (en) 1999-04-16 2000-04-14 Poly(propylene fumarate) cross linked with poly(ethylene glycol)

Country Status (9)

Country Link
US (4) US6384105B1 (en)
EP (3) EP1194463B1 (en)
JP (3) JP2002542339A (en)
KR (3) KR100696407B1 (en)
AT (3) ATE321803T1 (en)
AU (3) AU770579B2 (en)
CA (3) CA2370330C (en)
DE (3) DE60026983T2 (en)
WO (3) WO2000063263A1 (en)

Families Citing this family (142)

* Cited by examiner, † Cited by third party
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