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Biodegradable Epoxy-Poly (Ester Amide)s

#G-802


Biodegradable Epoxy-Poly (Ester Amide)s and Functional Polymers Based on Them

Tech Area / Field

  • CHE-POL/Polymer Chemistry/Chemistry
  • MED-DRG/Drug Discovery/Medicine
  • MED-OTH/Other/Medicine

Status
8 Project completed

Registration date
13.09.2001

Completion date
19.12.2006

Senior Project Manager
Zalouzhny A A

Leading Institute
Georgian Technical University / Research Center for Medical Polymers and Biomaterials, Georgia, Tbilisi

Collaborators

  • Cornell University / College of Human Ecology, USA, NY, Ithaca\nChubu University / College of Bioscience and Biotechnology, Japan, Aichi

Project summary

We propose to combine the expertise of FSU and USA scientists to pursue the general goal of developing advanced and innovative biodegradable polymeric-based materials for a variety of commercial applications, particularly in the biomedical, consumer and agricultural fields. Specifically, we plan to focus our efforts on the joint development of a new generation of synthetic biodegradable (bioresorbable) AA-BB type amino acid derived polymers [functional poly(ester amide)s] that could be used either for drug binding to provide better and more efficient drug administration or for the formation of innovative three dimensional biodegradable networks, including hybrid networks with unsaturated polysaccharides newly invented by the USA team (e.g. dextran’s double-bond containing derivatives) that would have the potential as the substrates for tissue engineering of injured or aged human tissues. The proposed project represents a significant advancement of the original AA-BB type amino acid based biodegradable poly(ester amide)s developed by the Georgian team leaded by Prof. R.Katsarava and the US team leaded by Prof. C.C. Chu. This advanced research and development will make the AA-BB type biodegradable poly(ester amide)s far more versatile in properties and processing, and commercially more appealing. There are 7 major tasks in this proposed cooperative research project: (1) Synthesis of new bis-electrophilic monomers having epoxy groups, such as active di-p-nitrophenyl esters of diacids containing epoxy groups [e.g., 2,3-epoxysuccinic acid, 3,4-epoxyadipic acid, and 3,4,5,6-diepoxyadipic acid]; (2) Synthesis of biodegradable epoxy-poly(ester amide)s (EPOXY-PEAs-3) using new and cost efficient active solution polycondensation of the bis-electrophilic monomers having epoxy groups (prepared in Task 1) with di-p-toluenesulfonic acid salts of bis-(a-amino acid)a,w-alkylene diesters. Active di-p-nitrophenyl esters of saturated fatty diacids (adipic and sebacic acids) will be used as the bis-electrophilic co-monomers for regulating epoxy groups concentration within the EPOXY-PEAs-3 backbones; (3) Use the EPOXY-PEAs-3 synthesized in Task 2 above as the foundation materials to synthesize new biodegradable polymers having useful chemical functional groups (FUNCT-PEAs-3) by transformations of epoxy groups in EPOXY-PEAs-3 so that they could be used for future attachments of either biologically active compounds for therapeutic application or photo sensitive groups for preparing photo-sensitive PEAs (PS-PEAs-3); (4) Synthesis of biodegradable three-dimensional networks by photo-induced cross-linkage of EPOXY-PEAs-3 or PS-PEAs-3, or hybrid networks by photo-induced cross-linkage of PS-PEAs-3 with the newly invented unsaturated polysaccharides (US Patents filed by the USA team in March 2001) that could be used as substrates for growing human tissues (e.g., skin, blood vessels, cartilage) for tissue reconstruction (tissue engineering). (5) Characterization of these new materials synthesized from Tasks 2-4 above by standard chemical, physico-chemical and mechanical means for confirmation of their chemical structure and correlation to their performance; (6) in vitro biodegradation study of the new biodegradable polymers synthesized in the presence of enzymes for the purpose of determining the structure-biodegradation relationship; (7) Assessing potential therapeutic value of these new generation biologically active biomaterials by covalent attachment of a particular biologically active compound in the family of the nitric oxide (4-aminoTEMPO) and antibiotics (e.g., Rapamycin) to the newly developed EPOXY-PEAs-3 and their functional biodegradable biomaterials prepared from Tasks 2-4 and subsequent evaluation of in vitro release kinetics of the incorporated nitric oxide derivative and Rapamycin from these new polymers; (8) Preliminary assessing the potential of EPOXY-PEAs-3 as tissue adhesives for wound closure via covalent interaction of the epoxy groups with functional groups of proteins in tissues (NH2, OH, etc.). Such adhesive materials are promising for various surgical applications, e.g. for post-operation closing of parenchimatous organs, wounds, to cover/heal stomach ulcers, etc.

The outcome of this proposed project will generate the required information to demonstrate the feasibility of the proposed new concept. Such a demonstration is required for both the FSU and USA teams to secure additional funding sources from industry or/and governmental agencies to proceed animal and clinical trials, intellectual property protection and eventual commercialization as both teams did successfully for their previous collaborative work in which a USA company sponsored research/development and a US patent was subsequently filed in August, 2000.

Abbreviations: the following abbreviations are used in this project description for distinguishing PEAs at various stages of preparation and transformations.

EPOXY-PEAs-3: the PEAs prepared according to Task 2, containing epoxy group moieties. They could be used for preparing functional PEAs (FUNCT-PEAs-3) which could be used for drug attachment and photo-curable tissue adhesives.

FUNCT-PEAs-3: the PEAs functionalized by polymer-analogous transformations from EPOXY-PEAs-3 according to Task 3, and containing functional groups useful for covalent attachment of bioactive substances, e.g. 4-aminoTEMPO and Rapamycin, photosensitive double bond moieties, etc.

PS-PEAs-3: the photo-sensitive PEAs obtained from FUNCT-PEAs-3 after further polymer-analogous transformations by attaching double bond containing compounds, e.g. acrylic, methacrylic and cinnamic acids, maleic anhydride, poly(ethylene glycol) methacrylate, etc.


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