title: Photocurable bioadhesive based on lactic acid.
abstract: Novel photocurable and low molecular weight oligomers based on l-lactic acid with proven interest to be used as bioadhesive were successfully manufactured. Preparation of lactic acid oligomers with methacrylic end functionalizations was carried out in the absence of catalyst or solvents by self-esterification in two reaction steps: telechelic lactic acid oligomerization with OH end groups and further functionalization with methacrylic anhydride. The final adhesive composition was achieved by the addition of a reported biocompatible photoinitiator (Irgacure® 2959). Preliminary in vitro biodegradability was investigated by hydrolytic degradation in PBS (pH=7.4) at 37 °C. The adhesion performance was evaluated using glued aminated substrates (gelatine pieces) subjected to pull-to-break test. Surface energy measured by contact angles is lower than the reported values of the skin and blood. The absence of cytoxicity was evaluated using human fibroblasts. A notable antimicrobial behaviour was observed using two bacterial models (Staphylococcus aureus and Escherichia coli). The cured material exhibited a strong thrombogenic character when placed in contact with blood, which can be predicted as a haemostatic effect for bleeding control. This novel material was subjected to an extensive characterization showing great potential for bioadhesive or other biomedical applications where biodegradable and biocompatible photocurable materials are required.
authors.affiliation: CIEPQPF, Department of Chemical Engineering, University of Coimbra, P-3030 790 Coimbra, Portugal.
authors.forename: D S
authors.initials: DS
authors.lastname: Marques
authors.affiliation: CIEPQPF, Department of Chemical Engineering, University of Coimbra, P-3030 790 Coimbra, Portugal.
authors.forename: J M C
authors.initials: JM
authors.lastname: Santos
authors.affiliation: CIEPQPF, Department of Chemical Engineering, University of Coimbra, P-3030 790 Coimbra, Portugal.
authors.forename: P
authors.initials: P
authors.lastname: Ferreira
authors.affiliation: CICS-UBI, Health Sciences Research Center, University of Beira Interior, P-6200 506 Covilhã, Portugal.
authors.forename: T R
authors.initials: TR
authors.lastname: Correia
authors.affiliation: CICS-UBI, Health Sciences Research Center, University of Beira Interior, P-6200 506 Covilhã, Portugal.
authors.forename: I J
authors.initials: IJ
authors.lastname: Correia
authors.affiliation: CIEPQPF, Department of Chemical Engineering, University of Coimbra, P-3030 790 Coimbra, Portugal.
authors.forename: M H
authors.initials: MH
authors.lastname: Gil
authors.affiliation: CIEPQPF, Department of Chemical Engineering, University of Coimbra, P-3030 790 Coimbra, Portugal. Electronic address: cristina@eq.uc.pt.
authors.forename: C M S G
authors.initials: CM
authors.lastname: Baptista
mesh_terms: D000269:Adhesives / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D001419:Bacteria / Q000187:drug effects; D001672:Biocompatible Materials / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D004912:Erythrocytes / Q000187:drug effects; D005347:Fibroblasts / Q000187:drug effects; D006801:Humans; D019344:Lactic Acid / Q000737:chemistry*; D055668:Photochemical Processes; D011817:Rabbits
chemical_list: D000269:Adhesives; D000900:Anti-Bacterial Agents; D001672:Biocompatible Materials; D019344:Lactic Acid
keywords: Bioadhesive formulation; Biocompatibility; Photocurable; Polycondensation; Telechelic lactic acid prepolymers