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      Low molecular weight ε-caprolactone- p-coumaric acid copolymers as potential biomaterials for skin regeneration applications

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          Abstract

          ε-caprolactone- p-coumaric acid copolymers at different mole ratios (ε-caprolactone: p-coumaric acid 1:0, 10:1, 8:1, 6:1, 4:1, and 2:1) were synthesized by melt-polycondensation and using 4-dodecylbenzene sulfonic acid as catalyst. Chemical analysis by NMR and GPC showed that copolyesters were formed with decreasing molecular weight as p-coumaric acid content was increased. Physical characteristics, such as thermal and mechanical properties, as well as water uptake and water permeability, depended on the mole fraction of p-coumaric acid. The p-coumarate repetitive units increased the antioxidant capacity of the copolymers, showing antibacterial activity against the common pathogen Escherichia coli. In addition, all the synthesized copolyesters, except the one with the highest concentration of the phenolic acid, were cytocompatible and hemocompatible, thus becoming potentially useful for skin regeneration applications.

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          Most cited references39

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          Biodegradable polymers as biomaterials

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            NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist

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              Anti-inflammatory properties of curcumin, a major constituent of Curcuma longa: a review of preclinical and clinical research.

              Curcuma longa (turmeric) has a long history of use in Ayurvedic medicine as a treatment for inflammatory conditions. Turmeric constituents include the three curcuminoids: curcumin (diferuloylmethane; the primary constituent and the one responsible for its vibrant yellow color), demethoxycurcumin, and bisdemethoxycurcumin, as well as volatile oils (tumerone, atlantone, and zingiberone), sugars, proteins, and resins. While numerous pharmacological activities, including antioxidant and antimicrobial properties, have been attributed to curcumin, this article focuses on curcumin's anti-inflammatory properties and its use for inflammatory conditions. Curcumin's effect on cancer (from an anti-inflammatory perspective) will also be discussed; however, an exhaustive review of its many anticancer mechanisms is outside the scope of this article. Research has shown curcumin to be a highly pleiotropic molecule capable of interacting with numerous molecular targets involved in inflammation. Based on early cell culture and animal research, clinical trials indicate curcumin may have potential as a therapeutic agent in diseases such as inflammatory bowel disease, pancreatitis, arthritis, and chronic anterior uveitis, as well as certain types of cancer. Because of curcumin's rapid plasma clearance and conjugation, its therapeutic usefulness has been somewhat limited, leading researchers to investigate the benefits of complexing curcumin with other substances to increase systemic bioavailability. Numerous in-progress clinical trials should provide an even deeper understanding of the mechanisms and therapeutic potential of curcumin.
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                Author and article information

                Contributors
                Role: ConceptualizationRole: Data curationRole: Formal analysisRole: Writing – original draftRole: Writing – review & editing
                Role: ConceptualizationRole: Data curationRole: Formal analysis
                Role: Data curationRole: Formal analysisRole: Writing – review & editing
                Role: Data curationRole: Formal analysis
                Role: Data curationRole: Formal analysis
                Role: Data curationRole: Formal analysisRole: Methodology
                Role: Data curationRole: Formal analysisRole: Writing – review & editing
                Role: Data curationRole: Formal analysis
                Role: Data curationRole: Formal analysis
                Role: Data curationRole: Formal analysis
                Role: Data curationRole: Formal analysis
                Role: ConceptualizationRole: Data curationRole: Formal analysisRole: Writing – review & editing
                Role: ConceptualizationRole: SupervisionRole: ValidationRole: Writing – review & editing
                Role: ConceptualizationRole: SupervisionRole: ValidationRole: Writing – original draftRole: Writing – review & editing
                Role: Editor
                Journal
                PLoS One
                PLoS ONE
                plos
                plosone
                PLoS ONE
                Public Library of Science (San Francisco, CA USA )
                1932-6203
                8 April 2019
                2019
                : 14
                : 4
                : e0214956
                Affiliations
                [1 ] Smart Materials, Istituto Italiano di Tecnologia, Genova, Italy
                [2 ] DIBRIS, University of Genoa, Genoa, Italy
                [3 ] Istituto di Biomedicina ed Immunologia Molecolare "A. Monroy", CNR, Palermo, Italy
                [4 ] Analytical Chemistry Facility, Istituto Italiano di Tecnologia, Genova, Italy
                [5 ] Instituto de Ciencia de Materiales de Sevilla, Centro mixto CSIC-Universidad de Sevilla, Isla de la Cartuja, Sevilla, Spain
                [6 ] Instituto de Hortofruticultura Subtropical y Mediterránea (IHSM), La Mayora Universidad de Málaga-CSIC Algarrobo-Costa, Málaga, Spain
                [7 ] Departamento de Biología Molecular y Bioquímica, Universidad de Málaga, Málaga, Spain
                [8 ] Nanomaterials for Biomedical Applications, Istituto Italiano di Tecnologia, Genova, Italy
                [9 ] Materials Characterization Facility, Istituto Italiano di Tecnologia, Genova, Italy
                University of Hyderabad, INDIA
                Author notes

                Competing Interests: The authors have declared that no competing interests exist.

                Author information
                http://orcid.org/0000-0003-3877-7985
                Article
                PONE-D-18-35069
                10.1371/journal.pone.0214956
                6453441
                30958838
                880d7ad7-4ca2-4c6f-a53e-9fd72cddbc73
                © 2019 Contardi et al

                This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

                History
                : 11 December 2018
                : 23 March 2019
                Page count
                Figures: 6, Tables: 2, Pages: 18
                Funding
                The authors received no specific funding for this work.
                Categories
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                Physical Sciences
                Chemistry
                Polymer Chemistry
                Macromolecules
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                Polymers
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                Earth Sciences
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                All relevant data are within the manuscript and its Supporting Information files.

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