Antioxidant and adsorption properties of bioinspired phenolic polymers: A comparative study of catechol and gallol

ACS Sustainable Chemistry and Engineering

Volumn 4, Issue 7, 2016, Pages 3857-3863

  Zhan, Kan ^a   Ejima, Hirotaka ^a   Yoshie, Naoko ^a  

^a INSTITUTE OF INDUSTRIAL SCIENCE   (Japan)

Author keywords

Bioinspired polymer; Catechol; Gallol; Polyphenol; RAFT polymerization

Indexed keywords

ADSORPTION; ANTIOXIDANTS; BIOCOMPATIBILITY; CHAINS; FREE RADICAL POLYMERIZATION; LIVING POLYMERIZATION; PHENOLS; PLANTS (BOTANY); POLYMERIZATION;

2 ,2-DIPHENYL-1-PICRYLHYDRAZYL; ANTI-OXIDANT ACTIVITIES; CATECHOL; GALLOL; OXYGEN RADICAL ABSORBANCE CAPACITIES; POLYPHENOLS; RAFT POLYMERIZATION; REVERSIBLE ADDITION-FRAGMENTATION CHAIN TRANSFER POLYMERIZATION;

POLYDISPERSITY;

EID: 84979032249     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.6b00626     Document Type: Article

References (64)

1. Demmig-Adams, B.; Adams, W. W. Antioxidants in photosynthesis and human nutrition Science 2002, 298 (5601) 2149-2153 10.1126/science.1078002
2. Ingold, K. U.; Pratt, D. A. Advances in radical-trapping antioxidant chemistry in the 21st century: a kinetics and mechanisms perspective Chem. Rev. 2014, 114 (18) 9022-9046 10.1021/cr500226n
3. Barclay, L. R. C.; Edwards, C. E.; Vinqvist, M. R. Media effects on antioxidant activities of phenols and catechols J. Am. Chem. Soc. 1999, 121 (26) 6226-6231 10.1021/ja990878u
4. Finkel, T.; Holbrook, N. J. Oxidants, oxidative stress and the biology of ageing Nature 2000, 408 (6809) 239-247 10.1038/35041687
5. Quideau, S.; Deffieux, D.; Douat-Casassus, C.; Pouységu, L. Plant polyphenols: chemical properties, biological activities, and synthesis Angew. Chem., Int. Ed. 2011, 50 (3) 586-621 10.1002/anie.201000044
6. Duthie, G. G.; Duthie, S. J.; Kyle, J. A. M. Plant polyphenols in cancer and heart disease: implications as nutritional antioxidants Nutr. Res. Rev. 2000, 13 (01) 79-106 10.1079/095442200108729016
7. Neshchadin, D.; Batchelor, S. N.; Bilkis, I.; Gescheidt, G. Short-lived phenoxyl radicals formed from green-tea polyphenols and highly reactive oxygen species: an investigation by time-resolved EPR spectroscopy Angew. Chem., Int. Ed. 2014, 53 (48) 13288-13292 10.1002/anie.201407995
8. Wang, Y.; Ho, C. T. Polyphenolic chemistry of tea and coffee: a century of progress J. Agric. Food Chem. 2009, 57 (18) 8109-8114 10.1021/jf804025c
9. Li, N.; Shi, J.; Wang, K. Profile and antioxidant activity of phenolic extracts from 10 crabapples (Malus wild species) J. Agric. Food Chem. 2014, 62 (3) 574-581 10.1021/jf404542d
10. Vallverdú-Queralt, A.; Odriozola-Serrano, I.; Oms-Oliu, G.; Lamuela-Raventós, R. M.; Elez-Martínez, P.; Martín-Belloso, O. Changes in the polyphenol profile of tomato juices processed by pulsed electric fields J. Agric. Food Chem. 2012, 60 (38) 9667-9672 10.1021/jf302791k
11. Sileika, T. S.; Barrett, D. G.; Zhang, R.; Lau, K. H. A.; Messersmith, P. B. Colorless multifunctional coatings inspired by polyphenols found in tea, chocolate, and wine Angew. Chem., Int. Ed. 2013, 52 (41) 10766-10770 10.1002/anie.201304922
12. Pandey, K. B.; Rizvi, S. I. Plant polyphenols as dietary antioxidants in human health and disease Oxid. Med. Cell. Longevity 2009, 2 (5) 270-278 10.4161/oxim.2.5.9498
13. Hong, S.; Yeom, J.; Song, I. T.; Kang, S. M.; Lee, H.; Lee, H. Pyrogallol 2-aminoethane: a plant flavonoid-inspired molecule for material-independent surface chemistry Adv. Mater. Interfaces 2014, 1 (4) 140013-140019 10.1002/admi.201400113
14. Le Deun, E.; Van der Werf, R.; Lebail, G.; Le Quéré, J. M.; Guyot, S. HPLC-DAD-MS profiling of polyphenols responsible for yellow-orange color in apple juices of different French cider apple varieties J. Agric. Food Chem. 2015, 63 (35) 7675-7684 10.1021/acs.jafc.5b00988
15. Rahimi, A.; Ulbrich, A.; Coon, J. J.; Stahl, S. S. Formic-acid-induced depolymerization of oxidized lignin to aromatics Nature 2014, 515 (7576) 249-251 10.1038/nature13867
16. Ejima, H.; Richardson, J. J.; Caruso, F. Phenolic film engineering for template-mediated microcapsule preparation Polym. J. 2014, 46 (8) 452-459 10.1038/pj.2014.32
17. Ejima, H.; Richardson, J. J.; Liang, K.; Best, J. P.; van Koeverden, M. P.; Such, G. K.; Cui, J.; Caruso, F. One-step assembly of coordination complexes for versatile film and particle engineering Science 2013, 341 (6142) 154-157 10.1126/science.1237265
18. Nadagouda, M. N.; Varma, R. S. Green synthesis of silver and palladium nanoparticles at room temperature using coffee and tea extract Green Chem. 2008, 10 (8) 859-862 10.1039/b804703k
19. Ross, J. A.; Kasum, C. M. Dietary flavonoids: bioavailability, metabolic effects, and safety Annu. Rev. Nutr. 2002, 22 (1) 19-34 10.1146/annurev.nutr.22.111401.144957
20. Wu, H.; Wu, C.; He, Q.; Liao, X.; Shi, B. Collagen fiber with surface-grafted polyphenol as a novel support for Pd (0) nanoparticles: Synthesis, characterization and catalytic application Mater. Sci. Eng., C 2010, 30 (5) 770-776 10.1016/j.msec.2010.03.013
21. Krogsgaard, M.; Nue, V.; Birkedal, H. Mussel-inspired materials: self-healing through coordination chemistry Chem.-Eur. J. 2016, 22 (3) 844-857 10.1002/chem.201503380
22. Isakova, A.; Topham, P. D.; Sutherland, A. J. Controlled RAFT polymerization and Zinc binding performance of catechol-inspired homopolymers Macromolecules 2014, 47 (8) 2561-2568 10.1021/ma500336u
23. Matos-Pérez, C. R.; White, J. D.; Wilker, J. J. Polymer composition and substrate influences on the adhesive bonding of a biomimetic, cross-linking polymer J. Am. Chem. Soc. 2012, 134 (22) 9498-9505 10.1021/ja303369p
24. Hasegawa, U.; Moriyama, M.; Uyama, H.; van der Vlies, A. J. Catechol-bearing block copolymer micelles: Structural characterization and antioxidant activity Polymer 2015, 66 (1) 1-7 10.1016/j.polymer.2015.03.080
25. Lee, H.; Lee, B. P.; Messersmith, P. B. A reversible wet/dry adhesive inspired by mussels and geckos Nature 2007, 448 (7151) 338-341 10.1038/nature05968
26. Lee, H.; Scherer, N. F.; Messersmith, P. B. Single-molecule mechanics of mussel adhesion Proc. Natl. Acad. Sci. U. S. A. 2006, 103 (35) 12999-13003 10.1073/pnas.0605552103
27. He, L.; Fullenkamp, D. E.; Rivera, J. G.; Messersmith, P. B. pH responsive self-healing hydrogels formed by boronate-catechol complexation Chem. Commun. 2011, 47 (26) 7497-7499 10.1039/c1cc11928a
28. Su, J.; Chen, F.; Cryns, V. L.; Messersmith, P. B. Catechol polymers for pH-responsive, targeted drug delivery to cancer cells J. Am. Chem. Soc. 2011, 133 (31) 11850-11853 10.1021/ja203077x
29. Holten-Andersen, N.; Harrington, M. J.; Birkedal, H.; Lee, B. P.; Messersmith, P. B.; Lee, K. Y. C.; Waite, J. H. pH-induced metal-ligand cross-links inspired by mussel yield self-healing polymer networks with near-covalent elastic moduli Proc. Natl. Acad. Sci. U. S. A. 2011, 108 (7) 2651-2655 10.1073/pnas.1015862108
30. Ahn, B. K.; Lee, D. W.; Israelachvili, J. N.; Waite, J. H. Surface-initiated self-healing of polymers in aqueous media Nat. Mater. 2014, 13 (9) 867-872 10.1038/nmat4037
31. Oh, Y. J.; Cho, I. H.; Lee, H.; Park, K. J.; Lee, H.; Park, S. Y. Bio-inspired catechol chemistry: a new way to develop a re-moldable and injectable coacervate hydrogel Chem. Commun. 2012, 48 (97) 11895-11897 10.1039/c2cc36843a
32. Holten-Andersen, N.; Jaishankar, A.; Harrington, M. J.; Fullenkamp, D. E.; DiMarco, G.; He, L.; McKinley, G. H.; Messersmith, P. B.; Lee, K. Y. C. Metal-coordination: using one of nature's tricks to control soft material mechanics J. Mater. Chem. B 2014, 2 (17) 2467-2472 10.1039/C3TB21374A
33. Xu, H.; Nishida, J.; Ma, W.; Wu, H.; Kobayashi, M.; Otsuka, H.; Takahara, A. Competition between oxidation and coordination in cross-linking of polystyrene copolymer containing catechol groups ACS Macro Lett. 2012, 1 (4) 457-460 10.1021/mz200217d
34. Harrington, M. J.; Masic, A.; Holten-Andersen, N.; Waite, J. H.; Fratzl, P. Iron-clad fibers: a metal-based biological strategy for hard flexible coatings Science 2010, 328 (5975) 216-220 10.1126/science.1181044
35. Lee, B. P.; Konst, S. Novel hydrogel actuator inspired by reversible mussel adhesive protein chemistry Adv. Mater. 2014, 26 (21) 3415-3419 10.1002/adma.201306137
36. Wang, Y.; Shi, D.; Tao, S.; Song, W.; Wang, H.; Wang, X.; Li, G.; Qiu, J.; Ji, M. A general, green-chemistry approach for the immobilization of inorganic catalysts in monolithic porous flow-reactors ACS Sustainable Chem. Eng. 2016, 4 (3) 1602-1610 10.1021/acssuschemeng.5b01541
37. Zheng, K.; Zhang, L.; Gao, Y.; Wu, Y.; Zhao, W.; Cui, Y. Enzymatic oxidative polymerization of pyrogallic acid for preparation of hindered phenol antioxidant J. Appl. Polym. Sci. 2015, 132 (12) 41592-41599 10.1002/app.41591
38. Oh, D. X.; Kim, S.; Lee, D.; Hwang, D. S. Tunicate-mimetic nanofibrous hydrogel adhesive with improved wet adhesion Acta Biomater. 2015, 20 (1) 104-112 10.1016/j.actbio.2015.03.031
39. Xie, J.; Schaich, K. M. Re-evaluation of the 2, 2-diphenyl-1-picrylhydrazyl free radical (DPPH) assay for antioxidant activity J. Agric. Food Chem. 2014, 62 (19) 4251-4260 10.1021/jf500180u
40. Tian, X.; Schaich, K. M. Effects of molecular structure on kinetics and dynamics of the trolox equivalent antioxidant capacity assay with ABTS+• J. Agric. Food Chem. 2013, 61 (23) 5511-5519 10.1021/jf4010725
41. Ou, B.; Hampsch-Woodill, M.; Prior, R. L. Development and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe J. Agric. Food Chem. 2001, 49 (10) 4619-4626 10.1021/jf010586o
42. Sierra, C. A.; Lahti, P. M. A photoluminescent, segmented oligo-polyphenylenevinylene copolymer with hydrogen-bonding pendant chains Chem. Mater. 2004, 16 (1) 55-61 10.1021/cm034708z
43. Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Antioxidant activity applying an improved ABTS radical cation decolorization assay Free Radical Biol. Med. 1999, 26 (9) 1231-1237 10.1016/S0891-5849(98)00315-3
44. van den Berg, R.; Haenen, G. R. M. M.; van den Berg, H.; Bast, A. Applicability of an improved Trolox equivalent antioxidant capacity (TEAC) assay for evaluation of antioxidant capacity measurements of mixtures Food Chem. 1999, 66 (4) 511-517 10.1016/S0308-8146(99)00089-8
45. Ejima, H.; Yanai, N.; Best, J. P.; Sindoro, M.; Granick, S.; Caruso, F. Near-incompressible faceted polymer microcapsules from metal-organic framework templates Adv. Mater. 2013, 25 (40) 5767-5771 10.1002/adma.201302442
46. Sauerbrey, G. Verwendung von schwingquarzen zur wägung dünner schichten und zur mikrowägung Eur. Phys. J. A 1959, 155 (2) 206-222 10.1007/BF01337937
47. Li, H. W.; Strauss, H. L.; Snyder, R. G. Differences in the IR methylene rocking bands between the crystalline fatty acids and n-alkanes: Frequencies, intensities, and correlation splitting J. Phys. Chem. A 2004, 108 (32) 6629-6642 10.1021/jp049106x
48. Saito, Y.; Yabu, H. Synthesis of poly (dihydroxystyrene-block-styrene) (PDHSt-b-PSt) by the RAFT process and preparation of organic-solvent-dispersive Ag NPs by automatic reduction of metal ions in the presence of PDHSt-b-PSt Chem. Commun. 2015, 51 (18) 3743-3746 10.1039/C4CC08366K
49. Goupy, P.; Dufour, C.; Loonis, M. Dangles, O., Quantitative kinetic analysis of hydrogen transfer reactions from dietary polyphenols to the DPPH radical J. Agric. Food Chem. 2003, 51 (3) 615-622 10.1021/jf025938l
50. Piras, A. M.; Dessy, A.; Dinucci, D.; Chiellini, F. 2-Methoxy aniline grafted poly (maleic anhydride-alt-butyl vinyl ether) hemiester: a new biocompatible polymeric free radical scavenger Macromolecules 2011, 44 (4) 848-856 10.1021/ma102309m
51. Wright, J. S.; Johnson, E. R.; DiLabio, G. A. Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects, and application to major families of antioxidants J. Am. Chem. Soc. 2001, 123 (6) 1173-1183 10.1021/ja002455u
52. Ganapathi, M. R.; Hermann, R.; Naumov, S.; Brede, O. Free electron transfer from several phenols to radical cations of non-polar solvents Phys. Chem. Chem. Phys. 2000, 2 (21) 4947-4955 10.1039/b005864p
53. Leopoldini, M.; Marino, T.; Russo, N.; Toscano, M. Antioxidant properties of phenolic compounds: H-atom versus electron transfer mechanism J. Phys. Chem. A 2004, 108 (22) 4916-4922 10.1021/jp037247d
54. Zhou, H. C.; Tam, N. F. Y.; Lin, Y. M.; Ding, Z. H.; Chai, W. M.; Wei, S. D. Relationships between degree of polymerization and antioxidant activities: a study on proanthocyanidins from the leaves of a medicinal mangrove plant ceriops tagal PLoS One 2014, 9 (10) e107606-e107616 10.1371/journal.pone.0107606
55. Sheih, I. C.; Wu, T. K.; Fang, T. J. Antioxidant properties of a new antioxidative peptide from algae protein waste hydrolysate in different oxidation systems Bioresour. Technol. 2009, 100 (13) 3419-3425 10.1016/j.biortech.2009.02.014
56. Carter, M. K. Correlation of electronic transitions and redox potentials measured for pyrocatechol, resorcinol, hydroquinone, pyrogallol, and gallic acid with results of semi-empirical molecular orbital computations-A useful interpretation tool J. Mol. Struct. 2007, 831 (1) 26-36 10.1016/j.molstruc.2006.07.020
57. Brigati, G.; Lucarini, M.; Mugnaini, V.; Pedulli, G. F. Determination of the substituent effect on the OH bond dissociation enthalpies of phenolic antioxidants by the EPR radical equilibration technique J. Org. Chem. 2002, 67 (14) 4828-4832 10.1021/jo025755y
58. Muzolf, M.; Szymusiak, H.; Gliszczyńska-Świgło, A.; Rietjens, I. M. C. M.; Tyrakowska, B. e. pH-dependent radical scavenging capacity of green tea catechins J. Agric. Food Chem. 2008, 56 (3) 816-823 10.1021/jf0712189
59. Chirdon, W. M.; O'Brien, W. J.; Robertson, R. E. Adsorption of catechol and comparative solutes on hydroxyapatite J. Biomed. Mater. Res. 2003, 66B (2) 532-538 10.1002/jbm.b.10041
60. Waite, J. H. Nature's underwater adhesive specialist Int. J. Adhes. Adhes. 1987, 7 (1) 9-14 10.1016/0143-7496(87)90048-0
61. Bastings, M. M. C.; Helms, B. A.; van Baal, I.; Hackeng, T. M.; Merkx, M.; Meijer, E. W. From phage display to dendrimer display: Insights into multivalent binding J. Am. Chem. Soc. 2011, 133 (17) 6636-6641 10.1021/ja110700x
62. Van Lent, B.; Scheutjens, J. M. H. M. Influence of association on adsorption properties of block copolymers Macromolecules 1989, 22 (4) 1931-1937 10.1021/ma00194a069
63. Misra, D. N. Adsorption from solutions on synthetic hydroxyapatite: nonaqueous vs. aqueous solvents J. Biomed. Mater. Res. 1999, 48 (6) 848-855 10.1002/(SICI)1097-4636(1999)48:6<848::AID-JBM13>3.0.CO;2-M
64. 2 Environ. Sci. Technol. 1996, 30 (5) 1604-1613 10.1021/es950615+