Effects of pH and Oxidants on the First Steps of Polydopamine Formation: A Thermodynamic Approach
We present a general thermodynamic top-down analysis of the effects of oxidants and pH on dopamine oxidation and cyclization, supplemented with UV–vis and electrochemical studies. The model is applicable to other catecholamines and various experimental conditions. The results show that the decisive...
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| Published in | The journal of physical chemistry. B Vol. 122; no. 24; pp. 6314 - 6327 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
21.06.2018
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| Subjects | |
| Online Access | Get full text |
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| Abstract | We present a general thermodynamic top-down analysis of the effects of oxidants and pH on dopamine oxidation and cyclization, supplemented with UV–vis and electrochemical studies. The model is applicable to other catecholamines and various experimental conditions. The results show that the decisive physicochemical parameters in autoxidation are the pK values of the semiquinone and the amino group in the oxidized quinone. Addition of Ce(IV) or Fe(III) enhances dopamine oxidation in acidic media in aerobic and anaerobic conditions by the direct oxidation of dopamine and, in the presence of oxygen, also by the autoxidation of the formed semiquinone. At pH 4.5, the enhancement of the one-electron oxidation of dopamine explains the overall reaction enhancement, but at a lower pH, cyclization becomes rate-determining. Oxidation by Cu(II) at reasonable rates requires the presence of oxygen or chloride ions. |
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| AbstractList | We present a general thermodynamic top-down analysis of the effects of oxidants and pH on dopamine oxidation and cyclization, supplemented with UV–vis and electrochemical studies. The model is applicable to other catecholamines and various experimental conditions. The results show that the decisive physicochemical parameters in autoxidation are the pK values of the semiquinone and the amino group in the oxidized quinone. Addition of Ce(IV) or Fe(III) enhances dopamine oxidation in acidic media in aerobic and anaerobic conditions by the direct oxidation of dopamine and, in the presence of oxygen, also by the autoxidation of the formed semiquinone. At pH 4.5, the enhancement of the one-electron oxidation of dopamine explains the overall reaction enhancement, but at a lower pH, cyclization becomes rate-determining. Oxidation by Cu(II) at reasonable rates requires the presence of oxygen or chloride ions. We present a general thermodynamic top-down analysis of the effects of oxidants and pH on dopamine oxidation and cyclization, supplemented with UV-vis and electrochemical studies. The model is applicable to other catecholamines and various experimental conditions. The results show that the decisive physicochemical parameters in autoxidation are the p K values of the semiquinone and the amino group in the oxidized quinone. Addition of Ce(IV) or Fe(III) enhances dopamine oxidation in acidic media in aerobic and anaerobic conditions by the direct oxidation of dopamine and, in the presence of oxygen, also by the autoxidation of the formed semiquinone. At pH 4.5, the enhancement of the one-electron oxidation of dopamine explains the overall reaction enhancement, but at a lower pH, cyclization becomes rate-determining. Oxidation by Cu(II) at reasonable rates requires the presence of oxygen or chloride ions.We present a general thermodynamic top-down analysis of the effects of oxidants and pH on dopamine oxidation and cyclization, supplemented with UV-vis and electrochemical studies. The model is applicable to other catecholamines and various experimental conditions. The results show that the decisive physicochemical parameters in autoxidation are the p K values of the semiquinone and the amino group in the oxidized quinone. Addition of Ce(IV) or Fe(III) enhances dopamine oxidation in acidic media in aerobic and anaerobic conditions by the direct oxidation of dopamine and, in the presence of oxygen, also by the autoxidation of the formed semiquinone. At pH 4.5, the enhancement of the one-electron oxidation of dopamine explains the overall reaction enhancement, but at a lower pH, cyclization becomes rate-determining. Oxidation by Cu(II) at reasonable rates requires the presence of oxygen or chloride ions. We present a general thermodynamic top-down analysis of the effects of oxidants and pH on dopamine oxidation and cyclization, supplemented with UV–vis and electrochemical studies. The model is applicable to other catecholamines and various experimental conditions. The results show that the decisive physicochemical parameters in autoxidation are the p K values of the semiquinone and the amino group in the oxidized quinone. Addition of Ce(IV) or Fe(III) enhances dopamine oxidation in acidic media in aerobic and anaerobic conditions by the direct oxidation of dopamine and, in the presence of oxygen, also by the autoxidation of the formed semiquinone. At pH 4.5, the enhancement of the one-electron oxidation of dopamine explains the overall reaction enhancement, but at a lower pH, cyclization becomes rate-determining. Oxidation by Cu(II) at reasonable rates requires the presence of oxygen or chloride ions. We present a general thermodynamic top-down analysis of the effects of oxidants and pH on dopamine oxidation and cyclization, supplemented with UV–vis and electrochemical studies. The model is applicable to other catecholamines and various experimental conditions. The results show that the decisive physicochemical parameters in autoxidation are the pK values of the semiquinone and the amino group in the oxidized quinone. Addition of Ce(IV) or Fe(III) enhances dopamine oxidation in acidic media in aerobic and anaerobic conditions by the direct oxidation of dopamine and, in the presence of oxygen, also by the autoxidation of the formed semiquinone. At pH 4.5, the enhancement of the one-electron oxidation of dopamine explains the overall reaction enhancement, but at a lower pH, cyclization becomes rate-determining. Oxidation by Cu(II) at reasonable rates requires the presence of oxygen or chloride ions. We present a general thermodynamic top-down analysis of the effects of oxidants and pH on dopamine oxidation and cyclization, supplemented with UV-vis and electrochemical studies. The model is applicable to other catecholamines and various experimental conditions. The results show that the decisive physicochemical parameters in autoxidation are the p K values of the semiquinone and the amino group in the oxidized quinone. Addition of Ce(IV) or Fe(III) enhances dopamine oxidation in acidic media in aerobic and anaerobic conditions by the direct oxidation of dopamine and, in the presence of oxygen, also by the autoxidation of the formed semiquinone. At pH 4.5, the enhancement of the one-electron oxidation of dopamine explains the overall reaction enhancement, but at a lower pH, cyclization becomes rate-determining. Oxidation by Cu(II) at reasonable rates requires the presence of oxygen or chloride ions. |
| Author | Marttila, Lauri Ouvinen, Tuomo Lukkari, Jukka Salomäki, Mikko Kivelä, Henri |
| AuthorAffiliation | Department of Chemistry University of Turku Graduate School (UTUGS) Turku University Centre for Surfaces and Materials (MatSurf) Doctoral Programme in Physical and Chemical Sciences |
| AuthorAffiliation_xml | – name: Department of Chemistry – name: Turku University Centre for Surfaces and Materials (MatSurf) – name: Doctoral Programme in Physical and Chemical Sciences – name: University of Turku Graduate School (UTUGS) |
| Author_xml | – sequence: 1 givenname: Mikko orcidid: 0000-0001-6190-2073 surname: Salomäki fullname: Salomäki, Mikko organization: Turku University Centre for Surfaces and Materials (MatSurf) – sequence: 2 givenname: Lauri orcidid: 0000-0002-8221-0954 surname: Marttila fullname: Marttila, Lauri organization: University of Turku Graduate School (UTUGS) – sequence: 3 givenname: Henri orcidid: 0000-0003-1414-8893 surname: Kivelä fullname: Kivelä, Henri organization: Turku University Centre for Surfaces and Materials (MatSurf) – sequence: 4 givenname: Tuomo surname: Ouvinen fullname: Ouvinen, Tuomo organization: University of Turku Graduate School (UTUGS) – sequence: 5 givenname: Jukka orcidid: 0000-0002-9409-7995 surname: Lukkari fullname: Lukkari, Jukka email: jukka.lukkari@utu.fi organization: Turku University Centre for Surfaces and Materials (MatSurf) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29787272$$D View this record in MEDLINE/PubMed |
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| Snippet | We present a general thermodynamic top-down analysis of the effects of oxidants and pH on dopamine oxidation and cyclization, supplemented with UV–vis and... We present a general thermodynamic top-down analysis of the effects of oxidants and pH on dopamine oxidation and cyclization, supplemented with UV-vis and... We present a general thermodynamic top-down analysis of the effects of oxidants and pH on dopamine oxidation and cyclization, supplemented with UV–vis and... |
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| SubjectTerms | anaerobic conditions autoxidation chlorides copper dopamine electrochemistry ions iron oxidants oxygen physical chemistry quinones thermodynamics ultraviolet-visible spectroscopy |
| Title | Effects of pH and Oxidants on the First Steps of Polydopamine Formation: A Thermodynamic Approach |
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