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Gas chromatography-mass spectrometry analysis of pheomelanin degradation products
Linköping University, Department of Clinical and Experimental Medicine, Clinical Chemistry. Linköping University, Faculty of Health Sciences. Östergötlands Läns Landsting, Centre for Laboratory Medicine, Department of Clinical Chemistry.
Linköping University, Department of Clinical and Experimental Medicine, Clinical Chemistry. Linköping University, Faculty of Health Sciences.
Linköping University, Department of Clinical and Experimental Medicine, Clinical Chemistry. Linköping University, Faculty of Health Sciences. Östergötlands Läns Landsting, Centre for Laboratory Medicine, Department of Clinical Chemistry.
2009 (English)In: Journal of Chromatography A, ISSN 0021-9673, E-ISSN 1873-3778, Vol. 1216, no 30, 5730-5739 p.Article in journal (Refereed) Published
Abstract [en]

Melanoma is most rapidly increasing in the white population and people with pheomelanin skin type are at high risk to develop melanoma. However, little is known about the pheomelanin structure and function, and further elucidation of this melanin is therefore an important task. A GC/MS method was developed based on hydriodic acid hydrolysis of pheomelanin in the urine. Derivatization was performed with ethyl chloroformate and ethanol:pyridine (4:1, v/v). N,O-Ethoxycarbonyl-ethyl esters were extracted with chloroform and analyzed by GC/MS. 4-Amino-3-hydroxyphenylaianine and 3-amino4-hydroxyphenylaianine together with one benzothiazinone and two benzothiazole compounds were detected and identified in hydrolyzed samples of synthetic pheomelanin and melanin from the urine of a patient with melanoma. These findings strongly suggest that heterocyclic pheomelanin-type units are incorporated in the pigment structures.

Place, publisher, year, edition, pages
2009. Vol. 1216, no 30, 5730-5739 p.
Keyword [en]
Alkyl chloroformate; Aminohydroxyphenylalanine; Derivatization; Gas chromatography-mass spectrometry; Melanin; Melanoma; Pheomelanin; 7-(2-Amino-2-carboxyethyl)-5-hydroxy-3, 4-dihydro-2H-1, 4-benzothiazine-3-one 6-(2-Amino-2-carboxyethyl)-4-hydroxybenzothiazole 6-(2-Amino-2-carboxyethyl)-4-hydroxy-2-methyl-benzothiazole; Benzothiazine; Benzothiazole; Benzothiazinone
National Category
Medical and Health Sciences
Identifiers
URN: urn:nbn:se:liu:diva-20135DOI: 10.1016/j.chroma.2009.05.063OAI: oai:DiVA.org:liu-20135DiVA: diva2:233390
Available from: 2009-08-31 Created: 2009-08-31 Last updated: 2017-12-13Bibliographically approved
In thesis
1. Pheomelanin markers in melanoma with reference to their excretion into urine
Open this publication in new window or tab >>Pheomelanin markers in melanoma with reference to their excretion into urine
2009 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Skin pigmentation is an important issue in most cultures. Until recently we have not understood the most important elements of pigmentation regarding detailed chemical structure. The synthesis of melanin is very complex, and although core enzymes, other important proteins, and parts of the melanin structure have been identified much information in this context awaits disclosure.

The function of the melanocyte and the deposition of melanin pigments into the keratinocytes are very important in the protection against UV light. Melanin pigments consist of high-molecular structures often described as brown to black eumelanin and yellow to red pheomelanin. Eumelanin is photoprotective, whereas pheomelanin is believed to be carcinogenic after UV radiation. There is strong evidence that people of fair complexion with freckles who tan poorly are at higher risk of developing melanoma. These people have a higher pheomelanin to eumelanin ratio in their skin.

Melanoma, one of the most widely spread cancers, is derived from melanocytes. There is accumulating evidence that pigment constitution is highly involved in the development of melanoma. We found that patients with advanced melanoma secrete substantial amounts of pigment structures into the urine, in particular those with diffuse melanosis. In subsequently performed experiments we purified these pigments and subjected the product to chemical degradation by either hydrogen peroxide oxidation or hydriodic hydrolysis. Several new chromatographic methods were developed for the structural analysis of these products. Structural analysis of new chromatographic peaks was performed. In conclusion, complex pheomelanin structures as well as low molecular weight pigments and free benzothiazoles have been identified in the urine of patients with melanoma and diffuse melanosis.

The present thesis provides new insight into melanogenesis and melanoma progression. This opens the doorway to further approaches to the investigation of melanins and can help to understand fundamental problems about the structure and biosynthesis of natural melanins.

Place, publisher, year, edition, pages
Linköping: Linköping University Electronic Press, 2009. 67 p.
Series
Linköping University Medical Dissertations, ISSN 0345-0082 ; 1143
Keyword
Pheomelanin, melanoma, benzothiazole, aminohydroxyphenylalanine, diffuse melanosis, HILIC
National Category
Other Clinical Medicine
Identifiers
urn:nbn:se:liu:diva-21486 (URN)978-91-7393-566-1 (ISBN)
Public defence
2009-10-23, Berzeliussalen, Hälsouniversitet, Campus US, Linköpings Universitet, Linköping, 13:00 (Swedish)
Opponent
Supervisors
Available from: 2009-10-12 Created: 2009-10-02 Last updated: 2010-01-14Bibliographically approved

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Nezirevic Dernroth, DzenetaKågedal, Bertil

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