Development of a method for isolation of melanin from archival FFPE tissues of human melanoma for structural studies by pyrolysis-gas chromatography-tandem mass spectrometry

[1] D’Orazio JA, Marsch A, Lagrew J, Veith WB. Skin pigmentation and melanoma risk In: Advances in malignant melanoma – clinical and research perspectives. InTech 2011: 39–68. D’OrazioJA MarschA LagrewJ VeithWB Skin pigmentation and melanoma risk In: Advances in malignant melanoma – clinical and research perspectives InTech 2011 39 68 Search in Google Scholar

[2] Simon JD, Peles D, Wakamatsu K, Ito S. Current challenges in understanding melanogenesis: Bridging chemistry, biological control, morphology, and function. Pigment Cell Melanoma Res. 2009; 22: 563–579. SimonJD PelesD WakamatsuK ItoS Current challenges in understanding melanogenesis: Bridging chemistry, biological control, morphology, and function Pigment Cell Melanoma Res 2009 22 563 579 10.1111/j.1755-148X.2009.00610.x19627559 Search in Google Scholar

[3] Wakamatsu K, Zippin JH, Ito S. Chemical and biochemical control of skin pigmentation with special emphasis on mixed melanogenesis. Pigment Cell Melanoma Res. 2021; 34: 730–747. WakamatsuK ZippinJH ItoS Chemical and biochemical control of skin pigmentation with special emphasis on mixed melanogenesis Pigment Cell Melanoma Res 2021 34 730 747 10.1111/pcmr.12970886180633751833 Search in Google Scholar

[4] Brenner MV, Hearing J. The protective role of melanin against UV damage in human skin. Photochem Photobiol. 2008; 84: 539–549. BrennerMV HearingJ The protective role of melanin against UV damage in human skin Photochem Photobiol 2008 84 539 549 10.1111/j.1751-1097.2007.00226.x267103218435612 Search in Google Scholar

[5] Ito S, Wakamatsu K, Sarna T. Photodegradation of eumelanin and pheomelanin and its pathophysiological implications. Photochem Photobiol. 2018; 94: 409–420. ItoS WakamatsuK SarnaT Photodegradation of eumelanin and pheomelanin and its pathophysiological implications Photochem Photobiol 2018 94 409 420 10.1111/php.1283728873228 Search in Google Scholar

[6] Meredith P, Sarna T. The physical and chemical properties of eumelanin. Pigment Cell Res. 2006; 19: 572–594. MeredithP SarnaT The physical and chemical properties of eumelanin Pigment Cell Res 2006 19 572 594 10.1111/j.1600-0749.2006.00345.x17083485 Search in Google Scholar

[7] Mitra D, Luo X, Morgan A, Wang J, Hoang MP, Lo J, Guerrero CR, Lennerz J K, Mihm MC, Wargo JA, et al. A UV-independent pathway to melanoma carcinogenesis in the redhair-fairskin background. Nature. 2012; 491: 449–453. MitraD LuoX MorganA WangJ HoangMP LoJ GuerreroCR LennerzJ K MihmMC WargoJA A UV-independent pathway to melanoma carcinogenesis in the redhair-fairskin background Nature 2012 491 449 453 10.1038/nature11624352149423123854 Search in Google Scholar

[8] Morgan AM, Lo J, Fisher DE. How does pheomelanin synthesis contribute to melanomagenesis? Two distinct mechanisms could explain the carcinogenicity of pheomelanin synthesis. Bioessays. 2013; 35: 672–676. MorganAM LoJ FisherDE How does pheomelanin synthesis contribute to melanomagenesis? Two distinct mechanisms could explain the carcinogenicity of pheomelanin synthesis Bioessays 2013 35 672 676 10.1002/bies.201300020403371523650156 Search in Google Scholar

[9] Napolitano A, Panzella L, Monfrecola G, d’Ischia M. Pheomelanin-induced oxidative stress: Bright and dark chemistry bridging red hair phenotype and melanoma. Pigment Cell Melanoma Res. 2014; 27: 721–733. NapolitanoA PanzellaL MonfrecolaG d’IschiaM Pheomelanin-induced oxidative stress: Bright and dark chemistry bridging red hair phenotype and melanoma Pigment Cell Melanoma Res 2014 27 721 733 10.1111/pcmr.1226224814217 Search in Google Scholar

[10] Premi S. Role of melanin chemiexcitation in melanoma progression and drug resistance. Front Oncol. 2020; 10: 1305. PremiS Role of melanin chemiexcitation in melanoma progression and drug resistance Front Oncol 2020 10 1305 10.3389/fonc.2020.01305742565532850409 Search in Google Scholar

[11] Premi S, Wallisch S, Mano CM, Weiner AB, Bacchiocchi A, Wakamatsu K, Bechara EJH, Halaban R, Douki T, Brash DE. Chemiexcitation of melanin derivatives induces DNA photoproducts long after UV exposure. Science. 2015; 34:, 842–847. PremiS WallischS ManoCM WeinerAB BacchiocchiA WakamatsuK BecharaEJH HalabanR DoukiT BrashDE Chemiexcitation of melanin derivatives induces DNA photoproducts long after UV exposure Science 2015 34 842 847 10.1126/science.1256022443291325700512 Search in Google Scholar

[12] Salopek TG, Yamada K, Ito S, Jimbow K. Dysplastic melanocytic nevi contain high levels of pheomelanin: Quantitative comparison of pheomelanin/eumelanin levels between normal skin, common nevi, and dysplastic nevi. Pigment Cell Res. 1991; 4: 172–179. SalopekTG YamadaK ItoS JimbowK Dysplastic melanocytic nevi contain high levels of pheomelanin: Quantitative comparison of pheomelanin/eumelanin levels between normal skin, common nevi, and dysplastic nevi Pigment Cell Res 1991 4 172 179 10.1111/j.1600-0749.1991.tb00435.x1816549 Search in Google Scholar

[13] Pavel S, Van Nieuwpoort F, Van der Meulen H, Out C, Pizinger K, Cetkovska P, Smit NP, Koerten HK. Disturbed melanin synthesis and chronic oxidative stress in dysplastic naevi. Eur J Cancer. 2004; 40: 1423–1430. PavelS Van NieuwpoortF Van der MeulenH OutC PizingerK CetkovskaP SmitNP KoertenHK Disturbed melanin synthesis and chronic oxidative stress in dysplastic naevi Eur J Cancer 2004 40 1423 1430 10.1016/j.ejca.2003.11.03515177503 Search in Google Scholar

[14] Dzierżęga-Lęcznar A, Kurkiewicz S, Stępień K. Detection and quantitation of a pheomelanin component in melanin pigments using pyrolysis-gas chromatography/tandem mass spectrometry system with multiple reaction monitoring mode. J Mass Spectrom. 2012; 47: 242–245. Dzierżęga-LęcznarA KurkiewiczS StępieńK Detection and quantitation of a pheomelanin component in melanin pigments using pyrolysis-gas chromatography/tandem mass spectrometry system with multiple reaction monitoring mode J Mass Spectrom 2012 47 242 245 10.1002/jms.295722359335 Search in Google Scholar

[15] Chodurek E, Dzierżęga-Lęcznar A, Kurkiewicz S, Stępień K. Exposure to valproic acid and 5,7-dimethoxycoumarin induces pheomelano-genesis in the human melanoma G-361 cells, as demonstrated by Py-GC/MS/MS study. J Anal Appl Pyrolysis. 2013; 104: 567–572. ChodurekE Dzierżęga-LęcznarA KurkiewiczS StępieńK Exposure to valproic acid and 5,7-dimethoxycoumarin induces pheomelano-genesis in the human melanoma G-361 cells, as demonstrated by Py-GC/MS/MS study J Anal Appl Pyrolysis 2013 104 567 572 10.1016/j.jaap.2013.05.012 Search in Google Scholar

[16] Dzierżęga-Lęcznar A, Kurkiewicz S, Tam I, Marek Ł, Stępień K. Pheomelanin content of cultured human melanocytes from lightly and darkly pigmented skin: A pyrolysis-gas chromatography/tandem mass spectrometry study. J Anal Appl Pyrolysis. 2017; 124: 349–354. Dzierżęga-LęcznarA KurkiewiczS TamI MarekŁ StępieńK Pheomelanin content of cultured human melanocytes from lightly and darkly pigmented skin: A pyrolysis-gas chromatography/tandem mass spectrometry study J Anal Appl Pyrolysis 2017 124 349 354 10.1016/j.jaap.2017.01.009 Search in Google Scholar

[17] Del Bino S, Ito S, Sok J, Nakanishi Y, Bastien P, Wakamatsu K, Bernerd F. Chemical analysis of constitutive pigmentation of human epidermis reveals constant eumelanin to pheomelanin ratio. Pigment Cell Melanoma Res. 2015; 28: 707–717. Del BinoS ItoS SokJ NakanishiY BastienP WakamatsuK BernerdF Chemical analysis of constitutive pigmentation of human epidermis reveals constant eumelanin to pheomelanin ratio Pigment Cell Melanoma Res 2015 28 707 717 10.1111/pcmr.1241026285058 Search in Google Scholar

[18] Lerche CM. Olsen P. Nissen CV, Philipsen PA, Wulf HC. A novel LC-MS/MS method to quantify eumelanin and pheomelanin and their relation to UVR sensitivity – a study on human skin biopsies. Pigment Cell Melanoma Res. 2019; 32: 809–816. LercheCM OlsenP NissenCV PhilipsenPA WulfHC A novel LC-MS/MS method to quantify eumelanin and pheomelanin and their relation to UVR sensitivity – a study on human skin biopsies Pigment Cell Melanoma Res 2019 32 809 816 10.1111/pcmr.1280531233275 Search in Google Scholar