The "benzothiazine" chromophore of pheomelanins: a reassessment

Photochemistry and Photobiology
Alessandra NapolitanoM d'Ischia

Abstract

The characteristic absorption and photochemical properties of pheomelanins are generally attributed to "benzothiazine" structural units derived biogenetically from 5-S-cysteinyldopa. This notion, however, conveys little or no information about the structural chromophores responsible for the photoreactivity of pheomelanins. At pH 7.4, natural and synthetic pheomelanins show a defined maximum around 305 nm, which is not affected by reductive treatment with sodium borohydride, and a monotonic decrease in the absorption in the range 350-550 nm. These features are not compatible with a significant proportion of structural units related to 2H-1,4-benzothiazine and 2H-1,4-benzothiazine-3-carboxylic acid, the early borohydride-reducible pheomelanin precursors featuring absorption maxima above 340 nm. Rather, these features would better accommodate a contribution by the nonreducible 3-oxo-3,4-dihydrobenzothiazine (lambdamax 299 nm) and benzothiazole (lambdamax 303 nm) structural motifs, which are generated in the later stages of pheomelanogenesis in vitro. This conclusion is supported by a detailed liquid chromatography/UV and mass spectrometry monitoring of the species formed in the oxidative conversion of 5-S-cysteinyldopa to pheomela...Continue Reading

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Citations

Dec 29, 2012·Accounts of Chemical Research·Alessandra NapolitanoMarco d'Ischia
Nov 24, 2011·Organic Letters·Youcai Hu, John B MacMillan
Aug 23, 2011·Chemical Communications : Chem Comm·Giorgia GrecoMarco d'Ischia
Aug 11, 2011·Pigment Cell & Melanoma Research·Giorgia GrecoMarco d'Ischia
Nov 1, 2012·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Emanuele FerrariLuigi Casella
Jul 5, 2011·Free Radical Biology & Medicine·Orlando Chiarelli-NetoMaurício S Baptista
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Oct 13, 2015·Progress in Neurobiology·Fabio A ZuccaLuigi Zecca
May 13, 2014·Pigment Cell & Melanoma Research·Alessandra NapolitanoMarco d'Ischia
May 20, 2016·International Journal of Molecular Sciences·Raffaella MicilloMarco d'Ischia
Apr 8, 2014·Bioorganic & Medicinal Chemistry Letters·Ismael GalvánFrancisco Solano
Sep 27, 2018·Physiological Reviews·Liliana D'Alba, Matthew D Shawkey
Oct 2, 2020·International Journal of Molecular Sciences·Laurien E HoutzagersMartine J Jager
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Aug 26, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Maria Laura AlfieriAlessandra Napolitano
Aug 4, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Maher Al KhatibRebecca Pogni
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Sep 26, 2017·ACS Chemical Neuroscience·Zülfikar TemoçinGregory F Payne
Jun 2, 2016·ACS Chemical Neuroscience·Eunkyoung KimGregory F Payne

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