Identification of sulforhodamine B photodegradation products present in nonpermanent tattoos by micro liquid chromatography coupled with tandem high-resolution mass spectrometry.
This article deals with the photodegradation of sulforhodamine B, a dye widely used in nonpermanent tattoos. Degradation evidence was obtained from both aqueous and sweat-simulating solutions of the dye after 9 days of Solarbox irradiation. The identification of the degradation products was achieved using a nontarget approach. For this purpose, a micro liquid chromatography method coupled with tandem high-resolution mass spectrometry was developed. In addition, the chemical structures of five degradation products and two dye impurities were elucidated. The degradation products were the same for both types of solution, whereas the degradation rate of the dye in sweat-simulating solution was slightly faster than that in aqueous solution. The method was also applied to samples of tattooed pigskin subjected to irradiation, in order to better simulate the irradiation effects on the dye used on the skin. None of the degradation products found in the sulforhodamine B solutions were identified in the degraded tattooed pigskin samples, but a new signal at m/z 637.3051 (positive ionization) was found, and the structure of the corresponding molecule was elucidated. The mutagenicity of the photodegradation products was evaluated using a quantitative structure-activity relationship approach, which gave negative results for all the structures elucidated. Graphical Abstract Comparison between tattoed pigskin before and after photodegration process. Strategies for the identification of sulforhodamine B degradation products.
Department of Science and Technological Innovation, University of Piemonte Orientale, Viale T. Michel 11, 15121, Alessandria, Italy, fabio.gosetti@uniupo.it.
Fabio
F
Gosetti
Bianca
B
Bolfi
Emilio
E
Marengo
D002853:Chromatography, Liquid / Q000379:methods*; D055668:Photochemical Processes; D012235:Rhodamines / Q000737:chemistry*; D053719:Tandem Mass Spectrometry / Q000379:methods*; D013653:Tattooing
D012235:Rhodamines; C022027:lissamine rhodamine B