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Sociedade Brasileira de Química, SBQ, Journal of the Brazilian Chemical Society, 2014

DOI: 10.5935/0103-5053.20140277

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Preparation, Characterization, Cytotoxicity and Antioxidant Activity of DOPA Melanin Modified by Amino Acids: Melanin-Like Oligomeric Aggregates

This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

Two new synthetic melanin-like oligomers inspired by the synthesis of pheomelanin (cys-DOPA) were prepared using L-DOPA as a precursor and the amino acids serine (ser-DOPA) and threonine (thr-DOPA) for modifications. The products obtained exhibited appreciable antioxidant activity. The compounds were characterized by liquid chromatography-mass spectrometry (LC-MS), elemental analysis and infrared spectroscopy. The pKa values of the groups present in each melanin suspension were determined in aqueous solution by potentiometric and spectrophotometric titration. Cytotoxicity assays showed an IC 50 > 500 mg L -1 resulting in non-toxic compounds for living cells. Finally, cys-DOPA, ser-DOPA and thr-DOPA exhibited antioxidant activity determined by the DPPH scavenging assay, with EC 50 = 7.69, 1.02 and 27.60 mg L -1 , respectively.