PMID- 11006597 OWN - NLM STAT- MEDLINE DCOM- 20001019 LR - 20131121 IS - 0951-4198 (Print) IS - 0951-4198 (Linking) VI - 14 IP - 19 DP - 2000 TI - Effects of ultraviolet irradiation on melanogenesis from tyrosine, Dopa and dopamine: a matrix-assisted laser desorption/ionization mass spectrometric study. PG - 1862-8 AB - Matrix-assisted laser desorption/ionization (MALDI) mass spectrometry experiments were applied to study the influence of ultraviolet (UV) irradiation in melanogenesis. Samples were prepared starting from three different precursors, tyrosine, Dopa and dopamine, in the presence or absence of tyrosinase, the enzyme responsible for the synthesis of melanin. Enzymatic reactions were carried out for 10, 30, 60 and 120 min under UV irradiation at 365 nm, and aliquots were then immediately ultrafiltered and lyophilized. Samples obtained by irradiation of tyrosine solution revealed the formation of 5,6-dihydroxyindole (DHI) oligomers up to pentamers at 120 min; the reaction kinetics were markedly enhanced in the presence of tyrosinase. In the case of Dopa, UV irradiation favored melanogenesis only in the presence of the enzyme; in this case, many reaction pathways were activated, originating various oligomeric species of Dopa, DHI and 5,6-dihydroxyindole-2-carboxylic acid (DHICA). Conversely, when dopamine was used as tyrosinase substrate under UV light, mechanisms of melanogenesis different from those generated by simple enzymatic reaction without irradiation were not activated, as the same oligomeric species were present. CI - Copyright 2000 John Wiley & Sons, Ltd. FAU - Bertazzo, A AU - Bertazzo A AD - Dipartimento di Scienze Farmaceutiche, Via Marzolo 5, 35100 Padova, Italy. FAU - Favretto, D AU - Favretto D FAU - Costa, C V AU - Costa CV FAU - Allegri, G AU - Allegri G FAU - Traldi, P AU - Traldi P LA - eng PT - Journal Article PT - Research Support, Non-U.S. Gov't PL - England TA - Rapid Commun Mass Spectrom JT - Rapid communications in mass spectrometry : RCM JID - 8802365 RN - 0 (Melanins) RN - 42HK56048U (Tyrosine) RN - 63-84-3 (Dihydroxyphenylalanine) RN - EC 1.14.18.1 (Monophenol Monooxygenase) RN - VTD58H1Z2X (Dopamine) SB - IM MH - Dihydroxyphenylalanine/*chemistry/*radiation effects MH - Dopamine/*chemistry/*radiation effects MH - Melanins/*chemistry/*radiation effects MH - Monophenol Monooxygenase/chemistry MH - Photochemistry MH - Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization MH - Tyrosine/*chemistry/*radiation effects MH - Ultraviolet Rays EDAT- 2000/09/28 11:00 MHDA- 2000/10/21 11:01 CRDT- 2000/09/28 11:00 PHST- 2000/09/28 11:00 [pubmed] PHST- 2000/10/21 11:01 [medline] PHST- 2000/09/28 11:00 [entrez] AID - 10.1002/1097-0231(20001015)14:19<1862::AID-RCM87>3.0.CO;2-U [pii] AID - 10.1002/1097-0231(20001015)14:19<1862::AID-RCM87>3.0.CO;2-U [doi] PST - ppublish SO - Rapid Commun Mass Spectrom. 2000;14(19):1862-8. doi: 10.1002/1097-0231(20001015)14:19<1862::AID-RCM87>3.0.CO;2-U.