PMID- 36835650
OWN - NLM
STAT- MEDLINE
DCOM- 20230228
LR  - 20230228
IS  - 1422-0067 (Electronic)
IS  - 1422-0067 (Linking)
VI  - 24
IP  - 4
DP  - 2023 Feb 20
TI  - A Model Eumelanin from 5,6-Dihydroxyindole-2-Carboxybutanamide Combining 
      Remarkable Antioxidant and Photoprotective Properties with a Favourable 
      Solubility Profile for Dermo-Cosmetic Applications.
LID - 10.3390/ijms24044241 [doi]
LID - 4241
AB  - The search for new synthetic melanin-related pigments that maintain the 
      antioxidant and photoprotective properties of naturally occurring dark 
      eumelanins, while overcoming their unfavorable solubility, and molecular 
      heterogeneity is presently a very active issue for dermo-cosmetic purposes. In 
      this work, we explored the potential of a melanin obtained from the 
      carboxybutanamide of a major eumelanin biosynthetic precursor, 
      5,6-dihydroxyindole-2-carboxylic acid (DHICA), by aerobic oxidation under 
      slightly alkaline conditions. Analysis of the pigment by EPR, ATR-FTIR and MALDI 
      MS indicated a substantial structural similarity to DHICA melanin, while 
      investigation of the early intermediates confirmed unchanged regiochemistry of 
      the oxidative coupling. The pigment exhibited a UVA-visible absorption even more 
      intense than that of DHICA melanin, and a noticeable solubility in polar solvents 
      of dermo-cosmetic relevance. The hydrogen- and/or electron-donor ability, and the 
      iron (III) reducing power as determined by conventional assays provided evidence 
      for marked antioxidant properties not merely ascribable to the more favorable 
      solubility profile, while the inhibitory action of the radical- or 
      photosensitized solar light-induced lipid peroxidation was more marked compared 
      to that of DHICA melanin. Overall, these results hint at this melanin, which 
      remarkable properties are, in part, due to the electronic effects of the 
      carboxyamide functionality as a promising functional ingredient for 
      dermo-cosmetic formulations.
FAU - Argenziano, Rita
AU  - Argenziano R
AD  - Department of Chemical Sciences, University of Naples "Federico II", Via Cintia 
      4, I-80126 Naples, Italy.
FAU - Alfieri, Maria Laura
AU  - Alfieri ML
AUID- ORCID: 0000-0002-4602-3633
AD  - Department of Chemical Sciences, University of Naples "Federico II", Via Cintia 
      4, I-80126 Naples, Italy.
FAU - Gallucci, Noemi
AU  - Gallucci N
AD  - Department of Chemical Sciences, University of Naples "Federico II", Via Cintia 
      4, I-80126 Naples, Italy.
FAU - D'Errico, Gerardino
AU  - D'Errico G
AUID- ORCID: 0000-0001-6383-8618
AD  - Department of Chemical Sciences, University of Naples "Federico II", Via Cintia 
      4, I-80126 Naples, Italy.
FAU - Panzella, Lucia
AU  - Panzella L
AUID- ORCID: 0000-0002-2662-8205
AD  - Department of Chemical Sciences, University of Naples "Federico II", Via Cintia 
      4, I-80126 Naples, Italy.
FAU - Napolitano, Alessandra
AU  - Napolitano A
AUID- ORCID: 0000-0003-0507-5370
AD  - Department of Chemical Sciences, University of Naples "Federico II", Via Cintia 
      4, I-80126 Naples, Italy.
LA  - eng
GR  - 2017YJMPZN/Ministry of Research/
PT  - Journal Article
DEP - 20230220
PL  - Switzerland
TA  - Int J Mol Sci
JT  - International journal of molecular sciences
JID - 101092791
RN  - Z3OC8499KG (5,6-dihydroxyindole)
RN  - 12627-86-0 (eumelanin)
RN  - 0 (Melanins)
RN  - 0 (Antioxidants)
SB  - IM
MH  - *Melanins/chemistry
MH  - *Antioxidants/chemistry
MH  - Solubility
PMC - PMC9961549
OTO - NOTNLM
OT  - 5,6 dihydroxyindole
OT  - antioxidant
OT  - carboxybutanamide
OT  - melanins
OT  - photoprotection
COIS- The authors declare no conflict of interest.
EDAT- 2023/02/26 06:00
MHDA- 2023/03/03 06:00
PMCR- 2023/02/20
CRDT- 2023/02/25 02:57
PHST- 2023/01/23 00:00 [received]
PHST- 2023/02/16 00:00 [revised]
PHST- 2023/02/18 00:00 [accepted]
PHST- 2023/02/25 02:57 [entrez]
PHST- 2023/02/26 06:00 [pubmed]
PHST- 2023/03/03 06:00 [medline]
PHST- 2023/02/20 00:00 [pmc-release]
AID - ijms24044241 [pii]
AID - ijms-24-04241 [pii]
AID - 10.3390/ijms24044241 [doi]
PST - epublish
SO  - Int J Mol Sci. 2023 Feb 20;24(4):4241. doi: 10.3390/ijms24044241.