PMID- 29899264
OWN - NLM
STAT- MEDLINE
DCOM- 20181010
LR  - 20230926
IS  - 1422-0067 (Electronic)
IS  - 1422-0067 (Linking)
VI  - 19
IP  - 6
DP  - 2018 Jun 13
TI  - The Late Stages of Melanogenesis: Exploring the Chemical Facets and the 
      Application Opportunities.
LID - 10.3390/ijms19061753 [doi]
LID - 1753
AB  - In the last decade, the late stages of melanin biosynthesis involving the 
      oxidative polymerization of 5,6-dihydroxyindole (DHI) and 
      5,6-dihydroxyindole-2-carboxylic acid (DHICA) have been extensively investigated. 
      Most of the information derived from a biomimetic approach in which the oxidation 
      of melanogenic indoles was carried out under conditions mimicking those occurring 
      in the biological environment. Characterization of the early oligomers allowed 
      for drawing a structural picture of DHI and DHICA melanins, providing also an 
      interpretative basis for the different properties exhibited by these pigments, 
      e.g., the chromophore and the antioxidant ability. The improved knowledge has 
      opened new perspectives toward the exploitation of the unique chemistry of 
      melanins and its precursors in cosmetic and health care applications. A 
      noticeable example is the development of an innovative hair dyeing system that is 
      based on the marked ease of DHI to give rise to black melanin on air oxidation 
      under slightly alkaline conditions. The advantage of this method for a step-wise 
      coverage of gray hair with a natural shade pigmentation on repeated treatment 
      with a DHI-based formulation with respect to traditional dyes is presented. A 
      variant of DHICA melanin combining solubility in water-miscible organic solvents, 
      an intense chromophore in the UltraViolet-A UV-A region, and a marked antioxidant 
      potency was evaluated as an ingredient for cosmetic formulations.
FAU - Panzella, Lucia
AU  - Panzella L
AUID- ORCID: 0000-0002-2662-8205
AD  - Department of Chemical Sciences, University of Naples "Federico II", I-80126 
      Naples, Italy. panzella@unina.it.
FAU - Ebato, Atsuko
AU  - Ebato A
AD  - Hair Care Products Research Laboratories, Kao Corporation, Tokyo 131-8501, Japan. 
      ebato.atsuko@kao.com.
FAU - Napolitano, Alessandra
AU  - Napolitano A
AUID- ORCID: 0000-0003-0507-5370
AD  - Department of Chemical Sciences, University of Naples "Federico II", I-80126 
      Naples, Italy. alesnapo@unina.it.
FAU - Koike, Kenzo
AU  - Koike K
AUID- ORCID: 0000-0002-6796-5785
AD  - Hair Care Products Research Laboratories, Kao Corporation, Tokyo 131-8501, Japan. 
      koike.kenzo@kao.com.
LA  - eng
PT  - Journal Article
PT  - Review
DEP - 20180613
PL  - Switzerland
TA  - Int J Mol Sci
JT  - International journal of molecular sciences
JID - 101092791
RN  - 0 (Hair Dyes)
RN  - 0 (Melanins)
SB  - IM
MH  - Animals
MH  - Hair Dyes/*chemistry/pharmacology/standards
MH  - Humans
MH  - Melanins/*biosynthesis/chemistry
MH  - Melanocytes/*drug effects/metabolism
MH  - Oxidation-Reduction
PMC - PMC6032422
OTO - NOTNLM
OT  - 5,6-dihydroxyindoles
OT  - antioxidant
OT  - chromophore
OT  - cosmetic formulations
OT  - hair dyeing
OT  - melanins
COIS- The authors declare no conflict of interest.
EDAT- 2018/06/15 06:00
MHDA- 2018/10/12 06:00
PMCR- 2018/06/01
CRDT- 2018/06/15 06:00
PHST- 2018/05/21 00:00 [received]
PHST- 2018/06/08 00:00 [revised]
PHST- 2018/06/08 00:00 [accepted]
PHST- 2018/06/15 06:00 [entrez]
PHST- 2018/06/15 06:00 [pubmed]
PHST- 2018/10/12 06:00 [medline]
PHST- 2018/06/01 00:00 [pmc-release]
AID - ijms19061753 [pii]
AID - ijms-19-01753 [pii]
AID - 10.3390/ijms19061753 [doi]
PST - epublish
SO  - Int J Mol Sci. 2018 Jun 13;19(6):1753. doi: 10.3390/ijms19061753.