Progress Towards the Study of Metal Chelating Properties

of Eumelanin-Inspired Small Molecules

Victor Ekehchiadi, Santosh Adhikari, Toby L. Nelson
Department of Chemistry, Oklahoma State University

Introduc1on   Results  and  Discussion     UV-­‐vis  spectra  of  DBI  and  Ph-­‐DBI-­‐Ph  

•  Melanin is a pigment that is produced by cells known as Synthesis

melanocytes in the skin of most animals, including humans. This
pigment comes in different shades, depending on the genetic make-
up of the individual. Melanin comes in two basic forms, and can
range from yellowish-red to dark-brown. The lack of melanin is
responsible for albinism.

MELANIN     Eumelanin
•  The most common form of
melanin, which is a brown-black, Conclusion  
Eumelanin Pheomelanin insoluble biopolymer, composed
black-brown yellow-red
of 5,6-dihydroxyindole carboxylic
acids (DHICA), and 5,6- •  Eumelanin-inspired core molecule (DBI)
dihydroxyindole (DHA). have been successfully synthesized.
Responsible Responsible
for for
•  Eumelanin-inspired small molecule have
Dark colored Red hair and been synthesized by Sonaghashira
skin
eyes and hair
freckles coupling reaction, and characterized by
NMR and UV-visible spectroscopy
•  The deprotection of methyl indoylene ether
•  Nelson et. al. showed that eumelanin-inspired small molecules had
has been attempted.
high light absorption ranging from UV to IR region (visible range).
They also demonstrated that optoelectronic properties of these
molecules can be altered by changing the different substituents at 5
and 7 positions.1
Future  Direc1on  
1.0
Normalized Absorbance

0.8 R λ abs (nm)

•  Deprotection of DBI methyl indoylene ether .
Br-I-Br 308
•  Synthesis of eumelanin inspired small molecule from
0.6 H 384, 298, 239

t-Bu 387, 301, 239

deprotected DBI molecule.
0.4 OMe 390, 353, 304, 241 •  Synthesis of eumelanin inspired molecules with
N(Me)2
415, 354, 310, 265,
239 different protecting groups in the 5,6 position
0.2 F 382, 297, 239
(esters).
•  Metal (Zn,Fe) binding to eumelanin inspired small
CN 401, 302, 241

NO2 423, 304, 280

0.0
300 400 500 molecules in the 5,6 position
Wavelangth (nm)

References  
•  Farmer and his co-workers worked on metal binding by melanin and
showed that melanin molecules have high affinity for metal ions. His •  S. Selvaraj, S. Adhikari, R. Hopson, S. Dai, A.
work also determined the nature of metal binding sites, and Rheingold, M. Borunda, T. Nelson :Journal of Materials
quantified binding affinities of different metals ions like copper and Chemistry C.2015,9.
zinc.3 •  Louise K. and J. Franz :Inorganic Chemistry. 2006. 45.
9. 3657-3664.
•  Szpohanicz B. Gidanian S. Kong P. Farmer P. Journal
of inorganic biochemistry. 2002.89.45-53

Acknowledgement    

•  The objective of this research is to synthesize eumelanin-inspired •  Wentz Research Grant

small molecule from vanillin extract and to study their metal •  Ok-LSAMP
chelating properties for their potential application in sensing
different metals ions and water remediation.