Dithizone is a sulfur-containing organic compound. It is a good
ligand
In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elec ...
, and forms complexes with many toxic metals such as
lead
Lead is a chemical element with the symbol Pb (from the Latin ) and atomic number 82. It is a heavy metal that is denser than most common materials. Lead is soft and malleable, and also has a relatively low melting point. When freshly cu ...
,
thallium
Thallium is a chemical element with the symbol Tl and atomic number 81. It is a gray post-transition metal that is not found free in nature. When isolated, thallium resembles tin, but discolors when exposed to air. Chemists William Crookes an ...
and
mercury.
Dithizone may be prepared by reacting
phenylhydrazine
Phenylhydrazine is the chemical compound with the formula . It is often abbreviated as . It is also found in edible mushrooms.
Properties
Phenylhydrazine forms monoclinic prisms that melt to an oil around room temperature which may turn yellow ...
with
carbon disulfide
Carbon disulfide (also spelled as carbon disulphide) is a neurotoxic, colorless, volatile liquid with the formula and structure . The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical n ...
, followed by reaction with
potassium hydroxide
Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash.
Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which exp ...
.
Dithizone is used to assess the purity of human pancreatic islet preparations used for transplantation into patients with type 1 diabetes. Dithizone binds zinc ions present in the islet's beta cells, and therefore stains the islets red. Exocrine tissue also present in the preparations does not bind dithizone, and is therefore not stained.
[{{cite journal , last1 = Ricordi , first1 = C , last2 = Gray , first2 = DW , last3 = Hering , first3 = BJ , last4 = Kaufman , first4 = DB , last5 = Warnock , first5 = GL , last6 = Kneteman , first6 = NM , last7 = Lake , first7 = SP , last8 = London , first8 = NJ , last9 = Socci , first9 = C , last10 = Alejandro , first10 = Rodolfo , last11 = Zeng , first11 = Yijun , last12 = Scharp , first12 = David W. , last13 = Viviani , first13 = Giorgio , last14 = Falqui , first14 = Luca , last15 = Tzakis , first15 = Andreas , last16 = Bretzel , first16 = Reinhard G. , last17 = Federlin , first17 = Konrad , last18 = Pozza , first18 = Guido , last19 = James , first19 = Roger F. L. , last20 = Rajotte , first20 = Ray V. , last21 = Carlo , first21 = Valerio Di , last22 = Morris , first22 = Peter J. , last23 = Sutherland , first23 = David E. R. , last24 = Starzl , first24 = Thomas E. , last25 = Mintz , first25 = Daniel H. , last26 = Lacy , first26 = Paul E. , title = Islet isolation assessment in man and large animals , journal = Acta Diabetologica Latina , volume = 27 , issue = 3 , pages = 185–95 , year = 1990 , pmid = 2075782 , doi = 10.1007/BF02581331 , display-authors = 8 , url = http://d-scholarship.pitt.edu/4513/1/31735062116805.pdf ]
File:Dithizone by Danny S. - 001.JPG, Dithizone
File:Dithizone by Danny S. - 002.JPG, Dithizone in Ethanol 96%
References
Thiocarbonyl compounds