4-Aminophenylmercuric Acetate
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4-Aminophenylmercuric acetate (CH3CO2HgC6H4NH2, also known as 4-(Acetoxymercurio)aniline or APMA), is an organomercurial compound and
thiol In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl gro ...
-blocking reagent used in experimental biology and chemistry to activate
matrix metalloproteinase Matrix metalloproteinases (MMPs), also known as matrix metallopeptidases or matrixins, are metalloproteinases that are calcium-dependent zinc-containing endopeptidases; other family members are adamalysins, serralysins, and astacins. The MMPs b ...
s and
collagenase Collagenases are enzymes that break the peptide bonds in collagen. They assist in destroying extracellular structures in the pathogenesis of bacteria such as ''Clostridium''. They are considered a virulence factor, facilitating the spread of ga ...
proteolytic enzyme A protease (also called a peptidase, proteinase, or proteolytic enzyme) is an enzyme that catalyzes (increases reaction rate or "speeds up") proteolysis, breaking down proteins into smaller polypeptides or single amino acids, and spurring the for ...
s. The material is highly toxic.


Properties

APMA has a molecular weight of 351.8 g/mol and appears as a white powder with a slight yellowish cast. Its melting temperature is 163–165 °C. APMA is soluble in water to concentrations as high as 5 mM, and in DMSO to concentrations of 10 M or more. In 100% acetic acid, an APMA solution of 50 mg/mL is a light translucent yellow.


Protein modification

APMA is known to activate matrix metalloproteinase enzymes and collagenase. APMA activates proteolytic enzymes by reacting with
cysteine Cysteine (symbol Cys or C; ) is a semiessential proteinogenic amino acid with the formula . The thiol side chain in cysteine often participates in enzymatic reactions as a nucleophile. When present as a deprotonated catalytic residue, sometime ...
s at the
amino terminal The N-terminus (also known as the amino-terminus, NH2-terminus, N-terminal end or amine-terminus) is the start of a protein or polypeptide, referring to the free amine group (-NH2) located at the end of a polypeptide. Within a peptide, the amin ...
domains that bind zinc, near the location of the enzyme
active site In biology and biochemistry, the active site is the region of an enzyme where substrate molecules bind and undergo a chemical reaction. The active site consists of amino acid residues that form temporary bonds with the substrate (binding site) a ...
.


Toxicity

APMA and APMA vapors are highly toxic or fatal in contact with skin, or if inhaled or swallowed.


See also

*
4-Chloromercuribenzoic acid 4-Chloromercuribenzoic acid (''p''-chloromercuribenzoic acid, PCMB) is an organomercury compound that is used as a protease inhibitor, especially in molecular biology applications. PCMB reacts with thiol groups in proteins and is therefore an in ...
- an organomercury compound that is used as a protease inhibitor *
Phenylmercury acetate Phenylmercuric acetate is an organomercury compound used as a preservative, disinfectant, and antitranspirant. Properties Phenylmercuric acetate forms colorless, lustrous crystals, and is soluble in ethanol, benzene, acetic acid, and sparingly ...
- a structurally related organomercury compound historically used as a preservative in paints


References

{{DEFAULTSORT:Aminophenylmercuric acetate, 4- Acetates Organomercury compounds