4-Aminophenylmercuric acetate

4-Aminophenylmercuric acetate

Names
IUPAC name Acetato(4-aminophenyl)mercury
Identifiers
CAS Number	6283-24-5
3D model (JSmol)	Interactive image
Beilstein Reference	3664749
ChemSpider	8082118
ECHA InfoCard	100.025.907
EC Number	228-497-1
PubChem CID	16682983
CompTox Dashboard (EPA)	DTXSID8064197
InChI InChI=1S/C6H6N.C2H4O2.Hg/c7-6-4-2-1-3-5-6;1-2(3)4;/h2-5H,7H2;1H3,(H,3,4);/q;;+1/p-1 Key: RXSUFCOOZSGWSW-UHFFFAOYSA-M
SMILES CC(=O)O[Hg]C1=CC=C(C=C1)N
Properties
Chemical formula	C8H9HgNO2
Molar mass	351.757 g·mol−1
Appearance	off-white powder
Solubility in water	5 mM
Solubility	DMSO
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H310, H330, H373, H410
Precautionary statements	P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Aminophenylmercuric acetate (CH₃CO₂HgC₆H₄NH₂, also known as 4-(Acetoxymercurio)aniline or APMA), is an organomercurial compound and thiol-blocking reagent used in experimental biology and chemistry to activate matrix metalloproteinases and collagenase proteolytic enzymes. ^{[1] [2]} 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. ^[3] 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. ^[3]

Protein modification

APMA is known to activate matrix metalloproteinase enzymes and collagenase. ^[4] APMA activates proteolytic enzymes by reacting with cysteines at the amino terminal domains that bind zinc, near the location of the enzyme active site. ^[4]

Toxicity

APMA and APMA vapors are highly toxic or fatal in contact with skin, or if inhaled or swallowed. ^[3]

See also

• 4-Chloromercuribenzoic acid - an organomercury compound that is used as a protease inhibitor
• Phenylmercury acetate - a structurally related organomercury compound historically used as a preservative in paints

References

1. Rosenfeldt, Mathias (2005). "The organomercurial 4-aminophenylmercuric acetate, independent of matrix metalloproteinases, induces dose-dependent activation/ inhibition of platelet aggregation". Thromb Haemost. 93 (2): 326–330. doi:10.1160/th04-08-0541. PMID   15711750. S2CID   11814137.
2. Sellers, Anthony; Cartwright, Elizabeth; Murphy, Gillian; Reynolds, John (1977). "Evidence that Latent Collagenases are Enzyme-Inhibitor Complexes". Biochemical Journal. 163 (2): 303–307. doi:10.1042/bj1630303. PMC   1164697 . PMID   194584.
3. "p-Aminotophenylmercuric acetate material safety data sheet" (PDF). sigmaaldrich.com. Sigma Aldrich. Retrieved 7 June 2018.
4. Lundblad, Roger (2014). Chemical reagents for protein modification (Fourth ed.). CRC Press. p. 234. ISBN   9781466571914 . Retrieved 7 June 2018.