3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||351.757 g·mol−1|
|H300, H310, H330, H373, H410|
|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).
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. The material is highly toxic.
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.
APMA is known to activate matrix metalloproteinase enzymes and collagenase. APMA activates proteolytic enzymes by reacting with cysteines at the amino terminal domains that bind zinc, near the location of the enzyme active site.
APMA and APMA vapors are highly toxic or fatal in contact with skin, or if inhaled or swallowed.
- 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
- 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. doi:10.1160/th04-08-0541. PMID 15711750.
- Sellers, Anthony; Cartwright, Elizabeth; Murphy, Gillian; Reynolds, John (1977). "Evidence that Latent Collagenases are Enzyme-Inhibitor Complexes". Biochemical Journal. 163: 303–307. doi:10.1042/bj1630303. PMC 1164697. PMID 194584.
- "p-Aminotophenylmercuric acetate material safety data sheet" (PDF). sigmaaldrich.com. Sigma Aldrich. Retrieved 7 June 2018.
- Lundblad, Roger (2014). Chemical reagents for protein modification (Fourth ed.). CRC Press. p. 234. Retrieved 7 June 2018.