4-Aminophenylmercuric acetate
| |
| Names | |
|---|---|
| IUPAC name
Acetyloxy-(4-aminophenyl)mercury
| |
| Identifiers | |
3D model (JSmol)
|
|
| 3664749 | |
| ChemSpider | |
| ECHA InfoCard | 100.025.907 |
| EC Number |
|
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C8H9HgNO2 | |
| Molar mass | 351.757 g·mol−1 |
| Appearance | off-white powder |
| 5 mM | |
| Solubility | DMSO |
| Hazards | |
| GHS labelling: | |
  
| |
| Danger | |
| 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.[1][2] The material is highly toxic.
Properties
[edit]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
[edit]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
[edit]APMA and APMA vapors are highly toxic or fatal in contact with skin, or if inhaled or swallowed.[3]
See also
[edit]- 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
[edit]- ^ 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.
- ^ 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.
- ^ a b c "p-Aminotophenylmercuric acetate material safety data sheet" (PDF). sigmaaldrich.com. Sigma Aldrich. Retrieved 7 June 2018.
- ^ a b Lundblad, Roger (2014). Chemical reagents for protein modification (Fourth ed.). CRC Press. p. 234. ISBN 9781466571914. Retrieved 7 June 2018.