4-Aminophenylmercuric acetate

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4-Aminophenylmercuric acetate
4-Aminophenylmercuric acetate.png
Names
IUPAC name
Acetyloxy-(4-aminophenyl)mercury
Identifiers
3D model (JSmol)
3664749
ChemSpider
ECHA InfoCard 100.025.907 Edit this at Wikidata
EC Number
  • 228-497-1
  • 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
  • CC(=O)O[Hg]C1=CC=C(C=C1)N
Properties
C8H9HgNO2
Molar mass 351.757 g·mol−1
Appearance off-white powder
5 mM
Solubility DMSO
Hazards
GHS labelling:
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
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]

References[edit]

  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. doi:10.1160/th04-08-0541. PMID 15711750.
  2. ^ 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.
  3. ^ a b c "p-Aminotophenylmercuric acetate material safety data sheet" (PDF). sigmaaldrich.com. Sigma Aldrich. Retrieved 7 June 2018.
  4. ^ a b Lundblad, Roger (2014). Chemical reagents for protein modification (Fourth ed.). CRC Press. p. 234. Retrieved 7 June 2018.