Disease relevance of ACAC

• The toxicity of acetylacetone has been demonstrated in various studies [1].
• Acetylacetone-cleaving enzyme Dke1: a novel C-C-bond-cleaving enzyme from Acinetobacter johnsonii [1].
• The potential energy surfaces of the C-O cleavage, rotational isomerization, keto-enolic tautomerization, and dehydration reactions of acetylacetone in the lowest triplet and ground states have been determined using the complete active space self-consistent field and density functional theory methods [2].
• Plant tumour producing Agrobacterium tumefaciens is effectively inhibited in vitro by the complex [VO(ACTSC-Na)(acac)]H2O (ACTSC-H2 = condensation product of acetylacetone and thiosemicarbazide) [3].

High impact information on ACAC

• This was confirmed by the identification of 3,5-diacetyl-1,4-dihydrolutidine by UV, visible, and fluorescence spectroscopy and by thin-layer chromatography of chloroform extracts of the reaction mixture of ascorbic acid solutions, acetylacetone, and ammonium acetate [4].
• Alteration of actin-tropomyosin interaction in 2,4-pentanedione-treated rabbit skeletal myofibrils [5].
• It has been possible to specifically label rabbit skeletal muscle actin at Lys-237 with 2,4-pentanedione, producing an enamine [6].
• Cr(acac)(3) (where acac is the deprotonated monoanion of acetylacetone) exhibits monophasic decay kinetics with tau = 1.1 +/- 0.1 ps following excitation into the lowest-energy ligand-field absorption band; the time constant is found to be independent of both excitation and probe wavelength across the entire (4)A(2) --> (4)T(2) absorption envelope [7].
• Clinical comparison of indium-111 acetylacetone and indium-111 tropolone granulocytes [8].

Chemical compound and disease context of ACAC

• A novel Fe+Zn containing oxygenase from Acinetobacter johnsonii catalyses 2,3-cleavage of acetylacetone to acetate and methylglyoxal has been purified [9].
• 2,4-Pentanedione (2,4-PD: CAS No. 123-54-6) is a volatile industrial chemical of moderate acute toxicity, centrally neurotoxic by repeated exposure to high vapor concentrations, fetotoxic, and clastogenic [10].

Biological context of ACAC

• 2,4-Pentanedione (2,4-PD; CAS No. 123-54-6), an industrial chemical, was investigated for its comparative pharmacokinetics in male Fischer 344 rats by a single intravenous (i.v.) injection of (4.3, 43, 148.5, and 430 mg/kg), or a 6-hr nose-only inhalation exposure (400 ppm) to 14C-2,4-PD [11].
• Acute intravenous and inhalation pharmacokinetics of 2,4-pentanedione in the Fischer 344 rat [11].
• Malondialdehyde, a product of lipid peroxidation, and acetylacetone undergo one-electron oxidation by peroxidase enzymes to form free radical metabolites, which were detected with ESR using the spin-trapping technique [12].
• Nanoparticles with a mean size of 1.0-2.4 nm are obtained through hydrolysis of aluminum isopropoxide in the L(2) phase of amphiphilic (PDMS-POE) polydimethylsiloxane-polyoxyethylene Silwet L-7607-octanol/acetylacetone-water mixtures [13].
• A stable derivative is formed by cyclization with acetylacetone, and the derivative is separated, purified, and concentrated by liquid-liquid solvent extraction [14].

Anatomical context of ACAC

• All of the patients were studied with granulocytes labeled with In-111 acetylacetone (In-111 GRAN), TPBS and 29 of these patients had Ga-67 studies as well [15].
• The exact nature of the stimulation of andien-beta synthase activity is unknown, but the andien-beta synthase activity obtained after treatment with acetyl acetone was directly correlated to total P450c17 activity in the untreated microsomes [16].
• The effect was dose-dependent, specific to acetyl acetone and was seen in both testis and adrenal microsomes [16].
• Acetyl acetone is necessary for effective labelling of erythrocytes with 113mIn [17].
• As this enzyme prodrug combination was highly cytotoxic for neutrophils and only requires the presence of a non-human peroxidase and acetylacetone, it might immediately be applied to research on the ADEPT techniques [18].

Associations of ACAC with other chemical compounds

• Selective modification of arginine is achieved by reaction with 2,4-pentanedione for long times at pH 9, followed by treatment of the protein with hydroxylamine [19].
• Modification of lysozyme with 2,4-pentanedione at pH 9 results in modification of 4 lysine residues and 4.5 arginine residues in 100 hr [19].
• Primary amines react with 2,4-pentanedione at pH 6-9 to form enamines, N-alkyl-4-amino-3-penten-2-ones [19].
• With both malondialdehyde and acetylacetone and the enzymes myeloperoxidase and chloroperoxidase, carbon-centered radicals were detected [12].
• With phenylglyoxal and 2,4-pentanedione as modifiers there was a selective activation of pseudocholinesterase alone with no effect on aryl acylamidase [20].

Gene context of ACAC

• The addition of acetyl acetone can potentially be used to assess the total potential of P450c17 to catalyze andien-beta synthase activity in vitro [16].
• The developmental toxicity of 2,4-Pentanedione (2,4-PD; CAS No. 123-54-6), a widely used industrial chemical, was investigated by vapour exposure, because of its widespread use, and potential for human exposure [21].
• 2,4-Pentanedione did not react with Arg residues of RTX-III even after 100 hr incubation [22].
• The results obtained by the present method show good correlation with those obtained by the glycerol kinase method (correlation coefficient, 0.989) or the acetylacetone method (correlation coefficient, 0.979) [23].
• THF:H2O (v/v) and hydrogen peroxide (0.082 mol/L) provided maximum yield of polymer (21.2% weight conversion of styrene to polystyrene) with 2,4-pentanedione as initiator [24].

Analytical, diagnostic and therapeutic context of ACAC

• The separation of diacetylacetonato-beryllium [Be(acac)2] from acetylacetone was achieved with micellar electrokinetic chromatography (MEKC) followed by subsequent beryllium analysis carried out using capillary electrophoresis [25].
• Modification of arginine residues in bradykinin, [1-5]-bradykinin, splenopentin and two synthetic pentapeptides with acetylacetone (pentane-2,4-dione) significantly increases the relative abundance of sequence-specific fragment ions produced by matrix-assisted laser desorption/ionization (MALDI) [26].
• A key step in the procedure, pre-column derivatization with acetylacetone, is performed under conditions that permit direct injection of the reaction mixture onto an HPLC column [27].
• Tautomer interconversion of 2,4-pentanedione during gas chromatography on an oxidized cyano-modified capillary column [28].
• Dopamine (DA) has been determined by spectrophotometry and by liquid chromatography as derivatives of acetylacetone (AA) [29].

References