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Amino Acid and Protein Targets of 1,2-diacetylbenzene, a Potent Aromatic Gamma-Diketone That Induces Proximal Neurofilamentous Axonopathy

Amino Acid and Protein Targets of 1,2-diacetylbenzene, a Potent Aromatic Gamma-Diketone That Induces Proximal Neurofilamentous Axonopathy

Min-Sun Kim, Seyed B Hashemi, Peter S Spencer, Mohammad I Sabri

Toxicol Appl Pharmacol. 2002 Aug 15;183(1):55-65.

PMID: 12217642

Abstract:

The gamma-diketone analogs 1,2-diacetylbenzene (1,2-DAB) and 2,5-hexanedione (2,5-HD), but not the delta-diketone 1,3-diacetylbenzene (1,3-DAB) or the beta-diketone 2,4-hexanedione, induce neuropathological changes in the rodent central and peripheral nervous systems. The molecular targets of these neurotoxic aromatic and aliphatic gamma-diketones, and of their nonneurotoxic structural analogs and ninhydrin, are examined by assessing their differential reactivity with neural and nonneural amino acids and proteins in vitro and in vivo. Whereas 1,2-DAB is chromogenic and forms polymers with amino acids (notably lysine) and proteins (especially lysine-rich proteins), 1,3-DAB lacks these properties. Ninhydrin forms a chromophore without evidence of protein polymerization. 1,2-DAB preferentially targets neurofilament over microtubule protein in vitro and in situ. Based on protein reactivity, 1,2-DAB is three orders of magnitude more reactive than 2,5-HD. Lysine-rich neurofilament protein subunits NF-H and NF-M are more susceptible than lysine-poor NF-L and beta-tubulin to 1,2-DAB. These observations correlate with the development of proximal (1,2-DAB) and distal (2,5-HD) neurofilament-filled axonal swellings and segregated intact microtubules observed during systemic treatment with aromatic and aliphatic gamma-diketones.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP704007	1,2-Diacetylbenzene		704-00-7	Price

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