77479-03-9Relevant academic research and scientific papers
Reaction of acetaldehyde with 5-aminolevulinic acid via dihydropyrazine derivative
Suzuki, Toshinori,Yasuhara, Naoki,Ueda, Takashi,Inukai, Michiyo,Mio, Mitsunobu
, p. 126 - 129 (2015/02/19)
When a solution of 5-aminolevulinic acid (ALA) was incubated with acetaldehyde at neutral pH, a product was generated. This product was identified as 3-ethylpyrazine-2,5-dipropanoic acid (ETPY). ETPY was stable at neutral pH. It has been reported that ALA dimerizes at neutral pH generating 3,6-dihydro-pyrazine-2,5-dipropanoic acid (DHPY), and subsequently resulting in pyrazine-2,5-dipropanoic acid (PY) by autoxidation. In the present reaction, DHPY generated from ALA reacted with acetaldehyde, resulting in ETPY. Preadministration of ALA 3 min prior to acetaldehyde injection supressed the toxicity of acetaldehyde in male mice. These results suggest that ALA may be useful as a scavenger for acetaldehyde.
Degradation mechanism and stability of 5-aminolevulinic acid
Bunke,Zerbe,Schmid,Burmeister,Merkle,Gander
, p. 1335 - 1341 (2007/10/03)
The physiological substance and precursor of the heme synthesis 5-aminolevulinic acid (ALA) is a promising prodrug for photodiagnosis and photodynamic therapy of epithelial tumors, particularly in urological and gynecological tissues. For the clinical use of this substance, a chemically stable and sterile drug formulation is required. In the present study, degradation mechanism of ALA in aqueous solution and possibilities to improve its stability were examined. A capillary electrophoretic method was developed that was suitable for the quantification of ALA and of two degradation products. The intermediate degradation product was 2,5-dicarboxyethyl-3,6-dihydropyrazine, which was further oxidized to 2,5-dicarboxyethylpyrazine. The structures of the degradation products were proven by 1H and 13C nuclear magnetic resonance spectroscopy. ALA degradation was very efficiently inhibited by adjusting the pH of the aqueous solution to a value 5 and by purging with nitrogen. Additives such as antioxidants did not improve the ALA stability. These results demonstrated that low pH ALA aqueous solution may be one possible dosage form to be considered for market introduction. (C) 2000 Wiley-Liss, Inc.
The nonenzymatic cyclic dimerisation of 5-aminolevulinic acid
Butler,George
, p. 7879 - 7886 (2007/10/02)
The nonenzymatic cyclic dimerisation of 5-aminolevulinic aid (5-ALA) leads to the formation of a pyrazine (3) and, under some circumstances, pseudo-porphobilinogen (1). On the other hand, the enzyme-catalysed process leads to porphobilinogen (PBG). The products of the former reaction were identified from their NMR spectra and mechanisms for their formation are proposed.
