Increase in 3-deoxyglucosone levels in diabetic rat plasma. Specific in vivo determination of intermediate in advanced Maillard reaction.
A specific assay of 3-deoxyglucosone (3-DG) was developed in our laboratory to help elucidate the relationship between advanced Maillard reaction and diabetic complications. 3-DG is known as a highly reactive intermediate of the reaction in vitro and a precursor of advanced glycosylation end products such as pyrraline and pentosidine, which have been previously detected in vivo. 3-DG was converted to a stable compound, 2-(2,3,4-trihydroxybutyl)-benzo[g]quinoxaline, by reacting with 2,3-diaminonaphthalene. Since the derivative had a characteristic UV spectrum, it was determined at 268 nm by high performance liquid chromatography. This method was sensitive enough to detect 10 ng/ml (61.7 nM) of 3-DG in vitro. A slight modification to this method allowed in vivo detection of small amounts of 3-DG. Plasma free 3-DG levels were significantly higher in streptozotocin-induced diabetic rats compared with controls (918 +/- 134 nM versus 379 +/- 69 nM, p < 0.001) and were suppressed with the administration of aminoguanidine, an inhibitor of Maillard reaction. Plasma pyrraline levels in diabetic rats also increased in parallel with elevated 3-DG levels but were only marginally suppressed by administration of aminoguanidine. Our results indicate that 3-DG is present in vivo under normal conditions and that its level increases in diabetic subjects. Determination of 3-DG represents a good tool to predict development and progression of diabetic complications and to assess the efficiency of inhibitors to Maillard reaction.
Yamada
H
H
Second Department of Internal Medicine, Kobe University School of Medicine, Japan.
Miyata
S
S
Igaki
N
N
Yatabe
H
H
Miyauchi
Y
Y
Ohara
T
T
Sakai
M
M
Shoda
H
H
Oimomi
M
M
Kasuga
M
M
D015081:2-Naphthylamine / Q000031:analogs & derivatives; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000097:blood; D003921:Diabetes Mellitus, Experimental / Q000097:blood*; D008401:Gas Chromatography-Mass Spectrometry; D015416:Maillard Reaction; D008297:Male; D009646:Norleucine / Q000031:analogs & derivatives / Q000097:blood; D011758:Pyrroles / Q000097:blood; D051381:Rats; D017208:Rats, Wistar; D012710:Serum Albumin, Bovine / Q000378:metabolism; D013056:Spectrophotometry, Ultraviolet
D011758:Pyrroles; D012710:Serum Albumin, Bovine; C026373:2,3-diaminonaphthalene; C059571:2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine; D009646:Norleucine; D003847:Deoxyglucose; D015081:2-Naphthylamine; C016350:3-deoxyglucosone