An active, aldehydic metabolite of the cell-differentiating agent hexamethylene bisacetamide.
6-Acetamidohexanal has been identified in human plasma and urine as a metabolite of the cell-differentiating agent, hexamethylene bisacetamide (HMBA). Synthesis of 6-acetamidohexanal was accomplished by oxidation of 6-acetamido-1-hexanol with pyridinium dichromate. A screen of 6-acetamidohexanal for cell-differentiating activity in HL60 human leukemia cells revealed a higher level of activity than HMBA or N-acetyl-1,6-diaminohexane, another active metabolite of HMBA. The results are consistent with a pathway which involves deacetylation of HMBA, oxidative deamination of the resulting N-acetyl-1,6-diaminohexane to yield 6-acetamidohexanal, and further oxidation to give 6-acetamidohexanoic acid.
Subramanyam
B
B
Department of Medicinal Chemistry/Pharmacognosy, School of Pharmacy, University of Maryland, Baltimore 21201.
Callery
P S
PS
Egorin
M J
MJ
Snyder
S W
SW
Conley
B A
BA
D000081:Acetamides / Q000378:metabolism* / Q000494:pharmacology; D000447:Aldehydes / Q000378:metabolism* / Q000494:pharmacology; D001711:Biotransformation; D002454:Cell Differentiation / Q000187:drug effects; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008995:Monoamine Oxidase / Q000378:metabolism; D013055:Spectrophotometry, Infrared; D014407:Tumor Cells, Cultured / Q000187:drug effects / Q000378:metabolism
D000081:Acetamides; D000447:Aldehydes; C061294:6-acetamidohexanal; D008995:Monoamine Oxidase; C014026:hexamethylene bisacetamide