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...

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Bibliographic Details
Published in:	Drug metabolism and disposition Vol. 17; no. 4; p. 398
Main Authors:	Subramanyam, B, Callery, P S, Egorin, M J, Snyder, S W, Conley, B A
Format:	Journal Article
Language:	English
Published:	United States 01-07-1989
Subjects:	Acetamides - metabolism Acetamides - pharmacology Aldehydes - metabolism Aldehydes - pharmacology Biotransformation Cell Differentiation - drug effects Gas Chromatography-Mass Spectrometry Humans Magnetic Resonance Spectroscopy Monoamine Oxidase - metabolism Spectrophotometry, Infrared Tumor Cells, Cultured - drug effects Tumor Cells, Cultured - metabolism
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Summary:	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.
ISSN:	0090-9556