Analogs of N-4909 (1), which had a stimulating activity for apolipoprotein E (apo E) secretion in Human hepatoma Hep G2 cells, were prepared and their activities examined. Cyclic analogs which had different kinds of amino acids or different number of amino acids from N-4909 (1) showed less effect on apo E secretion from Hep G2 cells. The length of acyl chain was found to be an important factor for the activity. Shorter chain reduced the activity. Linear analogs were also prepared. One of their analogs, N-5849 (17), which had six amino acids was found to have strong activity.

01 Jan 1999·The Journal of AntibioticsQ4 · MEDICINE

First Total Synthesis of N-4909 and Its Diastereomer; A Stimulant of Apolipoprotein E Secretion in Human Hepatoma Hep G2 Cells.

Q4 · MEDICINE

Article

Author: Makoto Yanai ; Shigeru Hiramoto

Both (R)- and (S)-3-hydroxy-13-methyltetradecanoic acids were prepared via a lipase-catalyzed enantioselective acylation. The total synthesis of N-4909 and its diastereomer were achieved by a coupling of either (R)- or (S)-3-hydroxy-13-methyltetradecanoic acid moiety with a hexapeptide moiety and by a cyclization with HATU (O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate) and HOAt (1-hydroxy-7-azabenzotriazole) in a high dilution condition. The R configuration of 3-hydroxy-13-methyltetradecanoic acid was found to be important for stimulating the activity of apolipoprotein E secretion in human hepatoma Hep G2 cells.

01 Jan 1996·The Journal of AntibioticsQ4 · MEDICINE

Stimulation of Apolipoprotein E Secretion in Human Hepatoma Hep G2 Cells by a Cyclic Acylpeptide, N-4909.

Q4 · MEDICINE

Letter

Author: Shigeo Hatanaka ; Nobuhiro Kinoshita ; Shigeru Hiramoto ; Haruo Seto

The isolation of the cyclic acylpeptide N-4909 from Bacillus sp. Number 4691, the determination of its structure and its identification as a subcomponent of isohalobacillin, and its stimulation of apolipoprotein E secretion by Hep G2 cells are described.

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Indication	Highest Phase	Country/Location	Organization	Date
Liver Cancer	Preclinical	Japan	Nisshin Flour Milling Co Ltd	02 Jan 1999
Hypercholesterolemia	Preclinical	Japan	Nisshin Flour Milling Co Ltd	-

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