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Isoprenoid


DATA No : IIP0009 INFORMANT : Yoshichika Yoshioka

NAME : [2E,6E,10E]-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenic acid

COMMON NAME: Geranylgeranic acid, geranylgeranoic acid
SYMBOL: GGA
FORMULA: C20H32O2 MOL.WT (average) : 304.467


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BIOLOGICAL ACTIVITY
Synthetic 4,5-didehydro geranylgeranoic acid, a potent ligand both for cellular retionoic acid-binding protein and for nuclear retinoid receptors, induced apoptosis in human hepatoma-derived cell line HuH-7 but not in primary hepatocytes, although all-trans or 9-cis retinoic acid did not induce any growth inhibition(Ref. 0081). A synthetic geranylgeranoic acid (GGA) induced apoptotic cell deth in a human hepatoma cell line, HuH-7, but not in mouse primary cultured hepatocytes. Prior to chromatin condensation, GGA induced a dramatic loss of the mitochondrial membrane potential in 1 hour and in a dose dependent manner in HuH-7 cells, but not in the primary hepatocytes. GGA induces apoptosis in hepatoma cells through derangement of mitochondrial function and subsequent activation of the cysteine protease cascade(Ref. 0082).
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CHEMICAL SYNTHESIS

METABOLISM
The product derived from geranylgeranyl diphosphate.
GENETIC INFORMATION

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REFERENCES
[0081]
AUTHOR:Nakamura, N., Shidoji, Y., Moriwaki, H., and Muto, Y.
TITLE:Apoptosis in human hepatoma cell line induced by 4,5-didehydro geranylgeranoic acid (acyclic retinoid) via down-regulation of transforming growth factor-alpha PubMed ID:8619789
JOURNAL:Biochem Biophys Res Commun.
VOL:219 PAGE : 100-104 (1996)
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[0082]
AUTHOR:Shidoji, Y., Nakamura, N., Moriwaki, H., and Muto, Y.
TITLE:Rapid loss in the mitochondrial membrane potential during geranylgeranoic acid-induced apoptosis PubMed ID:9020060
JOURNAL:Biochem Biophys Res Commun.
VOL:230 PAGE : 58-63 (1997)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.