All Photos(1)
Synonym(s):
6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one, mixture of (5E,9E,13E) and (5Z,9E,13E) isomers, GGA, Selbex, Teprenone, UNII-S8S8451A4O
Empirical Formula (Hill Notation):
C23H38O
CAS Number:
Molecular Weight:
330.55
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
assay
≥98% (HPLC)
Quality Level
form
oil
storage condition
protect from light
color
clear
solubility
DMSO: >5 mg/mL
storage temp.
−20°C
SMILES string
C\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CCC(C)=O
InChI
1S/C23H38O/c1-19(2)11-7-12-20(3)13-8-14-21(4)15-9-16-22(5)17-10-18-23(6)24/h11,13,15,17H,7-10,12,14,16,18H2,1-6H3/b20-13+,21-15+,22-17+
InChI key
HUCXKZBETONXFO-NJFMWZAGSA-N
Application
Geranylgeranylacetone has been used as an inducer of heat shock protein 70 (HSP70) to analyze its protective effects against cerebral ischemia/reperfusion (I/R).
Biochem/physiol Actions
Geranylgeranylacetone can induce expression of HSP70, HSPB8, and HSPB1. Induction of HSP70 expression is protective against the development of various diseases, such as inflammatory bowel disease, hypoxic/ischemic brain injury and spinal and bulbar muscular atrophy (cytoprotective and anti-inflammatory effects). Reports indicate that GGA protects against NSAID-induced gastric and intestinal lesions by induction of HSP70 expression. Other studies have shown that GGA induces expression of HSPB8 and HSPB1 and reduces the formation of amyloid oligomers as well as insoluble aggregates in HSPB5 R120G TG mice.
Geranylgeranylacetone is an acyclic polyisoprenoid that has been studied to exhibit protective effects against reperfusion injury, inflammation and organ transplantation. It is an anti-ulcer agent that is involved in the protection of gastric mucosa.
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Certificates of Analysis (COA)
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Yoko Ishii et al.
Investigative ophthalmology & visual science, 44(5), 1982-1992 (2003-04-26)
To study the effects of geranylgeranylacetone (GGA) on the expression of inducible (HSP72) and constitutive (HSC70) heat shock proteins (HSPs) on retinal ganglion cells (RGCs) in a rat model of glaucoma. Adult Wistar rats were given intraperitoneal injections of GGA
Kylie Kavanagh et al.
American journal of physiology. Endocrinology and metabolism, 300(5), E894-E901 (2011-02-18)
We evaluated heat shock protein 70 (HSP70) changes in diabetes mellitus (DM) in a nonhuman primate model. To this end, two studies were conducted in DM vervet monkeys. 1) Normal control and streptozotocin-induced DM monkeys (Stz-DM) that were differentiated into
Noritaka Fujimura et al.
Arteriosclerosis, thrombosis, and vascular biology, 32(1), 153-160 (2011-10-15)
Geranylgeranylacetone (GGA) induces expression of heat shock protein 90 (Hsp90), an adaptor molecule for assembly of endothelial nitric oxide synthase (eNOS) phosphorylation complex. The purpose of this study was to determine whether GGA enhances Hsp90 expression and augments endothelium-dependent vasodilation
Naoyuki Yoshikawa et al.
Anti-cancer drugs, 21(9), 850-860 (2010-08-21)
Geranylgeranylacetone (GGA), an isoprenoid compound, is a widely used antiulcer drug developed in Japan. GGA is structurally similar to plaunotol and geranylgeraniol, another isoprenoid reported to exert strong anticancer effects. In an earlier study, GGA was shown to inhibit ovarian
Deli Zhang et al.
Journal of molecular and cellular cardiology, 51(3), 381-389 (2011-07-13)
The most common clinical tachycardia, Atrial Fibrillation (AF), is a progressive disease, caused by cardiomyocyte remodeling, which finally results in contractile dysfunction and AF persistence. Recently, we identified a protective role of heat shock proteins (HSPs), especially the small HSPB1
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