Geranylgeranylacetone - CAS 6809-52-5
Catalog number:
6809-52-5
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C23H38O
Molecular Weight:
330.55
COA:
Inquire
Targets:
HSP
Description:
Geranylgeranylacetone is commonly utilized to protect the gastric mucosa in peptic ulcer disease can induce expression of HSP70, HSPB8, and HSPB1.
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Purity:
≥95%
Appearance:
Clear Pale Yellow Oil
Synonyms:
Teprenone; 6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one;
Solubility:
Soluble in DMSO
Storage:
Store at -20 °C
MSDS:
Inquire
Application:
An anti-ulcerative.
Quality Standard:
Enterprise Standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Quantity:
Grams-Kilos
InChIKey:
HUCXKZBETONXFO-NJFMWZAGSA-N
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+
Canonical SMILES:
CC(=CCCC(=CCCC(=CCCC(=CCCC(=O)C)C)C)C)C
1.[Role of Heat Shock Protein 70 in Retinitis Pigmentosa and a Novel Strategy for Treatment].
Koriyama Y1, Furukawa A. Brain Nerve. 2015 Dec;67(12):1523-31. doi: 10.11477/mf.1416200332.
Retinitis pigmentosa (RP) is a group of inherited disorders involving the photoreceptors of the retina and can lead to visual loss. There has been tremendous progress in the delineation of the biochemical and molecular basis of RP. Reactive oxygen species, calcium-calpain activation, and lipid peroxidation are known to be involved in the initiation of photoreceptor cell death, but the precise mechanisms of this process remain unknown. Heat shock protein 70 (HSP70) has been shown to function as a chaperone molecule that protects cells against environmental and physiological stresses. However, there are a few reports showing the role of HSP70 in photoreceptor cell death. Recently, we found that the production of 4-hydroxy-2-noneral caused the calpain-dependent cleavage of carbonylated HSP70 prior to photoreceptor cell death in RP model mice. Furthermore, HSP70 inducers, such as valproic acid and geranylgeranylacetone attenuated photoreceptor cell death.
2.Mediators and mechanisms of heat shock protein 70 based cytoprotection in obstructive nephropathy.
Mazzei L1,2, Docherty NG3, Manucha W4,5. Cell Stress Chaperones. 2015 Nov;20(6):893-906. doi: 10.1007/s12192-015-0622-z. Epub 2015 Jul 31.
Urinary heat shock protein 70 (Hsp70) is rapidly increased in patients with clinical acute kidney injury, indicating that it constitutes a component of the endogenous stress response to renal injury. Moreover, experimental models have demonstrated that Hsp70 activation is associated with the cytoprotective actions of several drugs following obstruction, including nitric oxide (NO) donors, geranylgeranylacetone, vitamin D, and rosuvastatin. Discrete and synergistic effects of the biological activities of Hsp70 may explain its cytoprotective role in obstructive nephropathy. Basic studies point to a combination of effects including inhibition of apoptosis and inflammation, repair of damaged proteins, prevention of unfolded protein aggregation, targeting of damaged protein for degradation, and cytoskeletal stabilization as primary effectors of Hsp70 action. This review summarizes our understanding of how the biological actions of Hsp70 may affect renal cytoprotection in the context of obstructive injury.
3.Geranylgeranylacetone Suppresses N-Methyl-N-nitrosourea-Induced Photoreceptor Cell Loss in Mice.
Koriyama Y1, Ogai K2, Sugitani K3, Hisano S4, Kato S5. Adv Exp Med Biol. 2016;854:237-43. doi: 10.1007/978-3-319-17121-0_32.
Retinitis pigmentosa is a disease characterized by the loss of photoreceptor cells. The N-methyl-N-nitrosourea (MNU)-induced retinal degeneration model is widely used to study the mechanism of these retinal degenerative disorders because of its selective photoreceptor cell death. As for the cell death mechanism of MNU, calcium-calpain activation and lipid peroxidation processes are involved in the initiation of this cell death. Although such molecular mechanisms of the MNU-induced cell death have been described, the total image of the cell death is still obscure. Heat shock protein 70 (HSP70) has been shown to function as a chaperon molecule to protect cells against environmental and physiological stresses. In this study, we investigated the effect of geranylgeranylacetone (GGA), an accylic polyisoprenoid, on MNU-induced photoreceptor cell loss. HSP70 induction by GGA was effective against MNU-induced photoreceptor cell loss as a result of its ability to prevent HSP70 degradation.
4.Improvement of Pharmaceutical Properties of Isoprenoid Compounds through the Formation of Cyclodextrin Pseudorotaxane-Like Supramolecules.
Higashi T1, Tanaka H, Yoshimatsu A, Ikeda H, Arima K, Honjo M, Iwamoto C, Motoyama K, Arima H. Chem Pharm Bull (Tokyo). 2016 Apr 1;64(4):340-5. doi: 10.1248/cpb.c15-00931. Epub 2016 Feb 5.
The purpose of this study was to design cyclodextrin (CyD)-based pseudorotaxane-like supramolecular complexes with various isoprenoid compounds, such as reduced coenzyme Q10 (R-CoQ10), squalene, tocotrienol, and teprenone, and to evaluate their pharmaceutical properties. Squalene, tocotrienol, and teprenone formed precipitates with β-CyD and γ-CyD in aqueous solution, whereas R-CoQ10 formed precipitates with γ-CyD aqueous solution. The results of powder X-ray diffraction and (1)H-NMR analyses indicated that these precipitates are derived from pseudorotaxane-like supramolecular complexes. The photostability of teprenone was markedly improved by complexation with CyDs, especially in the γ-CyD system. In addition, the dispersion rates of teprenone in the γ-CyD system were higher than those in the β-CyD system, compared with the corresponding physical mixtures. In conclusion, pharmaceutical properties such as photostability and dispersion rates of isoprenoid compounds were improved by the formation of pseudorotaxane-like supramolecular complexes with β-CyD and/or γ-CyD.
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CAS 6809-52-5 Geranylgeranylacetone

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