Garcinol CAS: 78824-30-3
MF: C38H50O6
MW: 602.80
A potent p300 and PCAF histone acetyltransferase inhibitor.

Garcinol (CAS 78824-30-3)

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Synonym Camboginol
Anwendungen A potent p300 and PCAF histone acetyltransferase inhibitor
CAS Nummer: 78824-30-3
Reinheit: ≥95%
Molekulargewicht: 602.80
Summenformel: C38H50O6
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Garcinol (camboginol) is a polyisoprenylated benzophenone derivative from the rind of Garcinia indica fruit and is a potent inhibitor of histone acetyltransferases p300 (IC50 ~ 7 μM) and PCAF (IC50 ~ 5 μM) in vitro. P300, also known as E1A binding protein p300, regulates cell growth and division via interactions with numerous transcription factors, and the p53 associated trancriptional coactivator PCAF (P300/CBP-associated factor) plays a direct role in transcriptional regulation. Reports show that garcinol represses the p300-mediated acetylation of p53 and promotes apoptosis through caspase-3 activation. Additionally, this compound predominantly down-regulates global gene expression in HeLa cells. Researchers found that garcinol exhibits dose-dependent cancer cell-specific growth inhibition in ER-positive MCF-7 and ER-negative MDA-MB-231 breast cancer cells. Additional research shows that garcinol exhibits anti-carcinogenic and antiiinflammatory properties through selective suppression of prostaglandin E2 synthesis and 5-lipoxygenase product formation.


Literaturhinweise

1. Matsumoto, Kenji., et al., 2003. Cytotoxic benzophenone derivatives from Garcinia species display a strong apoptosis-inducing effect against human leukemia cell lines. Biological & pharmaceutical bulletin. 26(4): 569-71. PMID: 12673047
2. Balasubramanyam, Karanam., et al., 2004. Polyisoprenylated benzophenone, garcinol, a natural histone acetyltransferase inhibitor, represses chromatin transcription and alters global gene expression. The Journal of biological chemistry. 279(32): 33716-26. PMID: 15155757
3. Mantelingu, K., et al., 2007. Specific inhibition of p300-HAT alters global gene expression and represses HIV replication. Chemistry & biology. 14(6): 645-57. PMID: 17584612
4. Koeberle, Andreas., et al., 2009. Identification of 5-lipoxygenase and microsomal prostaglandin E2 synthase-1 as functional targets of the anti-inflammatory and anti-carcinogenic garcinol. Biochemical pharmacology. 77(9): 1513-21. PMID: 19426689
5. Ahmad, Aamir., et al., 2010. Apoptosis-inducing effect of garcinol is mediated by NF-kappaB signaling in breast cancer cells. Journal of cellular biochemistry. 109(6): 1134-41. PMID: 20108249
6. Chen, Ching-Shyang., et al., 2011. Nicotine-induced human breast cancer cell proliferation attenuated by garcinol through down-regulation of the nicotinic receptor and cyclin D3 proteins. Breast cancer research and treatment. 125(1): 73-87. PMID: 20229177

Aggregatzustand :
Solid
Löslichkeit :
Soluble in ethanol (25 mg/ml), DMSO (25 mg/ml), and DMF (25 mg/ml). Insoluble in water.
LAGERUNG: :
Store at -20° C
Schmelztemperatur :
72° C
Sidepunkt :
~710.8° C at 760 mmHg (Predicted)
Dichte :
~1.1 g/cm3 (Predicted)
Brechungsindex :
n20D 1.56
IC50 :
histone acetyltransferases (HATs) p300: IC50 = 7 µM; PCAF: IC50 = 5 µM
Ki-Daten :
Histone acetyltransferase p300: Ki= 4900 nM
pK Werte :
pKa: 4.5
Ausschließlich für Forschungszwecke. Nicht Geeignet für Verwendung in Diagnostik oder Therapie.
Deutsche WGK :
2
PubChem CID :
3531
MDL-Nummer :
MFCD03700761
SMILES :
CC(=CCC1CC2(C(=O)C(=C(C3=CC(=C(C=C3)O)O)O)C(=O)C(C2=O)(C1(C)C)CC=C(C)C)CC(CC=C(C)C)C(=C)C)C

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Garcinol  Publikationen

Lesen Sie wie andere Anwender Garcinol eingesetzt haben. Klicken Sie auf den jeweiligen Eintrag um den entsprechenden PubMed-Abstract abzurufen .

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PMID: # 29174768  Ghosh, TK. et al. 2018. J. Mol. Cell. Cardiol. 114: 185-198.

PMID: # 29414668  Huang, WC.|Kuo, KT.|Adebayo, BO.|Wang, CH.|Chen, YJ.|Jin, K.|Tsai, TH.|Yeh, CT.| et al. 2018. J. Nutr. Biochem. 54: 140-150.

PMID: # 29740418  Simpson, S. et al. 2018. Front Microbiol. 9: 788.

PMID: # 25538147  Yao, XH. et al. 2014. Physiological reports. 2:

PMID: # 23644046  Du, T. et al. 2013. Experimental and molecular pathology. 95: 38-45.

PMID: # 30377593  Habibi, A.|Soleimani, M.|Atashi, A.|AkhavanRahnama, M.|Anbarlou, A.|Ajami, M.|Ajami, M.| et al. Avicenna J Phytomed. 8: 350-357.

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