Garcinol CAS: 78824-30-3
Garcinol is a potent p300 and PCAF histone acetyltransferase inhibitor..

Garcinol (CAS 78824-30-3)

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Garcinol is rated 5.0 out of 5 by 1.
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Nombres Alternativos: Garcinol is also known as Camboginol.
Solicitud: Garcinol is a potent p300 and PCAF histone acetyltransferase inhibitor.
Número de CAS: 78824-30-3
Pureza: ≥95%
Peso Molecular: 602.80
Fórmula Molecular: C38H50O6
Para Uso Exclusivo en Investigación. No está diseñado para uso en diagnosis o terapia.
* En el Certificado de Análisis específico de lote, puede encontrar información específica (como el contenido en agua).

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) both in vitro and in vivo. p300, also known as E1A binding protein p300, regulates cell growth and division through interacting 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 in vivo, promotes apoptosis through caspase-3 activation and predominantly down-regulates the 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 anti-inflammatory properties through selectively suppressing Prostaglandin E2 synthesis and 5-lipoxygenase product formation. Garcinol is also known as Camboginol, and 3-(3,4-dihydroxybenzoyl)-4-hydroxy-8,8-dimethyl-1,7-bis(3-methyl-2-buten-1-yl)-5-[(2S)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]-bicyclo[3.3.1]non-3-ene-2,9-dione.


References

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

Estado de Materia :
Solid
Solubilidad :
Soluble in ethanol (25 mg/ml), DMSO (25 mg/ml), and DMF (25 mg/ml). Insoluble in water.
ALMACENAMIENTO :
Store at -20° C
Punto de Fusión :
72° C
Punto de ebullición :
~710.8° C at 760 mmHg (Predicted)
Densidad :
~1.1 g/cm3 (Predicted)
Indice de Refracción :
n20D 1.56
IC50 :
histone acetyltransferases (HATs) p300: IC50 = 7 µM; PCAF: IC50 = 5 µM
Datos Ki :
Histone acetyltransferase p300: Ki= 4900 nM
Valores de pK :
pKa: 4.5
Para Uso Exclusivo en Investigación. No está diseñado para uso en diagnosis o terapia.
WGK Alemania :
2
PubChem CID :
3531
Número MDL :
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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Citaciones 1 a 6 de un total de 6

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.

Citaciones 1 a 6 de un total de 6
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