239802
Curcumin, Curcuma longa L.
A cell-permeable and irreversible antitumor and anti-inflammatory agent that acts as an inhibitor of 5-lipoxygenase (IC₅₀ = 8 µM) and cyclooxygenase (IC₅₀ = 52 µM).
Synonym(s):
Curcumin, Curcuma longa L., 1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, NOD2 Signaling Inhibitor I, Nucleotide-binding Oligomerization Domain 2 Signaling Inhibitor I, Histone Acetyltransferase Inhibitor I, HAT Inhibitor I, p300/CBP Inhibitor I
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About This Item
Empirical Formula (Hill Notation):
C21H20O6
CAS Number:
Molecular Weight:
368.38
MDL number:
UNSPSC Code:
12352205
NACRES:
NA.77
Quality Level
Assay
≥80% (HPLC)
form
solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
protect from light
color
orange-yellow
solubility
acetic acid: 10 mg/mL
DMSO: 5 mg/mL
shipped in
ambient
storage temp.
10-30°C
InChI
1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-13,22,24-25H,1-2H3/b7-3+,8-4+,16-13-
InChI key
ZIUSSTSXXLLKKK-KOBPDPAPSA-N
General description
A cell permeable antitumor and anti-inflammatory agent that acts as an inhibitor of 5-lipoxygenase (IC50 = 8 µM) and cyclooxygenase (IC50 = 52 µM). Confers significant protection against neurotoxic and genotoxic agents. Also inhibits the induction of nitric oxide synthase in activated macrophages (IC50 = 6 µM). Recently shown to inhibit the EGF receptor intrinsic kinase activity in the human epidermoid carcinoma A431 cells in a dose- and time-dependent manner. Also shown to be a p300/CREB-binding protein-specific inhibitor of histone acetyltransferase, inhibiting the acetylation of histones H3 and H4 with an
IC50 of ~25 µM. Does not affect p300/CREB binding protein-associated factor (PCAF).
IC50 of ~25 µM. Does not affect p300/CREB binding protein-associated factor (PCAF).
A cell-permeable and irreversible antitumor and anti-inflammatory agent that acts as an inhibitor of 5-lipoxygenase (IC50 = 8 µM) and cyclooxygenase (IC50 = 52 µM). Confers significant protection against neurotoxic and genotoxic agents. Also inhibits the induction of nitric oxide synthase in activated macrophages (IC50 = 6 µM). Recently shown to inhibit the EGF receptor intrinsic kinase activity in the human epidermoid carcinoma A431 cells in a dose- and time-dependent manner. Also shown to be a p300/CREB-binding protein-specific inhibitor of histone acetyltransferase, inhibiting the acetylation of histones H3 and H4 with an IC50 of ~25 µM. Does not affect p300/CREB binding protein-associated factor (PCAF).
Biochem/physiol Actions
Cell permeable: yes
Primary Target
5-lipoxygenase
5-lipoxygenase
Product does not compete with ATP.
Reversible: no
Target IC50: 8 µM, 52 µM, against 5-lipoxygenase, Cyclooxygenase, respectively; 6 µM inhibiting the induction of nitric oxide synthase in activated macrophages
Warning
Toxicity: Standard Handling (A)
Reconstitution
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Other Notes
Hung, S., et al. 2008. Mol. Pharmacol.74, 274.
Cui, L., et al. 2007. Antimicrob. Agents Chemother.51, 488.
Salvioli, S., et al. 2007. eCAM4, 181.
Balasubramanyam, K. et al. 2004. J. Biol. Chem.279, 51163.
Brouet, I., and Okshima, H. 1995. Biochem. Biophys. Res. Commun. 206, 533.
Korutla, L., and Kumar, R. 1994. Biochim. Biophys. Acta1224, 597.
Flynn, D.L., et al. 1986. Prostagland. Leuk. Med. 22, 357.
Cui, L., et al. 2007. Antimicrob. Agents Chemother.51, 488.
Salvioli, S., et al. 2007. eCAM4, 181.
Balasubramanyam, K. et al. 2004. J. Biol. Chem.279, 51163.
Brouet, I., and Okshima, H. 1995. Biochem. Biophys. Res. Commun. 206, 533.
Korutla, L., and Kumar, R. 1994. Biochim. Biophys. Acta1224, 597.
Flynn, D.L., et al. 1986. Prostagland. Leuk. Med. 22, 357.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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