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239802

Sigma-Aldrich

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:
458-37-7
Molecular Weight:
368.38
MDL number:
MFCD00008365
UNSPSC Code:
12352205
NACRES:
NA.77

Quality Level

100

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).
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
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.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

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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