Potent HDAC inhibitor
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HC Toxin

Item No. 10576

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(6R,9S,14aR)-3,6R-dimethyl-9S-(6-((S)-oxiran-2-yl)-6-oxohexyl)decahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetranone
CAS Number
83209-65-8
Synonyms
  • Toxin I (Helminthosporium carbonum)
Molecular Formula
C21H32N4O6
Formula Weight
436.5
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/mlMethanol: 10 mg/ml
λmax
232 nm
SMILES
[H][C@@]12C(N([H])[C@@H](C)C(N([H])[C@H](C)C(N([H])[C@](CCCCCC([C@@H]3CO3)=O)([H])C(N1CCC2)=O)=O)=O)=O
InChi Code
InChI=1S/C21H32N4O6/c1-12-18(27)22-13(2)19(28)24-14(7-4-3-5-9-16(26)17-11-31-17)21(30)25-10-6-8-15(25)20(29)23-12/h12-15,17H,3-11H2,1-2H3,(H,22,27)(H,23,29)(H,24,28)/t12-,13+,14-,15+,17-/m0/s1
InChi Key
GNYCTMYOHGBSBI-SVZOTFJBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    HC Toxin is a cell-permeable, reversible inhibitor of histone deacetylases (HDACs) (IC50 = 30 nM).1,2 Through its effects on HDACs, HC toxin has been shown to up-regulate the expression of 15-lipoxygenase-1 in colorectal cancer cells and induce fetal hemoglobin in human primary erythroid cells.3,4 HC Toxin is a cyclic tetrapeptide first isolated from H. carbonum (now C. carbonum), a pathogen of maize.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brosch, G., Ransom, R., Lechner, T., et al. Inhibition of maize histone deacetylases by HC toxin, the host-selective toxin of Cochliobolus carbonum. Plant Cell 7, 1941-1950 (1995).

    2. Darkin-Rattray, S.J., Gurnett, A.M., Myers, R.W., et al. Apicidin: A novel antiprotozoal agent that inhibits parasite histone deacetylase. Proc. Natl. Acad. Sci. USA 93(23), 13143-13147 (1996).

    3. Kamitani, H., Taniura, S., Ikawa, H., et al. Expression of 15-lipoxygenase-1 is regulated by histone acetylation in human colorectal carcinoma. Carcinogenesis 22(1), 187-191 (2001).

    4. Cao, H., and Stamatoyannopoulos, G. Histone deacetylase inhibitor FK228 is a potent inducer of human fetal hemoglobin. Am. J. Hematol. 81, 981-983 (2006).

    5. Walton, J.D. HC-toxin. Phytochemistry 67, 1406-1413 (2006).