Merck
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382191-M

Millipore

HMTase Inhibitor II, Chaetocin

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Synonym(s):
HMTase Inhibitor II, Chaetocin, EHMT2/G9a Inhibitor II, HMT Inhibitor II, Histone Lysine Methyltransferase Inhibitor II, HMT Inhibitor II, Histone Lysine Methyltransferase Inhibitor II, EHMT2/G9a Inhibitor II
Empirical Formula (Hill Notation):
C30H28N6O6S4
CAS Number:
28097-03-2
Molecular Weight:
696.84
MDL number:
MFCD00133163

Assay

≥97% (HPLC)

Quality Level

100

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white to off-white

solubility

DMSO: 1 mg/mL

storage temp.

−20°C

InChI

1S/C30H28N6O6S4/c1-33-21(39)27-11-25(15-7-3-5-9-17(15)31-19(25)35(27)23(41)29(33,13-37)45-43-27)26-12-28-22(40)34(2)30(14-38,46-44-28)24(42)36(28)20(26)32-18-10-6-4-8-16(18)26/h3-10,19-20,31-32,37-38H,11-14H2,1-2H3

InChI key

PZPPOCZWRGNKIR-UHFFFAOYSA-N

General description

A naturally occurring cell-permeable Chaetomium fungal epi-dithio-diketopiperazine that potently inhibits the H3K9 histone methyltransferase activity of Drosophila melanogaster SU(VAR)3-9 and its human homologue SUV39H1 (IC50 = 600 and 800 nM, respectively) in a SAM-competitive manner, while exhibiting much reduced potency against murine G9a or Neurospora crassa DIM5 H3K9 HMT (IC50 = 2.5 and 3 µM, respectively) and no activity against the H3K27 HMTase activity of Drosophila E(z), the H3K4 activity of bacterial SET7/9, or the H4K20 activity of bacterial PRSET7. Although the reduction of intramolecular disulfide bonds of Chaetocin does not affect its HMTase inhibitory activity in cell-free enzymatic assays, the integrity of the disulfide bonds is shown to be essential for its cellular uptake. Myeloma cell lines as well as myeloma cells isolated from patients are shown to be especially susceptible to death upon H2O2 or Chaetocin treatment due to their heightened sensitivity to cellular oxidative stress induced by these agents.

Warning

Toxicity: Harmful (C)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Isham, C.R., et al. 2007. Blood109, 2579.
Greiner, D., et al. 2005. Nat. Chem. Biol.1, 143.

Legal Information

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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